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When storytelling meets list-making.
I recently wrote an article about when to quit your job—and how quitting is about assessing your needs and value. I realized that, oddly enough, my employment and quitting history might be a fun peek into my growth as a person and how I finally began to see my value.
I also really like lists.
So, here’s a list of all the jobs, starting when I was 23, I’ve ever quit:
8th Grade Teacher, 2010: This is a story I tell a lot—it’s one of the defining stories of my life.
I had just finished my first year of teaching. It sucked. I was 23, I had graduated from college a year earlier, and I was miserable. Having the summer off was the greatest thing that could have happened to me. I randomly made friends with a guy with who I ended up spending my entire summer. We hung out almost every day, and towards the end of the summer, he said he needed money and was going to go work at a coffee shop.
That sounded so much better to me than going back to school. This was mid-August—about three weeks before the school year was about to start. We were sitting at El Beit, a shop that I don’t think exists anymore, and I remember thinking I needed to quit. Right then.
I got straight on the train, went to the school, and quit. I thought my principal would be mad, but he said, “You’re young. Fuck around. Come back when you’re 30.”
Quitting a job is usually seen as a door closing. Once the door is closed, you can never go through it again. This was the first time I quit a job and there was no animosity. It felt like I was just taking a detour, and everyone was ok with that. I felt confident that, if I wanted to, I could come back.
First Coffee Job, Midtown Manhattan, 2011: One of the best jobs I’ve ever had. My boss, Rachel, was fun, caring, and pushed me to take on responsibility and hone my skills.
I started as a barista, was then promoted to assistant manager—and then didn’t know what else to do. There wasn’t a clear path for me to advance, and when I asked about the future, no one had a good response for me. I worked for a small chain, so you pretty much had to wait for a new store to open to get a non-barista job (assistant managers still worked 40 hours on the floor). I quit because of the lack of opportunity at the time, but my boss understood. Although there was some friction when I left, no one was upset with me for going.
I didn’t want to talk about the jobs I had in college, mostly because these were part-time gigs that ended when the school year was over. I do think about one job I had in college where I stood in our business school’s lobby with a scanner and asked to scan people’s hands for a long-term study (something to do with the ratio between the length of your pointer and ring fingers and the hormones you’re exposed to in utero).
However, in my last article, I mentioned the very first job I ever quit. I glossed over it quickly, but writing about it brought up more feelings and I wanted to flesh out that experience further.
Movie Theater, 2005: A movie theater opened in my neighborhood, and almost all my friends got hired to work there. We were paid six bucks an hour to clean bathrooms and tell horny teens to stop making out in the theater. About a month in, I got a job offer from a store in a mall close by, and they offered me $6.50/hr, which was A. Huge. Deal.
I told my boss I’d have to put in my two weeks, and he told me over and over how I’d regret that decision. Perhaps I was slightly green—I had never done this before—but he made me feel really, really dumb. He said things like how selfish I was for quitting over money and that I’d ask for my job back soon, he was sure of it.
I haven’t thought much about that experience until now, and how utterly inappropriate and weird it was for him to say all that stuff to me. And this guy wasn’t even my direct boss. He was the manager of the entire theater and there were at least three other people who I had to go through to get to him. I don’t think I had ever talked to him before that moment.
My retail job was the fucking best. I got to hang in the mall, get free clothes, and still see whatever movies I wanted since all my friends still worked at the theater. I got to live my best 17-year-old life so fuck that guy.
First Management Job, Brooklyn, 2013: This is the first job I was ever fired from. I should have quit this job before that happened.
This is also the first job I ever had with real responsibilities. Barring huge things like finances and paying rent, everything was up to me. In a way, I relished it, but not in a healthy manner. I was definitely one of those bosses who thought working 60 hours a week meant I was doing it right—which I’ve detailed in a past article. I was nitpicky and strange and didn’t know how to trust people or take care of them well.
I thrived—until I didn’t. After about a year and a half, my relationship with my boss, the owner of the cafe, got really sour. I was mad at him all the time, I felt like he was lazy and incompetent (I was harsh) but I also felt like he expected too much from me. I’m not really sure who was right or wrong, but I was certainly quite a shit head. This should have been my cue to go.
But I didn’t. Instead, I pushed on and got more and more resentful—and more defiant.
I remember testing him one day. He had a meeting with a designer who was redoing our logo, a guy I had introduced my boss to (and happened to be dating because of course, I’m 25 so all the lines are blurry and you date pretty much everyone in front of you and stupidly recommend them for jobs that you maybe shouldn’t. I was real messy about combining my personal and professional lives).
I was out to dinner with this dude, and he mentioned this meeting. And I said I wasn’t going to go. I hadn’t been required to go, and the meeting fell on one of my days off. I knew, though. I was expected there, even if no one had said so. I knew what I was doing by not going.
When I came in for my next scheduled shift, my boss had a severance check, all my stuff in a bag, called me a car, and sent me home. I did file for unemployment and won an unjust firing case against him—I was definitely a jerk, but he never reprimanded me for my behavior. I never got in trouble at work, and according to the state unemployment office, because there was no record of any sort of poor performance, I was let go without just cause.
Management, to not management, to management, Manhattan, 2013: This is the job where I dared my boss to fire me.
I was so bummed when I got fired. I remember wanting to take a break from real responsibility, and just be a barista for a few months. I applied for a job at a small, prestigious coffee shop in the West Village opening up a new store in the East Village. I said I wanted just to be a barista, and the owner, a man who made me sit for an interview for almost three hours, told me I either had to manage or he didn’t have a job for me. So I agreed to run the store.
Turns out, he hired a different person to be the manager weeks later, and never told me. That became clear eventually, but not because the owner ever told me. The new manager was a guy who was widely hated by the staff for being a misogynistic fuck, and was quickly fired. I was finally promoted. However, I was working somewhere else during this time.
Second Job During This Time, 2013: This was one of the greatest places I’ve ever worked. I only worked here once a week, and for some reason the kind folks at this coffee shop let me hang around and learn more about coffee than I had ever learned in the three years I’d been a barista.
I also had a devastating crush on one of my coworkers. Again, blurry lines.
My boss at the other job, the prestigious West Village spot, hated that I worked there. He told me that there was “an understanding” that you only worked at one place, even though I was still a barista making $13 an hour with no benefits.
Eventually, when my non-management position turned into a management opportunity, I was told I had to choose (you don’t have to choose—there is no legal precedent for this and he’d have a hard time trying to fire me for it—but I didn’t know at the time), and I chose to pursue the management job. I quit, and everyone was so lovingly kind to me I almost changed my mind.
Back to the management job: My boss treated me like a mean kid in high school. He had favorites, he doted on some but not others, and would regularly ignore my texts and emails. He’d call me crazy when I asked him a question—a question I needed an answer to. He’d make fun of me, and encourage others to do so. One day, we got a drink together (at his wife’s insistence—I told her he hadn’t spoken to me in weeks) and he told me pretty much the worst things anyone has ever said to me. He said I was disingenuous, not nice, a fake person, and that he didn’t like working with me.
I asked if any of this had to do with my job performance. He said no.
I asked him to fire me if he hated me so much. He wouldn’t.
I didn’t know what to do. On the one hand, I thought, “Fuck this guy—if he wants to get rid of me, he needs to fire me.” On the other hand, I was so worn down. I felt deflated.
I saw a job opening at a coffee shop I’d always known as the Barista Retirement Home—where all the curmudgeonly baristas would eventually end up because the tips were good. I called the number in the ad as I sat on the floor, waiting for a bus from Boston to New York. They offered me the job, and I quit the next day.
Barista, Brooklyn, 2015: I was pretty happy at this job. I made more money than I’ve ever made working in any job not just in coffee, but ever. I had tons of freedom, and I started with this coffee shop just as they were on the brink of expansion.
A friend of mine had recently taken a job with a company in San Francisco, and sent me a job opening he thought I’d be interested in. I had no expectations when I applied and was sort of astonished when I got the job. I debated taking the job for weeks until one of my regular customers told me I could always come back.
I told my boss that I had gotten this new job, and he was quiet for a moment, thanked me for my time, gave me $500, and apologized for not giving me more. To this day, no one has ever shown me that level of kindness. I think about that moment all the time.
Coffee Trainer, San Francisco, 2016: I was hired to be a wholesale trainer, then lead trainer, for a prominent coffee roaster in San Francisco. This job was a bust from the get-go. I was promised a moving stipend—I didn’t get one. My salary was less than what I was making in New York, and I didn’t fully understand just how expensive San Francisco was. People started leaving my department left and right because the job was so awful.
Every one of my coworkers and bosses left at some point. I was promoted to the head of my department and told that my job wasn’t a promotion but “a shift in responsibilities.” I had a new account in San Diego, a coffee shop that was immediately busy from the day they opened. They didn’t anticipate the foot traffic and ran out of coffee on their very first day. I scrambled to get them more, pulling excess coffee from our training space and retail floor. At the time, we were in between bosses (I had no one to report to and no one to ask for help), and I thought I was being resourceful. The two owners, a set of brothers, reprimanded me for hacking together a solution. I was told I should have let them run out.
I realized I pretty much disagreed with every decision being made by “the brothers” (that’s literally how they were referred). I probably should have left day one when I was told that “no one remembered talking to me about a moving stipend” but I stayed for a year. No one said goodbye to me on my last day.
Cafe Manager, Oakland, 2017: The only other job I’ve ever been fired from. This job was really great—until it wasn’t.
Pretty much the moment I moved to the Bay Area I realized the salary I was being paid by the coffee roaster was in no way enough to live. I started working weekends at a local coffee shop just a few blocks from my house. I became really close to a lot of the regulars, I was incredibly tight with the staff, and there’s something truly special about working in the neighborhood you live. I’ve never felt more connected to a community.
My boss, the owner of the cafe, was sort of a bumbling idiot but harmless. He’d run into the shop with a wild idea and realize quickly how silly it was, but neglect important things like paying bills or giving people raises. Nothing was malicious, but he wasn’t the most competent leader.
I only ever saw this guy, and I assumed he was the owner, but then I found out that he co-owned the cafe with his wife—and they were getting divorced.
Because this was a neighborhood shop and everyone knew everyone’s shit, our customers would gossip about it with us but no one really knew what was going on. Eventually, she got the cafe as part of their divorce settlement. No one told us what was happening.
The change in leadership was strange. She pretended like nothing happened, that she had always been in charge. I had to keep reasserting systems and ideas that had already been challenged and debated—and decided upon—when he was in charge. He also never fully stepped back so it was just confusing and weird.
I can imagine a divorce is hard to go through and adding on a new business complicates things, but I was tired of managing up. At the time, I was going through a devastating breakup, and to this day I doubt she has any clue what was going on with me. I felt resentful that I was showing her so much patience and grace, and I felt like she didn’t give a shit about me.
I took one sick day—the only sick day I took in two years—and was reprimanded for not having a back up plan. My back up plan, with such a small store (we had four employees), should have been her covering my shift, but she didn’t know how to make coffee.
So I sort of tempted fate. I did the bare minimum I needed to do to get by. I started picking up shifts at other places in the neighborhood, building a foundation for the day I’d eventually leave, but I wasn’t going to quit. If they wanted me out, they’d have to fire me. And they did—epically, in one of the strangest series of Slack messages I’ve ever received.
Restaurant, Chicago, 2018: This story sucks to tell.
I moved to Chicago a few months earlier. I answered a post on Instagram from a restaurant I liked. I’ve never worked in a restaurant, and I was so intimidated. I was a food runner, which literally meant my entire job was to run plates from the kitchen to the dining room.
I was shaky at first, but I caught on quickly, and ended up doing really well. I knew my boss, the owner and head chef, respected me, and he usually let me expedite (call tickets to the chefs) and run food because he knew I could do it.
But then people started saying strange things to me. Some of the cooks called me “chef’s favorite”—at one point, I even snapped at a cook. The chef managed the back of house, and his wife managed the front of house. She wasn’t very nice to me, but I assumed she was just like that and I stayed out of her way. But then folks kept commenting on how she treated me. They asked me if I noticed how mean she was to me in particular.
I didn’t know what to do. While I wasn’t personally made uncomfortable by the chef, I realized everyone else was made uncomfortable by me. I started doubting if I was good at my job, I’d feel terrible anxiety that maybe he did have a thing for me that was weird or unfair. I remember listening to an episode of This American Life (about apologies and favoritism—it’s the second story they tell in the episode) where a television writer began second-guessing her talent after her boss became obsessed with her—and subsequently savage when she rejected him—and weeping in my car.
I quit saying I got a different job. I did, but it was definitely so I could get out. I went to the restaurant a few times after as a guest, but then one of the servers called me “chef’s favorite.” I never went back.
Coffee Manager, Chicago, 2018: I took this job to get out of the last one. I sort of knew from the beginning I wasn’t going to like working there, but I figured I should try it. This job had health insurance, a salary—things I desperately needed.
I set a deadline. If I didn’t like this job in two months, I’d leave. Two months came and went, I still hated this job, so I left.
In terms of ways to quit a job, this felt the healthiest to me. I had an idea of what I thought the job would be like, and when I realized the job didn’t align with my goals or values, I left. I made a clear list of the things I wanted, how they weren’t being served, and gave it to my HR manager. There wasn’t time for me to grow resentful or angry.
My Last Job, Chicago, 2019: Quitting this job was an exercise in acknowledging my value.
I write all these things about asking for raises, how managers should be clear with their staff about growth and feedback, how baristas can stand up for themselves. It took me an embarrassingly long time to realize I wasn’t demanding these things from my leaders or doing any of these things for myself.
I made some strides in my time at this job. I was in a restrictive—and, at best, legally questionable—non-compete agreement, and I got them to revise it. I slowly but surely got more money. But it never felt…good? I was never quite paid enough and felt icky that I had to even negotiate out of a non-compete. Something never quite sat well.
It took me a long time to name that unsettling feeling, and recognize that it meant I felt undervalued. If I valued my talent, I had to go.
This was a wild exercise. I’m not sure what I gained except being really sad and bummed out. But I do hope the way I approached quitting past jobs helps you.
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