What It’s Like to Quit Your Job During the Holidays

Photo by Alvin Engler on Unsplash.

I remember the exact moment I decided to quit my job. It was late fall 2014, and I was devoting time to self-reflection, as my therapist of a little less than a year had suggested. On construction paper, I’d scrawled out one of those idea webs you use to plan persuasive essays in elementary school. Only instead of filling all the little circles with reasons why hamburgers are better than hot dogs, I filled them with all the things I wanted to do with my life: career paths I was interested in, topics I wanted to write about, etc. etc. etc. I looked down and was struck by how little my job had to do with any of it.

I expected to have some buyers’ remorse over the decision. I knew I was really, really lucky to make a good salary at Groupon, writing blog posts about donut sandwiches and boozy snow cones. But after four years, I was very tired of writing twee coupons for a living, my other key job responsibility. Plenty of my coworkers had built thriving side hustles and creative careers while working at our company, but I found it hard to mentally separate myself from the place I was for 40 hours every week. I needed a clean break—and I needed it before I acquired a mortgage or children or any of the other expensive adult responsibilities that make it hard to move on from a stable job.

I envisioned my “time off” sort of like grad school, but without the student debt or onerous application paperwork. I signed up for a writing class at StoryStudio Chicago and bookmarked an online poetry course on Open Yale. To keep my hands busy while listening to discourses on blank verse, I invested in some bamboo knitting needles and fancy yarn. I envisioned myself cosseted in the easy chair by the window for hours each day, knitting increasingly complex scarves and slowly but surely figuring out what I wanted to do with my life.

As idyllic as that all sounded, there’s a reason that quitting your job with no back-up plan is not a move usually endorsed by career experts: it is not good for your finances. When I gave my two weeks’ notice in mid-December, my boss asked what I was moving on to. “Oh, tutoring, freelancing, stuff like that,” I said. It was a lie. All the tutoring jobs I found online were in the suburbs and required a car, which I didn’t have. When I gave notice in mid-December, I had exactly one freelance gig lined up. It paid a glamorous 3 cents a word.

That was okay, because my real plan was to live off $7,000 in savings for the next six months. (That wasn’t all of my savings—I already had a good amount stashed away.) The ACA had just been passed, and insurance for a healthy single person cost a mere $150/month (ha, remember those days?). Unlike many of my Millennial peers, I didn’t have any student debt. The rent on my “multi-room studio” apartment wasn’t exactly cheap, but it wasn’t unworkably expensive, either. I was gonna be fine. Right? I shot off a few applications to a few part-time jobs just in case.

And so I ended up in the lobby of the nearly empty Groupon office on January 2, 2015, taking goodbye selfies with the Spaceship Cat, uncertain of the future but also feeling way less dread in the pit of my stomach than I generally felt on the commute to work each day.

In the couple of weeks after, I kept busy. I read at a couple of live lit events and volunteered at 826CHI, a writing tutoring center. Then, unexpectedly, one of the jobs I’d applied to called me back. After a pleasant phone chat with the company co-founder, who didn’t seem put off by my lack of experience with business writing, I was hired for a part-time, freelance remote editing job in mid-January 2015. It paid $1,000/month, which I figured would at least cover my rent.

J/k, I totally didn’t understand freelancer taxes then. In real life, the stipend covered part of my rent. What it did actually do, though, was give me a kick in the pants to start taking my own writing seriously. After a few articles I’d worked on for clients ended up getting published in well-known online publications, I realized I should probably just get over my fear of pitching editors my own work. In the spring of 2015, I published my first paid freelance article in an actual magazine. That fall I published another.

By the time I reached the end of my “six months off,” my hours and pay had increased enough at the part-time job that I didn’t feel in a rush to return to an actual office. I finally did get a tutoring gig that didn’t require a suburban commute, which brought in a couple extra hundred a month, and got a little more aggressive about seeking out freelancing gigs. I still wasn’t making a lot—I couldn’t save at all, and I mostly went without new clothes—but I was no longer dipping into savings to make rent.

I never finished knitting my first scarf, never mind multiple; in my online Modern Poetry course, I never got past Hart Crane. But today, three years later, I’m still with the same company, and am now full-time with benefits (in part because I asked for it—always, always ask).

Things worked out well enough for me that I’m tempted to become a quit-your-job evangelist. But a lot has changed since New Year’s 2015. Before I got on employer insurance earlier this year, my ACA insurance cost triple what it did two years ago. Let’s not even discuss how much rent has increased since then. If I wanted to quit that same job today, I would need to set aside way more than $7,000. It’s also true that I was truly, incredibly lucky to find even a part-time job that was a good fit for me so soon. Job searches are usually much longer and harder than that.

That said, if you can afford it—and like I said, especially today that’s a big “if”—I don’t believe that quitting your job outright is always a bad idea. For me, it helped me take risks to build my career that I probably wouldn’t have taken if I’d been working full-time. I have no regrets.

Nathalie Lagerfeld is a writer and editor based in Chicago who has a lot of opinions about movies. Find her on Twitter @maviswillsaveus.

This piece is part of The Billfold’s Holidays and Money series.


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