At the beginning of your career, all you can think about is money.
You optimize for it. You tell yourself you’ll do everything to achieve it. The number becomes the north star, the ultimate validation of your worth.
After a few years, you realize chasing money for money’s sake doesn’t really work.
You discover Ikigai, personal growth, memento mori. You realign your work and life around deeper meaning. You realize the problems you solve, the niches you operate in, the rabbit holes you explore, and the large surface area for luck—these are what actually matter.
Then you start figuring it out. It all clicks together.
Fifteen years in, you’re a leader in your space. You have great self-awareness. You’ve developed a healthier relationship with money. You understand the game you’re playing.
Then begins your mid-life reinvention.
You work really hard to detach your work identity from your personal identity. This leads to an identity crisis: Who am I without my niche? Without FAANG on my resume? Without those fancy ARR outcomes?
Two things can happen here.
Path One: You successfully mold your work and personal identity into one cohesive whole. Your second coming becomes clear—founder, creator, consultant. You have a network that allows you to reinvent yourself into who you think you should be.
Path Two (the more common reality): The conflict becomes extreme.
You hold onto your work and keep getting hired for what you’ve done in the past. But it’s not appealing to you anymore. Your second coming isn’t clear. Maybe you’re not cut out to go out on your own.
At this point, you have a rich personal life—passions outside of work, kids, relationships, depth beyond your professional achievements.
And this is where you circle back to where you started.
All work can give you now is money. So you start optimizing for it again.
You fear ageism coming for you. You feel time running out before age and AI push you out of relevance. You start dreaming about “fuck you money”—every dollar becomes runway for the day you finally quit.
You fantasize: Maybe I’ll run a laundry franchise. Generate passive income. Become a farmer and grow my own food.
You’re comfortable with leisure now. You realize retirement isn’t about sipping mai tais (they’re too sweet anyway).
But you feel disconnected from your craft. You’re desperately trying to figure out your second act, your encore performance in this professional theater.
Here’s the uncomfortable truth: You’re not even halfway through life.
If you’re unlucky, you’ll live to 80. If you’re lucky, you’ll die sooner.
But if you end up with those extra decades, what’s your plan for the next 40-50 years?