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You are reading The How to Live Newsletter: Your weekly guide offering insights from psychology to help you navigate life’s challenges, one Wednesday at a time.

In the pantheon of workplace horrors, the bad boss reigns supreme—a figure both mundane and monstrous, capable of transforming the ordinary into a landscape of dread.

I've encountered my share of these petty tyrants, each leaving an indelible mark on the canvas of my professional life.

One of my earliest jobs was for a casting director who hurled staplers (not staples) at our heads if we didn’t answer the phone on the half-ring.

Later, as a Production Assistant (PA) on a film set, my direct superior (the 1st Assistant Director aka 1st AD) was the silicone upon which the LA bro mold was set.

One sweltering summer night, after a grueling shoot in the Bronx, we started wrapping up at 3 a.m. The 1st AD had me “police” the area—a euphemism for cleaning up.

I was in shorts and a tank top, sticky and sweaty from humidity and stress. Task completed, I approached the air-conditioned van, filled with the male PAs and the 1st and 2nd AD. The 1st AD rolled the window down, smirked, waved and wished me "Good luck!" and drove off, stranding me miles from home, without cash or ID.

The joke was on them, it seems. As I walked downtown in the middle of the night, I stumbled into a bar hoping someone might give me subway fare, only to find the producer and director mid-nightcap. They summoned a cab, paid for it, and fired the 1st AD.

But it's the pandemic-era tyrant who haunts me most—a white man in publishing who wanted to get into podcasting. He hired me to write, host, co-produce, and program a book podcast.

He dismissed all my ideas, calling my list of proposed authors “woke,” unless I mentioned any white women authors, whom he derisively called, “Park Slope moms.” He refused to hire any people of color because “we have to hire someone good,” paid me three times less than the engineer, and was sexually inappropriate at every turn.

When I recorded voice-overs, he’d sit in the studio, telling me I was untalented, worthless, incompetent, and not good at anything. When the pandemic hit, and I had to record in my closet, he’d call in and berate me the same way.

He tried to control my online presence, barraging me with abusive texts after I posted anything on my personal social media accounts. He constantly talked behind my back to the engineer, who confided in me everything that was said. This did not help matters.

I worked for two years for this person, during the pandemic when I was at my loneliest and most vulnerable, and he dismantled me layer by layer until there was nothing left.

The scars of these encounters reveal a universal truth: the power dynamics of the workplace can warp and wound in ways both subtle and profound. Yet, in sharing these stories, I hope to offer solidarity.

To suggest that perhaps, in the retelling, we might find a way to reclaim our narratives, to transmute pain into wisdom.

I asked people online to submit their bad boss stories. I’ve chosen three. The last one is the longest and juiciest.

May these stories of workplace tyranny remind you that you are not alone, and that you can find the strength to forge better paths—for yourselves, and for those who come after.

BAD BOSS ONE:

My bosses were so bad I developed a stutter. I realized that my speech was garbled, worked on it, realized that they still were not hearing me. 

These are Good Liberal People, in White Hat Savior jobs. 

I’ve witnessed surreal passive aggressive racism, tried to address it with them, and get confronted with “I don’t remember that” so often that I actually check my personal journals to confirm that my memory is accurate. 

This is a job I am stuck at, trying to manage keeping my sanity. 

When I actually get to do my job, I love it. But toxic, egomaniacal, racist bosses ruin everything for everyone.

BAD BOSS TWO:

First, he was pretty regressive in terms of gender norms and diversity. Once, when I challenged him to put together a more diverse panel than the all white male one he proposed, he testily told me he wanted to focus on hiring competent speakers.

Another time, he told me, a mother, that he didn’t think women could be successful mothers and successful in their career at the same time. I shared this with a mom colleague and she said he had told her much the same. 

But then, I was doing a ton of overtime and getting pretty burned out. After some testing, it turned out it wasn’t just burnout, but autistic burnout, and I got diagnosed autistic.

Rather than helping me through this burnout and diagnosis, he laid me off because he said everyone disliked me and no one wanted to work with me. 

Anyway, the tl;dr is it took me a year to recover from that toxic environment. I guess I’m grateful for the diagnosis. 

Although speaking of, when I shared the diagnosis his response was, “…What’s your prognosis?” Sir, it’s autism, it’s not terminal cancer.

When I told him that’s why I was burned out and people disliked me, he said no. He said everyone disliked my personality. “Well, maybe not this person and that person, but that’s because they just started and don’t know you yet.”

Can you IMAGINE saying that to someone?!

BAD BOSS THREE:

It was the fall of 2004, and it was my fist job out of college.

I was working for a Random House company (what was then the Doubleday-Broadway Publishing Group) at a new nonfiction imprint.

My boss had been poached from Penguin. She was in her mid-forties, and this was a big job for her, an executive vice presidentship with her own imprint, so she had a lot to prove. Honestly, it was exciting for me. Not only was I working in big publishing, but I was going to help launch a new imprint.

What became clear really quickly is that this boss was not a very stable person. She had a notorious temper, and she talked down to anybody and everybody she could, so long as they didn't outrank her, in which case, she'd treat you fawningly.

There were a few immediate red flags, the most obvious of which was that she demanded a few weird things, including that I come in early (like 8 or 8:30 a.m.) and turn on her office lamps and computer and log her in so that when she got there, she didn't have to, you know, turn stuff on herself.

I was also supposed to have a green tea ready for her whenever she came in, and she'd email me from her Palm Pilot to give me a 10 minute warning. If the tea wasn't ready, there was trouble. If I made it and it cooled too much, there was trouble. Because it was my first job, I made it a point to be extra deferential, and I sincerely worked hard to be helpful to people, including her, my colleagues, and our authors.

Somehow, though, she found me too deferential and often said things like "You're such a woman" or "Don't be such a woman," which I found interesting because, well, she was a woman. Early in my tenure there, my mom was on a business trip, traveling from California, and she came to visit me at the office and take me to lunch.

She met my boss briefly and exchanged pleasantries. When I got back from lunch, I overheard my boss shit-talking my mother to one of my colleagues, saying "No wonder he has no sense of style. Did you see his mother! Oh, my God! That hair! That blazer!"

It was really petty, mean-girl shit. I had to pass her door to get to my cubicle, and it was clear that I'd heard her.

This did not deter her. She went on and on about how people from the west coast inherently have no style and have to be "trained" by more sophisticated people.

One of the best stories (and worst moments) was this: My boss, REDACTED, was bicoastal, which she loved to mention to anybody who'd listen. She was a real know-it-all, so if you brought up anything, she had something to say about it. But especially if you were talking food, culture, shopping, television, fashion, etc., she always knew best.

She had a home in San Francisco and an apartment on Astor Place, and she often brought back teas and tinctures and traditional Chinese medicines from San Francisco.

One summer, she was mostly on the west coast and had left a big plastic bag of chrysanthemum tea in a drawer in her office. Because she hadn't been in NY for three weeks, when she returned to find that the tea had been infested with some sort of mite, she FREAKED OUT, ripped the bag open, and strew tea and mites all over her office.

She ran out to my cubicle with a box of tissues and demanded that I go into her office and "kill all the bugs." She pantomimed smooshing the bugs with a tissue, and she was nearly in tears. I told her I wasn't comfortable doing that, but that I'd happily call facilities and ask somebody to come up to vacuum and do pest control.

She got very angry at this and said, "I can't call facilities! They're already mad at me because I demanded the low-VOC paint in my office." This was true, to an extent, though facilities wasn't angry about the paint choice; they were angry because she talked to them like they were low-class morons.

Truly, she treated servers, assistants, delivery people, retail workers, and messengers like absolute trash, often criticizing their looks, their accents, and their job performance. She really enjoyed doing the voice of Apu from the Simpsons, too, and justified it by saying shit like, "I actually have so many Indian friends, and they find it uncanny and hilarious how good I am an an Indian accent."

Anywho, back to the bugs: I told her I REALLY felt that I couldn't do this, and she slammed the box of tissues down on my desk and yelled "Well, I certainly can't do it! I'm a buddhist! I took a vow not to kill!" She huffed off to a three-hour lunch with an agent at Molyvos, and while she was gone, I killed approximately 10,000 mites and picked little bits of tea out of her carpet, desk chair, keyboard, and drawers.

Not long after that, two of her former colleagues from Riverhead were poached, too, and given their own company (bigger than an individual imprint). This made her livid and she got extra hard on people.

She started demanding that when she was working from the West Coast that I maintain both NYC hours and SF hours. So, I'd come in at 8:30, and I've have to stick around until 5:30 pacific to answer her phones and such. So, I was working 12-hour days for $32,500/ year.

I was buying groceries at the Key Food in Astoria with a credit card. Eventually, I quit. Her next assistant developed stress-alopecia from working for her. A few months later, she got fired. Her name is REDACTED, and she edited the REDACTED when she was at Riverhead. Mention her to anybody who worked in publishing from 1990-2006, and they'll roll their eyes or run from you.

Truly, one of the most vapid, self-centered, dip-shittiest people I've ever known, let alone worked for.

Got a bad boss story to share? Leave it in the comments!

Until next week I will remain…