Annual Letter to Self
I’ve been operating by a set of unwritten rules. What does being a man today mean?
To provide and protect. Offer financial stability. Exude a sense of confidence and control. Take accountability. Never get dragged into embarrassing situations.
And so you do it.
Fifteen years ago, you told yourself you were just getting started. Ten years ago, you said it was time to get serious. And now, you’re staring down 37 with a good title and a decent salary (Rule #1: Provide), and a sinking feeling in your gut that you haven’t even scratched the surface of what you could’ve become.
I know that feeling. It’s a quiet, dull ache. Not failure, exactly— because you haven’t failed. You've provided. You've protected. But it's the absence of intensity. The creeping suspicion that your comfort has become a cage.
You’ve been told you’re “smart,” “high-potential,” “a great guy to have on the team.” And so you coast. You do enough to be respected. Not enough to be remarkable.
You tell yourself the stakes are too high to leap now. But if you’re honest, the real reason isn’t risk. It’s fear. It's the terror of breaking Rule #2. Fear of negative feedback. Fear of looking foolish. Fear that if you try with everything you’ve got and still fall short — then what? Then you haven't just failed a project. You've failed the entire job of 'being a man.'
So instead, you ration your effort. You spread your ambition thin. You tell yourself you’re playing the long game. But deep down you know: this isn’t strategy. It’s hiding.
I want to tell you something no one says out loud:
You can reinvent yourself now. At 37. In mid-career. With your resume full of safe choices and your mind full of late-night doubts.
There was a third, forgotten rule on that list: "Dreams and aspirations. Don't forget to put yourself first."
You don’t need permission to honor that. You need conviction. No one’s coming to rescue you. No manager, no mentor, no divine timing. The sooner you take radical ownership of that, the freer you become.
The corporate escalator got you this far. But the elevator doesn’t go to the top floor. From here, it’s a climb — hand over hand — with no guarantee of applause. And that’s why most people stay where it’s warm.
But here’s the trick: the climb doesn’t have to be dramatic. You don’t need to quit everything overnight or burn bridges. You just need to commit — deeply, privately, relentlessly — to becoming dangerous again
Start treating your time like it's sacred. Start doing hard things without telling anyone. Start acting like someone whose work will change the game — even if no one sees it yet.
Here’s what happens when you stop hiding:
— Your attention sharpens. — Your standards rise. — The right people find you. — And the monsters in your mind fade away.
You start saying no to work that flatters your ego but dulls your soul. You stop needing constant approval. You begin to trust your own taste, your own hunger, your own sense of timing. And slowly, without fanfare, your life catches fire.