"You Should Fire Me."

I dared my boss to fire me—here's what happened.

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The first time I ever quit a job was when I was 17. I was an usher in a movie theater—which mostly meant I swept popcorn off the floor and told other teenagers, likely some of my classmates, to stop dry humping during Herbie, Fully Loaded—and recently got offered a job in the mall, which was this Miami teenager’s dream come true in 2004. I went in, told my boss (a person I had never met) that I got another job that paid more, and he told me I’d regret it.

Fast forward about ten years, and I’m having a similarly crippling conversation with my boss.

I worked at a cafe that could be summed up in a series of painfully arbitrary moments. I remember one night closing with a friend of mine, and we danced around each other’s wages, trying to figure out what the other person made. When we figured out we were paid differently, we tried to understand why—we couldn’t. It was common to see someone be commended for something you were just reprimanded for. It was an everyday occurrence to see someone request certain shifts but then be told you were selfish for making a scheduling request.

Everything felt discordant, and I could only boil it down to one thing: either the boss liked you, or he didn’t.

I knew my boss, the owner of the cafe, didn’t like me from the beginning. In my initial interview, I told him I planned to go to Spain for a week, and when he forgot weeks later (he put me on the schedule but I insisted I told him), he gave me a hard time about the shifts he had to fill. I applied for a salaried position with another coffee company (at the time he paid me $13/hour with no benefits) and when I told him, he somehow felt both betrayed that I considered going somewhere else and disdain at my continued presence in his store.

And yet, I was still there. In fact, I was promoted. The owners (a husband and wife duo but I mostly interacted with the husband on a day-to-day basis) seem to either acknowledge my talents or simply need a warm body in their second location, and I fit the bill. I went to manage their newest store.

The moment I assumed my new position, we hit turbulent water. His general dislike turned into outward annoyance and aggressiveness. I remember texting my boss a question, and not getting an answer. It was something I needed to know, and after a few days, I texted him again. He told me I was insane—that I was acting crazy for texting him more than once. He avoided me regularly, skipping on visits to the store when he knew I was working. I remember one conversation with his wife where she asked why we weren’t getting along, and I told her he hadn’t spoken any words to me, to my face, in over a month.

So she made us get a beer.

I was no angel at this job. The minute I sensed he didn’t like me, I pretty much went negative. I trashed talked both of them (I apologized for trash talking his wife, truly the only regret I have at this job), I expressed my frustration constantly and openly—both with employees and with customers. I wasn’t bad at my job but it was clear that I hated being there.

Because it sucks to work somewhere when your boss so obviously dislikes you.

I’m not sure what I expected when we got this beer. Maybe an apology, or even just an acknowledgement that there was something off about our working relationship. But instead, he ripped into me.

He told me I was disingenuous, that I was disliked, that he didn’t trust me, and generally that he thought I was a bad person. I’m summing this up in a few words, but imagine hearing someone stammer out these sentences over the course of twenty minutes. You really can’t say much back—there’s no argument for someone telling you they hate your guts.

There was something so wild, sitting with this beer he bought me, warming up as I’m nursing it between my hands, and just feeling like you’re being torn in half. It’s surprising—you can almost picture yourself dropping the beer like you’re being told bad news—but you’re also paralyzed because you’ve never imagined this situation ever before and you have no idea what to do.

I remember being quiet. And then I remember saying, “you should fire me.”

I think that caught him off-guard. That wasn’t what he expected me to say. I think he thought I’d fight back, or apologize, or promise to do better. And I didn’t say it like I was ashamed of myself—I said it matter of factly, like I knew he had made up his mind. It was like a dare. I dared him to fire me.

I have no idea what came over me. I wish I could channel that confidence all the time because I usually shudder under confrontation. But in that moment, I think I knew that this path had only one logical conclusion. There was no circumventing his disdain for me. I couldn’t do anything to suddenly get in his good graces.

It’s like when you’re in high school, and there’s that one group of friends that’s always going to look down on you no matter what. As much as I could have strained for acceptance, I was never going to get it, and I couldn’t change anything about me to gain it.

More importantly, though, is that I did nothing wrong to prompt this dislike. I couldn’t go backwards and point to a moment where I should have changed my actions. The only thing to do in that moment was to fire me.

Did he? No, of course not.

Instead, he let me dangle in this weird hellscape where we both decided we didn’t like one another and had no idea what to do with it. We were suddenly more confrontational but it felt…weirdly peaceful? Like this was just how our world works now.

I suspect he didn’t fire me because I had enough ground to file an unemployment claim. I tried to wait it out and just tempt him to make a sudden decision but eventually I caved. I saw an ad for a coffee shop that was hiring in Brooklyn and sitting on the floor of a bus station in Boston I quickly accepted the new position, looking for any way out.

But I knew I had to go. And even though he didn’t fire me, he should have.

I struggle with the line on when it’s ok to fire someone. Part of me wants to say it’s never ok, and the other part wants to say it’s ok to fire whoever, whenever—not because you have the right to hate people arbitrarily, but because if you dislike someone, you’re going to treat them poorly and no one deserves that.

My boss should have fired me the moment he sensed he didn’t like me. I would have been mad, I would have been upset, but hey! I wouldn’t be telling you this embarrassing story of how I dared him to fire me after shitting all over me and he cowered like a chicken. I’m not saying he was right to dislike me, but it was worse for him to treat me the way he did. If he fired me sooner, I wouldn’t be carrying the scars of that conversation over beers, which I still count as one of the most hurtful moments of my life (remember folks, I had a live-in boyfriend with a secret girlfriend for months! and my friends knew about it!).

Before that conversation, we had never talked about me leaving, or about what breaking a working relationship would look like. I think there’s a certain acknowledgement of your weaknesses you have to face when you fire someone (that’s another topic but I think if you have to fire someone, there’s a trail of your failures you need to chase to examine how you got to this point) but for me, suggesting I be fired meant acknowledging my worth and acknowledging I’d run up against an unmovable force.

This is sort of all exists in a weird bad mucky void where there’s no pathway to a right answer. It’s making the best of a lose-lose situation, which tickles my Justice Sense—throughout this whole scenario, he was wrong! He hired me! He promoted me! Trying to make sense of an objectively terrible situation is weird, and feels sort of wrong. So am I trying to find answers in a place there might not be any? Sure. Could I have written a whole piece on how his hatred of me could have stemmed from misogynistic feelings about women in power? Sure. But that’s not what I think about to this day.

I think about that beer. I think about his words. And I think about that quiet moment where I dared him to take action.

In a way, this is a celebration of that moment—the moment I told him to fire me. In a sea of negativity and just god-awful shitty feelings, I feel like I found stable water. I found an answer. I finally said, “this isn’t working,” and I put my foot down. I wouldn’t be treated like this anymore. Instead of trying to make something that wouldn’t work suddenly work, I was cutting out. We were on this journey deeper into turbulent times, and I took a machete and created a new path out of the forest.

It felt violent, and powerful. I couldn’t see what was in front of me before I cut away the branches. The horizon in front of me looked promising as fuck.


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