I know how that sounds. Stick with me.
My dear elder millennials — like me — we got the degree. We took the job. We worked hard. We climbed the ladder. We maxed the 401k.
But are we…set?
Wasn't this all based on rules written *before* the unprecedented once-in-a-lifetime event(S!) we keep living through?
We were handed those rules and then — oh, just like — 9/11. The 2008 crisis, right when I and many of you graduated college. A decade of wage stagnation. Student debt that compounded faster than our salaries grew. A housing market that priced us out of what our parents bought on one income. A pandemic at every life stage. Inflation shock. And now, in real time, AI quietly repricing the white-collar work most of us built our careers on.
We did everything right. The math still doesn't work.
This is the part nobody in corporate leadership is going to tell you in a performance review: the version of the deal you were sold — the one your *parents* could mostly count on — hasn't really been on offer for most of your working life.
I know you already know all of this. But are you acting on it yet?
For you, I bet it comes down to one last variable: stability.
The old logic was *a job is stability, starting a business is risk*. That logic depended on pensions, on one income buying a house, on company loyalty being reciprocal, on your skills not being repriced overnight by a model trained on the internet.
Saying that out loud, doesn't it sound more like the 1960s than even the 2010s? (Much less, 2026.)
I know you're not sure you can stomach another 15 to 25 working years inside a system that has already broken its promises. Otherwise I wouldn't have your email address.
Now — I'm not telling you to quit your job tomorrow. Even after Tim was clearing $500 a day in profit with Tripped, we kept my 9-5 income going. We bank-rolled the next phase of the business with it. We staged it. That's the disciplined version of this.
What I am telling you is that the question has changed.
It's not *"is it risky to build something of my own?"* anymore.
It's *"which risk am I actually taking?"*
Because you're taking one either way.
Do the math your coworkers haven't done yet.
Fin
