All The Jobs I've Ever Quit

This is an embarrassingly long list...

Hi friends! This article will accompany a future episode of my podcast, Boss Barista, about quitting jobs. If you’ve never listened, you should check it out!

Listen here!

I recently wrote about when to quit your job, and I want to hear YOUR STORIES about jobs you’ve quit, jobs you wish you quit, and moments where quitting a job felt painful, freeing, impossible…anything! Here’s how to do it:

  • Find the voice memo app on your phone—most smart phones have them. If not, you can make a video on your phone and send that (I’ll only use the audio)

  • Record your story! All stories will be shared anonymously unless you specify otherwise

  • Send it away to bossbaristapodcast@gmail.com! That’s it!

And if you like this writing, consider donating to my Patreon. A lot of what I write challenges workplace norms, which as I stated above, pretty much make it impossible to incorporate paid work and the writing I do together.

[Ashley’s notes: I hate that I have to say this, but please be mindful that this isn’t reporting. These are just the things milling about in my head. I can write my quick and dirty thoughts on why you deserve a raise or how I am woefully unemployable—but anything that requires actual reporting, like asking questions and doing a bunch of research might be out of the scope of this project. Also, I should be paid for that work—more on that later in the month.]

Oh! And a quick reminder! If you’re not signed up for this newsletter, then welcome! I’m glad you’re here! But like, sign up, will ya? There’s a cute little button for you to do so.

Now! Onwards!


I recently wrote an article about when to quit you 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, since I was 23, I’ve ever quit:

Give Up GIF by ATTN:

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 just graduated college, and I was miserable. Having the summer off was the greatest thing that could have happened to me. I hung out with this dude who didn’t have a job (who I’m no longer friends with) pretty much every day that summer, and at one point, he told me 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 right then. 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 door closing. Once the door is closed, you can never go through it again. This was the first time quitting a job was ever presented differently. 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 ever 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.

**QUICK INTERLUDE**

I said I wasn’t going to include jobs from before I was 22 (most of my jobs growing up were part time or were things that ended from school year to school year. I did have one wild job in college where I stood in our business school’s lobby with a scanner and asked to scan people’s hands) but I was reminded of the very, very first job I quit—and how horribly mean my boss was.

My Very First Job, Movie Theater, 2004: 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. The store also closed way earlier than the movie theater, so I wouldn’t be out at work at 2 AM—my high school started at 7:30 so workdays were brutal.

movie theater GIF

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.

And 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.

Anywho. Back to it.

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 is untrue. I was nitpicky and strange and didn’t know how to trust people or take care of them well.

I did thrive here for awhile—until I didn’t. Sort of out of nowhere, 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 certainly harsh) but I also felt like he expected so much more out of me than of him. 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—although this guy was fine. He was totally competent but I was still real messy about combining my personal and professional lives).

I remember being 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, and called me a car and sent me packing. I did win a unjust firing claim against him with the state (I was definitely a jerk, but he never confronted me or 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) and filed for unemployment, but ended up not collecting any since I picked up another job quickly.

Management, to not management, to management, Manhattan, 2013:

I talked about this job in a previous article 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. That guy was widely hated by the staff for being a misogynistic fuck, and was quickly fired. Then, I was finally promoted. However, I was working somewhere else in tandem.

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 store let me hang around and learn more about coffee than I had ever learned in the three years I’d been behind the bar.

I also had a devastating crush on one of my co-workers. Again, blurry lines.

My boss at the other job, the prestigious spot in the West Village, 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 a larger position. 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—more than once. 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 quite what to do. On the one hand, I thought, “Fuck this guy—if he wants to get rid of me, he needs to actually do it.” On the other hand, I was so worn down. I felt deflated.

I remember seeing 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—and I called, sitting on the floor of a bus station in Boston. They offered me the job, I quit the next day.

Barista and Trainer, Brooklyn, 2015: I was pretty happy at this job, but it certainly wasn’t perfect. I made more money than I’ve ever made working in coffee (still—to this day), I had tons of freedom, and we were a growing company.

I had a friend who thought I’d made a great trainer for the company he worked at—in San Francisco. 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.

Lead 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 pretty much 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 co-workers and bosses left at some point. I was promoted to lead of my department and told that my job wasn’t a promotion but “a shift in responsibilities.” I had a new account open in San Diego and, when they ran out of coffee on their very first day (they had a line out the door all opening weekend—a huge success) I was reprimanded for scrambling to get them more coffee. I was told I should have let them run out.

I realized I pretty much disagreed with every decision being made by leadership. 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 is a job that 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 at the coffee roaster was in no way enough to live. So 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, and I had to keep reasserting systems and ideas that had already been challenged and debated—and decided upon—when he was in charge. She didn’t understand. I think, if she had shown any vulnerability, I might have helped her out more, but she just insisted that this was her cafe now. We had no moment as a store to get on the same page and develop a language of care and understanding.

I can imagine a divorce is hard to go through and managing a new business to boot, but I’m so 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 was mad I was asked to show her so much grace and she could give a shit about me. I took one—the only one in two years—sick day I had ever taken, and I 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—but she didn’t know how to make coffee.

So I sort of tempted fate. I started picking up shifts at other places in the neighborhood, but I wasn’t going to quit my cafe job. 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, and 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 meant that literally 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 snapped at one of them. The chef, my boss, 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) 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 pretty much only 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 and recognize their worth. 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? Like this was never the right amount of money for this job, or the fact that I ever had to negotiate out of a non-compete felt wrong and icky (I was a part time contractor [not an employee, which is very different] for them—imagine being a part time barista somewhere and being told you couldn’t make coffee somewhere else but you were never going to be give full time hours—which is something coffeeshops are now coming under fire for). Something never quite sat well.

It took me a long time to put that unsettling feeling together with the acknowledgement of my value. 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 when to quit and the myriad forms quitting a job took place in my life helps you.

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