As our world changes, more and more of us are making the leap to a non-traditional work arrangement. If you’re considering this path, here’s some thoughts from someone who has walked it for a while now.
My Backstory
Back in 2018, I worked as in-house compliance for a fantastic financial advisory firm. I had every perk a twenty-something could want from a job: unlimited PTO, intelligent and kind coworkers, flexibility, autonomy, great benefits, room to grow, and to top it all off, my company paid me handsomely.
But I was miserable.
At the time, I felt guilty and confused about not feeling satisfied. I had everything I could want in a job. Why was I so ungrateful? Was everyone else also miserable and just hiding it? If just about every other person I knew could function in a traditional work environment, why couldn’t I?
I finally accepted that maybe this structure worked for plenty of other people, but the classic nine-to-five work structure simply didn’t work for me. Now I don’t feel so uncommon in that respect. After the economic upheaval of the pandemic, I read almost every day about people quitting their jobs to pursue more fulfilling endeavors.
While I don’t think quitting your job is inherently good or bad, I do believe it only works if you understand what you’re getting into. The problem is that, in our society, we have two contradictory narratives about the entrepreneurial life—and neither of them, in my experience, tells the whole truth.
While I don’t think quitting your job is inherently good or bad, I do believe it only works if you understand what you’re getting into.
To show what I mean, here are two ways I can tell my own story, both of which are true.
Version One: Leap and the Net Will Appear
In January of 2019, my husband and I moved from Cincinnati, Ohio, which everyone will tell you is a “great place to raise a family” (translation: it’s cheap) to Washington, DC, one of the more expensive cities in the country. For some reason, I decided this was a great time to quit my job in finance and start a freelance writing career from scratch.
Did I have any experience as a freelance writer?
Nope.
Did I have any clients lined up?
Not a single one.
Did I know where to go to get clients?
No clue.
Fast forward two and half years. I have successfully built a freelancing portfolio that provides me the freedom and flexibility I always craved. I travel often, make my own hours, and can work from anywhere.
It sounds like the dream, doesn’t it?
Version Two: Pulling Yourself Up By Your Bootstraps
While still working in finance—before I knew I would ultimately quit—I saved half of my take home pay. Even with my decent salary, this required rigorous budgeting. I carried around color coded envelopes with cash, and when the cash ran out, I stopped spending. (My friends still tease me about those envelopes.) At the time, I had no plans for the money I saved; I simply knew money meant flexibility, so I kept saving.
But life with a nine-to-five job was grinding me down, so when I quit my job to move to Washington, DC, instead of looking for a new employer, I started freelancing.
In the beginning, I burned through my savings and lived in a constant state of stress about whether or not I would “make it.” When I could no longer stand working from my apartment, I would scrounge together nine quarters and go buy a small black coffee for $2.25 (including tax) at the coffee shop down the street and work from there.
What followed was a year of major stress. I regularly worked six or seven days a week and took almost no time off, so not surprisingly, I ended up supremely burned out. This forced me to undertake a whole new type of work – figuring out my limits and creating a schedule I could maintain long-term.
Finally, I felt like I had “made it” (no longer thinking any day I may have to give up and start sending out resumes) which didn’t happen until nine months in and I learned how to stick to a reasonable schedule. Even so, freelancing confronted me with plenty of challenges. For example, I didn’t truly appreciate the magic that is a sick day until I was throwing up for the third straight day while still taking calls and finishing a piece for a client. Even now, I can easily take off an afternoon, or sometimes a whole day, but anything more requires a ridiculous amount of planning and strategizing. Not to mention that—unlike my salaried days—when I don’t work, I don’t get paid.
Weaving the Narratives Together
In the first version of my story, I took a major risk, got super lucky, and ended up successful. In the second, I worked my ass off, lived frugally, and dealt with ongoing struggles in order to pursue my passion.
You’ve probably heard both of these narratives in some form before. Any number of successful self-employed people, from artists to entrepreneurs, tell us a simple story that mirrors either version one or version two. And this makes sense. Humans are natural storytellers, and we prefer a clean, cohesive narrative. Did you plan ahead or take a major risk? Was success due to hard work or luck? Is your current life glamorous or filled with ongoing challenges? For almost everyone who has ever struck out on their own, the answer to every question is a combination of both.
The problem, in my opinion, is that not nearly enough people share the whole, messy version. This makes it difficult for anyone contemplating leaving the world of more typical employment to decide if venturing out on their own is worth it.
Not nearly enough people share the whole, messy version. This makes it difficult for anyone contemplating leaving the world of more typical employment to decide if venturing out on their own is worth it.
Is working for yourself glamorous or a living hell?
For me, it’s both—a glamorous hell. If I could have found a way to feel satisfied in my salaried job, I would much rather be working for someone else. But I couldn’t.
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