Nobody Knows What They're Doing (Including Your Boss)

40 Before 40: 40 Life Lessons Before Turning 40 · Nov 2, 2026 · 3m

When you’re a kid, you assume the adults have it figured out. They seem to know everything. Then you become the adult.

In Lesson 2 of 40 Before 40, I report back from the rooms I used to think held all the answers. What I found there changed how I think about money, titles, ambition, and what success is supposed to look like.

In this episode: – What’s actually behind the curtain in the rooms you’re trying to get into – The trap of chasing a promotion you don’t even want – The one-question test I use before going after anything shiny

If you’ve ever measured yourself against a job title, a…