In Defense of Not Figuring Out Your Career in Your 20s

There’s a winding road ahead, enjoy the ride

Evan Wildstein
Index
Published in
4 min readMar 16, 2022

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Image: Tony Wu/Pexels

I turn the big 4-0 this year, which is equal parts terrific and terrifying. It also brings me near the 20-year mark in my career. Mixed feelings about that, as well.

I’m in a wildly different professional place than I was in my 20s — and most of my 30s, for that matter. One industry (social impact) has paid my bills this entire time, and I’ve tested the waters in varying roles. Operations, public events, fundraising, organizational development.

Maybe something about that winding road resonates with you?

Here’s the thing. Other than sleeping, you’ll spend more time in your life working than anything else. You might as well sit back, learn a few things along the way, and enjoy the ride.

Finding the winding road

Over the past two decades I’ve refashioned my career a few times — three to be exact. I believed I was on the chief executive track, so right out of college, everything I did was in service of that goal.

The longer I worked, the more I realized I didn’t know. I took different jobs, signed up for workshops, and networked like crazy to gain new skills. At the time, I believed I was building a portfolio of…

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