The lasting sting of a dysfunctional boss

It was supposed to be my dream job. Anna's reign of chaos made that impossible.

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About a decade ago I landed my dream job as an editor at a prestigious environmental non-profit organization. After years of working as a health editor, I was thrilled to make the switch, knowing I’d be producing content on topics like climate change and deforestation.

Right away, though, things seemed off with my boss “Anna.” Case in point: The time she organized a team-building event at a bowling alley that ended up with her committing minor theft.

Her trigger seemed to be the drink tickets. We each got two to use for adult beverages, but not everyone used them. Afterward, a few of us decided to walk to a nearby bar to keep chatting. Anna told us to go on ahead while she paid the tab.

About half an hour later, she arrived and sat down at our booth. A coworker asked if she wanted us to flag down a server.

“I’m good,” she said as she opened her coat, where she had tucked away one hand. She brought out a full glass of wine, presumably taken from the bowling alley.

I was stunned. My new boss was stealing wine glasses? No one said anything, but our expressions must have been telling.

“What? We had extra tickets, I didn’t want to waste them,” she said. As if that wasn’t embarrassing enough, our server, a bold-as-brass older woman, noticed the outside drink. 

“Did you bring that in from somewhere else?” she chastised Anna. She grabbed the wine glass and put it on her tray. “I can tell you’re the sort of woman who knows better. No outside alcohol is allowed, it says it right on the door. I really hope you didn’t steal this.”

Anna laughed it off, and we all tried to, too. Maybe this was just a one-time thing, when she got a little too tipsy and made a bad decision on the company’s dime?

‘Dancing, drinks, maybe more?’

If only. More red flags popped up, the worst being when she and I were trapped at a DC hotel on a work trip, during a snowstorm. As we ate dinner at the bar, she kept giggling at her phone. I made the mistake of asking what was funny.

“Oh, I just like to post on Craigslist’s random encounters when I’m on trips, as a way to meet new people,” she said, mentioning how she liked to make friends in different towns, making it sound relatively innocuous. For some reason, she said, her most recent post kept enticing men to send photos of their genitalia.

Later that evening, tucked into my hotel bed, I looked it up. Contrary to how innocent she made her habit sound, in this post she described herself as a woman in town for a few days, with curly hair and thigh-high boots, ready to meet men for “dancing, drinks, maybe more???”

Yeah.

Not my only boss to deal with

For several reasons, I could have gone to HR. But I didn’t, worried I’d somehow be the one getting fired. I’d long been keen to the fact that HR is not your friend.

But also, the situation was just so confusing. Anna was not mean or passive aggressive. She was charming and personable. Just a little… unhinged? And definitely flaky, rolling into the office unpredictably, the smell of whiskey and cigarettes lingering in her wake. Truth be told, I kind of admired that about her, how she boldly did whatever the hell she wanted.

Not surprisingly, regular check-ins were not a thing with her. Instead she mostly had me report to “Cathy,” a woman in a different-but-related department who was Anna’s opposite—not a heavy-drinking party girl, but awful in her own buttoned-up ways, constantly micromanaging me. Cathy would complain to Anna that I was too rogue, and Anna, who never kept tabs on what I was working on, would relay Cathy’s feedback to me, a weird game of telephone in which my career was on the line.

The hallmark signs of a dysfunctional boss

In spite of this, I stayed at the job for four years, hopeful things would improve. I told myself Anna wasn’t “toxic.” She didn’t belittle me or steal my ideas. She just had no idea how to manage people, preferring to be hands-off.

Apparently that’s a thing with dysfunctional bosses. These kinds of bad bosses tend to “under-manage,” expecting employees to come to them for guidance. Meanwhile, they are friendly and love to talk, especially about themselves. And not surprisingly, they lack boundaries, such as, oh, I dunno, viewing dick pics while at dinner with a horrified underling.

Sadly, things never got better, even though I always had stellar performance reviews. One cold winter day, Anna called me into her office and said it would be best if I found a new job. Cathy especially was tiring of me.

“Sometimes things just don’t work out,” she said.

The lasting impact

A few weeks later, I found a new job as a health editor. It took a long time to trust that my new supervisor wouldn’t say or do something inappropriate and then expect me to laugh it off. In the interim, I often wasted time analyzing our communications, trying to decipher if there was some sort of “hidden agenda” like there was at my previous job. I also was scared to make any mistakes, meticulously reading my edits several times before handing them over. I didn’t trust my instincts, which you need as an editor. Thanks to four years with a dysfunctional boss, my confidence had been crushed and it was going to take a while to get it back. (These are the kinds of things you can’t explain in a job interview, or, later when your new boss gives you feedback. Complaining about your old boss, and her toxicity? It makes you look like the crazy one.)

A few years ago I got updates on Anna and Cathy from a former colleague. After both of them rose up the ladder to VP titles, Cathy had been laid off in a “restructure.” Anna, meanwhile, was fired when she rolled into work several weeks after a two-week vacation at Burning Man was supposed to end.

The schadenfreude was deep, but brief. I felt validated, less crazy. But I still felt sad. None of it turned out how I wanted it to, and I’m still reeling from that loss: For a brief time, I had my dream job. They aren’t always meant to last.