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When your toxic, evil boss asks you to do something illegal, don't fucking do it. He can afford a better lawyer than you.

Are You Working on the Next Fyre Festival?: Identifying a Toxic Workplace

Ever had a dream job become a nightmare?

I did.

On paper, the job was everything I wanted and more. Sexy product with high growth potential; industry stars leading the initiative; the best Glass Door reviews I’d ever seen; snazzy downtown office with free snacks, free catered lunches, even beer on tap. I’d be working with a few beloved former colleagues, and oh, right—they were doubling my previous salary. I even got to interview and approve my own manager, who was hired after me.

This opportunity sparkled from every facet like a lovely jewel. I entered that job with this-close-to-literal stars in my eyes.

Wobble wobble.

Four months later, it was 8:05 a.m. on a Monday. I was lacing up my snow boots for the walk to the train station. And I couldn’t see the laces anymore because tears reduced everything to a wobbling blur. They were tears of pure dread. These tears had replaced the stars in my eyes and the job that had once thrilled me filled me with misery.

My train leaves at 8:31, I reasoned. It takes me twenty minutes to walk to the station. I have six minutes to kneel here and let the tears flow. Not the healthiest calculus.

I told myself I would give it a year. After all, I had known real hunger—I could do anything for a year. But I only made it to six months.

All my life, I’ve had instruction on how to identify people who want to abuse me. Peers who want to bully and backstab; husbands who want to beat and control; strangers who want to rape and kill. But nobody ever warned me about their institutional counterparts.

These are the hospitals that confound you with arcane billing procedures; colleges that frame their loans as special awards; police that may arbitrarily enforce or not enforce the law based on who you are; unscrupulous realtors who redline; vampiric MLMs who predate. The list ain’t short!

But worst of all, the place you are obliged to go for forty hours (or more) every single week: the toxic workplace.

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By the time I arrived at work, I was in control of myself, focused, and ready to rip throats out.

My Secret Weapon for Preparing for Awkward Boss Confrontations

I’ve had a lot of uncomfortable discussions with bosses. A few things I’ve told them that come to mind…

“You deliberately humiliated another employee on a group call, and that level of immaturity and pettiness is professionally unacceptable.”

Or…

“Your administrative assistant, whom you love like a son, says casually and openly racist things whenever you’re not in the room.”

Or…

“You need to pay me $20,000 more dollars.”

To be fair, I said that last one nicer. And I had some great PowerPoint slides to go along with it!

Unlike a lot of people, I am actually very comfortable with conflict. I would even say I thrive on it. (There’s no way to say that and not sound like an asshole, but I am what God made me: an ENTJ.) Of all people, I probably go into a confrontational situation with the least possible amount of anxiety.

Nevertheless, I need extra deodorant on those days. My hands shake. My voice trembles. Which I really, truly hate. It makes people think I’m nervous, when it’s more of an under-exercized-border-collie-looking-at-a-fat-city-pigeon-and-trembling-with-overwhelming-herding-instinct situation.

YA DAG CAUGHT MAH

Having a difficult conversation with your boss is really hard. They’re often terribly high-stakes. Depending on the nature of the conversation, you may feel like you’re ambushing your boss with new and unpleasant information. Your life and livelihood may feel like they hang in the balance. It is not easy to stay chill.

That’s why I have a secret weapon for going into such conversations.

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