I’ve Had A Lot of Jobs. Here’s What I’ve Learned


I’ve had a lot of jobs. Close to 20 if I’m being honest.

I’ve worked as a preschool teacher, a law office assistant, an online ESL teacher, a travel agent, a Walt Disney World Cast Member, an ice cream scooper, a camp director, a marketing manager… and the list goes on.

Girl behind the register at Walt Disney World
My time as a WDW Cast Member back in 2011

Until a few years ago, I was embarrassed by this constant shift in jobs. I thought it meant I was “scared, weak, non-committal.” I prepared reasons for these premature departures for imaginary interviews in my head, always making sure it was about THEM, not ME. It even became the running joke in my family, casually mentioned over Thanksgiving dinner or a reunion where the inevitable question, “So, what are you doing now?” always loomed.But, then I started to reconsider what a gift this diverse resume was. And how it’s led me to where I am today. I am a quick-learning employee and freelancer with a passion for seeking out projects that reflect my interests, and, simultaneously, a person who is able to define myself outside of work.

As I enter my 30s, I look back over the last 10-15 years, full of very hard, yet necessary lessons.

On one hand, I wish my high school teachers and college professors would have prepared me better for the struggle that awaited me, reinforcing that many people take time to find their elusive dream career. But, on the other hand, I’m also glad that I had to figure out all the things I didn’t like or that no longer served me. The job I had when I was 20 wouldn’t work well for a mother of two toddlers who wanted to be home. Who could have predicted that a global pandemic would turn everyone’s careers (including mine) on their side? My ability to shift directions has come in handy.

I’ve come to learn that there are seasons for everything.

I’m so grateful that I have stories to tell about my time working at Walt Disney World and the friends I made there. It was the hardest, least glamorous job of my life, but I’d probably do it again for the memories. I am also grateful for that one job (or two or three) that ended in painful tears when it became clear I no longer aligned with the company’s mission or vision.

A girl using a hula hoop in a big field
Working as a camp director at a YMCA in NJ in 2014.

I’m even glad for that master’s degree I have that I’ve struggled to put to use. Is it a line on my resume? Yeah. It is also a source of grit and gave me perspective on the investment that is getting an advanced degree.

I often consider how I’ll tell my children about “all the jobs” Mama has had. It’ll be fun to tell stories about that one time that I met a princess out of costume or when I organized a Christmas play full of a bunch of unruly kindergartners. But, I also want them to know a few other things about this path I’ve taken (and the one I continue to walk.)I want you to know these things too. Because if you’re like me, a millennial, a dreamer, unhappy in your current career, or the average American who switches their career 12 times during their lifetime, I hope you take comfort in knowing there’s value in quitting and seeking out new opportunities. Here’s a little about what I’ve learned:

There is no rule about how many jobs you should have

Thinking back, I’m not sure who first told me the appropriate number of jobs one should have in their lifetime. Was it my parents? Grandparents? The media?

Whoever it was, I know there’s been an unspoken rule that’s told me, “Too many jobs is bad.” But, I think there’s some necessary nuance that needs to come with that rule that I initially failed to consider. Like, it’s not great if I were to be fired from a bunch of jobs due to tardiness, failure to meet job expectations, etc. Those are things to work on, not run from. But, what about those jobs I left for better opportunities? Or to escape an unsafe situation?

I think digging into WHY I left a job is much more important than the number of jobs I left.

I can now confidently say that leaving a job because you lack passion for showing up most days, have found something better (inside or outside of work), or want to challenge yourself to learn something new are all good reasons for leaving a job.

Miss Julie written by students
Before I was Mrs. Julie and Mom, I was a lot of children’s “Miss Julie”

On The Job Training Is Crucial for Finding What You Do and Don’t Enjoy

No amount of “Find your Dream Job” quizzes are going to help someone like me find their “Dream Job.” Those tests can’t measure how I’ve grown and changed in five years, how great or awful my coworkers were, or how becoming a mother shifted everything for me. I wish I would have known what it was like, for instance, to balance a career while also wiping butts and singing lullabies, but unfortunately, those lessons are the kind you learn while on the job.

Instead, I’ve learned that by trying out a handful of careers I’ve discovered things about myself that I wouldn’t have known otherwise.

How, if I get too far from my passion for working with kids, I’ll likely lose interest quickly. Or that I really enjoy variety and embrace change better than most people. Whatever lesson I learned, perspective is a gift that I can only get by walking some long roads and trying on a few dozen opportunities that may or may not suit me.

You are strong and brave for quitting

I wish someone would have told me that there was strength in quitting.

Saying no was something I needed to practice just as much as saying yes. Along the way, I’ve managed to learn that it takes a lot of courage to have an honest conversation with my supervisors about who I am and what interests me. Sometimes, these conversations have led to my next career, and sometimes, they’ve allowed me to refine my current role to better suit my changing desires. (Sometimes supervisors have also been sour… which offers a lesson that you can’t please everyone.)

Be the kind of supervisor you needed

I’ve been lucky to have a handful of good mentors around me throughout these past jobs. What usually set them apart was the fact that they cared about who I was as a person, in addition to who I was as an employee. We chatted about our passions, they knew when I was having a rough day, and they challenged me to grow.

These supervisors are also the ones I’ve kept in touch with. They’ve provided me with good references, but more importantly, they’ve helped me to see that a job is about building relationships. At the end of the day, it was as though they were preparing me to leave all along, giving me the tools and skills I needed to be the best human I could be.

I’m still finding my way and learning new interests and/or hobbies. Alongside me, my kids are also growing and changing, and eventually might need me a little less for things like getting dressed or cutting up their food into 10,000 tiny pieces. In the meantime, my work as a freelancer continues to open new doors, allowing me to think strategically and work with clients from a variety of industries. Perhaps my work will deepen there, or perhaps it’ll shift entirely. Only time will tell. What I can share is that I continue to experiment, say no, and proudly declare that I’ve had a lot of jobs.


Pin this post and be sure to follow Vermont Mom on Pinterest!

camp counselor wearing a red shirtVermont Mom Insiders get exclusive content that you do not want to miss, so sign up today!


Please enter your comment!
Please enter your name here