I'm curious if there are any guys in their 40s or older who feel like they're actually living the life they envisioned back in their twenties. If so, how did you achieve that?
3 Answers
I got lucky by marrying someone who’s super driven and works hard, which took a lot of pressure off my shoulders. After college, I also decided to leave the U.S. and that change made a big difference for me!
I’ve always wanted to be an airline pilot since I was a kid. Now at 41, I’m a 747 captain! The journey wasn’t easy; it was about having supportive parents and a lot of patience. I had to go through tough times, but networking and having mentors really helped me out. It’s wild to think I’m living my dream, even if I sometimes feel like an imposter.
I'm 37 now, and looking back, I realized I achieved what I aimed for through my 20s—having a steady career in the arts and living comfortably. But honestly, I think I should have aimed a bit higher, like, shot for the stars!

Definitely! Sometimes playing it safe doesn’t take you to where you really want to go.