January 2020. I’m on a Zoom with my new boss, reviewing candidates who are interviewing for the role of becoming my “new” new boss.

On paper, they were all great. Well-experienced. They’d done the job before. They could probably survive in the crazy, chaotic environment we were in at the time.

But none of them blew me away. None of them were going to.

They were doing the job I was going to do next.

Even if they had been in the Director role for a few years, they didn’t feel that far ahead. How many 11th graders are all that impressed by a 12th grader?

The people were smart, but the conversations were the opposite of inspiring. For every good idea I heard, I’d listen to three (or ten) things I’d do differently.

My boss told me she put me on the search because I had a high bar. I was her recruiter — the one who brought her into the company. She knew how I operated.

But I still wonder if she saw it before I did (she usually saw things before I did) — nobody who wasn’t named Mike Radice was getting my endorsement unless they were the Recruiting Director equivalent of Derek Jeter.

The Silent Pattern

This has been the pattern through 17 years of recruiting and nearly a decade leading: the most qualified people aren’t a lock to get the job.

I know because I found people with better credentials than mine, presented them to my boss, and watched her choose differently.

I know because I’ve regularly passed up talented people with sexy resumes for people with scars and bruises.

Here’s the brutal truth (he said, longing for the days before AI ruined that phrase): it doesn’t matter how qualified you are on paper. Hiring managers will hire the person they feel they can work with. Enough skills to do the job. Room to grow. Coachability. A personality they’re comfortable with. Their vibe. Someone they can put in front of other stakeholders without getting a call later asking, “Why’d you hire that dipshit?”

I was presenting impressive candidates — she’d have known if I was sandbagging the search. They just weren’t impressive enough, not for what the company needed, and most definitely not what I needed in a boss.

We needed someone who could elevate the team. I saw myself as that guy, even if I hadn’t done it at this scale yet.

My boss had an inkling I wanted the job. I think that conversation confirmed it.

Mind The Gap

The external candidates had done the job. I hadn’t. And in hindsight, I credit that gap for most of my success.

I’ve stepped into roles where the job was familiar. After the newness wears off and you settle into the new routine, it’s the same gig — just different scenery and different toys to play with. Outlook instead of Gmail. This ATS instead of that one. Once you settle in, you realize: I’ve already done this.

But when you move into a role you’re not fully qualified for, you’re trying to prove something — to your manager, to yourself, to the voice inside that’s hounding you like a bleacher creature in the Bronx. You don’t know what you’re doing. You’re gonna fuck this up. You should’ve just stayed where you were. Know your place. There’s a hunger to learn, a willingness to be coached, a desire to become worthy of the new seat. That’s an element you find less frequently in people who’ve been there, done that.

I cringe to think of the leader I was back then. I remember a couple of ego-fueled team meetings in particular, chest-thumping and shit-talking, that still make my skin want to slither off my body. But you have to start somewhere.

Attitude and coachability beat hard skills. Every time. Because at some point, every hard skill atrophies. The skill that made you lethal ten years ago might be obsolete today. The person who can learn is always the safer bet, even if they have to learn a few things to handle the bigger job.

The “Prove It” Months

She told me straight: You could be the guy to run this department. But you’ve got a long way to go. There are gaps in your game, and we’re going to have to work on it together.

So that’s what we did.

Some weeks, it felt like I was progressing. I felt my mind stretching. My beliefs were being challenged. Sometimes, I’d get punched in the face — often in public settings — and have to think about where I went wrong to allow the blow to land. I’d do a better job with a direct report in a tough situation and know that, six months earlier, I’d have bungled it.

Other weeks, it felt like I was shredding fresh powder in Breckenridge, smooth heel-to-toe transitions while kicking up clouds. Dialed in. Executing at a high level. Popping my head up to see if anyone was noticing — and, oh shit, boss is out of office today.

Then a recruiter called.

In recruiting, it’s all about timing. Call someone on the right day and they’d never think of leaving. Call them the next day after a bad week and they’ll take every call they get. I wasn’t at “fuck this place” yet. But I was definitely at: is this promotion ever actually going to happen?

So I went through the process. Got all the way to an offer — better money, equity, the whole nine yards. The hiring manager seemed like a dude I could work with. It gave me something to think about.

In the end, I turned it down. I liked my boss, and believed she’d be true to her word — even if it wasn’t on my timeline. I also liked my team. And as crazy as the company was at the time, I knew my way around it, and I was working directly with C-level leadership. I’d seen enough candidates jump for the wrong reasons, just to find out the grass isn’t always greener.

So I kept chewing the grass I knew for another month.

Then I got promoted.

You Got What You Wanted. Let’s See If You Really Wanted It.

My loyalty was rewarded — the numbers were better than if I had jumped ship. (The guy who was going to hire me at the other company left a month later, too...so it goes).

Almost immediately, the peers who all wanted the same job — friends I had been through the wars with for years — started leaving, one by one. Within six months, they were all gone. I had to rebuild my leadership team from scratch and learn every department underneath me at the same time.

Another perk of the promotion: minimal air cover. I was appropriately deemed the “throat to choke” for all things recruiting, and everyone who had issues came to me. I didn’t realize how many issues there were.

(Much later, I’d come to understand that a leader’s job is mostly dealing with issues. For those who strive for the top spot in their org, leadership is summed up perfectly in this 2-minute scene from The Wire).

Tech Founder/CEOs are passionate about all parts of their business, so I’d occasionally link up with ours to talk about candidates. I’d get a Slack ping at 11pm with a “Mike, good to connect?” The next message (whether I responded or not) would be a Zoom link. Most often, this was to go through candidates that had applied to roles. Scrolling through our Applicant Tracking System, I’d have to walk through why one candidate got an interview while another didn’t, what the status was of a certain candidate, and so on. I never had context. I don’t think that really mattered.

There’s a real gap between wanting a thing and being ready for it.

I thought getting the title was going to make me feel a certain way. Like I’d “made it,” at least for a minute. That had been a milestone I had been working towards.

Instead it was: Welcome to the show. Let’s see if you know what the hell you’re doing. And if not, we’ll go find someone who does.

So you do the job. You get battle-tested. You do indeed fuck things up, but you also get a few things right. People see you’re trying. Some even want to help you. And you find out your CEO had a pretty good sense of humor at 11:30 at night.

Discomfort is Not Optional

The best advice I have for someone who wants to move up?

Get comfortable being uncomfortable.

I emphasize this for two specific reasons.

First, good leadership is all about the willingness to have difficult conversations. That includes the discussions that you have with your manager about getting into leadership. You need to speak up.

When my boss asked what I thought of those candidates, I could have told her the truth: I think I’d do better than any of these people and you’d get me for cheaper. But I didn’t. I waited for her to suggest it because I didn’t want to seem like my ego was too big. (She got to know it well, and it was too big. I have a tattoo to prove it.)

Still, that was stupid. You have to raise your hand and say, out loud, that you want to enter the ring. It’s going to change the relationship dynamic. You gotta be OK with that.

Second, when you’re stretching into something new, you’re going to have to become a version of yourself that doesn’t exist yet. That takes...as long as it takes. The missing 20% doesn’t sound like a huge gap to cover, until you remember that the last 10% of a project takes 90% of the time. It’s gonna be a minute until you’re good at the gig.

You learn as you go - meeting by meeting, situation by situation. You make some good calls and blow others. People like working for you — until some don’t. There will be gaps. You will fuck up. You’ll lose some sleep. You’ll learn from your mistakes.

That’s the point.

Hard to squeeze that into the “How was your weekend?” small talk on Monday.

It’s Sunday in the early afternoon. I’m solo parenting - Michelle’s out of the house, getting a breather of some kind (nails or a Starbucks working session...that was 5 days ago, who can remember 5 days ago??).

I’m sitting on a barstool at our kitchen island. Paw Patrol is on in the living room. Amazingly, all three kids are occupying themselves. Two of them are playing in another room, and the third is doing something with dinosaurs on the carpet while Rocky and Zuma argue about whose $2M (taxpayer-funded?) vehicle they take on a mission.

Seeing that I am both alone and unneeded, something that rarely happens when more than two people are home, I pop open my laptop. As a solopreneur, there’s always more to do, and today I need to banter with Claude over some tasks and outlines - stuff that can be interrupted, because it will be.

And five minutes later, it is. My four-year-old is standing in the kitchen, looking at me. He looks legitimately sad, which surprises me, because he was just having fun in the other room and I didn’t hear a scream or a slap.

“What’s wrong, little dude?”

“Daddy, I thought you didn’t have to work today.”

Oh, shit. Busted. He’s right. This is one of those moments that, if I had missed it, I’d want back - working instead of playing with him. I close the laptop immediately, thankful that he said something, and play with him for a little while...until I slink away to write for an hour at Starbucks before picking up a grocery order.

It wasn’t until journaling about it later that those nine words seriously fucked me up.

Sacred Hours

My wrist is vibrating. It’s 5 AM again.

I roll away from a snoozing Michelle, untangle myself from the sheets, and move before my inner bitch reaches up from the pillow and pulls me back. The exit from the bed is necessarily silent: waking the missus (or the snoozing pup in his cage at the foot of the bed) would ruin everything.

I peel my eyelids back and tiptoe into the bathroom. From there, I leave my phone charging (not today, Satan) and take the back way out into my kitchen: closet -> laundry room -> hallway. Somewhere along this dark journey, I will step on a Hot Wheels car or a rogue Lego.

In the kitchen, I procure two drinks: one for caffeine, one for hydration (LMNT for the morning win).

In my office, I sit at my “analog” desk, the one without any tech, and look at my tools: a notecard, a simple timer, a blank pad, and a pen. It’s 5:05. Time to get to work.

The analog desk is a new seat for my morning “ritual.” The temptation to fuck about on the internet - check email, check LinkedIn, check where the unnecessary impulse buys are en route to my house - proved too mighty for my slow-booting mental system.

I used to fight it. Now, I just avoid it entirely to start.

I look back at the notecard: three topics to write about. That’s all I get to pick from. One long-form, two short-form. Which one do my eyes circle back to more than once? That’s the first victim.

I set a 30-minute timer and begin to write.

The first sentences are trash - they wouldn’t hook a drunken salmon.

But I keep writing.

Some sentences look good. The rest could have been constructed by my six-year-old.

The scratch-outs begin. The rewrites are marginal improvements.

Holy shit! A truly great sentence out of nowhere. A gift from the Muse for doing the only thing I’m in control of: getting out of bed and planting my ass in this chair to write.

The page is more than half-full now. Soon, it’s full. I’m writing on the back.

The timer goes off. Now, I’m moving to my “digital” desk with my handwritten page (occasionally pages) to keep going. I look at the clock. 5:40. I have another hour til the kids are up.

I have momentum. My only job now is to not hit the brakes.

I’ve done this for nearly a year now, and now, I’ve done it another day.

I’ll do it again tomorrow. And the day after that, and the day after that. Whether I’ve slept well, slept like shit, stayed up too late, woke up with a whiny toddler at 4 AM...these are inconsequential factors.

I’ve had some solid wins, but not the breakthrough.

Don’t care. My job is to show up and do the work.

My wrist vibrates. Just like that, it’s 6:45. I hear Michelle walking up the stairs to wake the three kiddos. I’m into the kitchen to make breakfast and lunches.

The chaos of getting them out the door and driving them to multiple schools.

The day job.

The sports practices and playtime.

The dinner, bath, and bedtime routine.

The night-time chores.

Collapsing into bed, the last thing I do is check my wrist to make sure my alarm is set:

5 AM.

Writing My Way Into Hell

Of course, that’s the ideal. (Yes, right now, that’s my ideal).

But there are legit disruptions. Over the last 18 days, our family has had parainfluenza, croup, RSV, sinus infections, double ear infections, and now ‘human metapneumovirus’ (whatever the fuck that is).

Yeah, sorry. I’m not David Goggins or Jocko Willink. That derails the Radice clan.

So when the Sacred Hours are shortened or disappear altogether, I try to make up for it. Sometimes at Starbucks for a concentrated work block. Sometimes in the kitchen, in the margins, when the kids are playing, and I’m alternating between the scenery and the butler.

But journaling that night, I stumble upon a revelation that hurts so deeply that I almost wish I had stayed ignorant of it.

The disappointment in his voice.

It wasn’t “in-the-moment” disappointment, like when I tell him he can’t have Oreos at 10 AM. It was accumulated disappointment.

Which means this is not the first time he’s been sad that I’m working instead of being with him.

Glad I have a Miller Lite next to me as I write. I down it and keep going down the gruesome rabbit hole.

The kids know not to interrupt Dad when he’s working. It still happens because they’re still kids, but on the whole, they’re pretty good about it. And they know I do a lot of work on a computer.

So...anytime I’m doing work around them, I’m sending the signal not to bug me. Which means, I’m sending the signal that I’m unavailable.

The Miller Lite is now empty. I need another one.

I thought I was in the background. Instead, I was a “road closed” sign.

How many moments had this adorable little kid wanted to play with me, but didn’t approach me because he saw me typing? Let’s triple the terror, because if it’s happened with him, it’s happened with his older and younger brothers, too.

My perspective had been totally different. I thought I was modeling something for them: that you have to work hard for your dreams, that your Mom and Dad put in a lot of effort to build something that matters to them. I was hoping to inspire them to follow their passions and get good at something that brings them joy.

My four-year-old doesn’t care about that, though. He’s not thinking of career paths or following passions or avoiding getting stuck on the non-partner track at a consulting job or whatever particular brand of corporate poison I hope he can avoid.

He wants to play King Kong fighting Godzilla. And instead of attacking, King Kong is arguing with a fucking robot.

What’s worse: King Kong is sending the signal that “work” is more important than Godzilla.

I close the journal and go get another beer.

Prioritizing Failure

The day before I went live with The 2nd Act Launchpad, my biggest worry was that if I filled all five founding slots in the first few days, I wouldn’t have enough time to get to all five clients every week or so.

I didn’t need to worry about that at all.

A week after the launch, nobody had purchased a single slot.

Sitting in the kitchen, I’m not grinding away on client deliverables or something else that would have signaled success. I’m disassembling a failure. I am surprisingly emotionally detached from it, so I guess I have grown up a little bit, but still - that’s what was on the task list for the day.

So when I hear, “Daddy, I thought you didn’t have to work today,” it’s pretty easy to close the laptop. Both because I want to be with him, and because I am happy to walk away from a turd of an assignment. As a company of one, turds are still my responsibility, but I’ll procrastinate on them like the rest of us.

Playing is...play. It’s refreshing. It’s pretty hard to be anything but present when you’re a titan battling a titan half your size (meaning any punches thrown default to hitting you in a sensitive region).

After the kids go to bed and the chores are done, I head to the office for my fifteen minutes of journaling, and proceed to ruin my night.

Hundreds…or Thousands?

The problem isn’t that he caught me working on a day I said I wouldn’t.

It’s the revelation that when I’m working around them, I’m signaling that I’m off-limits.

And that’s a painful realization for two reasons. First, the signal that I was sending was both obviously the wrong one AND something I was completely oblivious to. That’s a blind spot that a drunk rapper could drive a semi-truck through. Not ideal.

The second was a math equation trying to answer a dark question: how many moments? How many for my four-year-old? My six-year-old? My two-year-old? My instincts know that I have to start counting in the hundreds. I’m starting to get really, really scared that I need to count in thousands.

How many times was I in the room but miles away?

How many times did they walk up, excited to show me something, only to see me typing, then turn and walk away, their bulbs dimming a little bit?

How many times did they say something cute or sweet or heartfelt that I missed because I was staring at my goddamn phone?

Such a waste.

And here’s the real problem: this is the concluding section of this newsletter. I do not have this figured out. It’s an open loop that’s eating away at me.

I thought I’d feel better writing about it. I don’t. I might actually feel worse.

I know the discipline of my Sacred Hours is important.

I know that raising a family while working a full-time job and building a side business is an impossible equation.

I know that I am a human trying my best, and that even an asshole like me deserves a little grace.

I know that everything worth having in life requires sacrifice.

But I need to get a hell of a lot better at figuring out what I’m paying before I pay it.

Because right now, I don’t want to look at my tab.

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I hit send on the text to Michelle and put my head in my hands, dejected.

I’m sitting in Red Horn Brewing, one of my favorite work spots...cool enough to still feel like Austin, but there’s no electric scooters littering the front walkway. It’s a coffee shop and a brewery, though my time here usually involves more dark roasts and espressos than lagers or IPAs. I’ve spent the last few hours on the coffee side of the equation, writing and preparing for the call with the guy from the academy.

The unexpected unemployment has now dragged on for 3 months. What started as confidence in my skills and reputation has devolved, first into frustration, then anger, and recently, legitimate fear. The call is my first uncertain step towards an even more uncertain career pivot.

At 38 with 3 kids under 4 and a wife who was laid off the same week I was, there’s not a lot of margin for error.

I went into the call with a ton of excitement. I got a glimpse into a future I felt I could legitimately pursue. The freedom to be my own boss, do work I had become passionate about over the last few years, and build something that can’t be taken from me in one phone call.

Everything was energizing, but my Spidey sense was tingling as the conversation drew to a close. The sales rep re-stacked all of the benefits I’d be getting, building up the value...a play I now recognize straight out of Hormozi’s offer stack. Then he hit me with the number.

Before the conversation, I had anchored Michelle on a much lower number.

I just heard 7x what we had discussed.

I squirm, visibly uncomfortable for the first time in the conversation, and tell the sales rep that’s way more than I could pay right now. The rep pushes to close me anyway. But a career in negotiations has taught me how to stall, so I tell him I’ll either talk to him in 24 hours or we’re done.

His last lines to me aren’t parting shots, but questions that feel a little too intimate for someone who’s just met me:

“What’s the real fear here, Mike? Is it really about the money, or is it not believing that you can be successful?”

My phone vibrates. Michelle’s written back. “We’ll talk when you get home, babe. I love you.”

Yeah, right. We’ll talk about how I’d need to peel off nearly a month of our expenses in a time we’re draining both our severance packages to chase a new dream.

I go back up to the register. Instead of closing out my tab, I switch to beer.

THE COUCH

Hours later, all three kids are miraculously asleep at the same time.

We’re tucked into the white L-shaped couch that, back in 2022, I insisted was a ridiculous purchase. With two boys already in the fold, we’d need a cleaning crew on standby. But it wasn’t a hill worth dying on, and the joke’s been on me: it’s comfy as hell (and cleaners come once a quarter to perform miracles in my living room).

She sits in the “money” spot - that long side, facing the TV, where you can kind of melt into the corner. I’m opposite her on the chaise.

She’s relaxed. I’m not.

Usually, I can journal my way to a solution before we’re on the couch, but not tonight. Tonight, things are just too big. I need to talk this shit out.

“And, look, the guy walked me through a realistic path to hitting $20k a month by the time severance is up. He admitted it’s aggressive, but said it’s been done. So if it’s been done once, it can be done again, right?”

Michelle is at her best when I’m at my most frantic. She sits in a calm where my energy doesn’t seem to touch her, which is a good thing tonight, because I’m radioactive.

“So what are you scared of?”

I’m standing now, beginning to circle the couch and stretch - a routine that comes out when my inner tension is nearing its peak. Sometimes, the stretching prevents the panic attacks. Sometimes, not.

“He was reaching.” A decade and a half of attentive interviewing gives you access to the micro-tells and what they mean. “There’s been, like, one guy who’s done it. Maybe two. One lucky client outreach could get you there.”

She’s quiet for a pause. I work on my hamstrings.

“But that’s not what’s holding you back. You said, even if it takes longer to get to $20k, you can see this being successful, right?”

“Oh yeah, totally. I could make way more than I’m making now.”

“So what’s holding you back?”

Now I’m the one pausing, but what looks like silence to her is violence to me. I can hear my heart as increasingly rapid thuds in my eardrums. If I let my breath get out of control here, the attack will set in, and the universe will be giving me my answer:

You can’t fucking cut it, Mike.

Instead of breathing deeply, I throw myself face-down on the chaise and force myself to say it out loud.

“That I can’t fucking cut it. That I’ll spend the money and not be able to make it work. That the business will flop just like the album flopped, but instead of just my ego, I’m jeopardizing our future and my family’s ability to live in this fucking house.”

I want to throw up. It’s fine, I tell myself, because the cleaners are coming next week. I lift my head up and look at her, feeling weak and vulnerable and not anywhere near enough.

She waves her hand like she’s swatting a fly.

“Oh. I’m not worried about that at all.”

BELIEF IS A BEAUTIFUL ARMOR

Back when we started dating in 2012, John Mayer was on anytime we drove anywhere. We listened to him on our first (real) date, and we danced to for our first (married) dance. We see him anytime he’s in town.

The first weekend I drove up from Houston to visit Michelle in San Antonio, I had his brilliant Where The Light Is live album on repeat. His cover of Hendrix’s Bold As Love came on, and while it’s an awesome song, John goes on a bit of a tangent in the middle of the bridge (the topic, unsurprisingly, is love). But in the midst of the outpouring, two sentences hovered above the rest and tattooed themselves on my brain:

“I don’t mean, like a Roman candle, firework, Hollywood, hot pink love. I mean, like, I’ve got your BACK love!”

I’d heard it thirty times before and never thought about it once. But after he said it, Michelle, looking out the passenger window, smiled and said, “I want that kind of love.”

So did I.

On the couch on the verge of a panic attack with my 3-month-old in the next room, I know one thing in this universe to be true:

I’m lucky enough to have ‘I’ve got your BACK’ love.

“Seriously? That doesn’t worry you? Me fucking this whole thing up?”

Her head shake is immediate.

“No, not at all about that. I mean, yeah, the tight runway makes me uncomfortable. And I’d feel more comfortable if you kept applying to jobs, just in case something comes up that can help us sooner. And, I don’t want you to miss all of the baby’s time as a baby because you’re stressed out building a company. But, no, I’m not worried about you failing.”

I feel like someone is both taking a load off my shoulders and wrapping me in a blanket that just came out of the dryer. The storm in my head is quieting. My pulse is taking the escalator down.

These were logical concerns. They were risks that could be mitigated. More importantly, they weren’t my crippling self-doubt, my generationally-inspired tendency to play small, or my inner bitch.

They were just problems to solve for. Keep the important things the main things. Mitigate the risk where possible. Minimize the downside.

THE CLOSER

The next morning, I am ready to go at 6 AM, but the call isn’t until 12:30. I get on the Zoom and do the dude’s job for him. Run the card, already, woulda ya? Yeah, yeah, onboarding emails. Slack invites. Fine. Let’s go.

The receipt hits my inbox. My butthole tightens to pinhole width. I wonder if Chase will let me report this as a fraudulent charge if I call in the next 5 minutes? Is that a thing?

Then, beginning to model the erratic mood swings of a true founder, the guy born last night is back, and Mike Radice is an entrepreneur, baby. I’ve wanted this for a long, long time. I’ve got a wife who believes in me. Other than raising a newborn and two toddlers, I have no other commitments. Time to actually pull this off. LFG.

Within a week, three (3) recruiting leadership roles with impressive companies materialize from nowhere in 4 days.

Well, that changes everything. But that’s why we agreed on the guardrails in advance. I thought I’d get longer than a week at this, but I have my priorities clear.

So life happens (again), and the ghostwriting thing temporarily goes from the whole meal to the sauce simmering on a side burner. It’s there—you smell it every time you come in the room—but it doesn’t have your full attention.

And that’s fine. Because I didn’t need the ghostwriting business to crush it. I didn’t need to escape from corporate America - and honestly, I’m glad I didn’t. I’ve already made some life-long friends at this new gig.

What Michelle unlocked that night on the couch was more than a career choice. It was a total perspective shift. The moment someone believes in you more than you believe in yourself rewires something inside of you.

For me, it was recognition that my life partner, the one who will tell me (with pleasure) when I’m out of my goddamn mind, doubled down on me instead.

That’s real.

I’ve spent more time out of my comfort zone over the last two years than I did in the prior decade. I’m a far-from-perfect, pretty-damn-good dad. The ghostwriting business turned out to be the on-ramp to building 2nd Acts.

I’m not here without that.

I’m not here without her.

This has been playing on a loop in my head since December 2023.

23 days after my son was born, I got laid off. My wife’s pink slip was 5 days behind mine.

3 kids under 5, and in less than a week, 100% of our income stream fucking evaporated. And I didn’t have a backup plan.

Looking at my son, finally disconnected from the wires and tubes of the NICU and sleeping peacefully in his bassinet, that’s when the mantra started.

That was the starting point for what I’ve been building.

What I’m launching today.

What I Found When I Went Looking

At that point, I was pretty fed up with the corporate shit, so I decided to go look at alternative ways to build a life. Getting outside funding or investing in a business idea was out. Besides, that wasn’t really what I was interested in at the time. I had been writing, and whether as the main thing or a part of it, I knew that’d be prevalent in my next chapter.

The only problem was that for the last two years, all I had been writing was fiction.

The list of hyper-profitable post-apocalyptic sci-fi writers is pretty short, and nobody other than my wife and siblings had laid eyes on my work. Odds of me hitting it big...right up there with the Jets winning a Super Bowl.

So I needed to figure out how the hell to become a professional writer with no prior writing experience (if you don’t count lambasting unsuspecting candidates and harassing hiring managers who refused to return my fucking calls).

I found a number of great courses and even ended up joining a cohort that had a ton of value. But the assumptions were the same everywhere. You had large blocks of time to dedicate to courses, live calls, hot seats. You were going to follow one prescribed path toward one specific thing. You could fuck around all day in Slack channels and recorded call archives to seep yourself in knowledge.

And if you had no idea what you wanted to build yet [me], there was basically nothing for you.

Most of these courses were put together by people in completely different life circumstances. Young entrepreneurs who were smart to jump on digital creation early and got to teacher status in a fast sprint.

That wasn’t my life at all. I couldn’t move back in with my parents or subsist on a studio apartment on ramen and Miller Lite if my business venture didn’t work out. I have a wife. Three kids, including this 23-day-old little nugget who is going to need formula. A mortgage. I’m the kind of guy who had 10 hours a week to build if I was lucky — and at that point, they were the sleep-deprived hours that come with a newborn.

Nobody had built anything for people like us.

Realistically, by the time I was taking those courses, I was already behind, and I fucking knew it. I needed runway. The time to start building was two years ago.

What I Built

Still, I wasn’t just going to spend the next few months smashing Easy Apply on LinkedIn and having coffee dates, showing up in another goddamn Starbucks somewhere around Austin in a button-down and reeking of survival desperation.

So I took the courses. Went through all of the AI trainings, the prompts, the Notion pages and templates. I wrote copious notes. Filled notebooks. Journaled through the whole experience. Voice notes on walks and in the cold plunge. I did it all.

And then I went and built the thing I wish I could have handed myself two years ago.

The 2nd Act Launchpad is designed for people at our stage of life — leaders and seasoned operators who are good at what they do, but with real obligations and commitments. Smart people who see layoff after layoff and know they need to be building their life raft while they’re still on the boat. Like, right now.

The program is eight weeks long, but you can do it in four if you’re all in. Five one-on-one calls and a 21-prompt AI system that you work through between sessions, so you’re not waiting on me (or anybody else) to get shit done. Two tracks: one for people who have no idea what they want to build yet, and one for people who already know but can’t get it off the ground.

At the end of the eight weeks, you leave with a validated direction, a complete offer, a 90-day roadmap, a discipline system, and an AI brain tailored to your situation, designed to help you run your new thing.

The Honest Founder Truth

I would love to spend all of my time with my fellow builders, swinging a machete by their side, helping them out of the woods. But that’s not my reality. I have five spots. It’s legit all the time I have because I’m building this in my own 10 hours a week. I’m still all in on my day job. I’ve got a wife, kids, t-ball, jiu jitsu, the whole nine yards.

For everybody jumping in on the founding cohort, it’s a win-win. You’re getting a better price and more direct access to me. I’m getting honest feedback and a result I can point to.

And I’m guaranteeing that you get on your path. If you show up every day and document what you’re doing, it works — or you get your money back.

If you’ve made it to the end of this, you’re still reading because you already know. You know the moment is coming for you, or it already has. You’ve felt that stomach-dropping, shame-caked feeling of standing over your sleeping kid, unsure how much longer you’re going to be able to provide for them.

I don’t know if I’ve ever felt worse as a parent. Fear and uncertainty are a powerful fucking cocktail.

When you’re in that moment, you tell yourself the same thing I told myself:

Never again.

If you’re ready, head here:

The text came through on a late Sunday afternoon in early December. I put my phone down.

I knew that text. I’d sent that text.

Our newborn son was 23 days old. The last 3 weeks had been some of the most emotionally draining weeks of my life. Our little dude arrived just early enough for a mandatory NICU stay to help his little lungs finish developing. For 8 days, Michelle and I were ships passing in the night. Instead of bringing baby brother home to his eager older brothers, we were alternating shifts at the hospital during visiting hours. The non-NICU parent would be at home with two toddlers and two ailing dogs, running operations to try to keep the home life “normal.”

Now, the night before I was supposed to return to work, “normal” was about to be on the receiving end of a hand grenade.

What I Thought I Was Building

My time at this company had been the most successful arc of my career. Following 3 unsuccessful stints, making me question whether I had “lost it” as a recruiter, I joined this organization as an individual contributor in an attempt to rebuild.

I knocked it out of the park.

4 promotions in 5 years. I started as an Enterprise Sales Recruiter, then moved to Executive Recruiter, helping the CEO reshape the executive team. From there, I led a small Corporate Recruiting function, then moved into the Director seat. That’s when things got wild.

These were the early-COVID hyper-growth times. As a remote-first company, we had a massive competitive advantage in the market. We scaled rapidly, and my team had to scale to match. We grew from 15 to 58 in 18 months. I had 6 leaders reporting up to me. Somewhere in the chaos, I was promoted to VP (skipping AVP entirely, which my boss had to pause to tell me, “This doesn’t happen”).

The peak was a full-team offsite in Dubrovnik, Croatia, where I had nearly 60 people from 13 countries together for a few days of work and fun with King’s Landing as a backdrop. One night, we chartered an old pirate ship and cruised around the beautiful harbors of the Adriatic Sea at sunset. Stepping back onto land, I remember how light I felt. I was proud of what we’d built.

But unease was growing. It had started with that VP promotion. I should have felt like I “made it.” Instead, I looked above me and saw the end of the line - my boss’s job, the Chief People Officer gig. And I knew there was no way in hell I’d ever take that job. I’m not really an “HR-intervention” guy.

And so, at 37 years old, I had to ask myself, “Is this as good as it gets? Is this what I’m going to be doing for the next couple of decades?”

I’d seen this happen to candidates for years. Guys in their 50s coming in for meetings, and 10 minutes into the conversation, I’d be thinking, “You’re going to have to change so much for anyone to even sniff at your background.” The road ahead was clear.

And my exit strategy? Well, the “rock star” dream had been squashed a few years earlier with an album release that went nowhere. The current project was writing a fiction novel - something that was a ton of fun to learn, but pretty dicey to call a “career back-up plan.”

The Slow Dismantling

Five months after Croatia, I arrived in Napa for a People Leadership Team offsite. Within moments of checking into the little hotel, my boss pulled me aside.

“We’re going to have to do a layoff. And it’s going to hit your team hard.”

Huh? The CEO had prided himself on never having done a layoff in the 8 years the company had been in business.

But a week later, I was saying goodbye to a third of the team that I had built. Good people. People who, as they were losing their jobs, were asking ME how I was feeling, acknowledging how hard it had to be for me.

That was fucking brutal.

Round two came a few months later and was even worse than the first. These were people I really didn’t want to lose. As I went through those rounds of Zoom calls, the dialogues already committed to memory, I started to feel what these actions were costing me. Friendships (because who’s returning calls from the guy who takes away your livelihood?), but also pieces of me. I remember every face, every conversation...but I was having to numb the part of me that felt deeply about these people.

Round three brought the team down to the size it was when I became director. I was fed up. This amazing thing we had built had been stripped and sold for parts, and had nothing to do with our performance. Life was unfair. My disdain for the job was through the roof.

My text came before the fourth wave.

Day 23

I don’t have any complaints about the way it all went down. My boss, always my biggest supporter (and toughest critic), sat in her bed while I sat in my office. We chatted like we had thousands of times over the last 5 years together. The strategic work had dried up. I was expensive. My #2 was more than capable of running the team. It wasn’t personal. The package was fair. We were parting as friends.

The next morning, I joined a Zoom call with the team to say goodbye. The people I’d been in the trenches with through the build, the crazy requests from the founder CEO, the last-minute offers for “mission-critical hires” that broke all of our processes, the tech implementations, the brainstorming sessions, the life events we celebrated together. 17 little boxes on a screen. I didn’t cry. But I felt it all.

Then I closed the laptop...and the longest professional chapter of my life.

The prevailing thought in the curtained-off NICU square was always “I want to get him home now.” But once that chatter cleared, my thoughts turned to big-picture stuff. The instability at work. The lack of any meaningful backup plan.

That came into clear focus on day 1 of unemployment. Yes, there was relief: no calendar notifications, no red dots on Slack, the knowledge that I wouldn’t have to tell anyone else that their paycheck was gone. But I’d stand above my son in his bassinet, watching him sleep, and the thoughts were anything but relief:

Look at this little guy.

What did you just bring him into?

You could lose the house because you never built a fucking backup plan. What kind of father does that?

But it was a few weeks before Christmas. I had a decent package to carry me into the new year. I decided to lean into the unexpected surplus of family time, confident that I’d find something in February or March.

Then Michelle got laid off 5 days later.

158 Applications. 3 Interviews.

The next few months were difficult. The holidays were a great family time, but when you’re unemployed, every moment has a shadow hanging over it. I’d see my kids’ faces light up as they unwrapped Christmas presents, as I mentally calculated the cost of each gift. You know you shouldn’t be doing it, and your brain does it anyway.

Shortly after Christmas, we had to put one of our dogs down. It wasn’t wholly unexpected - he was diabetic, blind, and most daily actions were a struggle. Our most emotionally-intuitive pet, we assumed he stuck around to meet the baby, then said his goodbyes.

A month later, our second dog went, too. Surprise kidney failure.

In 60 days, we’d lost 2 jobs, 2 dogs, and 100% of our income stream.

This was about the time I started panicking.

The market had been shit when I went into it, but I still held onto the confidence that I had a hell of a success story to tell. Meanwhile, the voice in the back of my head was already jawing at me: “What? Do more of the same? You already hit that mountaintop, remember?” But when I looked at the dwindling numbers in my bank account, it was easy to shut that voice up.

As my applications without interviews hit triple-digits, I started having a different thought:

“Nobody is coming to save you.”

Fuck.

I’ve been giving the same advice for job searches for as long as I can remember:

“Do it for an hour or two a day and then stop. Go do something else, or you’ll drive yourself crazy.”

For once in my life, I actually followed my own advice. In the hours that weren’t spent job-seeking, bottle-feeding, diaper-changing, or serving as the nap station for our newest addition (one I didn’t mind, since I got to hold him without tubes and wires attached), I was thinking about what else I could do to earn a living.

I had spent the last couple of years learning how to write fiction. And I saw plenty of people writing online, brands that needed help telling their stories, and books with famous names and smooth prose that didn’t match the intellect of their subjects.

Maybe I could become a ghostwriter.

I’ve found that, when you open your mind to a new possibility, the universe tends to answer. A couple of guys I followed on LinkedIn, Dickie Bush and Nicolas Cole, were teaching people to write online. Cole had even written a book on The Art and Business of Ghostwriting. It seemed straightforward enough.

They had a cohort-based course teaching how to build a solo ghostwriting agency. I said, “fuck it,” and booked a call with their sales team.

The Cruel Joke - And The Never Again

How I ended up enrolling in the cohort and becoming a ghostwriter is the subject of an upcoming article, so we’re going to fast-forward through that scene for now. The TL;DR - while continuing to clock an hour a day on a job search I expected to yield nothing, the rest of my time was spent learning how to become a ghostwriter and building a business.

By mid-February, I had “the conversation” with Michelle - that I was fucking done with the job search and was going all-in on ghostwriting. I’d do whatever it took to be successful. She backed me. I got the LLC, stopped the bullshit LinkedIn applications and coffee-meeting requests, and declared to the universe, “I’m an entrepreneur.”

The universe does what it usually does in those moments: it laughed in my face. “Like hell you are.”

The next Monday, I got a note that turned into a coffee date. An old CMO pal told me her company was contemplating a confidential TA leadership change. That afternoon (no shit), I got a cold outreach from a recruiter about a global head of TA job. The coup de grâce was the Wednesday text from a tech founder whose software I’ve relied on for years - and the best networker I know. “So and so is looking for a TA leader,” he tells me. “She’s awesome. You’re awesome. You two need to know each other.”

3 months of dead airtime. Then 3 viable opportunities in as many days.

Writers don’t put shit like this into movies, because real life tends to be too unbelievable for fiction.

I went through all of the interview processes—still building my ghostwriting business, but suddenly looking at the prospect of replacing my paycheck by next month instead of (maybe, if I was lucky) Halloween. Job offers came in.

Three kids under 4, one of them a newborn. A wife mired in the same job-search muck I had been in; lots of effort, zero prospects.

It wasn’t a question. I signed with my current company. While I filled out the DocuSign, I heard two words repeating in my mind:

“Never again.”

In April, I rejoined the corporate ranks and put the ghostwriting business on ice as I ramped up in the role. But this experience had altered the way I thought about my career. Gone were the thoughts of company loyalty. I no longer believed that I was indispensable. I didn’t look for my job to provide me meaning.

Once I had things in a stable place at work, I resumed building. Evolving. Refining. I saw ghostwriting as an awesome skill to have, and I’ve been able to help out a few clients... but it’s not all I’m meant to do.

What I’m doing today—helping people build their 2nd Acts without burning down their first—is.

Because we’re all at risk. We’re all one phone call away from having our livelihood taken from us. Every parent hovering over a bassinet, wondering if they’ve done enough.

We can either bury our heads in the sand and pray it won’t happen to us.

Or we can build our life raft while we’re still on the boat.

I know my answer. It’s summed up in two words:

Never again.

---

P.S. If this landed, later this week, I’m opening 5 spots for the founding group of the 2nd Act Launchpad - an 8-week, 1:1 coaching, AI-powered approach to figuring out what and how to build something that can’t be taken from you. If you’re interested, reply. If you’re curious, stay tuned.

It doesn’t happen overnight. At 26, I was a single dude living in Houston, no kids, no dogs, no “real” responsibilities (besides keeping myself alive). Blink and you’re 40 with a wife, 3 little boys, a house you built, a career, a passion for a thing that doesn’t pay you a lot yet, and a puppy (because why not?).

But I’m walking around with the same cup I had at 26. I’m still the same guy (at least when it comes to name, rank, and serial number). So how am I expanding my mind to fit all of this?

The Cup Is Overflowing

The real answer: I’m not.

I’m losing stuff. Moments. Memories. Whole years, it seems. Flashes of insight that I wasn’t quick enough to write down. And I can’t stop thinking about what living the life I’m living right now will cost me in the end. The life I keep opting into, day after day.

It’s the Impossible Equation. If you’re a working parent, you already feel the pinch. Needing to be in three places at once. Countless demands on your time and attention at rates that would be unfathomable to our ancestors two generations ago. We’ve spent decades dissecting “work-life balance,” like it’s a benefit a company can provide or some attainable state. It’s bullshit. The minute we could get email on our phones, the best we could hope for was “work-life integration.” Nobody has the playbook for that. Which is why most of us suck at it (myself included).

But there are others like me who see that whole picture and go, “Yeah, I see the partner and the kids and the mortgage and the day job and the cute puppy whose recent dump stunk my office up for an hour...But I have this thing I have to build. And I need to do it now.”

God help us.

Because it’s the dumbest time to build. And we’re going to do it anyway.

I’ve always had some outlaw in my way of thinking. Rebellious teenager energy mixed with a confidence that whatever moves I make, I’m gonna get away with ‘em. Chalk it up to rumored mafia connections a few generations back.

It’s my version of the pull to break away from the well-trodden path.

Despite my ancestry, my draw was never a career that ended in a cell or a cemetery. I always wanted to create things: first music, then books, businesses, and solutions to problems. Building my own thing to contribute to improving my little corner of the world, and along the way, freeing me from the “default mode” way of living.

And I’m looking at this dinky cup that I’ve been holding all my adult life. It certainly wasn’t built for this...not even if I’d upgraded to one of those 32 oz Erin Pub mugs that Villanova kids would obliterate after a night at the local Irish bars could it hold this.

On top of that, I’m not operating like I was when I was young and optimistic. I’ve seen too much.

Financial insecurity. Broken relationships. The loss of loved ones. The scars of interpersonal conflicts, traumatic experiences, layoffs, and health scares.

I don’t know about you, but my cup’s beat to shit. Hairline fractures are adding to the spillage. Memories I wanted to keep slipped out and pooled around the base of the cup. Ideas I had for my business - some really goddamn good ones. The important stuff is seeping out, too. I used to have every millimeter of my wife’s face mapped in my mind: now, I’m happy that I can remember her eye color.

The Permanent Guilt Loop

Theatrics aside, I’m in it now. I’m building my 2nd Act while working hard to ensure I don’t dynamite my current life. It means trade-offs I hadn’t thought about, skills I hadn’t cultivated, and mental disciplines I hadn’t fully developed.

Take my perpetual guilt loop as an example:

When I’m with my kids, I feel like I should be building. I’m watching my boys wrestle in the game room and take swings in the batter’s box, but my mind is racing. “I’m behind. The deliverables are stacking up. This is what’s jeopardizing my launch timeline. I still have to learn how to do X. Y didn’t configure properly, now I have to troubleshoot. HOW DO YOU MIGRATE YOUR CUSTOM DOMAIN TO SUBSTACK IN TIME FOR THIS NEWSLETTER??” I’m right here. And I’m miles away...missing memories.

When I’m building, I feel like I’m robbing my family. I’m writing this at a Starbucks 1.7 miles from my home. It’s a Monday morning on a day the kids have off from school. I could be snuggled up watching Paw Patrol, or making kids pancakes I promised I’d make for 3 days (and didn’t, I’m realizing as I type), or tossing the tennis ball with the pup. I’m right here. Advancing my dream. And I’m miles away...missing opportunities.

All the while, I’m going to war with the voice in my head.

“You’re missing the good stuff right now.” No, I’m nailing this newsletter.

“Your son is getting better at t-ball, and you’re missing that stage of evolution because you’re distracted.” Well, yeah, but when else am I going to do it? And what am I really missing? He’s on his butt, building a dirt pile at 2nd base while ignoring his coach.

The tension is always there. It’s like a cancer, slowly eating away at me. When I’m with my family and I haven’t launched yet, I’m thinking about the business. When I’m working on the business, I’m thinking about Michelle and the boys. It never stops.

It doesn’t matter where I am. I’m always in the wrong place. Building while parenting feels selfish. Parenting while needing to build feels like I’m pushing my dream further away. I can’t win.

But in addition to coming from gangster bloodlines, I’m also extremely stubborn. Which means I’m not giving up on any of it. So how am I, and all the others like me, supposed to keep going?

The Margins ARE The Business

People like us don’t get 4 hours of focused work blocks following our morning walk, workout, or cold plunge. We write ideas in the notebook between meetings. We type notes in the stands (on the rare occasions we’re not coaching). We sit in the driveway to get our thoughts down before dragging the groceries into the house.

This newsletter’s proof. I outlined the damn thing on Sunday afternoon, driving downtown to hit La Barbecue with some out-of-town family (which ended up becoming Terry Black’s after the La Barbecue brisket and ribs sold out. Sad, but TB’s is a solid consolation prize).

My 2-year-old was asleep in the back seat, pacifier in his mouth, sunglasses sliding off his nose. I was whispering a nine-minute voice note, which was interrupted by me yelling at (yet another) Austin driver who doesn’t understand right-of-way laws. When I got home, after the kids went to sleep, I dumped out the transcript and started hunting for ideas to structure what you’re reading. I’m writing it during this guilty Starbucks session.

This IS the system. The margins aren’t a consolation prize for people who don’t have the luxury of focus time. They’re where the work gets done.

The Fundamental Truth They Don’t Tell You

All the productivity advice lives somewhere between mediocre and irresponsible.

“Quit your job and follow your passion” means I’ll lose the house.

“I’ve made $8 million over the last 3 years” is irrelevant when I’m still trying to make my first $10k.

“You need to go all-in.” Sure, after getting the kids to school, working the day job, exercising, eating, taking the kids to practice, and going through the epic bedtime saga, I’m all in...on the 90 minutes a day I have to myself (because I wake up 90 minutes earlier than everyone else).

Here’s what people like us need to hear before we start:

If you’re going to build in this stage of life—as a working parent with young kids and a full schedule—THIS is the experience you’re going to have. The tension will always exist. The guilt loop is permanent. The margins are the system. Accept it or don’t build.

This is chosen suffering. We’re choosing to build under these life conditions. I’m not an idiot: I know it’s the wrong season. I should have done this shit when I was 29, but I didn’t. The flip side is wait until I have more bandwidth.

Well, my youngest is 2, so....a decade? Longer? I’m 40. My mom passed away at 56, and my grandfather was gone by 52.

I think about that every day. Fuck waiting.

But there’s a difference between choosing a worthy struggle and self-imposed suffering. It’s never more apparent than when I want the conditions to be different. “How fast could this thing launch if I could focus on it for two uninterrupted weeks?”

Doesn’t matter. The conditions are the conditions. Every time I let myself get frustrated that things aren’t different, I’m cutting open my flesh, dropping the knife, and reaching for the salt.

The Argument For Doing It Anyway

The above paragraphs are like taking little kids out to dinner in public. If you’re a couple contemplating kids, watch a full meal of parents wrangling toddlers before you make your decision. Like kids, you’ll never feel fully ready. I wrote this to scare off the people who aren’t ready. If you don’t have some serious resolve and have a willingness to take a beating (a la Tyler Durden not fighting back in the basement of Lou’s Tavern), turn away now.

But some of those optimistic couples will have kids soon. Just like plenty of you are saying, “Doesn’t matter. I’m doing it anyway.”

Good. If you’re going into this thing with eyes wide open, there’s a smaller chance of you getting knocked out of the race you’re about to run.

Because there are really, really good reasons for doing it anyway.

Anybody who’s watched the economy over the last two decades knows one thing for certain: we are all at risk.

If your company’s underperforming or the market shifts, you might get laid off.

If you got a new boss, you might be shown the door. If your job can be done by AI, it will be...and soon.

Building your own thing BEFORE you need it is great for two reasons:

1. It gives you sovereignty. If you do it right, 12-24 months from now, nobody can tell you which of your kids’ events you can or cannot attend. At the minimum, you’re building the life raft while you’re still on the boat.

2. It provides a value to the world that doesn’t exist yet (at least, not your version of it). All the world’s religions point to service for a good reason. We’re here to be useful.

Both are good reasons. Both are also necessary. Marry your desire for sovereignty with doing the most amount of good for the most amount of people, and you’re likely to solve the money problem at the very least. But if you can dial that balance in, your life’s ceiling goes way, way up.

So lean into the crazy-believer energy. Build in the margins. Try to make something of your own. Recognize it’s going to cost you something (or multiple somethings) you care about, and hold an honest accounting with yourself before you go into it. But go into it. Empty the cup of the non-essential (seriously, how much Netflix and Instagram do we all need to make it through a Tuesday?) and make room for the important stuff. Patch the cracks as best you can, and get on with the fucking thing.

Because the kids that you think about while you’re building?

They’re watching. They’re downloading your OS.

And they’re either watching you build someone else’s dream, or you’re modeling the path to building your own.

I haven’t yet paid a therapist enough money to figure out exactly where it came from, but I have a general idea.

All families are fucked up in their own way, and ours was no different. Mom’s side were a particular breed of Massholes: parents who withheld affection and sisters with sharp claws and small minds. Her mom and dad didn’t even show up to her wedding because they didn’t like my dad.

They were nothing if not consistent, because they walked out on us grandkids, too.

It was a sunny summer afternoon in 1996 in Upstate New York, the day before we were supposed to visit the Baseball Hall of Fame in Cooperstown. I didn’t hear the full conversation at the kitchen table, but it ended with my grandfather standing up and saying, “I don’t have to take this shit.”

They were packed in less than 10 minutes.

Mom: “You don’t have to do this.”

Grandma: “We have four other kids.”

Then they were gone. Leaving my 8-year-old cousin at our house.

I spent years wondering what was wrong with us. Why were we so easy to walk away from?

That pattern followed me everywhere. Middle school edges of friend groups. High school pretending to fit in. Business school teaching me to please clients and kiss ass. Recruiting, where success meant people liking me.

Somewhere in my 30s, I snapped. I let the kid out—the one who spent hours reading Calvin and Hobbes, coming home with grass stains and blood on his shirt. The high schooler at punk shows on the edges of mosh pits.

And for the first time in two decades, I liked myself.

I needed this book when I was 22. I found it at 39.

THE COURAGE TO BE DISLIKED

Authors: Ichiro Kishimi and Fumitake Koga

Published: December 12, 2013

Length: 288 pages

Buy: ​https://amzn.to/3OstrMV

WHY THIS BOOK MATTERS

I picked this book up when I was almost 40, years after I’d already made the choice to stop playing the approval game.

I had three kids under 5. A demanding corporate role. And I was building a business in the margins of my life—posting publicly, knowing it could damage my career, doing it anyway.

The book didn’t teach me something new. It validated every risk I’d taken since that “fuck it” moment in my 30s.

Kishimi and Koga are a philosopher and a writer who spent years translating Adlerian psychology into something functional. They packaged it as a dialogue between a teacher and a student—the student brings up every possible objection (to the point where I wanted to tell them, “All right, we fucking get it”), but that thorough examination leaves no room to dodge the truth.

The big idea: your unhappiness is a choice. And you can choose differently.

I’d already chosen. This book explained why it was the right choice.

If you’re building something that matters while everyone around you is asking why you can’t just be happy with what you have—this book will make you feel less alone. And it’ll give you the framework to keep going.

THE ESSENTIALS: 3 CORE IDEAS

#1: Your Unhappiness is a Goal You’ve Chosen

At 22, I was selling corporate sponsorships for two professional sports teams, the Philadelphia Flyers and 76ers.

My friends from Villanova had landed those Big 4 consulting jobs in New York that I told myself I didn’t want to take. But come senior year, I found myself a little jealous of the prestige of that whole operation. Offer letters months in advance. Manhattan apartments. Partying in Frank Sinatra’s city.

But I landed a gig working with NHL and NBA teams. I’d run into professional athletes in the hallways (including almost knocking over the now-GM of the Flyers right after he was traded to Philly as a player). In my mind, my career was just as credible as those of my consulting buddies.

I worked 80-100 hour weeks making just enough money to make rent. Cold calling all day. Suit jacket on to entertain clients (not mine) in the suites at night.

I fucking hated it.

Six months in, after working my thirteenth straight day, I drove myself to the ER on a Sunday night.

I was convinced I was having a heart attack. It ended up being a panic attack (the first of many, as it’d turn out).

Hooked up to an EKG machine, I saw the situation clearly: I was going to kill myself doing a job I hate. And for what? So I can tell people I work in pro sports?

I quit the next day with nothing else lined up.

My boss asked me what I was going to do next.

My response: “I don’t know, but it can’t be this.”

#2: The Approval Game is Rigged (and You’re Playing It Anyway)

I thought I’d learned my lesson after the sports job. Nope.

I ran away from corporate America and worked in a friend’s living room for almost two years at a startup that was going nowhere serious. I was broke—$30k a year broke, with shitty health insurance—but at least I wasn’t having panic attacks.

Eventually I needed to grow up and make money. I got into recruiting like most of us do: by accident. $18.50 an hour, no commission, but I was glad to have it.

And of course, I picked another profession where success was entirely contingent on people liking me.

I’d leave myself voicemails to practice my cold call pitches, then listen back and hear this fucking gross “customer service” version of my voice that I hated. But that’s who I thought I needed to be to get hiring managers and candidates and VPs to like me enough to do business with me. It worked well enough to make good money and get promoted. It didn’t make me happy, but having money and a little status was way better than being broke and lost.

As I tried to make strategic jumps to advance my career, I failed at two consecutive recruiting jobs in my 30s. I was about to quit my third because I went from having an amazing boss to a terrible one. My “fuck this place” energy was through the roof.

Then I hired my next boss. Instead of playing the game and putting on the political face, I was totally honest with her about where I was. I told her how I felt, what was broken, and that I was getting my resume ready. And something wild happened:

She listened.

More than that, she actually made my old boss apologize to me in person. Then empowered me to go do good work.

I’d spent a decade trying to control what other people thought about me. Every hiring manager, every candidate, every VP I worked with—I’d given all of them permission to determine whether I was having a good day or a bad one.

Ask any married person if they think they can control what their spouse thinks about them.

I’d built my entire career on that stupid assumption. But it ended up that having the courage to be honest – and not give a shit about what the other person thought or said – was the actual way to get what I wanted.

That was a huge paradigm shift for me.

#3: Happiness is Believing you’re Useful to Someone

I’d been repressing the kid in me. In that “fuck it” moment when I opened up to my boss, I finally let him out, because the alternative was burning my whole life down and starting over.

I was a 30-something handing the controls back to the kid who’d spend hours reading Calvin and Hobbes, his days exploring the woods and riding bikes and coming home with grass stains, blood on the shirt, and a smile. The high schooler who felt most at home at punk shows, taking hits on the edges of mosh pits in sweaty venues.

My career took off. My marriage got better. And for the first time in two decades, I genuinely liked myself.

Like all pendulums, it swung too far in the opposite direction. I pissed off my wife plenty. I frustrated the hell out of that good boss of mine. I was an impatient father.

But things eventually settled. Instead of acting like a rebellious, self-destructive teenager, I was channeling that energy into building. That’s where I became a professional. Where I turned pro.

Kishimi’s whole point: you can’t find happiness chasing others’ approval. You have to source it internally. The only way to do that is to shift your focus from something you can’t control—what others think—to something you can: how you contribute to the world you’re in.

I know my kids love me just because I’m their Dad. Michelle might occasionally kick me out of bed when I mouth off, but she still smiles when she’s telling me how annoying I am.

THE ENDURANCE FACTOR

The trap doesn’t change. We’re wired to want people to like us. We also all want to be ourselves.

Our parents faced it. Our kids will face it. So will theirs. They’ll grow up with the same bullshit we did—systems and institutions designed for conformity, not individuality. They’ll have to find their way back to being themselves.

The book builds a compounding skill—the ability to separate your self-worth from others’ opinions. It helps you stop asking, “What will they think?” and start asking, “What do I want?”

I needed it at 18. I found it in my 30s. Give this book to a high school kid before they pick a major to impress their parents.

Thanks for reading. You’re part of a growing, ambitious group striving towards something—a career move, an entrepreneurial venture, a 2nd act.

If this landed, share it with someone who needs to stop anchoring their happiness in the minds of others.

And if you’re feeling trapped by the golden handcuffs—building something on the side while trying not to burn down what’s working—grab the ​Golden Handcuffs Diagnostic​. It’s free, and it might clarify some things.

Up next, we’ll dive into a book that’s all about getting shit done in a way that ensures you love the journey as much as the destination.

Until then—keep building, keep growing, and keep going.

Mike

I’d done everything right. In bed by 10:30. Alarm at 5. A water bottle with an LMNT packet, a chilled Neutonic to caffeinate. My Sacred Hours were locked and loaded—90 minutes to work on the business before the chaos begins.

And then my 4-year-old appears at the bottom of the stairs. He’s scared. He doesn’t want to go back to sleep. He wants to hang with Dad.

And my first thought was, “You’ve gotta be fucking kidding me.”

I know my 80-year-old self will hate me for that. But it’s the truth. A flood of frustration hijacked my brain—immediate and justified.

Because I’m doing everything right. I’m sacrificing sleep. I’m protecting this time. I sit down at the desk ready to give it my all while most people are still asleep.

And the universe doesn’t give a shit.

The rest of my day was spent scrambling to find the hour I just lost—the hour that was mine.

You know this feeling. The sick kid call from school. The partner who needs you when you’re already overstimulated. The Slack message at 7:42 PM from the colleague who doesn’t believe in your ‘bedtime routine’ boundaries. The list of perfectly reasonable explanations for why your inner peace gets hijacked.

Here’s the uncomfortable truth I keep having to relearn: that frustration? That sense of being a victim of my circumstances? It’s a trap. A sneaky one, because the frustration feels so goddamn earned.

And yet—the lesson remains. The 4-year-old isn’t the obstacle to my stillness practice.

He is the practice.

So, around 11PM that evening, when I finally clawed back that hour and finished my newsletter, I looked at my bookshelf. My eyes wandered over the familiar spines to see which book I’d revisit next for this series.

My brain wasn’t perusing. It was scanning. Because as soon as I saw Ryan Holiday’s ​Stillness is the Key​, I thought back to my morning visitors: my son and my frustration.

And I knew I needed to re-read it. Again.

STILLNESS IS THE KEY

Author: Ryan Holiday

Published: October 1, 2019

Length: 288 pages

Buy: ​https://amzn.to/4qn3SLv​

WHY THIS BOOK MATTERS

I first picked up this book in 2019. I’ve been a Ryan Holiday fan since The Obstacle is the Way (Book 3 in this Outlast Yourself series), so this was a day-one buy. And I fucking needed it.

My wife was pregnant with our first. I was working a demanding corporate job. And I was also spending mornings and nights trying to record a rock album with my brother—jamming as much as I could into my “free time” so I could have it done before the baby came.

[NARRATOR: It wasn’t done before the baby came. In fact, it took another 18 months to complete.]

My mind was in a thousand places. Contemplating fatherhood. Feeding the insatiable beast of my own creative ambitions. Climbing the corporate ladder like a good little business school grad. And somehow trying to be present for a wife whose body was literally building another human.

But at night, I started reading. And it felt like he’d written this one specifically for me.

Six years later, I still pick this book up twice a year. The circumstances have evolved—three kids under 5 now, a bigger title, a business I’m building in the margins, and (because I apparently despise peace) a new puppy.

But the core tension hasn’t changed. My life is louder. Fuller. More demanding. And stillness feels more essential—and more elusive—than ever.

Here’s what this book forces you to confront: like most things in life, your inner peace is entirely on you.

Most people are waiting for the right conditions to find stillness.

Holiday’s message is: nope.

The conditions are right now. They always will be. And if you keep outsourcing your peace to things outside your control, you’ll spend your entire life waiting for a calm that never comes.

Stillness isn’t a destination. It’s a muscle you build. And like any muscle, it can either atrophy without use or strengthen under resistance.

THE ESSENTIALS: 3 CORE IDEAS

1. Stillness Is a Practice, Not a Prize

Most of us are clinging to a fantasy: someday, when the chaos settles, we’ll finally have peace.

When the kids are older. When the business is profitable. When I hit that number in my bank account. When I get the promotion. Then I’ll be able to think clearly. Then I’ll meditate. Then I’ll journal. Then I’ll take the long walks and find the stillness everyone keeps talking about.

This is a lie. And like all dangerous lies, it’s deadly because it sounds so reasonable.

Holiday’s core argument is that stillness isn’t something you achieve and then possess forever. It’s a practice—like exercise, like writing, like any skill that degrades without repetition. You don’t do one workout and stay fit for life. You don’t journal once and have a clear mind forever.

The 4-year-old showing up at 5:57 AM isn’t interrupting my stillness practice. That moment—the flash of frustration, the choice of how to respond, the opportunity to either spiral into resentment or breathe and be present with my scared son—that is the practice.

Every interruption is a rep.

The Stoics understood this. Marcus Aurelius didn’t write his Meditations from a spa retreat. He wrote them while running an empire, fighting wars abroad, wrestling with politicians and plagues, and burying his children. The obstacle wasn’t blocking his path to stillness—the obstacle was the path. (Sound familiar?)

You have to stop thinking your chaos is preventing you from developing stillness. The chaos is the training ground to strengthen your stillness muscle.

This reframe is the liberating permission you need to start now. Not when things calm down. Now. In the mess. With the puppy barking and the computer pinging and the phone vibrating and the toddler telling you that Chase is the best dog in the Paw Patrol for the forty-seventh time today.

2. You Have to Actively Protect Your Mental Space

Holiday uses a metaphor from Daoist philosophy that’s stuck with me for years: think of your mind as a pool of muddy water.

When thoughts churn, the mud churns too. When you’re constantly reacting—to news, to notifications, to the endless scroll of other people’s curated lives—the water never settles. You can’t see what’s beneath the surface. The turtles, the plants, the rocks at the bottom, all obscured by the mud you keep stirring up.

Stillness requires letting the mud settle.

This sounds passive, but it’s actually one of the most active things you can do. The world we live in is designed to keep your water churning. Holiday puts it bluntly: “Every time we open an app, there are a thousand people on the other side of the screen trying to keep us engaged.” Engineers, psychologists, slot machine designers, all optimizing to mine one thing: your attention.

And we wonder why we can’t think clearly. The minute we pull out our phone when we’re bored, we’re fighting an army of PhDs…which means we’re already fucked.

Protecting your mental space requires what Holiday calls “limiting your inputs.” You’re not going off the grid. You’re just being picky about what gets in. You don’t need to be constantly informed—that’s ego talking. Fear of looking ignorant. Fear of being left out. But most information isn’t urgent or important or even relevant to your day-to-day. Consuming it in real time does nothing but churn the water.

Holiday’s practical advice: don’t consume in real time. Wait a few days. What’s actually important will still be important. What’s not will have resolved itself.

Napoleon famously waited three weeks to open his mail—and loved noting how many “urgent” issues had simply disappeared. I’ve been implementing this practice with email threads. I can’t go three weeks (I need to keep my job, and I can’t blame the delayed responses on horses dying in transit), but I am more intentional about batching when I check and respond to emails. If there’s a thread with 8 names on it, I weigh in only when absolutely necessary. And, lo and behold, there’s a bunch of shit that didn’t require my attention to begin with.

It’s also why I guard my Sacred Hours like a psycho. 5:00-6:30 AM. No email. No LinkedIn. No news (I stopped reading the news a year ago and have ‘missed’ absolutely nothing. People tell me what I need to know). That time is for the work that matters most, done in the stillest part of the day, before the world puts an outboard motor into my little lake.

It’s not enough to want stillness. You have to build walls around it.

3. Mind, Body, and Soul Are Non-Negotiable Partners

Letting the mud settle is step one, but it’s not enough. Holiday is clear: the mind cannot achieve stillness without the body and soul being in alignment. The three are inseparable.

You can’t think your way to peace while running on five hours of sleep. You can’t journal your way to clarity while your body is screaming for a walk. You can’t meditate your way to contentment while your soul is starving for meaning.

The body piece: We’re overstimulated, overscheduled, and chronically under-rested. We skip the workout to squeeze in another meeting.

Holiday calls bullshit on the “glorification of busy.” You are not your job. Time is literally your life—every task you take on, you’re trading a piece of your life for it. Is it worth it?

Walking isn’t just exercise. Kierkegaard saw it as necessary for keeping the mind agile. It’s moving meditation. He believed sitting too long would make you sick—you need to move the body to still the mind. So he’d walk miles and miles until his thoughts settled.

The paradox is real: sometimes stillness requires motion.

I won’t preach about the value of sleep, because I’m terrible at prioritizing it. But I’ll just say this: sleep isn’t laziness. It’s how you recharge the system that makes everything else possible. You can’t make good decisions while exhausted. You can’t be present for your family while running on fumes. My worst choices come on the heels of a bad night’s sleep. Do as Holiday says, not as I do. Prioritize your sleep.

The soul piece: This is where I’m doing the most work right now. Holiday argues that without a connection to something greater—God, Source, the universe, whatever you call it—life becomes meaningless.

Meaning is essential to stillness. Without it, you’re just managing chaos until you die.

I’m on my own journey back to spirituality after years away from the Catholicism I grew up with. I don’t have this figured out. But I know Holiday is right: you can’t have a still mind while your soul is in turmoil. The virtue piece, the meaning piece, the connection to something beyond yourself—it’s not optional. It’s foundational.

Mind, body, soul. Neglect one and the others suffer.

THE ENDURANCE FACTOR

Why will this book matter in 10, 20, 50 years?

Because distraction isn’t going away. The forces competing for your attention will only get more sophisticated. The chaos of modern life—the information overload, the always-on work culture, the thousand people on the other side of your screen—it’s not a temporary condition. It’s our new baseline. (Hooray).

And yet, the human need for stillness is ancient. The Stoics wrote about it. The Buddhists built entire philosophies around it. Every wisdom tradition in human history has pointed toward the same truth: inner peace isn’t found in external circumstances. It’s cultivated internally, through practice, through discipline, through the slow work of letting the mud settle.

The tactics will evolve. But the fundamental human struggle—to find calm in chaos, to be present in a distracted world, to access the deeper thoughts beneath the noise—that’s timeless.

This book isn’t a hack or a shortcut. It’s a manual for the under-rested, overstimulated masses to help us fight one of the oldest battles humans have ever fought: the war against our own restless minds.

Thanks for reading. You’re part of a small (but growing), ambitious group who are striving towards something—a career move, an entrepreneurial venture, a 2nd act.

If this landed, share it with someone who needs the reminder that stillness isn’t waiting for them at some future finish line.

And if you’re feeling trapped by the golden handcuffs—building something on the side while trying not to burn down what’s working—grab the ​Golden Handcuffs Diagnostic​. It’s free, and it might clarify some things.

Next installment: a book about the courage it takes to stop living by other people’s expectations. The title alone pisses some people off. Can’t wait.

Until then—keep building, keep growing, and keep going.

Mike​

You’ve heard of the phenomenon. Drop one crab in a bucket, and it usually claws its way out. But put a bunch in there? As soon as one hits the rim, the others will reach up, grab its legs, and pull it back down into the pile.

My immediate family has always been supportive of my efforts to better myself. But extending beyond the nuclear family, it was a mixed bag, to say the least. I had aunts and grandparents who had big dreams but failed to deliver on them. I had a mom who was an artist in the kitchen who refused to open her own bakery. One (toxic) branch of my family tree could be the dictionary definition of “playing small.”

I’m 40 years old and finally filtering through childhood baggage I ignored for decades. Some of that “playing small” mindset seeped into me as a kid, and I’m confronting it now. This version of me is building my 2nd Act while holding down a senior leadership job with a global team, trying to be a good husband, and raising three feral boys.

There’s nothing small about my life today.

And while the public comments might be supportive (especially on LinkedIn, where people are a bit nicer than the trolls on X or IG or risk losing their jobs), I’m in plenty of conversations that feel different.

Resistance. Skepticism. “Concern” that’s actually masking someone else’s insecurity.

Here’s what it sounds like:

“How do you have the time to do all of that? You’ve gotta be dropping something.”

“That’s a lot. It’s only going to get harder as it picks up.”

Or, the simplest (and most regular): “You’re fucking insane, man.”

I’m in my Lonely Chapter. It’s that long, quiet stretch where you’re breaking free from your old crowd but haven’t been invited into your new tribe yet.

And it’s also when, if you’re not careful, your mental crabs can drag you right back down into the bucket of your old life.

In circumstances like this, I find it helpful to default to action. Make decisions. Do shit. Keep moving. Be useful — and steal from people who’ve already escaped the bucket.

So I looked to a guy who’s had not one, not two, but three successful acts.

Surely, he figured some shit out.

BE USEFUL: 7 TOOLS FOR LIFE

Author: Arnold Schwarzenegger

Published: October 10, 2023

Length: 288 pages

Buy: ​https://amzn.to/4baMncu​

WHY THIS BOOK MATTERS

Yeah, it’s Arnold. It’s easy to write him off as the meathead action star or the “Governator.”

But look at the freaking scoreboard.

This man didn’t just have a career — he conquered three completely distinct, high-barrier worlds:

1. Bodybuilding: 7 Mr. Olympia titles. In the GOAT conversation.

2. Hollywood: Became the highest-paid leading man in the world (with an accent everyone said would ruin him and a name nobody can spell).

3. Politics: Ran California — the world’s 5th largest economy — through a financial crisis.

I picked this up because I wanted to know: What’s the through-line? How does someone pull off that level of reinvention — not once, but three times?

The uncomfortable answer is one that’s a recurring theme through my ​Outlast Yourself​ series:

You’re not stuck because of your circumstances. You’re stuck because your vision is foggy and your reps are low.

We love our excuses. “I don’t have time.” “The system’s rigged.” “It’s too late for me to start over.”

Arnold — who grew up in a house with no plumbing, with a physically abusive father, in post-war Austria — looks you dead in the eye and says: “Bullshit.”

If you’re stuck in your golden handcuffs, this book serves as a mirror…and a lock pick.

THE ESSENTIALS: 3 CORE IDEAS

1. Dream So Big It Embarrasses You (Then Sell the Shit Out of It)

Arnold’s first rule isn’t “have a vision.” It’s have a vision so big that saying it out loud makes you feel like an idiot.

A kid in a tiny Austrian village deciding he’s going to be a famous American movie star is fucking delusional. Full stop. But Arnold held that image with such clarity that every single decision filtered through it. The delusion became the compass.

But having the dream isn’t enough. As much as it might suck to hear for all the introverts, you have to become the Chief Sales Officer.

When Arnold came to America, bodybuilding was a fringe subculture for weirdos lifting in basements. He didn’t just compete — he became the ambassador. Wrote pamphlets. Traded magazine appearances for plugs. Controlled the narrative.

The hardest sale usually starts with the one in the mirror. You need to believe in this thing when nobody else does—because, for most of your journey, nobody else will. So even though your vision should (and will) scare the shit out of you, it’s your job to be all-in on its success.

From there, go public with it. When you tell people your goal out loud, you create a public commitment. Now your reputation’s on the line. Now you have to execute.

I spent months building in silence, convinced the work would “speak for itself.” It doesn’t. You have to sell the vision — to your spouse, your future customers, your mentors — until they see what you see.

The crabs in the bucket will try to pull you back. Your ambition holds up a mirror to their fear, and they don’t like what they see.

Your job isn’t to convince them. It’s to use their doubt as fuel.

And then put something in their hands that overdelivers on all of your talk.

2. No Helicopters to the Mountaintop

Arnold tells the story of Sir Edmund Hillary, the first climber to summit Mount Everest. Swarmed at base camp by reporters, he was asked if the view was amazing. His answer was that it was—because he saw other peaks he hadn’t climbed and was already thinking about the next route.

Then Arnold asks: Do you think anyone who helicoptered to that same summit would feel the same thing?

Not a chance.

He’s relentless on this — almost annoyingly clear: The hard work is the point. As Hormozi puts it, “Hard work IS the goal.” It’s not a necessary evil. It’s the price of admission for doing anything meaningful. The actual point.

He’s not romantic about it either. The work won’t be fun. It’ll be grueling and monotonous. You’ll want to quit. But reframe it: that discomfort is data—good data. It’s the signal you’re actually making progress.

I think about this constantly during my Sacred Hours.

5:37 AM. House is dark. I’m staring at a blank page, coffee going cold, trying to find the thread of an idea before my 2-year-old wakes up and the day detonates. It’s not glamorous, and there are no dopamine hits during this slog. It’s just me and the reps.

That perspective kills my patience for other people making excuses about why they can’t find time (especially healthy single people – you have no fucking idea how much time you have right now).

Arnold’s math on time is also confrontational (albeit more supportive): “You really can’t find an hour or two?”

He walks through his schedule as a young immigrant — bricklaying during the day, training five hours, acting classes, English classes at night. Running on fumes and still building multiple empires.

His answer to “I don’t have time” is simple: Stop lying to yourself.

If you’re not doing the work, you don’t want the goal badly enough.

And if you need more time? “Sleep faster.”

3. The “Self-Made” Man is a Myth

Arnold Schwarzenegger — the guy whose entire brand is built on self-reliance and iron will — says pulling yourself up by your bootstraps is bullshit.

Every step forward, he says, was made possible by someone else. The mentors who taught him to train. The people who gave him a shot in Hollywood. The voters who trusted him with California.

Nobody does it alone.

As a guy who doesn’t like asking for help, this one hit me in the chest.

The Second Act journey can feel incredibly isolating. You’re building something no one else can see yet. The Lonely Chapter stretches on way longer than any Instagram success story suggests. And when you’re deep in it, it’s easy to believe you have to figure it all out yourself.

But Arnold’s point goes further: receiving help creates an obligation.

Once you’ve been lifted, you lift others. That’s the deal.

He talks about his work with the Special Olympics, his charitable efforts. His view is that nothing in his career — not the titles, not the box office records — felt as good as being useful to someone else.

This reframes the whole project.

You’re not just escaping your golden handcuffs for you. You’re building a platform that lets you eventually reach back and pull someone else up. The person 30 steps behind you who just needs to see that it’s possible.

Being useful isn’t a soft afterthought to success.

It’s the whole point.

THE ENDURANCE FACTOR

This isn’t a book about hacks. It’s about physics.

Arnold’s whole philosophy boils down to something brutally simple: input equals output. Doesn’t matter if you’re building a bicep, a movie career, or a political campaign. The mechanics don’t change. See it clearly. Do the work. Sell it to the world. Use the rewards to help everyone you can.

That’s it. That’s the whole book.

No manifestation. No vision boards. No “attracting abundance” while you sit on your ass and wait for the universe to deliver.

You have to lift the heavy-ass weight. Arnold did it with barbells. Then with scripts. Then with legislation. The weight changes. The lifting doesn’t.

Fifty years from now, people will still be looking for shortcuts. And this book will still be sitting there, arms crossed, saying:

There aren’t any.

Thanks for reading. You’re part of a small (but growing), ambitious group who are striving towards something—a career move, an entrepreneurial venture, a 2nd act.

No fluff, no formulas, just fuel for the life you’re actually trying to build.

If this hit something real for you, it’ll probably land with someone like-minded who you care about. Send it along and help them out.

Follow me on LinkedIn for daily writing about ambition, parenthood, and the daily grind of building your 2nd Act.

If that sentence sounds ridiculous, it’s because it absolutely is.

Michelle had a girls’ night away. I’d put the kids to bed solo the night before, then worked until 1 AM on my content strategy. Pancakes for breakfast were the incentive for the boys to stay in their rooms, and I’m a man of my word.

But I had fallen asleep (passed out?) before I had finished what I needed to do, and I was the only parent in the house, and I have a day job that I care about…so, my rationalization was that I needed to “maximize my productivity.”

This included being questioned by an AI interrogator while I supervised a 5 and 4-year-old mix flour, sugar, butter, milk, eggs, etc., with Bluey on in the background.

It wasn’t until later – when I saw how little progress I had actually made during my self-created breakfast chaos – that I asked myself the right question:

What the fuck am I actually producing right now?

The answer: trash.

Which always seems to be the case when I multi-task, split my attention, or try to serve two masters at once.

Ironically, I knew this approach was idiotic as I was doing it. I had just finished reading Cal Newport’s ​Deep Work,​ and knew that there were strategies and tactics for getting meaningful work done.

And to the surprise of no one, “getting pancake batter on your MacBook while your kids tell you to stop working” is not one of them.

DEEP WORK: RULES FOR FOCUSED SUCCESS IN A DISTRACTED WORLD

Author: Cal Newport

Published: January 5, 2016

Length: 304 pages

Buy It Here: ​https://amzn.to/3XREAbO​

WHY THIS BOOK MATTERS

I’m glad this sentence appeared in the early pages, because it caught my attention and anchored the way I read the book this time around.

Hearing a succession of mediocre singers does not add up to a single outstanding performance.

Talent isn’t a commodity you stack. Neither is effort. You can’t combine six half-focused hours and call it three hours of real work. That’s not how any of this works.

Newport calls the real thing “deep work”—professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit.

The opposite is shallow work: the emails, the Slack & Teams pings, the meetings about meetings. Necessary, sure. But if that’s all you do, you’re replaceable. Sadly, those who’ve made their bones in the shallows are finding that out in real time, as AI munches through their inbox and spits out the few details that actually matter.

And that’s the point. The world is always changing, but the spread of AI has a “car replacing horse” kind of energy in its impact. It’s changing everything. And the people who are only capable of doing the work AI replaces are going to be the first to be, well, replaced.

Those who are going to come out on top of the global economic shift are going to be the ones who live in the depths, not the shallows. The ones who come up with the ideas, sit in silence until insights arrive, then leverage the new technology to make their “thing” happen more efficiently.

None of us can afford to ignore deep work if we still want to be relevant five years from now.

THE ESSENTIALS: 3 CORE IDEAS

1. Rhythmic Deep Work: The Only Strategy That Survives Real Life

Newport outlines several philosophies for building deep work into your life.

• There’s the monastic approach—eliminate all shallow obligations, become a hermit. (Many days, this is my mental escape fantasy).

• The bimodal philosophy alternates between periods of deep isolation and normal life. (Many days, this is my backup mental escape fantasy).

• Then there’s rhythmic: transform deep work into a simple regular habit. Same time, same place, every day.

For anyone following my tagline of building their 2nd act without torching their first, rhythmic is likely your option. You’re not disappearing to a cabin to work uninterrupted hours at a time – what if the daycare app pings that your kid just threw up on the magna-tiles? If you’re lucky (like I was in 2022), you can take a sabbatical, but that time away tends to show you how much MORE you can be doing…just to drop you back into your regular life and force you to limit your options.

Life is getting the kids dressed, fed, out of the house, working the day job, trying to stay somewhat healthy by getting a workout or a walk in, and then the bracing for the kid’s re-entry that keeps you occupado until bedtime (including all the trips to walk them back to bed).

Cue: Jerry Seinfeld’s famous “don’t break the chain” method. He kept his comedy writing habit by marking an X on a calendar every day he wrote. The goal wasn’t word count or quality—just don’t break the chain. Show up, do work.

That’s why the rhythmic approach tends to be the way busy builders can get shit done. It’s why I write about sacred hours so often. I’ve read tons of biographies and how-to and self-development books (clearly, given the tone and topics of the newsletter), and this is one of the immutable laws of creation. Block time when nobody can bother you. Make yourself indistractable. Do it at the same time every day.

My Sunday morning pancake disaster happened because I was undisciplined and worked too late on Saturday night, causing me to miss my sacred hour window on Sunday. It was a structure problem.

Of course what I captured in between pancake flips and juice box delivery ended up being shit. And guess what? The stuff I did at 12:46 AM wasn’t all that fine, either.

We’ll all slip up and get ourselves out of rhythm. While Seinfeld is the ambition, James Clear’s advice is what I adhere to most: “Never miss twice.”

2. Embrace Boredom—or Keep Producing Nothing

If you’re constantly seeking stimulation, you’re training your brain against deep focus. Every podcast in the car, every scroll between tasks, every filled gap—you’re teaching your brain that boredom is intolerable.

His prescription? Take breaks from focus, not from distraction.

He also introduces what he calls “productive meditation”—using time when you’re physically occupied (driving, walking, showering) to work on a single problem. Not consuming content. Processing.

Until recently, I had it backwards. Every free moment had an earbud in: audiobook, podcast, tutorial. Walking, driving, sauna—always something playing. I was convinced this was how you learn.

Then a few weeks ago I got about 30% through a podcast and realized I’d listened to the entire fucking thing the week before on a different platform. None of it had stuck. Not a single concept.

I listened to the rest of the pod like Nate Bargatze watches history documentaries: ​on the edge of my seat​.

After that, I forced some changes. No music when I’m journaling. Quiet car when I have a drive by myself. Walks without earbuds.

Sometimes, I hate it. I have FOMO over all the cool shit I could be learning if I just had the newest Modern Wisdom episode on. (Lately, it’s Dan Koe guidance about how to be better at the content creation game – and I got to listen to one of ’em twice).

But now, I keep a 2nd notebook next to my journal – it’s where I jot the ideas that pop up out of my subconscious. I transcribe my voice notes from my drives or walks and cannot tell you where the ideas came from. Sometimes it’s fun hearing yourself and saying, “Damn, I sounded pretty smart for a minute there.”

I’m only 3 weeks in, but this is the highest ROI I’ve had for any activity. Just by making a little space. The audiobook can wait.

(Related: this newsletter shipped a week late. So I’m still dialing in the new system).

3. When You Can’t Control the Boundaries, Control the Quality Gate

“Attention residue” may be my favorite takeaway from this book. It’s a simple concept that, for some reason, is not common knowledge nearly 10 years after publication. When you switch from Task A to Task B, your attention doesn’t follow cleanly. Part of your brain stays stuck on the previous task. This residue builds up and degrades your performance on everything.

It’s why you can’t get back into writing that email after you responded to your teammate’s DM. Or why you can’t fully lock into the KPI dashboard when your wife texts you, “Did you get the winter comforter down from the attic yet?” (No, it’s on the list, you only asked me to do it 3 weeks ago. Don’t rush me). Whatever just hijacked your attention sticks with you into the next task. You find yourself thinking, “Did I see the comforter when I was up there changing the air filters?”

Newport’s solution? A shutdown ritual at the end of each workday. Review what’s incomplete, capture what needs capturing, then completely disengage until the next morning.

It’s good advice. For some people, it’s even possible.

But for many of us—especially those leading teams across time zones or juggling day jobs with second acts—a clean shutdown isn’t realistic. I lead a global team. Pings come in during workouts and the evening rush. Those pings require attention later. And even when my phone is quiet, unresolved problems from work eat away at creative capacity.

On distracted nights, I can tell immediately—my writing is shit.

The skill I’ve developed isn’t a flawless shutdown ritual. It’s recognizing when attention residue is degrading my output. When the writing feels a little too much like a guy who just wants to go viral on LinkedIn. And when I catch it, I make a choice: perform surgery, toss it in the drawer for later, or trash it altogether.

I don’t publish mediocre work and pretend it’s good (though I post plenty of stuff I’ll cringe at 3 months later). That’s the line I can hold regardless of my schedule.

THE ENDURANCE FACTOR

Damn near everything created by the minds of humans has required deep work.

Books get written in focused periods. Swords get forged by craftsmen who aren’t checking notifications. Architects design buildings in stretches of uninterrupted thought. This isn’t new.

But the defense required to protect it is intensifying every year.

The world will only get more connected. AI might make parts of our jobs easier—or it might turn the two-lane road of information into a twelve-lane highway blasting content directly into our skulls.

Doesn’t matter. Whoever solves the next problem, paints the next masterpiece, finds the insight that changes everything—they’re doing it from a place of focus and concentration. Not from a kitchen counter with batter on their hands.

Newport puts it simply: “A deep life is a good life.”

Master this now. The demands on your attention aren’t getting lighter.

Thanks for reading. A bit of housekeeping (see: mea culpa):

I was planning on launching The 2nd Act Protocol on December 17th. That’s getting pushed for the same reason this entry was delayed – a great idea during a journaling session (embrace boredom, it works) that’ll 10x the value. Building it is scaring the hell out of me and stretching me outside of my comfort zone, but it is the way forward.

So, in the proud tradition of ambitious solopreneurs who’ve had to delay a release, The 2nd Act Protocol drops in the new year.

But I built something to give you now: ​The Golden Handcuff Diagnostic​. A FREE, AI-powered PDF with killer prompts that’ll push you if you’re stuck, help you see what’s holding you back, and show you where you could be headed (the good and the bad).

Early results are promising:

My hope is that this helps a lot of people. If you or someone you know is stuck, give it a shot. It’ll get you thinking about your life through a different perspective.

Next week, someone who’s had not one, not two, but three full acts in the public light…including the part where he blew up his family.

Until then—keep building, keep growing, and keep going.

Mike

More directly: I wasn’t crystal clear on my vision, which left me doing a lot of different things to stay busy.

We had moved to Denver a year prior, which meant I had spent the prior 12 months acquiring new hobbies – snowboarding, hiking, camping, and sampling every Colorado-brewed IPA in an 80-mile radius.

These were just piled on top of the important things that already existed in my life: I was a husband, a dog dad, had a career I was trying to breathe life back into as I learned a new city, and a handful of songs written that I was aiming to turn into an album.

And, to the surprise of nobody other than the “Renaissance Man” flitting around the Rockies, adding inches to his waistline, I was making very little progress in anything.

My career was still stuck, despite legitimately working my ass off.

The songs were never quite done.

I kept getting myself in trouble on the mountains, having to use the ol’ falling leaf tactic to work my way down black diamonds like one of those lil’ ripper toddlers. (In truth, I watched toddlers pass me on those trails more than once).

Nothing was a priority, yet everything felt essential.

And while I was mildly annoyed, I wasn’t yet frustrated enough to change.

Michelle and I shot out to Vancouver for the wedding of a high school friend. She was in the wedding, so while my wife juggled bridesmaid commitments, I had the freedom to explore a new city. To belly up to a random bar on a Thursday afternoon and make a friend or two.

Instead, I sat in my hotel room with my Kindle and highlighted the fuck out of Greg McKeown’s ​Essentialism​.

ESSENTIALISM: THE DISCIPLINED PURSUIT OF LESS

Author: Greg McKeown

Published: April 5, 2014

Length: 304 pages

Buy it here: ​https://amzn.to/4rppAzo​

WHY THIS BOOK MATTERS

McKeown earned the right to write this by actually studying what worked. He spent years with Silicon Valley companies, watching some scale and others implode. The pattern was brutal and consistent: the ones who won weren’t doing more – they were doing less, but better.

I thought I learned this lesson in 2016. I got better at work. Started time blocking. Learned to say no graciously. Started asking “Is this essential?” before taking on projects.

But here’s what I’m realizing almost a decade later, rereading this with three kids under six and only 5-6:30 AM to build what matters: I applied Essentialism to my job. I never applied it to the rest of my life – including my dream.

2016 me had TIME. I had flexibility. I could have built 100x what I’m capable of now if I’d actually gotten serious about what I wanted instead of just getting better at what I was paid to do.

Now? Three boys, a global leadership role, and the quiet acceptance that I need to murder everything I can live without if I’m going to build anything that outlasts me.

THE ESSENTIALS: 3 CORE IDEAS

1. The 50% Buffer (or: Why You’re Always Wrong About Time)

Every time estimate you make is a lie.

Not because you’re dishonest. Because you’re human. And humans are systematically, predictably terrible at estimating how long things actually take.

McKeown’s solution is almost insultingly simple: multiply every time estimate by 1.5.

Always.

That presentation you think will take two hours? Block three. That newsletter you can definitely write in one sitting? Plan for two. Those sacred morning hours where you think you can knock out a framework AND respond to emails AND review your posts? Pick one.

At my best (which I’ll admit is infrequent), I use the 50% buffer. When I don’t, I end up writing my newsletter for 3 consecutive nights instead of the 1-2 sittings it should take.

Here’s why this matters for parents building in the margins: you don’t have time to be wrong.

If you’ve got 90 minutes before the kids wake up and you budget 90 minutes of work, you’ve already lost. The coffee takes longer to kick in. Your brain has to wake up and switch into “get shit done” mode, which feels like yanking a lawnmower starter cord until your shoulder’s burning.

But if you budget that 90 minutes as 60 minutes of actual work? You might actually finish something.

The 50% buffer isn’t pessimism. It’s refusing to lie to yourself about physics.

It’s also a forcing function. When you add 50% to everything, you immediately see you can’t do it all. You can’t fit seven things into your sacred hours if each of them actually takes 1.5x longer than you think. So you’re forced to choose.

Which is exactly the point.

Stop optimizing for the best-case scenario. Start planning for reality.

The best-case scenario almost never happens. Reality always does.

2. “Which Problem Do I Want?” Choose Your Hard.“WHICH PROBLEM DO I WANT?”

Trade-offs aren’t losses. They’re choices about which hard thing you prefer.

This is the reframe that changes everything.

Most people avoid trade-offs. They try to have it all. They straddle – McKeown’s term for keeping your existing strategy intact while simultaneously trying to adopt a competing strategy. It’s how Continental Airlines tried to copy Southwest to be both a low-cost carrier AND a premium carrier and ended up being neither.

It’s also how parents try to be fully present at home AND crush it at work AND build a side business AND maintain friendships AND stay in shape AND…

You know how this ends. Mediocrity on all fronts. Frustration and resentment across the board.

Essentialists ask a different question: “Which problem do I want?”

There are no solutions. There are only trade-offs. – Thomas Sowell

You’re not choosing between problems and no problems. You’re choosing between different problems.

Want to build something meaningful in the margins? Great. You’re choosing between the problem of “never getting traction on what matters” versus the problem of “dealing with FOMO and saying no to good opportunities.”

Want to be present with your kids? You’re choosing between the problem of “missing their childhood” versus the problem of “slowing your career trajectory.”

Both are hard. So pick your hard.

The power of “What problems do I want?” is that the question strips away the fantasy that you can avoid hard things. You can’t.

But you CAN choose which hard things you’re willing to tolerate.

And problems you’ve chosen are easier to tolerate than problems you’ve “let happen” to you.

3. If You Don’t Prioritize Your Life, Someone Else Will

Here’s the existential truth that should terrify you: every single day, you’re either designing your life or defaulting to someone else’s design.

The way of the Essentialist means living by design, not by default. Instead of making choices reactively, the Essentialist deliberately distinguishes the vital few from the trivial many.

And if you just let life happen to you, you’ll learn something quickly: other people are REALLY good at prioritizing your life for them.

Your boss prioritizes your life around their OKRs.

Your kids prioritize your life around their immediate (always fucking immediate) needs.

Your inbox makes everyone else’s urgency your problem.

Social media shows you all the experiences you “should” be having.

Society pushes you towards consumption and consumerism.

None of these are evil. They’re just optimizing for their goals, not yours.

If you’re not deliberately, systematically, relentlessly prioritizing your own life? You’re going to wake up at 45 with a calendar full of everyone else’s priorities.

And you’ll be fucking furious with yourself.

This hits differently for me right now, when I’m three weeks from launching my first digital product.

Because launching means I have to prioritize myself in a way that feels borderline transgressive. I am protecting my sacred hours. I’m saying no to good experiences and opportunities. I’m disappointing people. All because I’m choosing my life over other people’s expectations of my time.

I wrote out this Viola Davis quote and have been looking at it a lot lately:

“When it comes down to disappointing other people or disappointing yourself, choose other people all the time. Your job in life is to disappoint as many people as you can so that you do not disappoint yourself.”

THE ENDURANCE FACTOR

​Essentialism​ will matter more in 10 years than it does today.

It matters more to me now than it did a decade ago.

We’re finite beings with infinite demands on our attention. That problem only gets worse. More tools, more platforms, more opportunities – all creating the illusion we can have it all.

The ability to discern what matters from what doesn’t isn’t a skill you’ll use once. It compounds. The earlier you develop it, the more years you get to spend cranking on things that actually count.

This book is for anyone who’s felt the gap between what they say matters and what their calendar says matters. For parents who want to be present without abandoning ambition.

Dare I say…for people building their second act without torching their first?

Thanks for reading.

I’ve been thinking a lot about what it means to build something that outlasts you while three kids under six are actively prioritizing every minute of my life.

It’s a brutal truth: you can’t build what lasts if you’re spending all your time on what doesn’t.

Once you’ve stripped away the non-essential, you need the ability to knock out focused work. Next week’s entry is the bible for getting shit done in a distracted world.

Until then—keep building, keep growing, and keep going.

Mike

​​mikeradice.net

Judi Radice was one of one.

An Ivy League graduate from Boston, she met my dad at college, ignored all of the obvious warning signs, and was married to him for 33 years.

She was kind and witty and funny and could talk shit with the best of them. Her cold shoulder made the Night King look like Baymax: I remember one time, following of my many high school transgressions, she spoke to my best friend visiting from NY with all the sweetness in the world while completely ignoring me. For four straight days.

But on the flip side, if you got her rolling with laughter, there was no better sound.

And man, could that woman bake. Every single person who ate her treats told her she should open a bakery. It was a quiet dream of hers.

Watching her waste away from an aggressive form of uterine cancer – from diagnosis to deathbed in 10 months – was the most brutal thing my family and I have endured.

Losing her hurt. But I wasn’t prepared for what came after – a different kind of suffering entirely.

I lay awake at night, thinking about the experiences she’d never have. She’d never open her bakery. She’d never meet her grandkids.

And when I looked at my family, I saw her as the best of us. Here I was, a freewheeling degenerate – drinking, partying, contributing very little to society or the people around me (at least, that’s how I saw myself).

Now she was gone. And I was still here to…what? Continue down this “nothing” path of mine?

Was this just how life was? Or a cosmic-level fuck-up?

It was around this time that I first came across Viktor Frankl’s Man’s Search for Meaning.

It shifted my entire way of thinking.

In an obvious sense, nothing puts your own suffering into clear focus like hearing a man’s story of survival in Auschwitz. But in a more practical sense, Dr. Frankl’s book wasn’t just a recounting of camp life. It had a through-line – how suffering has not only the power to destroy, but also to transform.

He was a better person for having survived the atrocities committed by the Nazis.

Could I become a better person through the experience of losing my mom?

MAN’S SEARCH FOR MEANING

Author: Viktor Frankl

Published: 1946

Length: 184 pages

Buy: https://amzn.to/4rckUwu​

WHY THIS BOOK MATTERS

Viktor Frankl was a psychiatrist and neurologist who survived Auschwitz. He’s a man who lost everything—his wife, parents, brother, all the way down to the unfinished manuscript of his first work in the concentration camps. As the founder of logotherapy – a practice that insists that meaning is the central motivational force in human beings – he anchored his camp experience through the lens of a psychotherapist.

When I read it, I was searching for meaning – it might have been the first time I’d found a book whose title promises to address the exact issue I was wrestling with. Meaning. Why I’m here. Big topics that I was not equipped to handle on my own. This book helped me in ways that made me emotional re-reading it preparing to write about it now.

Spending the bulk of my career in recruiting, I see it all the time – people stuck in an existential vacuum, struggling to find meaning in their work. I saw it with my mom, dying with her bakery dream inside her. It’s the motive power behind my building of the 2nd Act Protocol, designed for people waking up somewhere between 35-50 and realizing they’re unfulfilled. I can’t think of a greater pain than dying with unfulfilled dreams, and my goal is to help as many people as possible avoid that fate.

Life is not a quest for pleasure or power, but a quest for meaning.

If you don’t have meaning, you won’t build anything that outlasts you – you’ll just survive until you don’t anymore. This book helps you find meaning even when circumstances seem hopeless. And being written by a concentration camp survivor, it eliminates 99% of the “yeah, but I have it worse” cries.

THE ESSENTIALS: 3 CORE IDEAS

​

1. You Need a Future Worth Suffering For

My mom’s dream was her bakery. Frankl held on to the manuscript he needed to rewrite. We all need something that keeps us going when shit gets hard. Because shit always gets hard.

Frankl saw it in the camps. “Any attempt to restore a man’s inner strength had to point out to him a future goal.”

He saw it in suicidal prisoners – the ones who kept going had a child waiting for them, or an unfinished book series. The prisoners who lost faith in their futures were doomed. One of Frankl’s visions that kept him alive was him imagining lecturing about camp psychology after liberation.

His key insight? “Suffering ceases to be suffering when it finds meaning.”

You’re not going to eliminate suffering in your life – don’t bother trying. Your goal is to have something that makes it worth enduring. Nietzsche said it the century before Frankl experienced it: “He who has a Why to live can bear almost any How.”

Most people stay stuck because they’re trying to escape their pain. I’ve seen it throughout my recruiting career. The better part of two decades watching people stay stuck in meaningless work. The ones who stayed miserable had nothing pulling them forward. The ones who made moves and took chances had a clear vision of what they were building toward.

The question shouldn’t be, “How do I stop feeling unfulfilled?” Instead, you should be asking yourself, “What future am I building that’s worth this discomfort?”

Your goal won’t eliminate suffering, but it will imbue it with meaning. Every hard day becomes a day you endured FOR something.

​

2. Life is Questioning You: Stop Asking What You Want

Most of us get tripped up here, asking ourselves, “What do I want from life?” That’s irrelevant. Life doesn’t give a shit what you want. So stop asking. Instead, listen to the question you’re actually being asked: “What does life want from you?”

If you’re not sure what you want, believe me, you’re not alone.

Frankl’s studies saw that 60% of American students felt “inner emptiness” or “a void within themselves.” They suffered from “Sunday neurosis” – a depression that kicks in when the busy week ends and emptiness becomes visible.

To get yourself out of it, you need to shift your thinking. Stop sitting in the paralysis that comes with asking yourself “What should I do?” Life is already asking you questions through your unhappiness and dissatisfaction. Feeling bored at work? That’s the question. The moments you feel most alive? That’s your answer. The more you close that gap, the more your unhappiness will dissipate.

Everyone has his own specific vocation or mission in life to carry out a concrete assignment.

You find your answer by moving, not by contemplating all of your options until you’re paralyzed.

If you need help sorting out where to start, a simple exercise is to “track the void” for two weeks. When you’re feeling empty or hopeless, write it down. When you’re feeling alive and excited, write that down, too. Over the course of a couple of weeks, the patterns will begin to reveal what life is quietly asking you to become. From there, it’s your responsibility to act.

Stop waiting for clarity about what you want. Start listening to what your life situation is demanding of you. The question you’re avoiding is the question you most need to answer.

Your emptiness isn’t the problem. Ignoring what it’s telling you is.

​

3. You’re Free Right Now. Choose Your Response.

If you’re in my stage of life – spouse, kids, mortgage, endless social commitments – you can feel trapped. But you’re not as trapped as a victim in Auschwitz. Frankl lost everything in his life and was still free.

Forces beyond your control can take away everything except one thing: your freedom to choose how you will respond.

Even in a concentration camp, prisoners could choose their attitude. There were people who gave away their last piece of bread to a comrade, or shared a blanket, or took a beating to protect a friend. The guards could attack and threaten death at every turn, but they could not strip a person of their choice of how they would respond to the moment.

You’re not trapped by your circumstances. You’re trapped by believing your circumstances determine your response. If people under constant threat of death could choose not to be victims, so can you.

Your job doesn’t make you miserable. Neither does your boss.

How you respond to your job, or your boss, is what’s keeping you unhappy.

Which means you can change your response now. Today.

You can transform through suffering. The suffering itself is neutral. Your response is what gives it meaning.

Every day you don’t take action, every day you choose to stay stuck in the discomfort – that’s you choosing to remain in that state of mind.

In the end, we’ll all have one last question to answer – one that many in Auschwitz had to answer far earlier than they expected.

How will you meet your death? Proud of the life you lived? Filled with regret?

Ask yourself the question now, as if today were your last.

And if you don’t like the response, start doing the work to make sure your final answer is one that reflects the meaning of your life.

THE ENDURANCE FACTOR

This book was written in 1946 and has sold over 16 million copies. It’s still selling.

It’s because the core truth doesn’t change: humans need meaning more than comfort.

Every generation has an existential vacuum, it just manifests in different ways. So ignore the circumstances and focus on the skills you can develop – skills that compound:

• Finding meaning in what you create

• Finding meaning in who you love

• Finding meaning in your response to suffering.

I’ve returned to this book many times since I first read it. Anytime I’m feeling lost, directionless, or trying to make sense of my current situation. Anytime I’m wrestling with cosmic injustice. Anytime I’m taking on a new challenge, and need a philosophical framework to remind me why it’s worth the effort.

Because it’s our “why” that powers everything else in our lives. It’s how we endure when things are difficult. Why we don’t quit when everyone else would.

And it’s how works that outlast their creators are born.

Like this book. Frankl passed away nearly 30 years ago, but is still helping the lost and directionless today.

We should all strive to leave that kind of impact.

Thanks for reading. You’re part of a small (but growing), ambitious group who are striving towards something—a career move, an entrepreneurial venture, a 2nd act.

If you like this, subscribe to get these in your inbox.

Or follow me on LinkedIn, where I talk about building your 2nd Act without burning down your 1st.

For three years, my brother Tommy and I self-recorded ​a rock album​.

It took a long time for two major reasons: we both had full-time jobs, and we lived across the country from each other.

So it was a passion project. Nights, weekends, and any other spare time I could afford was spent on “the music.” Writing lyrics and melodies, recording guitar parts, screaming into a condenser mic in a New Jersey basement.

We did the whole thing as a team of two, which meant figuring ourselves out as songwriters while also learning sound engineering, mixing, mastering.

It was a very fun, DIY punk rock kind of attitude. A ton of my favorite artists started with self-recorded EP’s or short albums. It felt cool to be walking down the same path as theirs. We were making something to share with the world.

And for the most part, everything worked:

• We have an album out in the world.

• Four years later, I still like the songs (even if though I hear plenty of opportunities for re-do’s).

• My kids will always have an album their dad and uncle rocked out on.

This, my friends, is what we call a moral victory.

Because, in reality, the album release was a complete flop.

It took me awhile to figure out where we made our mistakes, but over time, one screw-up loomed largest:

Other than telling some friends, nobody knew we were recording an album.

We didn’t build an audience. We didn’t leak songs to social media. I didn’t take videos of myself doing the work because I was writhing with imposter syndrome and self-doubt.

What if nobody likes the music?

What if people hate my voice?

What, I’m just supposed to just put a tripod here in the basement and film myself playing guitar like an asshole?

So we didn’t do it. We booted up a few socials, we shared some posts before the singles released, we dropped a couple of singles over a few months, and pushed our debut for a week.

Release day came. I stayed up until midnight to see it on Spotify and listened to the songs I was sick of hearing until two in the morning. So did Tommy.

Other than that, nobody else really gave a shit.

We had kind-hearted friends give it a listen. Some buddies bought CD’s or digital downloads. My team actually streamed one of the songs when I came onto a meeting, which was a really cool moment (good lookin out, Hoose).

But we had failed to properly develop an audience. Nobody cared about us because we hadn’t found people who liked us enough to care.

Because we didn’t show our work.

And so when I found Austin Kleon’s ​Show Your Work!​ and read it a year after our release, I wanted to throw it against a fucking wall.

Here’s the manual I needed during the pandemic.

SHOW YOUR WORK!

Author: Austin Kleon

Published: March 6, 2014

Length: 224 pages

Buy it Here: ​https://amzn.to/49PITvg​

WHY THIS BOOK MATTERS

Austin Kleon has always seemed to me like the exact kind of person I’d hope to meet in Austin, Texas. He’s got a cool, laid back vibe. He’s messy. He cares deeply about his craft and takes chances with it. He’s kinda brilliant – and would probably hate being referred to as such.

I respect his work – not only because it exists, but because I know about it. And I know about it because he put his money where his mouth was.

He showed every step of his process as he built his blog’s audience and started cranking out straightforward, high-octane books on creativity.

I found him via “Steal Like An Artist” when I was trying to figure out how to write songs. His ideas directly contributed to me figuring out my voice and style. He gave me permission not to know it all – but borrow from enough of YOUR greats and mix and mash their ideas, and you end up finding something that works. Then you refine the thing that works ’til it’s yours.

See? Fucking brilliant.

The ironic thing about this whole album release snafu was that I knew the book existed – it came out in ’14. The information was there for me. But I think a part of me was afraid of what was in the pages. It was something that was going to demand massive vulnerability.

I needed to do it to be successful. But, in the moment of truth, I blinked. I gave in to my inner bitch who let me stay in my comfortable shell – and watched my album rack up a whopping 250 streams in its first month.

You know what that feels like? Three years of my life poured into this project. Strained my marriage, spent less time with my son, overextended myself. All for moral victories, sunk costs, and expensive lessons.

It feels the way Brady feels losing not one, but two Super Bowls to Eli.

So why is this book essential? It saves you from the biggest mistake I made in my creator journey.

One I’m not making as I build the 2nd Act Protocol (a minor plug to come at the end).

THE ESSENTIALS: 3 CORE IDEAS

Ok, those first two sections were a bit longer than usual, but they were fun stories to tell. I’ll jump in and out of these ideas with more efficiency.

Kleon makes it possible because his writing is undeniable. You just read the shit and go, “Yeah, that’s totally right.”

1. Learn in Public (and Share Your Process Daily)

Documenting making a rock album wouldn’t have been hard. In fact, it probably would have been cool. I would have met other musicians, connected with other artists, and created some genuine fans.

I regret not doing it for other reasons, too.

I would have liked to see myself in the late nights, the moments I nail a solo or get the mix dialed in perfectly.

I would have liked to watch myself botch 24 takes…and nail the 25th. (This was me a lot in the vocal booth).

I was smart enough to capture the moment when I opened the box of our CDs, but I didn’t share it with anyone.

I had the wrong frame. In typical Mike fashion, I made it all about me. “What will people think about me?”

I wish I had shifted my frame to look at it from a more productive angle: the impact my sharing could have had on others.

“Would my making mistakes and sharing what I’m learning help other people making music on their own?”

Yes. 100%. I love learning from people somewhere near me on the path telling me something that tripped them up. My days as a 2nd Act Builder with a family and a full-time gig are all rolled ankles, bruised arms, shoulder and lower back pain. I’m trying to miss a punch or two instead of leaning into every one.

Tim Cook can’t teach me a damn thing about ducking and weaving.

But another dad trying to build a side business while still being Dad who still has a day job and has a more profitable side hustle? That guy has something to teach me. A bunch of somethings, probably. I’d follow him in a heartbeat.

Kleon shares great, easy advice. “Become a documentarian of what you do.” Share one small piece daily.

Put yourself out there. Literally, as I’m writing this, a visiting neighbor poked her head in my door and said, “I love your LinkedIn posts, I read every one. I don’t like them all so people don’t think I’m obsessed with this guy, but keep going!”

You never know who you’re helping.

2. “Scenius” Over Genius (Nobody Does it Alone)

So how do you find those people who will connect with what you’re doing?

Everybody thinks they need to “go get followers” to build an audience.

Musician Brian Eno looks at creativity differently – that great work comes from scenes, not lone geniuses. The “scenius” model suggests that great ideas come from groups of creative individuals, “A whole scene of people who were supporting each other, looking at each other’s work, copying from each other, stealing ideas, and contributing ideas.”

The nice part about the internet? It’s a massive scenius with no geographic limitations.

Which makes finding your little scenius in the bigger scene as simple as sharing your work.

“Make stuff you love and talk about stuff you love and you’ll attract people who love that kind of stuff.”

It’s not cold networking through cringe DMs – it’s pinging someone whose work moved you and telling them, “Hey, this thing you made landed with me” and linking to their thing.

This is how this newsletter came about. I had no authority on books, other than I like to read them and try to extract value out of what I ingest. I have thoughts and opinions about them. I try to leverage their wisdom in my day-to-day.

So, unlike my rock album, I just started talking about this stuff in public.

Leadership. Parenting. Trying to get better. Listening to my inner voice to chase a new calling. A bunch of fantastic books have helped me with all of that. So I talk about them now.

Slowly but surely, the right people have been showing up. Readers. Writers. Parents building something.

And that’s how I’ve waded into a cool little scenius of like-minded folks who I’d definitely have a beer with.

3. You’re Already Naked (So Stop Hiding)

The more I started sharing online, the more I began to realize a common theme:

Good ideas got some traction.

Personal stories got more eyeballs.

But the visceral stuff? The topics that made me hover over the “schedule post” button for a long time?

Those end up being what really connects me with people.

Steve Jobs said it best: “Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You’re already naked.”

When you’re building your first act, as Alex Hormozi puts it, you have “unlimited shots on goal.” You’re unknown. Who cares if you screw up? You’re just another anonymous voice in a sea of them.

But building a second act is different. You have status, reputation, something you’re scared of losing. And building something new – in public, no less – is admitting you don’t know everything. Which is admitting vulnerability.

There’s really only one question: hide that vulnerability, or share it?

How you answer that determines how quickly you connect with others.

People watching me fail in real-time (instead of building a rock album in a lab for 3 years and failing in one moment) has taught me something really valuable: nobody cares if you stumble.

Because everybody stumbles. We all trip up and fall down and run into things. It’s the reason the videos of people getting hurt – the ones I share with my wife and watch her laugh until she’s crying – have millions of views. We like seeing humans do human stuff. And humanity is inherently uncoordinated. Our life is all trial and error. So stop wasting energy protecting yourself and start spending it on creating.

And when someone does criticize you? Well, what of it? Channel some of David Goggins’ timeless wisdom: “You will never in life meet a hater doing better than you.”

Put out lots of work, let people take shots, and make more work. Kleon has the truth of it: “The more criticism you take, the more you realize it can’t hurt you.”

Stop treating your work like it’s precious. Treat it like practice.

Share more, learn faster, get feedback, and find your people sooner.

THE ENDURANCE FACTOR

Platforms are gonna change. TikTok might be dead in five years (or banned in America in a few months). LinkedIn might become something different altogether. Who knows.

Learn from my album release flop – the visibility you need comes from consistent sharing, not one big launch.

“The people who get what they’re after are very often the ones who just stick around long enough.”

The skills that help you stick around are skills that compound: documenting daily, sharing generously, learning in public, and building relationships with people who are near you on the path.

F. Scott Fitzgerald said “There are no second acts in American life,” but Kleon calls bullshit on this. “If you look around you’ll notice that there are not only second acts, there are third, fourth, and even fifth ones.”

For those of us building our second act (or third, or fourth), we can’t wait for gatekeepers. We can’t afford to tinker until our thing is “perfect.” We need allies and opportunity to build momentum. And we need them now.

If you’re building something that might outlast you, people need to know it exists. You need people to care about it. You also need people to help you make it better.

This book teaches you how.

Most of my Villanova business school classmates had a cleaner story. Many of them hopped on I-95 and went up to NYC to slot into EY, PwC, Deloitte, or KPMG, making real money from paychecks from real companies.

My first paycheck’s logos were impressive as I started in sports marketing – NBA & NHL teams look good, that’s why they sell jerseys. But six months in, I was failing hard. The Sunday night ER trip for my first panic attack made it official – that wasn’t the play.

I followed that with the total anti-corporate move into a friends’ start-up. Those were a fun couple of years working with people I liked out of a 2-bedroom apartment on the Main Line outside of Philly. But I was flat-broke with no upward career mobility, and when I turned 25, I finally said, “Shit, I need to start making money.”

So, career three—a newly-minted Resource Development Manager at an IT staffing firm—needed to stick. And that’s when I first read Ayn Rand’s controversial book, The Fountainhead.

My problem hadn’t been bad career choices (though there were definitely a few that weren’t fully thought out). The problem was that I wasn’t taking personal accountability for anything happening in my life. I was jealous of my friends who looked confident, who seemed to have direction, who weren’t constantly second-guessing every decision. I craved external validation and was getting none of it.

For a kid who had been an honors student his whole life and graduated cum laude from a solid school, I felt like I had devolved into a meager, floundering fuck-up. I’d still be chest-out with my buddies at our annual fantasy football draft, but it was a defense mechanism. Inside, I felt like a fraud.

Turns out, this is the exact mindset of what Ayn Rand calls a “secondhander” – someone who doesn’t create for themselves but expects others to provide for them. Someone who looks outside for validation instead of building from within.

My brother’s college buddy Oz recommended The Fountainhead right as I was starting career number three. (Shout out to Tommy and Oz). The timing was perfect, though I didn’t know it yet.

Reading that book was devastating in the best possible way. Here was protagonist Howard Roark – everything I wanted to be. Maybe not the emotional detachment—I’m not all that upset that I tear up watching Pixar movies from time to time— but the self-knowledge. The confidence. The way he ran everything through his own filter before making any decision.

I was so far from that ideal, I didn’t know where to start. So I started with how I was interpreting my life.

I wasn’t a good-for-nothing fuck-up. I wasn’t a helpless victim of circumstance, either.

I just hadn’t learned the language of my internal voice.

THE FOUNTAINHEAD

Author: Ayn Rand

Published: 1943

Length: 720 pages

Buy it here: https://amzn.to/48S9tDK

WHY THIS BOOK MATTERS

Today, I’m in what many call the lonely chapter. The weird middle where my future isn’t solidified, but I know it’ll look different from my past.

I’ve moved away from some people. I’m moving toward others – but I’m not invited to those conversations yet.

So you work with what you have. Podcasts, novels, people in your life who are a few miles down the path. Back when I needed him most, Roark became part of my advisory board. I still find myself seeking his counsel today.

If you’re investing your time in this Outlast Yourself series, you know the lonely chapter. Whether it’s behind you—something you made it through—or within sight, it’s going to be a part of your story. When you’re building something while still figuring out what that something is, it’s a mandatory stage.

The Fountainhead matters because Roark exemplifies staying true to your vision when you’re surrounded by people who think you should be doing something else. When the safe path seems smarter. When everyone’s telling you to compromise (just a little bit) to make your life easier.

Roark doesn’t bend. Ever. And the book shows you exactly what that costs – and what it’s worth.

THE ESSENTIALS: 3 CORE IDEAS

1. Run Everything Through Your Own Judgment First, No Matter The Cost

The most powerful scenes in the book aren’t Roark’s occasional triumphs. They’re his dark periods. The stretches when he was unemployed because he refused to compromise one iota of his architectural vision.

Roark would take any job to survive – working in a granite quarry, doing menial labor – but he wouldn’t connect his mind to work that violated his principles. Even when survival was on the line, he protected his core.

Pure Viktor Frankl energy: maintaining your essential self under pressure.

For six months after reading the book, I asked myself “What would a guy like Roark do?” in every situation. When things hurt – well, what of it? Push through. Don’t give yourself another option, because to do so would betray the essence of your soul.

To say “my soul” was tied up in an agency recruiting job would be a tad dramatic, but in another very real sense, I was redefining my identity.

I needed to become something else than what I was. Someone who:

• set his own course and moved towards his own vision

• kept the promises he made to himself

• went all-in on something and become really, really fucking good at it.

So I built my filter and used the hell out of it.

Did I still get stuff wrong?

Fuck yes. All the time.

For all the books I read, I seem incapable of learning anything without picking up my own scars.

But in my mind, it was an entirely new experience.

Who got it wrong? ME. Not suboptimal circumstances, unlucky breaks, or being dealt a bad hand. The guy making the decisions was the one who fucked it up.

It was liberating. I wasn’t at anyone’s mercy. The only thing that drove me was my mind, and the only thing that limited me was my abilities. And I could develop them.

I quadrupled my earnings in a year.

Within 18 months, I went from being too broke for a night out every week to living in a cool Midtown apartment with a great view of the Houston skyline. I bought my dream guitar – a PRS Custom 24 in Sapphire Smokeburst. (Clearly, I did not take on Roark’s frugal approach).

And that borrowed Roark filter? It’s now my filter – modified, customized, tailored.

It was functional in 2010. It is lethal today.

2. Being Selfish and Self-Directed is One of the Best Things You Can Do in This Life

Watch Roark in flow state and you’ll see something beautiful – a violent shift from aloofness to lethal with a pencil in his hand. A direct channel to Source, moving with confidence, speed, and precision that is the closest encounter creators have with the divine.

Compare that to Peter Keating’s hollow accomplishments that left him completely empty. Keating spent his whole life trying to become what other people wanted him to be. He succeeded by every external measure – money, status, recognition – and ended up with nothing.

Because secondhanders like Keating always flame out. If you can’t create original ideas, you’re destined for a life serving others or a life vacant and devoid of meaning.

I had plenty of Peter Keating in me when I read this book. Insecurity. Looking for external approval and validation. Terrified to find out who I actually was – because what if that person wasn’t good enough? Could I handle that realization?

The book made it easy to see what I wanted to run toward (Roark’s self-mastery, control, discipline, conviction) and what I wanted to run from (Keating’s emptiness).

Rand’s virtue of selfishness (a consistent theme in her work that first emerges in The Fountainhead) isn’t about stepping on others. It’s about taking full responsibility for your own fulfillment instead of expecting the world to provide it for you. Becoming useful instead of staying a dependent.

When you know who you are and what you’re building, you create more value for everyone around you. Self-direction isn’t selfish – it’s how you become most useful.

3. The World’s Continuous War is Between Those Who Know Themselves and Those Who Don’t.

Every field has its archetypes, and they’re all represented in this book:

Henry Cameron – The OG renegade who only listened to himself.

Howard Roark – The torch carrier who builds on the foundation.

Peter Keating – The secondhander who copies without understanding.

Ellsworth Toohey – The manipulator who controls through influence.

Toohey is the most dangerous because he’s a quiet, subtle Hitler who moves others around the chessboard. He doesn’t want to control the output of prime movers – he wants to control the men themselves. Titans of industry by proxy.

What Rand nailed: these guys always start small and unassuming. You don’t take them seriously until they’ve eaten through the foundation, put their people in key positions, and set themselves up for control.

Men like Toohey are primeval. They marginalize excellence and celebrate mediocrity. The more vanilla the world gets, the more we all suffer.

Always be watchful for the Tooheys in your life. They’ll disguise their control as collaboration. They manipulate via mentorship. They orchestrate the social tides, making you think you need them to succeed.

The inverse is more important: align yourself with the Roarks and Camerons of the world. The men and women who stand on their own two feet in the arena, face reality, and will die before compromising who they are. One or two of those in your life are rocket fuel for your journey (actual humans are better than fictional replicas in this case).

The war isn’t about success versus failure. It’s about authenticity versus conformity. And it will outlast us all.

THE ENDURANCE FACTOR

These character types exist in every era, every field. The renegade who breaks new ground. The successor who carries the vision forward. The follower who copies without understanding. The manipulator who controls through influence.

Rand didn’t create these archetypes – she didn’t need to. She just needed to personify them, and did an excellent job driving each archetype to their inevitable conclusion.

That’s why the book feels as relevant today as it did in 1943.

The names change (good luck finding an Ellsworth in the wild), but the dynamics don’t.

The book builds skills that compound over time:

• Recognizing your authentic voice versus borrowed opinions

• Developing internal standards that don’t require external validation

• Identifying the difference between influence and manipulation

• Building something that can only come from you

In ten years, the specific tactics for building your career will be different. The technology will be different. The opportunities will be different.

But you’ll still have to choose between authenticity and conformity.

You’ll still need to decide if it’s prudent to dilute yourself.

You’ll still shoulder the sacrifices that come along with your chosen path.

Authenticity is expensive.

Staying true to yourself means carrying weight.

“Conscious do cost,” as Butchie tells Omar in The Wire.

It’s up to you to decide if you’re willing to pay the price required to be yourself.

KEY QUOTES

I came here to say that I do not recognize anyone’s right to one minute of my life.

I don’t build in order to have clients. I have clients in order to build.

The question isn’t who is going to let me; it’s who is going to stop me.

The creator’s concern is the conquest of nature. The parasite’s concern is the conquest of men.

To say ‘I love you’ one must first know how to say the ‘I’.

The man who lets a leader prescribe his course is a wreck being towed to the scrap heap.

Who’s in your circle of fictional allies? What character keeps you grounded when the path gets unclear? Hit reply and tell me about the voice that guides you through your own lonely chapters.

I read every single response. Because we’re all figuring this out together, and sometimes the best advice comes from someone a few steps ahead on the same path.

If someone forwarded this to you and it landed, you can sign up at outlastyourself.net. They drop (most) Thursdays, with the caveat that I’m a working dad with 3 kids under 5 who’s on a plane every month. Sometimes, life gets in the way.

You can also check out the whole archive of The 52 Books That Will Outlast You on my blog.

Next week, we’ll hit that cool creative book that I mentioned last week. Another fellow Austinite represented by the 52 (not like I’m biased or anything).

Until then – keep building, keep growing, and keep going.

Last year in July, I went to Spain with Michelle for our 10th anniversary. Five days without ankle-biters needing snacks or entertainment—our longest escape in over 5 years.

We celebrated properly. Too much jamón, more vermouth than jamón. An “exercise routine” that peaked with one leisurely tour of Alhambra.

Back in Texas, I stepped on the scale and cringed. Heaviest weight of my adult life.

And the rest of my life wasn’t much better: online writing abandoned when it got hard, novel languishing in stops and starts, body falling apart with aches everywhere, and the cardio capacity of a sloth. I was married to a bilingual Spanish speaker, and despite “trying to learn Spanish” for years, I still couldn’t order coffee after a week in Spain.

So, where to start? Did I have the balls to tackle my health? My stalled writing career?

Nope. Took the path of least resistance.

I downloaded Babbel, bought a lifetime subscription to force commitment, and started learning Spanish. And one tiny feature in the app changed everything for me: the streak tracker.

Seven days in, I set a simple goal—don’t break the streak for a year. The minimum viable effort (a 2-minute vocabulary review) meant I could always keep it alive. But something else was happening. I was becoming someone who keeps promises to himself.

Once I saw that showing up daily could change my identity, I started applying it everywhere: working out 4 days and walking 3, writing for an hour daily, cold plunging after my fantasy football buddies dared me (nothing beats an ice bath after a sweaty Texas “fall” workout), adding sauna sessions because why not stack another habit.

On day 365 of my Spanish streak, I looked around at the rest of my life and was kind of shocked:

• 40 pounds lighter.

• Four workouts a week paired with walking on the off days.

• Cold plunging 6x a week, sauna 3-4x.

• Third draft of my book complete, posting online 5x a week.

No hero effort. Just small stuff, every day, for a long time.

When I re-read Atomic Habits over the weekend, I kept saying “ohhhh” out loud.

I’d accidentally implemented damn near every tactic author James Clear teaches.

ATOMIC HABITS:
AN EASY & PROVEN WAY TO BUILD GOOD HABITS AND BREAK BAD ONES

Author: James Clear

Published: October 16, 2018

Length: 320 pages

Buy it here: https://amzn.to/4oqxJkK

WHY THIS BOOK MATTERS

Clear earned his lessons the hard way.

He took a baseball bat to the face at 16 and ended up in a medically-induced coma. Upon waking, he had to rebuild his entire athletic life through small, boring habits that nobody noticed. That pattern helped him play college baseball, graduate with stellar marks, and start a newsletter that gained enough traction to warrant him writing a book about his findings.

I first read Atomic Habits in 2019—a time when my habits needed massive upgrades. But like most books, the lessons evaporated the moment I picked up the next one. Nothing changed.

(Perhaps the underlying reason I’m doing this series? A fair guess.)

Fast forward to this past weekend. I’m listening to the audiobook while staining my back porch stairs, and with every chapter I’m shocked at how much my subconscious retained.

Habit stacking. Environment design. Identity transformation.

All there in my life, implemented without conscious thought.

That’s when you know someone discovered something real: when their framework explains your accidental success better than you can explain it yourself.

THE ESSENTIALS: 3 CORE IDEAS

​

1: The Mathematics of Self-Destruction vs. Self-Construction

Clear gives you the math that should terrify anyone who’s honest about their trajectory:

1.01^365 = 37.78.

0.99^365 = 0.03.

The compound interest of getting 1% better every day for a year makes you 37 times better. The compound interest of getting 1% worse? You’re basically at zero.

What Clear doesn’t hammer home hard enough—and what my scale screamed at me—is that 1% worse happens with the kind of effortless momentum that would make physics professors weep. You can destroy months of progress in days without even trying. The slow drift toward becoming someone you don’t respect doesn’t feel like falling off a cliff. It feels like a vacation.

The Spanish app became my North Star, though not for the reason you’d think (after all, Michelle yells at me in English). The lessons became daily, accumulating proof that I was the person who does what he says he’ll do.

And once that identity started solidifying, the rest of my good behaviors started falling in line with minimal effort. Workout complete? Well, a cold plunge wouldn’t feel bad in this 102-degree garage. Morning pages written? Spanish lesson takes two minutes, let’s keep the momentum going.

Clear has great labels for all of these—habit stacking, temptation bundling, environment design. I had a simpler framework: might as well since I’m already sweaty. The chiller purchase for my cold plunge wasn’t some strategic environmental optimization. It was pure laziness—I got tired of hauling five 20-pound ice bags from the town ice machine like some kind of suburban Sisyphus.

But that laziness was the point. Make the right thing the easy thing. Remove friction from what you want to do, add friction to what you don’t. It’s not motivation, it’s architecture.
​

2. Motion vs. Action: The Mental Masturbation of Preparation

Clear draws a distinction that should be tattooed on every productivity junkie’s forearm: motion is not action. Motion is researching the perfect Spanish learning app for two weeks and watching YouTube videos about language acquisition theory. Action is downloading Babbel and doing lesson one while you’re taking a shit.

Most people live in motion because motion is safe. It’s all the dopamine of feeling productive without the messy reality of potential failure. You can spend months “preparing” to start a business, “researching” the perfect workout routine, “planning” your novel. Meanwhile, someone dumber and less qualified than you is actually doing the thing and getting better at it.

I know this because I’ve been that guy—the one with seventeen Moleskines full of ideas that go nowhere, or the optimized workout plan started on Monday and abandoned on Thursday. Motion addicts love to optimize systems they’ll never use.

The Spanish streak broke this pattern by accident. I didn’t research apps, didn’t study methodology, didn’t give myself time to build the perfect learning environment. The Instagram algorithm advertised a “lifetime license sale” (likely because it heard my shitty attempts to order a coffee). The app had decent reviews, so I just said “fuck it” and started. Two minutes a day. Every day. No optimization, no preparation, just repetition.

462 days later, I’m sure of one thing: Action compounds. Motion doesn’t. Every half-assed Spanish lesson moved me forward. Every hour researching “the best way to learn Spanish” would have kept me exactly where I started—monolingual and blissfully ignorant when my in-laws slipped into their native tongue around me.

Clear’s framework explains why this works: action creates evidence, evidence shapes identity, identity drives behavior. You can’t think your way into being a good writer. You have to write your way there, two shitty pages a day.

The beautiful thing about choosing action over motion? You find out real quick if you actually give a damn about the thing you’re pursuing. Motion lets you fantasize indefinitely. Action forces you to face whether you actually want the result or just like the idea of it.

​

3: Your Habits Are Your Operating System Export

My kids aren’t just watching my behavior—they’re downloading my operating system. When I do my Spanish lessons on the couch, they’re not learning Spanish—they’re learning that Dad practices something every day. When the boys come dip their hands into the 46-degree water, they’re not studying cold exposure benefits. They’re learning that comfort is negotiable, that hard things can become routine.

Clear’s framework says every habit is a vote for who you become. What’s written between the lines: those habits are also a vote for who others believe is possible to become. My 3-year-old comes in the gym and does curls, squats, and push-ups—not because I’m training him for the NFL, but because he sees that’s what the men in our family do (and because he wants to show his jiu-jitsu coaches his big muscles).

The ripple effect extends beyond blood relations. I’ve had multiple colleagues tell me they’ve picked up the journaling habit because I’ve talked to them about mine. I have four friends who have purchased cold plunge rigs over the last year after talking through my experience with them. That’s the bigger picture we all miss—we’re not just building habits. We’re building permission structures for what others think is possible.

Because we’re all always being watched. Every small, boring habit is either expanding or limiting what someone believes they’re capable of. Your kids, your colleagues, that friend who’s stuck—they’re all downloading your source code, whether you realize it or not.

This is how you outlast yourself—not through some LinkedIn hall of fame achievement that dies when you do, but through the operating systems you install in others. The person you become through your habits becomes the template others unconsciously follow. Your consistency becomes their possibility.

THE ENDURANCE FACTOR

Atomic Habits works because it’s not about productivity porn or life hacks. It’s about the unglamorous truth of how humans actually change: through small, boring, daily actions that nobody notices until they compound into someone different.

Clear didn’t invent some new system. He documented what already works—that identity follows behavior, that systems beat goals, that 1% daily improvements create exponential results. The math doesn’t care about your motivation. The compound effect doesn’t need your passion. It just needs you to show up.

The book endures because it explains why I became a writer by doing Spanish lessons. Why I get twitchy after a few days without a sauna and cold plunge session (two things that are regarded by most as self-torture). Why my 3-year-old does pushups because he sees me do them, not because I tell him to.

Every habit is a vote for who you become. But more than that—every habit is a vote for who others believe they can become.

That’s the part that matters. Passing on your good habits to others who are watching.

That’s the only way to outlast yourself.

Thanks for reading. You’re part of a small (but growing), ambitious group who are striving towards something—a career move, an entrepreneurial venture, a 2nd Act.

No fluff, no formulas, just fuel for the life you’re actually trying to build.

If you know more people like you, please think about sharing this. If this hit something real for you, it’s apt to land with someone like-minded who you care about.

Next week…I’ll be honest, I’m torn. I have a badass creativity book that is one of my favorites, and I have a foundational fiction book in the library. I’m honestly just in disbelief that it’ll be the 20th volume of this. Again, more proof of Clear’s tactics. Some would call it slow and steady. I like to think of it as relentless.

Keep building, keep growing, and keep going.

And you. And your spouse. And your boss, your grown kid, your neighbor, and anyone trying to live in the diluted-attention economy that is 2025.

Need proof? Check the state of your “unreads” at the end of the night. Mine:

• Personal email: 52 unread.

• Work email: 332 unread.

• Side-hustle email (mostly newsletters and coaches promising to help you grow): 2,847 unreads.

• Texts: 15 unread.

• WhatsApp fraternity chat: 33 unread (150+ if it’s Monday Night Football).

• LinkedIn: 25 unread.

The sick joke? Most of my days are really productive.

I crush tasks. I move the needle at work. My house isn’t falling apart. My family feels loved and supported. I get shit done (like writing this newsletter) and feel good about what I’m doing.

Yet I’m always behind.

And always will be.

Oliver Burkeman’s ​Four Thousand Weeks​ does the math: on average, that’s how long we all get. If that sounds short to you, it’s because it is. And on the scale of recorded history, our existence equals the flash of a camera in a dark room.

And when you realize that, in the long run, we’re all dead (killer opening chapter title, pun intended), something funny happens:

• You breathe a little easier.

• Those emails seem less important.

• You don’t care if you miss the fundraiser.

• You’re fine letting those “we should catch up soon!” notes drift into their deserved oblivion.

In an age of productivity advice, this book is the anti-productivity guide high performers need. Because being productive is not about your new system, timer, or app.

It’s about making the time to do the things that really matter, then being present for them.

Because, if you’re reading this, you have less than 3,000 weeks left.

​FOUR THOUSAND WEEKS: TIME MANAGEMENT FOR MORTALS​

Author: Oliver Burkeman

Published: August 10, 2021

Length: 290 pages

WHY THIS BOOK MATTERS

Confession time: I’ve done the productivity geek thing. I buy notebooks like finding the perfect one will solve all of my problems. New AI tool to improve my efficiency? Signed up for it, canceled the next month. Weekly / monthly / quarterly goal tracker? I had my friend in the UK grab me a copy of a notebook I couldn’t get in the States.

Guess how much it helped me get done? How many of those systems are still in operation? Hint: I’m writing this on a brand new app I downloaded today…

My quest hasn’t ended. Just like yours probably hasn’t. Getting on top of our to-do lists will always be one app away, just over the horizon.

Here’s why Burkeman gets it: He was a productivity columnist for The Guardian who spent years testing every time management hack. Then had the same realization I did: It’s all bullshit. Not because the tactics don’t work, but because they’re solving the wrong problem.

The real problem? We’re not trying to manage our time. We’re trying to avoid the uncomfortable truth that we’re mortal, limited, and fundamentally not in control. Every productivity system is just a more sophisticated form of denial.

THE ESSENTIALS: 3 CORE IDEAS

1. You’ll Never Be Caught Up—And That’s The Point

Burkeman discovered something that should be obvious, but isn’t: The better you get at email, the MORE email you get. It’s not a bug. It’s a feature.

Edward T. Hall’s metaphor for this is perfect: Time feels like a conveyor belt bringing you tasks. The more productive you get, the faster the belt moves. You don’t end up failing at productivity – you succeed yourself into exhaustion.

This was studied by Ruth Schwartz Cowan in relation to washing machines (or, as Michelle calls them, “the bane of her fucking existence.”) When washing machines were invented, laundry didn’t take less time—standards just got higher. Now we wash clothes after we wear them once instead of when they smell. Every hour you ‘save’ just get filled with new demands.

So what does that mean for all of us hanging on to a fantasy? You know the type:

• “When I finally get the workload under control…”

• “When I get promoted…”

• “When I finally have enough money saved…”

It’s all the same lie: That someday, you’ll have arrived. In reality, when you arrive, you’ll be handed more tasks…and again feel like you need to catch up. To quote one of my old executive partners, “It’s like a pie eating contest where the prize is more pie.”

I liked the highlight of Hofstadter’s Law: Any task takes longer than you expect, “even when you take into account Hofstadter’s Law.” Time actively resists your attempts to control it.

Burkeman’s tactical shift? Approach your work with a fixed volume. You’re only going to do so much. It’s a vast mental shift from how I typically approach my work, which looks more like, “I’m done when I collapse onto my keyboard.”

He recommends keeping two lists:

• Open list (the nightmare – everything you need to get done in all areas of your life).

• Closed list – The 10 tasks you’re working on right now.

You check something off the Closed list, you can add something from the Open list. But you can’t add to Closed until something’s done. This allows you to decide in advance what you’re going to fail at. If “drop 20 pounds” is on the Closed list and “Keep the kitchen clean” is on the Open, so be it. You’re gonna stare at dirty dishes more frequently and concentrate on the scale.

2. Your Attention is Your Life (And it’s Under Siege)

Here’s some tough math: We can consciously attend to about 0.0004% of information bombarding our brains at any moment.

But attention isn’t just some resource you manage—it IS your life. As Burkeman puts it: “Your experience of being alive consists of nothing other than the sum of everything to which you pay attention.”

Sit with that for a second. Your life is literally made of what you pay attention to. Nothing more, nothing less.

Meanwhile, every time you pull up Instagram or TikTok because you’re bored, “there are a thousand people on the other side trying to keep you there.” An army of PhDs and engineers focused on one mission: dwell time. Keep you on the platform. You think these people give a fuck about your mental health? It’s capitalism, baby.

If you’re a human being, it gets worse—you’re their accomplice. Because deep down, we all WANT to be distracted. Mary Oliver called it “the self within the self, that whistles and pounds upon the door panels.” We seek distraction because focusing on what matters is uncomfortable. It forces us to confront our limitations, our mortality, our fundamental lack of control.

Remember when 3 million people watched BuzzFeed wrap rubber bands around a watermelon for 44 minutes? Not because it was compelling. Because it was easier than sitting with ourselves. (I didn’t catch that one, but I’ve burned plenty of hours on equally mindless shit – Homestar Runner cartoons come to mind.)

The cost isn’t just time. It’s reality itself. Every hour on social media warps your picture of the world, generates anxiety even when you’re offline, and trains your brain to crave the next hit.

The philosophical shift? Accept that the discomfort of focus is the point, not something to avoid. When it feels hard to stay present, that’s your brain trying to avoid the weight of being human. Because, yeah, it’s fucking heavy being a human. But the only way you can carry the weight is to get stronger – rep by rep.

3. Stay On The Fucking Bus

Photographer Arno Minkkinen gave his students this advice about creativity, but it applies to everything:

The Helsinki bus station has 24 platforms. Multiple buses leave from each platform. For the first several stops, ALL buses from the same platform follow the same route.

You start a project. Three years in, someone says you’re derivative. So you quit, start over. Same thing happens. You keep jumping buses, searching for your “original” work.

Minkkinen’s solution? “Stay on the fucking bus.”

Eventually the routes diverge. That’s where distinctive work begins. But it ONLY happens for those patient enough to endure the derivative phase.

In a world built for instant gratification, the capacity to resist hurry becomes a superpower. Jennifer Roberts makes her Harvard students stare at one painting for three hours. First 40 minutes: torture. Hour two: something shifts. You stop fighting. The painting reveals what you miss when you’re looking at it long enough for your iPhone camera to focus.

But my favorite part of this chapter is something I’ve been circling in a few areas of my life: cosmic insignificance therapy (thanks, Hormozi).

The universe is 13.8 billion years old. Human civilization? 6,000 years. That’s 0.00004% of cosmic history. You could fit all of recorded human existence into a single commercial break on the universe’s timeline.

In 4 generations, everyone who knows anything about your existence will be gone. Your hopes, fears, dreams, achievements – gone, just like you will be.

So why, exactly, are you so upset that your 2-year-old just colored your white fireplace stones with black sharpie?

In the right frame, how little anything we do matters in the scheme of the cosmos is more liberating than terrifying. Time’s undefeated – we all get a death prognosis the moment we take our first breath. It’s dumb that we fight it (by we, I mean I.)

Why run yourself into the ground justifying your existence with your achievements? Believing you need to “make a dent in the universe?”

How much of a dent can a blink really make?

So, what if preparing meals for your kids matters as much as anything could? What if your novel is worth writing even if twelve people read it? What if any career is worthwhile if it makes things marginally better for the people around you?

We don’t need cosmic significance. We need local presence. Stay on the bus. Accept you’re a speck. Then get to work on the only thing you can: whatever’s right in front of you.

THE ENDURANCE FACTOR

This book will outlast the usual productivity porn because it’s not selling you another system. It’s not promising you’ll ever feel “in control.” It’s offering something harder and more valuable: reality.

The fundamental truth: You have 4,000 weeks if you’re lucky. You’ll never get everything done. You’re not in control. You’re not that important.

And once you stop fighting those facts, you can start living.

The attention economy is getting MORE sophisticated, not less. AI will accelerate this, not solve it. The pressure to optimize will intensify. Which means people who can accept limitation will have an increasingly rare advantage.

This builds the skills that matter: Patience in an impatient world. Focus in a distracted world. Acceptance in a world built on denial. Presence in a world obsessed with the future.

And, if we’re fortunate, something more valuable than a skill.

Peace of mind.

KEY QUOTES

The day will never arrive when you finally have everything under control… and that’s excellent news.

Strategic underachievement is the only way to achieve anything meaningful.

Missing out on something—indeed, on almost everything—is basically guaranteed.

Hope is the opposite of acceptance; it keeps you leaning forward into a future that never arrives.

Reality is always this moment, which is never quite the one you had in mind.

Stay on the bus. The scenery changes.

It’s 2020. I’d been with my company for years, promoted multiple times, and had a gold star next to my name. But the big job I was striving for had been hanging out there for six months, a carrot being dangled, as I continued to “grow into the role.” And I knew I was ready.

So I started taking calls.

One of them ended up clicking. It was for the big job at a bigger company. My potential future boss thought I was ready, too.

The offer came.

Bigger money than I had ever made in my life.

Pre-IPO equity – the kind that could change my family’s trajectory.

But there was something in my head telling me it wasn’t right.

My rebellious voice, the one born with a visceral disdain for the safe path. And when decision-time came, that voice’s whispers had become a stern warning:

“Come on, Radice – you know this ain’t it. Stay the course. You see the road ahead. And that side thing you’re working on? It’s starting to take shape.”

So I turned down the offer.

The recruiter couldn’t believe it. “Seriously? You’re turning it down?”

The hiring manager told me he was “gutted.”

And, returning to the current job on Monday morning, I thought to myself, “What the fuck did I just do?”

But my outlaw voice had it right.

The guy who would have hired me? I saw him celebrate the move to a new company on LinkedIn a month later.

And the company I stayed at? The big job came a few months later. The bigger money came. I grew into the leader I needed to become, all while quietly working on the craft that would come to define my second act.

That rebellious voice lives in all of us. The outlaw. The renegade. The person who wants to flip the bird at the system because they weren’t consulted when the goddamn rules were made.

Oscar-winning actor Matthew McConaughey details how he learned to listen to his inner voice in his nontraditional memoir ​Greenlights​.

It’s genuine. It’s undeniably him. And if he was telling you this story on the barstool where you were grabbing dinner, you’d be shocked when the lights came on at last call, hoping he could squeeze in the ending before they tossed your ass outta the bar.

GREENLIGHTS

Author: Matthew McConaughey

Published: October 20, 2020

Length: 320 pages

WHY THIS BOOK MATTERS

Greenlights isn’t your typical celebrity memoir. It’s 35 years of journals distilled into outlaw philosophy, a handsome Texan who rom-com’d his way to superstardom, then walked away from it all to become the actor he wanted to be.

I picked this up when it came out – during the COVID pandemic. We were all at a crossroads, all looking for safety, all suppressing our inner outlaws. The first time through, I saw it as a fun read by an excellent storyteller. But certain ideas kept bubbling back up from my subconscious at different decision-points in my life. So I revisited it now, half a decade older, hopefully a little wiser, to see if it made the cut. And what did I find?

This is the blueprint for the second act pivot. Not the sanitized version—the real one, where you have to earn the right to break the rules before you break them, and when you do break them, you’re paying a steep price today for a better day down the line.

THE ESSENTIALS: 3 CORE IDEAS

1. Outlaw Logic: Master The Rules Before You Break Them

McConaughey was raised on what he calls “existential outlaw logic.” His parents divorced twice and married three times—to each other. In his house, if something wasn’t true, it ought to be.

His dad’s philosophy was simple: “You better follow the rules until you’re man enough to break ’em.” You got your ass whipped for breaking rules, but you got punished worse for getting caught.

At 18, McConaughey went to Australia as an exchange student. The Rotary Club wanted him to sign a contract promising not to come home early when the homesickness inevitably hit. His response?

“I’m not signing that paper, but I’ll shake on it.”

Handshake over contract. His word was the deal. When things got brutal—and they did, in some bizarre ways—he stayed the full year. Not because of a paper, but because he shook on it, and that handshake meant something to him about who he was.

You might read outlaw logic and think “chaos,” but you’d be mistaken. It’s earned rebellion. You prove you know the game well enough to know when the rules are bullshit. Then you break them with integrity – an integrity you define for yourself.

You can’t pivot successfully if you never mastered your first act. The outlaw move only works when you’ve earned the credibility to make it. McConaughey didn’t walk away from rom-coms on day one. He dominated them first. Then he burned the bridge.

2. “Don’t Half-Ass It”—The Only Permission That Matters

As the best debater in the household, McConaughey was groomed to be the family lawyer. Blue-collar family from Texas with a few failed lawsuits under their belt, he was ready to play the part, and enrolled at University of Texas in the pre-law program.

But at his core, he knew it didn’t feel right. What did? Film school. Telling stories (like this book, which is a masterclass in barstool storytelling).

So he did what any 18-year-old in college would be scared shitless to do: he decided to call his dad and break the news.

At 7:36pm, after he knew dad would be fed and have the first drink in his bloodstream, he phoned home.

“Dad, I don’t want to go to law school anymore. I want to go to film school.”

Five seconds of silence.

“Is that what you wanna do?”

‌”Yes sir.” No hesitation from the kid taking the reins of his life.

Another five seconds.

“Well… Don’t half-ass it.”

Of all the things his dad could’ve said—disappointment, concern, “are you sure?”—he gave him the only permission an outlaw needs: total commitment.

Not “good idea.” Just “if you’re doing it, fucking do it.”

McConaughey took that seriously and won big. After exploding with “A Time to Kill,” he ended up getting typecast in rom-coms. Shirtless guy on the beach, working with the sexiest women in Hollywood, printing money. Living the dream, right?

For a time, yeah. But then the work became automatic. All challenge disappeared. And he started to hear it again – the quiet, insistent voice that he needed some more resistance in his life.

“I was more alive in my life than in my movies.” Sure, that’s the balance all of us would want if we could only settle for one or the other. But who says we have to settle?

So he turned down rom-com after rom-com in search of challenging dramatic work.

One studio offered $5 million. He passed.

$8 million. Nope.

$10 million, $12.5 million, $14.5 million.

(Well, he re-read the script at $14.5 million. I think we all would. That’s a ton of cash to do something you can do in your sleep.)

But in the end, he passed. And industry finally got it: he wasn’t rom-com guy anymore.

Twenty months. Zero work. His agent stopped hearing his name. Hollywood forgot him.

With their firstborn infant in her lap, his wife Camila backed him up: “If we’re gonna do this, we’re gonna do it all the way. No half-assin’ it.”

So he waited. He questioned himself. He looked at alternate vocations – the world always needs more teachers, right?

But as the months passed, the conversations in Hollywood shifted:

“Holy shit, this guy’s committed. Nobody turns down that kind of cash. He must have a plan.”

Then: “What’s McConaughey up to? He might be a unique choice for…”

The offers that came nearly two years later? Lincoln Lawyer. Killer Joe. Mud. True Detective.

His take on it? “I was remembered by being forgotten.”

He became a novel idea by disappearing. How he drew it up? Maybe, maybe not. But it worked because he didn’t falter – even when studio execs threw NFL money his way.

That’s the move. Not hedging. Not keeping one foot in. Go all in, or don’t bother.

3. The Greenlights Come When You Stop Asking

McConaughey got offered the role of Van Zan in Reign of Fire as a dragon-slaying badass. He shaved his head for the character (also because he was losing his hair—outlaws aren’t exempt from the global curse of the balding man).

The studio executive called: “You did NOT shave your head.”

“Yes I did.”

The exec then sent a letter: “This would be a tragedy… it may bring you very bad karma.”

The threat was meant to make him back down. Instead, McConaughey bought a custom Gucci suit, tanned his shaved head by the pool for five days until it was bronze and shiny, then showed up to an industry party looking like a goddamn Greek statue.

Executive called Monday: “I love the shaved head! You look original!”

But the real proof came with Dallas Buyers Club. He was attached to the script for five years. Nobody would finance it with him in the lead. Even his agent told him, “There is NO movie, Matthew.”

McConaughey: “We’re shooting in October.”

He lost 47 pounds on faith. Still no money.

“We didn’t ask permission. We didn’t flinch. We took the hill.”

Someone finally put up $4.9 million (they needed $7 million). They made it in 25 days. He won his first-ever Oscar for Best Actor, fulfilling a lifelong goal.

Nobody validates your outlaw path. That’s your job – to sign on the line for the decisions that will define your life. Your greenlights appear when you stop waiting at someone else’s intersection and start moving.

THE ENDURANCE FACTOR

This isn’t McConaughey’s invention—it’s ancient outlaw wisdom. Your dad had it. His dad had it. I strive to live so that my kids remember me having it. Every generation has the outlaws who create their own greenlights and the rule-followers stuck at yellow lights.

The book’s been out since 2020 and it keeps resonating because the pattern doesn’t change:

• Master your craft

• Go all in on the pivot

• Stop asking permission

Twenty years from now, someone will read Greenlights during THEIR crossroads moment and realize: the greenlights were always there. They just needed the balls to stop asking and start taking.

The bottom line: Outlaw logic isn’t about being reckless. It’s about being relentless. It’s about earning the right to break the rules, then not half-assing it when you do.

More outlaw = more greenlights. Not because you’re breaking rules—because you’re playing by your own. And at our peak, that’s the best any of us can hope to do.

KEY QUOTES

These are the ones I wrote down: no commentary needed, you can hear him saying every line – even the ones that aren’t his.

“Style is knowing who you are, what you want to say, and not giving a damn.” — Gore Vidal

“One in a row. Any success takes one in a row. Do one thing well, then another.”

“I have never had any trouble turning the page on the book of my life.” — Darryl K Royal

“I never wrote things down to remember; I always wrote things down so I could forget.”

“It is not about win or lose, it is about do you accept the challenge.”

You know the kind – where every surface is sticky, padded, and kids still find a way to injure themselves.

My 5-year-old is chasing “Purple Girl” around at light speed – in socks.

My 3-year-old launches himself down a slide headfirst into another child climbing up the same slide.

The 1-year-old is crying on my shoulder, drool pooling on my Yankees shirt.

And everywhere, there is screaming.

My brain’s running its usual program: irritation about the noise, deliverables piling up, parental guilt for checking baseball score while my kids play. The knot in my chest—that familiar tightness that comes from trying to control everything while controlling nothing—pulls tighter.

Purple Girl walks up to me and says, “Your son (the 5-year-old) pushed us down the slide.” My 1-year-old is screaming at the top of another slide because he has no one to ride down with him. My 3-year-old is holding on to my ankle, yelling, “Daddy, I want you to walk!” Michelle is in San Antonio – blissfully ignorant.

“Siri, define overstimulation.”

And, thanks to Eckhart Tolle’s ​The Power of Now​, it is in this moment that I access inner peace.

​THE POWER OF NOW: A GUIDE TO SPIRITUAL ENLIGHTENMENT​

Author: Eckhart Tolle

Published: 1997

Length: 256 pages

Buy: https://amzn.to/46PHcvu

WHY THIS BOOK MATTERS

Most spiritual books promise you’ll find peace once you meditate enough, forgive enough, or finally let go of your ego. Tolle’s different. He says you can access that peace right now – even when you’re holding a screaming toddler while your other kids are weaponizing slides.

I read this book over a decade ago after it was recommended by my good friend Nic, a man living a parallel life to mine but a few miles ahead on the path.

When he recommended Tolle while standing in a take-out line to bring dinner back to his family, I was in a pretty dark place. I was still grieving my mother’s death without the emotional tools to do so correctly.

Over the years, I had also been moving away from Catholicism. It wasn’t so much a firm decision as a drift. After Mom’s passing, it had accelerated to a brisk walk. I had a tough time reconciling how my mom, a generally fantastic person, could get “called home” early after 58 years of being good. Meanwhile, I was left here to continue my sprint on the hedonic treadmill, hearing “You’re such an asshole” with regularity and smiling because I knew it to be true.

It was a good time to look at my life from a different angle.

Enter Tolle. He was 29, on the verge of suicide, when he was “awakened.” And his advice feels like it. A guy fed up with the mechanics of life who found a gateway into something better, then made it his life’s work to share the map.

I like my wisdom digestible and accessible. In that moment, in the state I was in, it was mana in the desert.

Tolle wasn’t telling me to fix my situation. He was pointing out that my suffering wasn’t coming from the situation – it was coming from my resistance to it.

That distinction changes everything.

Fast forward to the screaming and leg-pulling.

A new stage of life. A new drift – a season of transformation and burning of old things to make way for new things. An inkling two weeks prior that this should be the next book I write about.

And, in true ​Outlast Yourself​ fashion, it held up.

It served me differently this time around, as I am not the same man I was when I last stepped into this literary river. But it reminded me of something important:

Sometimes – often – my only job in life is to accept what “is.”

THE ESSENTIALS: 3 CORE IDEAS

1. The Pain Body

Tolle has a term for what most of us carry without realizing it: the pain-body.

It’s the accumulated emotional pain living in your nervous system. Every layoff. Every time you felt powerless. Every moment you chose security over growth and resented yourself for it. That pain doesn’t disappear. It stacks up. It waits.

The pain-body feeds on situations that create more pain. It magnifies minor irritations into major disruptions. Your kid asking for snacks becomes evidence that your life is chaos. Your wife’s question about dinner becomes an indictment of your worth as a provider.

You’re not reacting to what’s happening. You’re reacting to everything that’s ever happened, all at once.

This is why you snap at your kids when they’re just being kids. Why Sunday nights feel like dread even when Monday looks manageable. Why you can’t just enjoy the play gym – you have to control it, because chaos feels like a threat to your already-fragile sense that you’re holding everything together.

Tolle says the first step isn’t to fix it. It’s to see it. To catch yourself and realize: “This reaction is way bigger than this trigger.”

That awareness creates a gap. And in that gap, you have a choice you didn’t have before.

2. Becoming Transparent

Tolle uses the relatable example of a car alarm to highlight this. It’s a peaceful night, and a car alarm goes off. It chirps for the requisite amount of time. So you sit there. With each bray, more frustration floods into your body and hits a wall. It stays with you. Your pain body feasts like a stoner on a couch, watching Rick and Morty, Double Stuf Oreos disappearing at record speed. (I don’t know anyone who does this).

And all of a sudden, you’re fucking angry. And you stay angry, even when that asshole finds the keys and the soothing double-beep signals that the whole misery is over.

But what if you had a veil instead of a wall? Something transparent, lightweight, a linen sheet in a breeze? What if you could let the noise pass through you instead of resisting it? Feel it, then release it.

That’s what I did at the play gym.

I let everything pass through me – Purple Girl’s complaints, one kid’s sad screams, the other kid’s laughing screams. I just…was.

What changed about my external state? Nothing.

How did I feel? Like someone removed a 1.5 pood kettlebell from my chest.

3. Everything You’re Clinging to is Already Gone

Twelve years ago, this was a jarring thought for a faithless kid who was wrestling with loss and mortality.

During my recent re-read, it was also jarring – for very different reasons.

At the book’s core, Tolle is teaching impermanence. Everything changes, disappears, or stops satisfying you. Your job title, your salary, your professional identity. But also: the father who tries not to miss tee-ball, the provider and protector, the husband who keeps trying to figure out how he’s supposed to talk to his wife.

On a long enough timeline, they all disappear. You retire. The work keeps going. Your kids are off to college. Tee ball is still going on at the park. If you’re fortunate, your marriage is intact. (I saw first-hand what it’s like when it’s not, and that’s a whole different experience).

And then, it all fades away. Because you fade. So will I. So will everyone telling you they love you—along with everyone telling you they hate you, or don’t believe in you, or wish you could be a little more emotionally intelligent when you bring up certain topics

Time is undefeated.

And there’s something about that knowledge that, while scary, is truly liberating.

When you stop clinging to those identities – when you accept they’re temporary anyway – you can actually be present. Not the perfect provider or the perfectly present dad. Just… there. Actually available instead of mentally elsewhere.

Once I accept that old Mike is dead, current Mike will be gone, and future Mike will eventually be dust too, a certain clarity comes.

Nothing matters except the stuff I choose to let matter. And even then, it only matters to me while I (and the people I care about) are here.

That awareness is an ally. It gives you permission to let go of all of it – your past grievances, your expectations, your chubby fuck of a pain body.

And just be.

THE ENDURANCE FACTOR

This book will outlast your current crisis because it’s not about your current crisis.

Twenty-seven years after publication, people are still discovering Tolle during their own personal apocalypses – the layoff, the divorce, the diagnosis, the moment when the life they built stops fitting. Each generation thinks they’re the first to realize that clinging to temporary identities creates suffering.

We’re not.

The Stoics knew it. The Buddhists knew it. Tolle just translated it for people who won’t sit on meditation cushions but will read a book on a Delta flight while their old life burns down behind them.

Your current transition will resolve one way or another. You’ll find your next thing or you won’t. Your kids will grow up either way. But the question Tolle poses remains: Will you spend your limited time here clinging to identities that are already dying, or will you actually show up for the life you have right now?

That question doesn’t age. Neither does the answer.

KEY QUOTES

The pain-body doesn’t want you to observe it directly and see it for what it is. The moment you observe it, feel its energy field within you, and take your attention into it, the identification is broken.

My anger at the play gym wasn’t about Purple Girl or the screaming kids. It was every accumulated disappointment trying to stay alive by feeding on chaos. The second I caught myself – “wait, this reaction is way too big” – the spell broke. That’s the whole game. Just see it.

Instead of having a wall of resistance inside you that gets constantly and painfully hit by things that ‘should not be happening,’ let everything pass through you.

Most of your suffering comes from three words: “This shouldn’t be.” You shouldn’t have to reduce your team. The job search shouldn’t take this long. Your kids shouldn’t melt down at bedtime. Delete “shouldn’t” from your vocabulary and half your problems disappear.

Nothing lasts in this dimension where moth and rust consume.

Your VP title? Gone. Your current crisis? Temporary. Your kids’ tee-ball phase? Blink and you’ll miss it. Everything you’re desperately trying to control is already slipping through your fingers. So maybe just show up for it while it’s here.

There’s no collapse, no breakdown, no cinematic moment.

One day you’re fine.
The next day you’re still fine but coffee doesn’t work anymore.
Then your favorite music sounds like noise.
Then writing—the thing that used to feel like breathing—feels like drowning.‌

I know because I’m there now. Present tense. Writing this from inside the weird, hollow place where high performers go to die and get reborn. (Which, for me, happens to be on a Delta flight at 30,000 feet.)

The first time I read Rick Rubin’s ​The Creative Act: A Way of Being​, I was focused on the first three words of the title. I was trying to find myself in this weird pivot from musician to writer (while maintaining the umbrella personality of leader and provider). I wanted to become a “creator.” I had already dropped an album with my brother, but it went nowhere, and I didn’t feel like I was truly an artist. Why not grab some advice from arguably the most famous and prolific music producer of all time and one of Time’s “100 Most Influential People in the World?”

Need proof? Look a subset of his roster. If none of these names are in your Spotify library, I’ll eat one of my many Yankee hats: The Beastie Boys, Run-DMC, Kesha, Adele, Ed Sheeran, Lady Gaga, Metallica, Slayer, Red Hot Chili Peppers, Rage Against The Machine, System of a Down, AC/DC, Audioslave, Weezer, Aerosmith, Linkin Park, Slipknot, The Avett Brothers, Tyler Childers, Kid Rock, Johnny Cash.

You’re probably thinking what I thought the first time I pulled up Rick’s Wikipedia. “How?”

​The Creative Act​ is a glimpse into his how.

Re-reading it this time, it was the second half of the title, A Way of Being, was what caught me. This was supposed to be reviewing another productivity book, with a slant for my fellow creatives out there. Some new tools for the toolkit.

Instead, it became a mirror showing me why none of my tools were working anymore.
Why pushing harder was making everything worse.
Why the source I’d been trying to squeeze dry was never inside me to begin with.

And why I was smashing my head into my keyboard getting my posts together for the week.

​THE CREATIVE ACT: A WAY OF BEING​

Author: Rick Rubin
Published: January 17, 2023
Length: 432 pages

WHY THIS BOOK MATTERS

Rick Rubin’s The Creative Act isn’t really about making music, despite Rubin’s legendary status as a producer. It’s about the deeper practice of being a vessel for creative work—and what happens when we mistake ourselves for the source instead of the channel.

Since I came up with the idea for ​The 52​ (in the shower – no shit, that happens in real life), I knew Rubin would make the list. But when it came time to write about it, I picked up this book thinking I’d find productivity hacks for creating while exhausted.

What I found instead was a mirror reflecting back why I was exhausted in the first place. Instead of tapping into Source and letting it flow, my big ol’ ego had been telling me I WAS the source – and then squeezing me like a bookie I owed money.

THE ESSENTIALS: 3 CORE IDEAS

1. You’re Not The Source, You’re The Vessel

We begin with everything: everything seen, everything done, everything thought, everything felt, everything imagined, everything forgotten, and everything that rests unspoken and unthought within us. This is our source material, and from it, we build each creative moment. This content does not come from inside us. The Source is out there.

Rubin doesn’t teach you how to push harder. He says to stop pushing altogether.

For those of us who have built our entire identity around effort, that’s terrifying.

I’ve been trying to squeeze creativity out of myself like the last bit of toothpaste from the tube. Rubin suggests the opposite: we’re not the source, we’re the vessel. The harder we squeeze, the more we block the flow.

He talks about creating “a space so free of the normal overpacked condition of our minds that it functions as a vacuum. Drawing down the ideas that the universe is making available.”

When did you last have a vacant space in your mind? When did you last stop long enough for an idea to find you instead of hunting ideas down like a bounty hunter?

2. Breaking Is Part Of The Process

In Japanese pottery, there’s an artful form of repair called kintsugi. When a piece of ceramic pottery breaks, rather than trying to restore it to its original condition, the artisan accentuates the fault by using gold to fill the crack.

I’ve read about kintsugi in a ton of productivity books (surprise, surprise), but this time, these lines got a thick underline. I’ve been treating my increasing exhaustion, my shortening temper, my inability to be present as failures to fix. Problems to solve. Weaknesses to overcome through more discipline, better systems, harder work.

What if the breaking is the point?

What if burning out isn’t failure but transformation? What if the cracks appearing in my perfectly optimized life aren’t meant to be hidden but highlighted?

Rubin writes: “The scar also tells the story of the piece, chronicling its past experience.”

Maybe those of us breaking under the weight of our own ambition aren’t failing. Maybe we’re being prepared to hold something different.

3. Discipline Means Harmony With Time, Not War Against It

Discipline and freedom seem like opposites. In reality, they are partners. Discipline is not a lack of freedom, it is a harmonious relationship with time.

Navy SEAL Jocko Willink’s “Discipline Equals Freedom” crept into my esoteric creative space, crossing genres just like Rick. (“Clever Girl,” says Muldoon right before the raptor eats him.) I’ve been using discipline as a weapon against time—trying to extract more from each hour, optimize every margin, turn every moment productive. That’s not discipline. That’s a sick form of violence, where I’m both perpetrator and victim.

Real discipline, according to Rubin, means creating “sustainable rituals that best support your work.” It means accepting the universe’s timetable instead of imposing your own. It means working with your natural rhythms instead of declaring war on them.

It’s a lesson I keep re-learning over and over again, usually in the shower or in a tin can floating above Earth: I’m better when I’m still. Not because stillness is lazy, but because stillness is where the work actually happens.

THE ENDURANCE FACTOR

This book will outlast your current crisis because it’s not really about your current crisis. It’s about the eternal tension between effort and grace, between pushing and receiving, between being the creator and being the created.

Every generation discovers this truth in their own way. The Stoics called it amor fati—love of fate. The Taoists called it wu wei—effortless action. Rubin calls it being a vessel. But the message endures: the harder we grasp, the less we hold.

Your burnout will pass. Your current project will ship or it won’t. Your metrics will go up or down. But the question Rubin poses will remain: Are you willing to empty yourself enough to be filled with something worth sharing?

KEY QUOTES

If you start from the position that there is no right or wrong, no good or bad, and creativity is just free play with no rules, it’s easier to submerge yourself joyfully in the process of making things.

For those battling imposter syndrome, read this again. There’s no right way or wrong way. What matters is YOUR way. You’re the only person who’s ever existed, who’s ever seen the world from your POV. The fact that the work comes from you is what makes it “right.”

When making art, the audience comes last.

‘Write a song people will like.’ ‘Make the movie that’ll be the summer blockbuster.’ But whose movies get remembered? Tarantino. Scorsese. Nolan. When’s the last time you saw a summer blockbuster that wasn’t a green screen and a shit script? Make it for you. Because you like it. You’ll find your people.

To the best of my ability, I’ve followed my intuition to make career turns, and been recommended against doing so every time. It helps to realize that it’s better to follow the universe than those around you.

When you need to figure out the best path forward, listen to your gut. It’s your work, your art, your life. Trust the signal you’re already hearing.

The work reveals itself as you go.

I’m seeing this happen in real time as I write my novel. Characters do unexpected things. Settings fall into place. For too long, I thought you find the path in the planning. But you find it in the doing.

When you’re on a roll in the Craft phase, work toward a full first draft. Maintain the momentum. If you reach a section of the work that gives you trouble, instead of letting this blockage stop you, work around it.

Sharing this one for my fellow creators. The work doesn’t need to happen sequentially – it needs to happen eventually. If you’re stuck, skip that part and hit something else.

We’re not playing to win, we’re playing to play.

I occasionally get tattoos for things I need to keep top of mind. This might be next.

I was an individual contributor.

This was “pre-kids” Mike, so my IDGAF muscle (which you’ll learn more about ahead) was in prime condition. Unfortunately, the rest of my life wasn’t.

I had moved my wife across the country for a job that was the wrong fit. My reputation as a rising star had just taken its third consecutive hit—and the gig I moved us to New Jersey for wasn’t even close to what I needed.

Oh, and we were broke.

So I joined this scaling startup as a Sales Recruiter, ready to make a difference. The company was fast-paced and future-thinking. My boss was amazing. It felt right.

Then in week three, the CEO made a mandate about recruiting. Something I knew would hurt us.

He had an open-door, “anybody can ping me about anything” policy. Or at least, he’d said he did in the all-hands I’d just watched.

So I did what any sensible new guy would do: I texted my wife to let her know I was about to challenge the CEO.

Then I did it—in a Slack channel with the CEO, HR, and the entire recruiting team watching.

Should I have been shit-canned? Maybe. I later saw others shown the door for less.

But I wanted to win. I thought the service had real potential. I believed that if we could get the right people in the door, we could build something special. And I knew his mandate would hurt our chances.

More than that, I was probably just fucking tired of losing.

Twenty minutes later, the CEO called. We had a good dialogue. I listened to his rationale. I shared my perspective.

Did I “win” that conversation?

No. He was the founder and CEO. I was the FNG who hadn’t even registered for benefits yet. I told him we’d do things his way and track the results.

But did that conversation help get us—and eventually me—closer to winning?

To quote Walter White: “You’re goddamn right.”

​WINNING: THE UNFORGIVING RACE TO GREATNESS​

Author: Tim Grover

Published: May 18, 2021

Length: 240 pages

Buy it here: ​https://amzn.to/4lSEJ8j​

WHY THIS BOOK MATTERS

Tim Grover trained Jordan, Kobe, and Wade—not just their bodies, but their minds. ​Winning​ is his response to everyone who read his first book, ​Relentless​, and whined: “But it doesn’t tell me what to do!”

Grover’s response? “Why the hell would you want to be told what to do?”

This book isn’t for people who need instructions. It’s for people who already know what needs to happen but keep apologizing for knowing it. Who’ve been told their intensity is “too much” and their standards are “unrealistic.”

You know that voice that told me to challenge the CEO? The one that doesn’t give a fuck about timing or politics or playing it safe? Grover says that voice is your superpower. Not your problem.

Most books tell you to find balance. To be a team player. To consider everyone’s feelings.

This one tells you the truth: Winning doesn’t care about your work-life balance. It laughs at being well-rounded. And it doesn’t give a shit if people think you’re difficult.

Because while you’re in another meeting about having a meeting, someone with half your talent and twice your selfishness is taking your spot.

THE ESSENTIALS: 3 CORE IDEAS

1. The Four Rings That Separate Winners From Everyone Else

Picture a target with four rings. Most people think they’re in the center. Most people are lying to themselves.

• Outer Ring: Talent. Everyone’s here. Your parents told you that you were special. So did everyone else’s. Congrats on having a pulse.

• Second Ring: Intelligence. You figured out how to use what you’ve got. Better than the outer ring, but still crowded.

• Third Ring: Competitiveness. You’ll fight for it. You understand nothing gets handed to you. But plenty of people talk about competing until it’s time to actually take something from someone else.

• Center: Resilience. This is where winners live. You’ll keep fighting when you’re bleeding. When you’ve been blindsided. When everyone else would understand if you quit.

Resilience is the power to stay in the fight when your fear is telling you to run.

It’s not inspirational. It’s the NFL kicker who misses the game-winner and has to line up again next week. It’s flopping through three consecutive jobs and still showing up to challenge the CEO at job number four.

Without resilience, the other three rings are just hobbies you talk about at parties.

2. Selfishness Isn’t Wrong - It’s Strategy

Winning requires selfishness. Winners don’t care what you think.

Read that again. Let it piss you off. Then ask yourself why you’re mad.

Grover calls it your IDGAF (I Don’t Give A Fuck) muscle - that part of you that can make decisions without polling the room first. Most people let theirs atrophy. They need consensus. Permission. Approval.

The world will call you an asshole for protecting your time. For saying no without explaining. For ending conversations when they stop serving you.

Good. Let them.

“Selfish winners give to themselves so they can ultimately give to others. They give themselves confidence, courage, clarity. They give themselves time and space and focus.”

Grover’s “No List” isn’t some productivity hack. It’s a declaration of war against your own bullshit. Those projects you’ll “get to someday”? The favors you keep postponing? The coffee meetings with people you don’t even like?

“Either do them or admit you’re never doing them and move on. Managing that back burner is a ridiculous waste of time and energy.”

You can’t win if you’re managing everyone else’s feelings. You can’t lead if you’re constantly checking if it’s okay to lead. And you sure as hell can’t build anything meaningful if you’re apologizing for the space it takes up.

3. Your Dark Side Is The Fuel That Actually Matters

Let’s get specific about what your dark side actually is: the mental list you keep of everyone who said you couldn’t. The boss who passed you over. The ex who said you’d never amount to shit. The parent who loved you but never quite believed in you.

It’s 2 AM revenge fantasies where you show up to the high school reunion successful as fuck. Checking LinkedIn to see if that guy who got promoted over you is still stuck in middle management. That guilty, delicious satisfaction when someone who doubted you fails.

We’re taught this is petty. Unhealthy. That successful people “rise above” and “wish everyone well.”

Bullshit.

Stop lying to yourself about who you are and why you’re that way. That’s your fuel, not something to hide.

Jordan didn’t forget being cut from varsity. He used it. Kobe kept a running list of every perceived slight. They called it psychotic. He called it motivation.

Your dark side remembers everything. While your conscious mind tries to forgive and forget, your dark side converts pain into premium unleaded. It doesn’t need meditation apps or gratitude journals. It runs on the fumes of every time life kicked you in the teeth—and it’s huffing like ​Charlie Day huffing spray paint while singing Dayman​.

The people who tell you to let it go? They’re not wrong—they’re just not trying to win like you are. They want peace. You want victory. Both are valid. Only one changes the world.

Here’s what becoming friends with your dark side looks like: You stop pretending you’re motivated by altruism when you’re really motivated by “fuck you.” You stop apologizing for keeping score. You stop feeling guilty for wanting to win so badly it hurts.

You shake hands with the monster in your closet and put it to work.

Because that monster will work longer hours than inspiration ever will. It’ll push harder than passion. It’ll endure more than purpose.

Your dark side isn’t your enemy. It’s your employee of the month. Every month. Forever.

THE ENDURANCE FACTOR

This book will outlast every life hack and morning routine because it’s not trying to fix you. It’s unleashing what you’ve been apologizing for.

In 20 years, people will still be pretending they want balance while secretly craving more. Still asking permission to be ambitious. Still waiting for the “right time” to stop playing nice.

​​Winning​ doesn’t age because the truth doesn’t age: Most people would rather be liked than be great.

The business books will keep coming. The frameworks will get prettier. But they’ll all dance around what Grover says directly: You already know what to do. You’re just scared of what it’ll cost.

That voice telling you to challenge your CEO three weeks into a new job? To come off mute when you’re low on the totem pole? To go against your boss because, fuck the politics, it’s necessary?

It’s the same voice that’ll be whispering to someone else in 2045. The details change. The technology evolves. But that moment when you choose between being reasonable and being right? That never changes.

This book endures because it’s giving you permission to trust the system you already have—the one everyone’s been telling you to ignore.

The one that wins.