Making career decisions that seem crazy

A person might discover that they prefer making guitars to playing them. (Image by endri yana yana)

Years ago, I moved to a new city with only the slimmest of job prospects (that was crazy decision number one).

I managed to find a part-time, temporary gig as an assistant teacher of music classes for older adults. We were teaching them how to play keyboard instruments, but the goal was really to sell them fancy home organs so complex that their array of buttons and dials resembled the cockpit of a 747 (the price was similar to that of an aircraft, too).

Right away, I was not liked by my direct supervisor. One factor was my habit of arriving at the studio three minutes after I was supposed to be there. Another was the fact that I genuinely wanted to teach these seniors how to play music instead of just encouraging them to push buttons to get the organ to play “How Are Things in Glocca Morra?” My purpose was not aligned with the program.

So at the end of my six-week trial, my supervisor made an offer: $10 an hour, 30 hours a week. Two weeks of (non-paid) vacation per year, with no additional opportunity for time off.

I realized that this was an offer that was designed to be turned down. She didn’t have the courage to tell me that I wasn’t a fit, so the ball was in my court. And even though the only other thing I had going was music lessons for one family, I said no.

I spent the next several weeks working on getting some more music lessons going. That was a slow process, so I got a gig as a breakfast waitress. But just a couple of months later, I was teaching enough music lessons that I could focus exclusively on those, making in eight hours what I would have made in a week at the organ dealer. And the company I founded to teach music lessons still exists today.

I could use this story to make a few different points: Running a business carries a risk, but the rewards might outweigh those of the steady gig. Hustle hard enough and you will make it. Have the courage to hold out for a better offer.

Valid theses, but here’s another one: The opportunity that looks good on paper isn’t necessarily the best one. To me, the most important part of the story is the breakfast waitress part. I mean, I had a degree in music education. I should have enjoyed the easy and relatively peaceful job teaching senior adults how to play the organ, but I dreaded going. Meanwhile, I loved working at the restaurant. That’s where I felt valued, competent, and appropriately challenged (and got free food).

Too often, we stay miserable in a position that we think we should like or should be successful in when it’s just not a fit. We double down to try to fix our attitude or improve our work when we could look for something else.

People slog away trying to start a business even though they long for the stability of a traditional job. Or they resent their employers and catalog their boss’ faults but refuse to quit, forcing someone else to make that decision for them. Or, for example, they work in the field of massage therapy even thought they secretly love bookkeeping (or vice versa). They’re following rules without realizing that they’re the ones who made them up.

I’m not suggesting that it’s easy to find something new — especially not right now. But there may be opportunities we’ve overlooked because they don’t match our “shoulds” or the way we’ve always seen ourselves. A dear friend whose work in PR led her to late nights at parties and restaurants found an abiding happiness as a writer and Pilates instructor. She now wakes up early and revels in the solitude. A colleague who is an actress and singer has discovered an unexpected penchant for spreadsheets and sales. And another good friend continued his satisfying career as a fine-dining server even after he finished his degree in political science. There are no right or wrong choices here — we get to design the life we want.

It’s so hard when our identity or self-worth gets wrapped up in making a success out of one specific thing. A few years ago, I worked on a project that I found grueling and didn’t enjoy. However, it was for a prestigious organization and I wanted to like it. When the project was over, they thanked me for my work and that was that. I was upset that they didn’t ask me to continue on a new project — even though I didn’t even want to continue! I wanted them to want me, and I made that more important than what I wanted.

It’s better to choose for ourselves instead of leaving these decisions in the hands of someone else. If you’re struggling with similar career challenges, you might examine your own preferences, assumptions, and narratives about work. What roles have you come to understand are “beneath you”? What industries would you never consider working in? What skills are you no longer developing? What do you automatically assume you would like or dislike? Behind each of these questions are answers you can reconsider and layers you can lift to see what’s under there.

Even though you may have years invested in a particular field, you don’t have to stay there. You’re in control, you get to choose, and you don’t have to pursue your career the “right” way or using the approach you “should” take. Like me, you might find that saying no to your best option reveals even better options, or that you are excited to say yes to something that everyone scoffs at. Have fun — even if fun means that your hair smells like a western omelet for the rest of the afternoon. It’s your life, your decision, and your path.