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

 I turn the big 4–0 this year, which is equal parts exciting and terrifying. It also brings me near the 20-year mark in my career. I 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 (nonprofits) has paid my bills this entire time, but I’ve tested the waters in varying roles. Operations, public events, fundraising, organizational development.

Maybe something about that winding road resonates with you? If you clicked into this story, I suspect that might be true.

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 proficiencies that would help me rise in the “right” way.

But something didn’t feel right.

For one thing, I wasn’t finding many nonprofit CEOs to admire or model myself after. Plenty of them had been promoted up in their careers for specific skills, landing in management positions with no business being there — you may hear about this referred to in the work world as the “Peter Principle.”

After 10 years of hard skill-building, I realized something needed to change. This inspired me to think about the more nuanced side of organizational life. I began a different journey of learning soft skills and having conversations with colleagues about failure.

That was hugely interesting — the idea not only that failure happens all the time, but people want to talk about it.

In business, we often rally around success and throw caution to the wind. Too many people pridefully wear “hustle” as a mask that covers burnout and exhaustion, and there’s a lot we can learn from those who are willing to take off the mask and share their messy stories.

I find myself sharing messy stories a lot these days. Frankly, I wish I had these stories at the onset of my career. In some ways, I feel as though I wasted a lot of time talking myself into certain decisions (and out of others) based on faulty expectations and industry standards.

Had I realized — or had someone told me — I didn’t need to figure it all out in my 20s, the past 20 years would have looked markedly different.

Driving the winding road

There’s some irony in figuring out your career by not figuring out your career. Had I read something like this in my 20s, I’d have brought some unfounded skepticism to the conversation.

And I get all that.

But as I inch closer to my 40th birthday, I’m about to enter the third “wave” of my career — one I never imagined and certainly never could have predicted. The one-time post-grad in me expected to be running a burgeoning, well-respected nonprofit in New York City, not unintentionally joining the great resignation in Houston, Texas.

Maybe this doesn’t apply to you? Maybe you’re 100% on that c-suite track, and no geriatric millennial is going to convince you otherwise. In that case, congrats! I’m ecstatic for you and all your future success.

However, if you’re a few years into your career and feeling an unexplainable itch, perhaps consider asking yourself Whitney Johnson’s fabulous five questions:

  • Does your business occupy an otherwise unoccupied niche?
  • Are you playing to your strengths?
  • Based on your answers to the previous questions, have you assumed the right risks?
  • Do you find your work difficult but not debilitating?
  • Are you gaining momentum?

My professional third-wave was the result of asking these questions — because I didn’t have immediate answers for a few of them. I concluded that there is more I can be doing that I’m not yet doing.

Last words

It would be unfair to write a story like this and not admit that the workplace is incredibly frustrating and weird right now. Thirteen percent more people quit their jobs in 2021 than in 2019.

That’s staggering data for anyone, especially those who are five or 10 years into their career. I’m not immediately suggesting you should depart your job, but do seriously reflect on where you are and where you’d like to be.

This is especially important when we realize how quickly our hard skills expire — entrepreneur Jeffrey Wald advises that happens in as few as six years. Think about that: the abilities you learned in college less than a decade ago may quickly no longer be relevant.

Careers really are a winding road, but lean into the journey. You may find a path you never dreamed of — the unknown can be exciting like that.

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