Be Smarter About Finding Your Career Fit

Too Many Misfits

How many people do you know who seem tailor-made for their vocation?

In my experience, not nearly enough. I blame the way society guides us to approach finding a career fit. It’s messed up. It holds us back. And it mangles us.

Look at finding a career fit like picking out shoes. Our education system, media, and culture push racks of mass-market options in front of us. We’re told to grab onto the best we can. Then we shove ourselves in and try to look good and outperform. 

Some of us do what we can to force a fit. Some trudge along, looking forward to the day we can hang ‘em up for good. And some soothe ourselves with self-justification and spa retreats.

More and more often, we say, “Screw it,” and risk an exchange. The next fit is often better because we learn from our mistakes. But it’s rarely close to ideal.

Oh, The Devastation!

Imagine having intensive sessions with a coach who’s like a certified master shoemaker for your professional path. 

You tell him all about your interests, values, and past successes and failures. He performs his own assessments of you and consults with those who know you well. Then he analyzes the evidence, sits you down, and tells you what he believes your true calling is.

If this sounds interesting to you, good news! This sort of fit-finding service exists.

The bad news is that it can be extremely painful. Here’s what investor Jeremy Giffon said about experiences with one such coach, Jack Skeen:

“I’d had a few highly accomplished people tell me that it was the most devastating thing they’d ever done in their life.”

Giffon asked Skeen why it hurts so much:

“Well, if I tell someone who is a very successful investor that they need to be a third-grade teacher, do you think that would be devastating if it weren’t true?”

Bad Fits Hurt Everyone

It’s hard to feel bad for any “devastated” wealthy investor who realizes they invested in the wrong career path. They’re literally fortunate to be in their shoes.

Similar can be said about all of us who have the luxury of career choice. But that’s no excuse for complacency. While finding a calling is a First World problem, it’s still a problem. Think of all the kids who could have benefited had that investor channeled their 80,000 hours toward their education.

The point of finding a career that fits like custom-made Vibram FiveFingers isn’t just to feel good. It’s to be useful. The better the match, the better off everyone is, including those who don’t have the luxury to shop around.

Feeling Around for Fit

You know the parable of the blind men and the elephant?

One man touches the tail and guesses it’s a rope. Another grabs an ear and thinks it’s a big leaf. A third suspects a leg is a tree. Etcetera.

That’s kind of what it’s like trying to figure out a career fit, but instead of a trunk, tail, legs, and ears, you’ve got talents, values, traits, and interests. You can’t see them, so you can only grope around and make educated guesses about how it all comes together.

You’ve also got an extra challenge the blind men don’t: finding a vocation that your unusual shape fits into. This takes time, patience, open-mindedness, creativity, and willingness to get your hands dirty. It’s an important task, though, so why don’t we put more effort into it?

A Cinderella Story?

We face a lot of social pressure to hurry up, jump into the best job that will accept us, and get moving to keep up with everyone else—financial pressure, too. 

But it’s short-sighted. What if we slowed down to make the effort to find a great fit? 

Imagine saving yourself from grinding through the aches and pains of an ill-fitting job—or coasting nowhere in a boring one. Imagine thriving and feeling forever fresh, covering new ground on your unique, unfollowable path, and contributing in ways you were made for. After 80,000 hours, you’d probably want to keep going.

Carl Rogers called this congruence. Abraham Maslow called it transcendence. Many might call it a fairy tale, but I believe in it. 

My Next Step

Ten years after slipping off the loafers of my corporate finance career, I’m still feeling around, trying this and that on for size.

(Too bad I can’t afford Jack Skeen.)

But I deserve even less pity than Skeen’s devastated clients because, even though I haven’t covered much ground, I’ve had a great time. I also learned a lot about how to cobble together a decent fit. 

This led me to a potential epiphany:

I love puzzles, mixing creativity with analytics, devising systems that challenge convention, and interacting with misfits. My track record hints at those being the rare few things I might be unusually adept at. So rather than hire Jack Skeen, maybe I can try putting myself in his shoes!

Maybe my fit is creating something that helps you find your fit.

APEX, Here We Come!

Since listening to Jeremy Giffon’s podcast in late July, I’ve been thinking about and researching a systematic approach for helping others and myself find uniquely fantastic fits for life.

I’ve still got endless thinking and learning to do, but I do have a broad outline and a name:

APEX: Afford Patience, Explore the Extraordinary.

It’s a take on FIRE (Financial Independence, Retire Early), but instead of targeting retirement, the goal is endlessly fulfilling contribution. 

I introduced APEX’s first essential component, affording patience last issue. In future issues, I plan to share much more about this APEX approach. Because no matter where you are in your career, I bet you’ve got at least a little wiggle room for a snugger fit.

Related Content

• ⚡️ The story of my pretirement and subsequent years of search.
• ⚡️ How to afford patience for ten years and counting.
• 🎧 Jeremy Giffon on the Invest Like the Best Podcast
• ⚡️ How useful are you?
• ⚡️ The surprising science of personality traits.
• ⚡️ Maslow’s hierarchy’s a boat, not a pyramid.
• 📗 The Good Enough Job. I’m halfway through and enjoying it. Simone Stolzoff makes the counterargument that we tie our identities so tightly into work that it makes our lives stink.