In my romantic life, I’ve been either a resigned celibate or resolute monogamist1.
For most of my working life, I’ve been a profligate polyamorist.
In the days that I’ve been procrastinating about writing this essay2 , I’ve been trying to think of a time when I only had one job at a time for longer than a couple of months and I’m coming up empty.
I started babysitting when I was about 12 and always had multiple families eager to pay me below minimum wage so they could get a date night. When I turned 16, I kept babysitting but also became a lifeguard at two different private pools and a restaurant hostess. In college the list of jobs I held included: working in the admissions office, working in the tutoring center, working in the fundraising office, being a lifeguard at the campus pool3 , babysitting, being a waitress at Don Pablos, working at the Speedo store at the mall, and a short stint filing papers at an insurance agency. Every single one of those jobs overlapped with another and I usually had three things going at a time.
After college, I started my professional career in admissions but quickly got side gigs babysitting. I spent several years working at Bath and Body Works, doing SAT tutoring classes, and working early morning weekends at a breakfast restaurant. This was a practical decision. I needed more money than my “real job” paid me (My first salary was $25,500 and I was in about $55,000 of debt between credit cards, student loans, and a car note). It was also an emotional one: I knew I was on my own in the world. I had no financial safety net, no family money to fall back on. The idea of having only one source of income was scary. What if I got fired? Where money was concerned, it has always felt safest to have more than one source of income. When you are living paycheck to credit card to paycheck, it feels good to always have another paycheck on the horizon or to end every weekend with an apron filled with dollar bills that smelled like maple syrup.
Over time, I paid off all my debt4 and continued to advance in my career. My second professional job paid $31,500. My third got me to $35,500. My fourth to $45,000. My fifth to $65,000 (please remember I work in higher education, so $65,000 felt like a GIANT accomplishment). But still I kept the side hustles going: more SAT tutoring, some college consulting, and even a brief stint in an MLM (where, somewhat miraculously given how trash the MLM model is, I didn’t actually lose money).
But then something amazing happened: I got my first freelance writing job.
I’d been writing online for a few years by that point. I had a personal blog with a very small following and also contributed to a fitness related blog. I never saw a dime from either of those, but I didn’t really care. I was learning how much I love to write and how good it feels when people told me that something I wrote resonated with them or made them laugh. When I finally got the chance to be paid for the thing I was happily doing anyways? MAGICAL.
Since that time (around 2012ish), I’ve written for multiple websites. I’ve been paid as little as $25 and as much as $1000 for a piece (the $1000 is SO VERY MUCH THE EXCEPTION). For 10 years, I’ve been writing consistently for one site more than any other and it has been largely a good experience. They’ve given me the chance to write about some things I care deeply about and also about fluff and silly celebrity culture. I’ve written literally hundreds of pieces for them, so many that sometimes I’ll be searching for a story about a particular topic, see an intriguing headline and then be startled to discover that I’m the one who wrote it. In this job I’ve learned a lot and I’m grateful for it.
Which is part of the reason why I’m struggling so hard with the simple truth that I really, really want to quit.
(Quick note: I’m putting a paywall on this one because this post feels a little vulnerable and also, to be honest, there are a few people I’m hoping don’t read this)
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