“So the plan’s...what? To be a writer?”
“You know don’t make a lot of money. And you’re making good money now. You’ve busted your ass to get here.”
“Things are good. You kind of throw away everything you’ve done to this point if you go that route, right?”
I leaned back in my chair on Zoom call number 11 of the day. I’m annoyed by the fact that this call still has another 20 minutes scheduled.
Talking with one of my mentors was supposed to be the thing that gave me energy to wrap up the day. That’s why I scheduled it in the late afternoon.
Instead, I felt like I was necking with a vampire.
I mumbled something about the novel being a first draft, and this idea was still years from happening, if it happened at all. I downplayed any chance of it being important, despite the fact that waking up early and writing had been the most intellectually stimulating part of my life for the last three months.
Fifteen minutes later I stood up, walked to the back porch to let the dogs out, and sat on the steps leading down to the yard. It was a standard issue 100-degree-day in Texas. I sat there long enough for sweat stains to form on my belly and back of my shirt.
The call had drained the last of my energy. What the fuck was I supposed to do now?
I had come to the conclusion months earlier that staying on my current path was not right for me. The writing had been the thing that I was enjoying the most out of my days. But here was someone who I trusted, who had my best interest at heart, telling me it was a side quest. That it wouldn’t amount to anything.
At that point, the back-and-forth in my head became more violent.
One voice: “You have kids now. Who cares if you’re happy? Your job is to provide.”
The other: “Fuck that. If my kids see a miserable dad, what am I modeling? Why don’t I deserve to be doing something that lights me up?”
I sat out there for a long time as the voices went back and forth, two Spartans beating the shit out of each other on the training ground.
By the time I stood up, belly sweat and all, the dejection was gone.
So was the gag I had been chewing on. The gag I hadn’t even known was in my mouth, but had been there for years: soaking up my saliva and silencing the Spartan I needed to be listening to.
The Conveyor Belt & The Ceiling
You have a gift inside of you. And so many gifts...so many stories of overcoming never fucking happen because people’s friends and family have beat this idea of modesty, humility, be nothing, do nothing, accept your gruel, and shut the fuck up. And that hurts society.
- Andy Frisella
According to our upbringing, we’re supposed to want the good life. Just not too good.
That’s why so few of us feel we have it.
I call this the gratitude gag order. It’s the external script that tells you wanting more is ingratitude.
The default script is familiar to everyone: do good in school, get a good degree, get a good job, get promoted, make money, rinse and repeat until you retire or die.
When you’re young, you follow it because you’re directionless. “You’ll figure it out later.”
Blink and you’re in your forties. Now you’re locked in; spouse, kids, mortgage, and a pile of responsibilities. And it always seems to feel like the realization comes when you’re most encumbered. You get the promotion, land the gig at your dream company, move into the house you’ve been picturing for years. Then, after a few weeks of fulfillment, you feel nothing.
“Oh my God, it was always like this. Is this all there is?”
The gag order was built on a half-truth. It’s true, you might have a great life. Compared to every prior generation, quality of life is higher for us. But the ceiling, “and that’s all you’re allowed to want,” is the part that lives underground.
The social script that keeps us in these systems comes from your environment: your experiences, the norms of the people around you, the tribes and factions you belong to. If you’re not around people who have broken the script, you default to the same programming as everyone else.
Self-sabotage was the armor you built against your own ambition (knowingly or not). On the flip side, the gratitude gag order is armor the system built to protect itself from you.
The external message (”you have a good life, quit bitching”) gets internalized over time. You hear it from enough people that, eventually, it sounds like your own thought.
The gag feels plausible. There are hundreds of excuses why you stay comfortable (wrong time, bad market, not enough expertise, nobody’d pay me for that), but they all funnel to the same place:
“I have it good enough. Why risk it?”
That’s how people choose a predictable hell over an unpredictable future dream.
The “responsible” choice is actually the fragile one. The risk of staying is invisible until it isn’t.
The risk is your salary.
Salary Buys Silence Twice
Your salary buys your silence twice: once from your employer, once from your own conscience.
The salary keeps you quiet at work. You don’t rock the boat because you need the check.
It keeps you quiet at home, too. You don’t let the idea that you deserve more sit too long, because the paycheck covers the baseline. The base of your hierarchy of needs is met. So why risk it?
The first muzzle, being quiet at work, is a systemic requirement. If everybody walked around their offices like Hunter S. Thompson recently returned from the Mint 400, HR teams would double in size and turnover would be north of 80%.
But the one at home, that one’s a deadly little motherfucker. “You’re safe, why risk it?” That voice is insidious because it sounds like common sense.
Until you flip the frame.
Because in truth, the thing buying your silence is a single point of failure.
A layoff in a shit market wipes out a decade of savings. A reorg makes you redundant. AI continues to compress the leadership layer: people might be complicated to manage, but agents seem to do what they’re told. How many Managers, Directors, and VPs are going to be needed when each of your employees is handling a handful of robots who follow directions?
And what’s that salary actually buying you, anyway? Think about the breakdown of a standard leadership job (you know, that thing you’re working 50+ hours a week to attain):
10% strategic thinking
20% dealing with difficult people and big egos
30% on draining status calls, most of which you only need your appearance, not your attention
40% cleaning up other people’s messes
Yuck.
We’re high-paid janitors for someone else’s system.
Which makes “comfortable” the most expensive word in the corporate world, because unspoken misery compounds.
But what if wanting more isn’t a problem?
The Dangerous Question
“Is this all there is?”
Like death, that question is coming for all of us.
After a promotion, or a raise. When you get the dream car or the dream house or the dream guitar (a Paul Reed Smith Custom 24 for me).
For a minute, life is fucking incredible.
But only for a minute.
Then we’re back to regularly scheduled programming. That tightness in your chest that you’re not quite fulfilled. “Well, shit, that achievement (or thing you bought with your new achievement money) didn’t make me feel what I thought it would.”
A few days later, that feeling moves from your chest to your gut. It’s icy. Because the question is heavier.
“Is this all there is?”
The gag order sees that as a dangerous fucking question. It threatens everything you’ve built.
But kids ask it constantly. Artists ask it. Titans of industry ask it. If there’s someone you like to listen to on a podcast or on TV, they asked it, too.
And that question has a hidden weight, because underneath it is the question you’re more afraid to ask:
“What if it all worked out?”
That question means you still want more. The social script has a word for that: ungrateful.
Wanting more isn’t ingratitude. In fact, I see it as a virtue, not a vice.
Maybe it’s the Ayn Rand streak in my 20s talking. Or maybe it’s because, when I’ve had the guts to ask for more out of my life, I’ve been rewarded with...well, more.
That’s why this newsletter exists. I want more.
Now, that doesn’t mean you have to become an entrepreneur or start bleeding out emotionally on the internet (done a bit of that, too. isn’t it fun, sucking in public?). But you have a version of it.
Starting a non-profit. Putting out a workout program. Making music or art or films. Opening a bakery.
Your family and friends truly believe they’re looking out for you. They don’t want to see you embarrassed or broke or exhausted or sad.
It’s not their fault. They’re just running the same default programming that, up until now, you’ve been running. They think they’re protecting you.
But what if it all worked out?
The Life Raft
The good news: if you want to try something new in your life, you do not have to quit your job.
You don’t have to blow up your marriage.
You don’t have to stop seeing your kids.
You don’t even have to empty your bank account.
As grown-ups, there’s an alternative approach here that few talk about.
We’re going to build the life raft while we’re still on the boat.
Nights. Mornings. Weekend mornings. Skipping Netflix for an earlier bedtime for the earlier alarm clock.
These don’t cost you anything other than your time. And isn’t it about time you were intentional with that time? Sitting down to brainstorm about something you love instead of plopping your cheeks on the couch, usually with a snack, to donate your attention to HBO?
You’re sitting on a decade or more of skills and experience.
You’re not sold on the fact that your current path is the right one for you anymore.
You have things that excite you (even if you have to dig around for them). Things you want to learn. Things you’re interested in.
The job is to look for where some of these things intersect: the parts of your work that give you energy, the things people come to you for, the topics you can’t stop rabbit-holing on, and the things you’d be willing to suck at long enough to get good.
Because...what if it all worked out?
Thanks, as always, for sticking around. I’ve been on Substack for about 6 months now, and I mean it when I say, the early time you’re investing in my work means a ton.
Speaking of work, it’s been busy. Here’s all the different ways I’m trying to put stuff out into the universe to help people along their 2nd Act path:
2nd Act Launchpad: Where you go if you’re getting serious about starting something new (and want some 1:1 face-time with me).
Golden Handcuffs Diagnostic: Where you go if you’re pretty sure you want to cheat on your day job, but you’re not ready to go all the way yet. 3 prompts, 60-minutes, and it’ll make you uncomfortable if you’re doing it right.
Instagram: A new daily series called 100 Days to Your Own Business (Without Quitting Your Day Job). It’s on day…12 today, I think? Easy enough to catch up if you’re interested, since it’s mostly sub-90 second quick hitters.
YouTube: Long form (this newsletter + added riffs or whatever’s top of mind) and short form (100 Days series). A one stop shop for all “Mike talking” content.
LinkedIn: Short form writing if you can’t stand my voice / face / both (in which case, let me also warn you against investing in the 2nd Act Launchpad).
On one hand, I don’t love typing up a footnote of self-promotion.
On the other, most of this shit didn’t exist a year ago.
So it feels pretty good to have a wall of links to be able to show YOU what’s possible when you stop “thinking about it” and decide to get after it for 12 months.