“Where are you working now? I can barely keep up anymore with all your job hopping, haha,” a friend of mine remarked off-handedly with a chuckle.

She didn’t mean anything by it, but the comment stuck with me and made me wonder, what’s wrong with me? Why can’t I stay in a job for multiple years like everyone else? Even staying in a single job for just 2 years seemed like a stretch given my track record.

If this sounds familiar, know that you’re not alone. In this article, I’ll walk through my own story, how I was able to veer away from a traditional career path and forge my own path, what I discovered along the way, and how you can create your own “uncareer” path.

My Uncareer Path Story

In the 10 years following college, I had 9 different jobs. I started out as an elementary school teacher with Teach For America, then left the classroom to study video game design so I could make educational games. After a few years in the games industry, I then went on to adult learning and corporate training before starting my own business, in yet another industry – real estate investing.

I never set out to be a serial job hopper. I don’t think anyone really aspires to be a job hopper; it’s certainly not the easiest path to success.

In fact, I grew up with dreams that were the complete opposite. I wanted to be a perfectly “normal” adult. My plan was to go to college, then med school, and become a doctor. I just assumed that most successful adults chose a single career path, then ascended a single career ladder for life.

All through elementary, middle, and high school, I did everything I was told. I studied hard, got straight A’s, then went on to an Ivy League school. I figured that because I did everything “right” and by the rules, that I was on the path to success, and that everything would be laid out for me.

Veering Away From The Traditional Path

My first clue that there might be a different path was during freshman year. After years of getting straight A’s and being valedictorian of my high school class, I’d gotten my first C in freshman biology class. 

I was discouraged and disappointed, but I wasn’t about to give up. I met with my counselor to tell him about my plans for the second half of my freshman year, which included more of the same traditional pre-med track classes – the next level biology class, calculus, etc.

I’ll never forget the moment he looked across the table and told me, “You know, you don’t HAVE to take biology. Or you could take a break and come back to it while you explore other things.”

It seemed like such a simple thing, but it was something I’d never considered before. I never knew that I had an option to take a different path or to forge my own path. I’d always kept my head down and blindly forged ahead without really reflecting on what I really wanted, what I loved to do, what drove me, or who I really was.

That second semester of freshman year, I ditched all the “traditional” classes I’d planned to take and instead tried out courses I’d never previously explored – psychology, sociology, anthropology, photography, and more.

It was a period of true freedom and self-discovery as I learned to shed what I thought I “should” do and shifted instead to what I wanted to do and felt called to do.

Job Hopping & Self-Discovery

After graduating college, a similar journey of self-discovery began again, and I found myself becoming an unintentional serial job hopper. Same as before, I had assumed that an Ivy League degree would set me up for life, and that I would keep my blinders on and climb the career ladder without issue.

However, with every job I held, I would inevitably bump up against systems, processes, or someone telling me, “Well, you can’t do that because this is the way things have always been done,” which limited the impact I wanted to have and the creativity and innovation I wanted to bring to each role.

I watched as my friends pursued traditional career paths, staying in a single job for years and years, all while I waffled back and forth, moving from job to job and industry to industry.

Uncareer Path & Unschooling

Honestly, it wasn’t until recently, when I started exploring a concept called unschooling (i.e., self-directed education) for my kids, that I reflected on my own unconventional career journey, and suddenly, it clicked. 

In case you haven’t heard of unschooling, it’s a form of homeschooling in which there’s no set curriculum; the parents support the child in learning whatever the child is interested in.

What’s so appealing to me about unschooling is that it’s all about letting each individual child explore their own interests and deep-dive into their passions, rather than forcing a traditional curriculum on them and imposing arbitrary standards and tests.

It’s about living and experiencing life to the fullest, rather than focusing on testing and grades, and it’s the same path I’ve taken since graduating from college and trying to find my place in the world – constantly reflecting on who I am, what I love, and where I want to go. 

As I have learned more and more about unschooling, I have seen the parallels between unschooling and the unconventional journey I’ve experienced in my own career exploration and self discovery.

In a way, my career path has been the exact opposite of a typical career path; an “uncareer” path, if you will.

It is my sincere hope that through sharing my experiences and being open, honest, and transparent about what I’ve learned and discovered along the way, I can help to normalize this otherwise abnormal and unconventional path, to connect you with others who are just like you, and to provide resources that might help you on your journey.

Your Uncareer Path

Did anything in my story resonate with you and your journey? Perhaps you’ve experienced the same job hopping or have questioned the path you’ve chosen for yourself or just want to know it’s okay to try something new.

The idea behind an uncareer is that there are no rules. You don’t have to follow a predetermined path, because you’re unique, and your interests will evolve over time. What you were interested at age 19 as a freshman in college is unlikely to be the same thing you’re passionate about when you’re 40. And that’s okay.

You don’t have to trudge along, counting down the days to retirement. There’s another way, and more and more people are embarking on an uncareer path journey, more now than ever before.

So, if you feel like a square peg in a round hole, start by asking yourself what you love and don’t love about where you currently are. What are you passionate about, and where do you want to go?

Then, start connecting with people who are doing the things you want to be doing. See if you can shadow them or just take them out for coffee (or a virtual lunch date). Start to try on your next potential career move and see how well it fits.

As you do so, you’ll start to gather the courage to make the move. And as you do so, you’ll become a true uncareer trailblazer.