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Advice / Career Paths / Exploring Careers

The Top 3 Lessons I've Learned From Having 25 Jobs

My resume is painfully long. I keep at least half my jobs off of it in order to maintain a reasonable length. Those forms on applications that require you to fill in your former companies, start and ending dates, your past supervisors, and salaries, are my nemesis. I have to ask myself how badly I want to apply, because filling in all of my past employment history will take well over an hour. Oftentimes, I decide the position is just not worth that much effort.

Though I was once turned down for donating plasma—yes, that’s a paying job, and yes, I was rejected—my experience includes working in fast food, at a card and balloon store, and mystery shopping. I have worked as a substitute teacher, a high school teacher, and a school counselor. I’ve been in movies, commercials, and TV shows. I’ve written standardized test questions and scored nationally standardized test essays. I’m a published author with two novels and dozens of articles under my belt.

One year, when money was tight, I delivered flowers on Valentine’s Day for a local florist. I’ve worked as an editor and the social media agent to a New York Times best-selling author. I’ve taught college psychology. I worked as a travel agent on my breaks from college and in the media Services office when I was in school. I sold makeup. I’ve babysat and taught preschool. I’ve modeled.

Looking back, there have been some jobs I enjoyed more than others. And there have definitely been jobs that paid better than the rest. But am I sorry I accepted any of them? Absolutely not. (And not just because they provided material for my future novels.) I learned a lot from working in varied settings that required different skills and knowing what I know now, I would never trade my path for a more linear one. How else would I have learned these three basic, but often overlooked, career lessons?


1. There’s More to Gain Than a Paycheck

I’ve taken most of my jobs because of a desire for a salary, but what I took away from many of the positions were lasting relationships. While I wasn’t destined to blow up mylar balloons for the rest of my life, I’m still friends with some of the women I worked with at that little shop. I was the youngest, by far, and the wisdom they imparted was invaluable. For example, they taught me that, though the customer is always right, I should never let someone talk down to me just because of my age.

I’ve walked away from almost all my jobs with at least one or two close friends. And though I may look back at the company where we met with disdain, I never regret having been there because it led me to some incredible people who changed my life for the better. Not to mention, in some cases, those relationships led to a better career in the future.

So, don’t act like you’re a contestant who’s “not here to make friends.” Keeping your head down and focusing solely on the task on hand may sound virtuous, but it’ll shortchange you from what you could’ve really gained.

Related: 4 Valuable Lessons You Learn From Working a Job You Hate


2. The Grass Is Always Greener (Always!)

Don’t get me wrong, I love that I’ve found so many “work from home” jobs. I’ve graded essays, written articles and books, and edited manuscripts—all of these from the comfy perch at my kitchen table. (And sometimes—confession: oftentimes—from my bed.) It’s allowed me to attend my kids’ field trips and school plays and class parties. When my daughter calls to say she forgot her art project at home, I’m able to walk six feet, pick it up off the dining room table, and drive it to her school. All of which is awesome.

Having said that, working from home is still difficult. For one, it’s distracting. I have to force myself to stay awake as I’m typing from my bed. It’s easy to feel overwhelmed by the dishes in the sink that are, literally, in view. The shows I DVRed the night before call my name as I work. It’s also lonely. There’s also no one else around. There’s not gossip around the water cooler—there’s not even a water cooler!

So, before you think, I’d be happy if I only I had a job that let me do X, remember there are always trade-offs. It may be that no situation is perfect: Instead, look for a position in which the benefits outweigh the drawbacks.


3. Sometimes, You Have to Take What’s Available

As I mentioned, I once accepted a job delivering flowers on Valentine’s Day—and it was the most challenging day of my life (partly because it was in the pre-GPS era and I had to use a map, and partly because I was six months pregnant). Up to that point, I’m embarrassed to say that I had no idea how hard delivery people work, how difficult it can be to find parking, and how ungrateful people can be when you hand them a bouquet of roses!

I cursed that job for the 10 or more hours I did it. (Yes, even in 10 hours, I still couldn’t make all the deliveries!) My feet were killing me, my back hurt, I was starving, and I got lost more times than I can count. And while it it wasn’t what I pictured when I was writing my thesis, I needed the money to pay for my son’s preschool tuition—and I made money.

Don’t beat yourself up for taking a temp job to pay the bills during a long job search or some other time when you need extra income. Odds are, you won’t do whatever that gig is for the rest of your career, but it could get you through a tight spot.



At more than 25 jobs, I’m guessing I’ve held more than the average person. Some of them were winners, others not so much. But there isn’t one I regret. I always managed to take away something valuable. (And learning how to do that in any situation is a skill within itself.)

So, if you, too, have a resume that’s starting to look an e-book—or if you fear taking a job because it doesn’t fit into the five-year plan you so carefully created—I suggest you jump in, feet first, and give it a shot. You might find it’s where you were meant to be all along, or you might last a week. But, I can promise you, you’ll learn something from the experience, and I’d love to hear what that is.

Reach out to me on Twitter and we’ll share war stories over a virtual cup of coffee.


Photo of person thinking courtesy of Fred Froese/Getty Images.