The Gentle Violence of Staying Put

Do you know what you actually want?

The last time I used my office key card at Pluralsight in April 2024 in Utah it felt heavier than it should have. Not physically but with the dense, numbing weight of a life I had meticulously built and was about to abandon. I had climbed the ladder, managed huge teams, and spoken the language of strategic imperatives with what I believed to be fluent ease.

I was a good soldier in the "Meeting Industrial Complex". My calendar a testament to a life of perpetual motion and often what felt like minimal progress.

These achievements felt like borrowed clothes, tailored for a person I was pretending to be. In that moment I realized a truth: my ambition had been a sophisticated form of hiding. It was an elaborate performance of someone else’s definition of a life well-lived. Lucky me… I would have three days to ponder these thoughts as I drove myself back across country to my home in Washington D.C.

You tell yourself you're building something meaningful. That the 12-hour days of back-to-back meetings are investments in a future where you'll finally have time to pursue what you actually want. But here's what they don't tell you about climbing ladders: each rung takes you further from the ground where real things grow.

I didn't always want to be an executive. At twenty-one, I wanted to write code that sang, build products that made people's eyes light up, create something from nothing with my own hands. But somewhere between the first promotion and the fifth, I convinced myself I was best at amplifying teams. I started wanting what I was supposed to want. Corner office. Seven-figure equity. The knowing nod from other executives at conferences. The subtle hierarchy of who speaks first in meetings.

You know this feeling. You've felt it creeping through your veins like a slow poison. It’s sweet at first. The wants you've inherited from mentors, from LinkedIn or X influencers, from the ambient pressure of what "successful" looks like in your particular corner of the world. These borrowed ambitions fit like a tailored suit. Impressive from the outside, suffocating from within.

There is a neuro-chemical high of imagining transformation. That rush when you picture yourself as a creator, an artist, a digital nomad, builder or founder. It is your brain's way of keeping you exactly where you are. Every time you read another essay about someone who quit—or was quit from their job—to follow their passion (yes, like this one) you get a hit of dopamine that feels like progress. This is called the intention-action gap. Your brain rewards you for the fantasy, then settles back into the familiar groove of your actual life.

You bookmark the article. You share it with a comment about "someday." You return to your spreadsheets.

This Moment is a Mirror

Here we stand at one of history's most profound inflection points. AI can now write code I spent years learning, create art that moves, compose music that has a real chance to make real people weep. The previously impossible has become a $20 or $200 monthly subscription. Claude, ChatGPT and Gemini sit ready to amplify any digital dream into your actual reality.

And what do we do with this newfound power?

We use it to write emails faster. To summarize meetings we shouldn't have attended. To generate slightly better slide decks for presentations nobody will remember. We're rearranging deck chairs on the Titanic while AI offers us the blueprint for lifeboats, wings and entirely new ships.

You tell yourself you're being "strategic" about AI adoption.

Really you're terrified.

Not of AI replacing you. That's the obvious fear. The one you can name.

You're terrified of what happens when the excuse disappears. When you can no longer say "I would create that app/write that book/start that company if only I knew how to code/write/build."

The tools that could liberate you instead become another layer of optimization for the life you're already living.

Another way to do the wrong thing more efficiently.

The Mythology of Prerequisites

“Not yet.”

Two words that feel like prudence and function as camouflage. The right credential. The perfect timing. Six more months of savings. We confuse rehearsing with readiness. We call the waiting “preparation” to avoid calling it “hiding.” I did this myself for years. Instead of starting what I wanted to start I moved from different job to different job that I thought would be great. Each time the story was sensible. Each time it was a stall.

At a certain point I realized the list of prerequisites was growing, not shrinking. That’s the tell. When your requirements multiply as your conviction rises, you’re building a fortress, not a bridge.

But here's what I learned the hard way that fateful day in late April 2024.

You will never, ever feel ready. The credentials will never be enough. The timing will never be perfect.

The market doesn't care about your MBA. Users don't care about your years of experience. The universe doesn't pause for your perfect moment. While you're collecting prerequisites, someone with half your talent and quadruple your ambition is building the thing you're still planning.

This is why many of us cling to the script we’re handed as we begin to co-create it. It’s not just easier… it feels safer. If the shape of your wanting matches the market’s, you never have to explain yourself.

Or is it your reputation that’s bothering you? But look at how soon we’re all forgotten. The abyss of endless time that swallows it all. The emptiness of all those applauding hands. The people who praise us—how capricious they are, how arbitrary. And the tiny region in which it all takes place. The whole earth a point in space—and most of it uninhabited. How many people there will be to admire you, and who they are. — IV. 3

The Creator's Paradox

At 1 AM, three months after leaving Pluralsight in late July 2024 I sat in my office at my house staring at a blank Cursor window. No team to delegate to. No product managers to define requirements. No designer to make it pretty. Just me, the cursor (and Cursor) and the terrifying freedom of creation.

I can tell you it hit me like cold water: I'd spent nearly two decades managing people who built things, optimizing processes for building things, strategizing about things to build. But I'd forgotten how to build. Worse. I'd forgotten the raw terror and ecstasy of making something from nothing.

You understand this intellectually.

You know that creation requires vulnerability. That the first version will be embarrassing and that failure is a teacher. But between knowing and doing stretches an abyss that swallows most dreams.

The first few lines of code I wrote along with Cursor was wrong. By line fifty, I was certain I'd made a catastrophic mistake. This wasn't the PowerPoint version of creation… clean, linear, with smooth transitions between slides.

I was confronting error messages that made no sense to me. Dependencies that fought each other. Code that kind of worked until it didn't.

A few days later, I shipped my first app. It is horribly ugly. Despite my enthusiasm hardly anyone used it.

But it was the most alive I'd felt in years.

The Violence of Transformation

We call it "disruption" when it happens to industries. When it happens to humans, we call it crisis. But it's the same phenomenon of breaking something old down and something new emerging from the wreckage.

Your current identity will not survive your transformation. This is not a bug. It's the entire point. The you who clings to stability, who knows exactly what comes next, who has a five-year plan and a retirement strategy. That person has to die for the next you to be born.

This is the violence we avoid. Not the violence of failure or poverty or judgment. Those are just stories we tell ourselves.

The real violence is the dissolution of who we thought we were.

I know this because a year forward the person who wore suits to our quarterly board meetings and delegated to my lovely assistant is now gone.

Sometimes I catch glimpses of him in the mirror. The “executive presence”, those calculating eyes, that practiced smile and reserved posture that knew exactly when to cross my arms. He was made to be so certain about everything.

What success meant. What mattered. What he wanted.

Now I know less each day and somehow that feels like progress.

I’ve had friends who have gone through similar transitions and they’ve been concerned about what they should say to their family or friends. The question: How do you tell those who envied your trajectory that it was killing you slowly, meeting by meeting, quarter by quarter?

You don't. You just start building. You let the work speak. You accept that some people will see this as failure or as a mid-life crisis (I’m turning 40 in two weeks so maybe it was?)

You stop needing them to understand.

Do you know what you actually want?

Strip away the performance. Peel back your borrowed ambitions. Dig beneath the sophisticated rationalizations. What's left?

Maybe it's smaller than you expected. Maybe it's bigger. Maybe it's so foreign to everything you've been pursuing that recognizing it feels like meeting a stranger who's been living in your house all along.

Most people don't really know what they want because knowing would obligate them to act.

And action would mean abandoning the elaborate infrastructure of fake desires they've spent decades constructing. The mortgage on the house they don't love. The career that sounds impressive at reunions. The life that photographs well but feels hollow.

You tell yourself these are "responsibilities." But really they're agreements you made with a version of yourself that no longer exists.

So here you sit, reading this in your carefully optimized life. Your calendar is full. Your trajectory is clear. Your future is planned.

And yet…

You can feel that flutter in your chest when you imagine something different. That voice at 1 AM whispering about paths you have not taken. That moment between sleep and waking when you forget who you're supposed to be and remember who you are.

What would you do tomorrow if you admitted what you actually wanted?

Not what would impress your network. Not what would justify your education. Not what would make your parents proud or your friends jealous or your inner critic finally shut up.

What would you do if you admitted the truth that's been sitting in your chest like an unexploded bomb, ticking quietly beneath every sensible decision, every strategic move and every borrowed dream?

The tools are all here. And the barriers have well dissolved. The only thing standing between you and that truth is the story you keep telling yourself about why you can't.

But you already know, don't you?

You've always known.

The question isn't what you would do.

The question is whether you'll finally stop pretending you don't know.

Whether you'll stop using your ambition as procrastination, your goals as hiding places, your endless preparation as an excuse to never begin.

Whether you'll admit that the life you're optimizing isn't the life you want.

And whether tomorrow: not someday, not after the next promotion, not when you're finally ready—tomorrow, you'll do the one thing that terrifies you more than failure:

Start.