20 Jobs in 10 Years — and Why I Finally Stopped Running

How many jobs have you had? A handful? Several? I bet I’ve had more.

For much of my adult life, I’ve switched jobs several times a year. I’d get excited about a new position, love it for a few months, hate it by the third, and be on my way to the next one by the fourth.

I know it sounds bad, but I’ve never been one to stick around in places that didn’t feel right for me. Sometimes I left the job, sometimes I got fired, but it always came down to one thing: I couldn’t see myself working those jobs long term. Even when I got fired, it was because I’d already stopped caring.

Time after time, I switched jobs hoping to find the one that felt different. Today, I can count at least 20 jobs I’ve held in the last ten years—most of them crammed into the first five.

Don’t believe me? Here’s the list:

Building horse troughs and feeding horses, lube technician at an oil shop, IT printer tech for a university, website manager for an art gallery, videographer and editor for a financial trading company, captioning agent, food vendor, media specialist for multiple companies, Sportsman’s Warehouse customer service associate, loan processing assistant, various yard work and window cleaning jobs, carpet cleaner, RV/trailer technician, hiking guide, assembly line worker, high school paraprofessional, sales agent, nanny, news reporter/journalist, network engineer apprentice, and finally, middle school STEM teacher.

Yeah… I’ve racked up quite the résumé, haven’t I? The only problem is that I held each of those for such short times, they hardly do me any credit.

Fortunately, each one gave me another piece of the puzzle. Some taught me the kind of work I despised, while others pointed me toward what I loved: writing and teaching.

It’s still wild to me that I managed to become a teacher. I’m a month in, and it doesn’t feel real yet. Today I shared my job list with one of my students, and they asked: If you switched jobs so much, why did you settle on teaching?

The answer was simple—because I love it.

That moment brought something to the surface I hadn’t fully realized. As I’ve shared in other posts, teaching is challenging. It’s hard work. But that doesn’t matter to me.

I’m not saying I’ve found the be-all, end-all job. But this is the first one I can actually see myself doing for a long time.

Even if my books take off, my gut tells me I’ll still want to keep teaching. When that kid asked why I do it, I realized it’s because I feel a sense of purpose here. And that feeling allowed me to look him in the eye and say: I wouldn’t trade this profession for any other in the world.

What about you? Have you had more jobs than me? Have you found a job you love? Or are you still on the hunt? I’d love to hear your answers in the comments.