How to Deal With Terrible Bosses

There's even an upside

Photo by Kate Owen

“Everything happens for a reason” is bullshit. Same goes for, “What doesn’t kill you makes you stronger.” They’re words I’ve heard dribble almost exclusively from the patronizing mouths of privileged, older (white) people who’ve never had a bad thing happen to them. They were the go-to platitudes from teachers when I first got sick; maybe you associate these phrases with a pat on the head from a terrible aunt.

Thankfully, this is not a rant about terrible aunts, but terrible bosses. Before I began working for myself, I worked for other people. From the ages of 18 to 28, I held all manner of 9-to-5s, with a variety of different kinds of bosses. For whatever reason, a lot of them were terrible. I’ll never ascribe to the philosophy that “everything happens for a reason,” but I might take solace in the jaws of Jagger: “You can’t always get what you want… but you might find you get what you need.” I have enough anecdotes about terrible bosses to fill a dozen articles, which leads me to believe I needed those terrible bosses to push me into doing what I do now.

My stint as a production company receptionist was perhaps the most mind-numbing job of my early 20s. I laid out breakfast every morning, ordered lunches every afternoon, and transferred calls in between. This terrible gig was made 1,000 times worse because I was also the assistant to the CEO, Fern*. She was smart, stylish, and, at first, encouraging. After two weeks, the honeymoon was over. I started getting yelled at about anything and everything, but my favorite gripe had to do with the plants. I was required to maintain everything growing in the loft, including the orchid in her office. Now, I’ll be honest: I have a black thumb. I’ve killed cacti! And I told Fern about it beforehand. On a level of one to 10 on the difficulty scale, orchids are an 11. When the flower inevitably died a few weeks later, she angrily shouted, “How am I supposed to trust you to do anything around here if I can’t trust you to keep a plant alive?” Fern’s lack of faith in me affected my desire to perform—and even be there in the first place—and I have no doubt it showed. But it was a teachable moment: How you treat others directly impacts their work. Being mean doesn’t always get results, it often has the opposite effect.

My worst boss was Mike*, who managed the boutique where I worked before starting my brand full-time. He looked like Jersey Shore’s “The Situation,” and dressed like a sailor (yes, there was a cap involved) on his way to the gym. Mike loved you until he hated you; on a long enough timeline, he hated everybody. He was a perfectionist with anger problems and would yell at us in front of customers, print out critical emails and tape them up in all of the available bathrooms, and even throw chairs. It goes without saying that his behavior was inappropriate. But I loved the people I worked with and I loved that store, so I made it work. I was lucky that my eyewear began to take off, so I had a safety net if I couldn’t deal anymore, but I was definitely developing full-blown retail PTSD, jumping at every phone call in fear and waking up with a sense of dread on days I had to work. Even after I left the store, it took a full year before I could walk by the display window without shaking like a chihuahua. In hindsight, this taught me that nothing is worth voluntarily staying in such a stressful environment.

There’s an upside to terrible bosses: They teach you about the kind of person you don’t want to be. Knowing what it’s like to be treated terribly as an employee made me a much better boss when it was time to bring on interns and a full-time assistant for my own brand. I was sympathetic toward schedules and sensitive to people’s strengths and weaknesses. I made sure to explain things thoroughly, and was understanding when things went wrong. I trusted the people that worked for me and would check in only when necessary. Terrible bosses helped me created an environment based on kindness and trust, where the only rules were: show up, work hard, be nice. And you know what? It freakin’ worked.

In a weird way, I’ve also learned to sympathize with my past tormentors. No one wants to be a bad boss! But being in charge means the buck stops with you, and there’s a lot of stress that goes along with it. There are times in owning and running a business where I am simultaneously pulling CEO and intern duties at once. It can be tiresome, monotonous, and exhausting. But I learned early on not to take that out on others. I’m fortunate to have the ability to sit back and remind myself how much worse things could be, and I’m grateful that I have the opportunity to run my own show. I wish younger me had the kind of boss who could share these insights.

On that note, I’d be remiss to leave you here thinking all bosses are terrible. My last music marketing job was the first employment I found after going into remission. Reverse commute to Newark aside, the duties were in my wheelhouse, with great coworkers and *Joe, a truly wonderful boss. When you go from being very sick every day to being someone who can live life without any physical limitations, you reevaluate everything, whether you want to or not. I spent the three months at this marketing job trying not to have an emotional breakdown at the office. I finally had my life back, and all I was doing was promoting bands? Without knowing anything about my situation, my boss took me aside in a professional yet truly kind way. He met with me in his office every few weeks for constructive reviews of my (inability to) work, until he had no choice but to fire me. Even then, he listened with a sympathetic ear while I told him what I had been going through (and I’m pretty sure ugly-cried throughout). He gave me some invaluable advice that I still keep to this day.

Joe reminded me that life is long and that if you’re smart and passionate, you have a lifetime to live on your terms. He saw a lost, snot-covered girl sitting in front of him and told her to spend a year at a job that had nothing to do with a career; making coffee (or, in my case, working at a store where a sailor threw chairs) and taking the time to heal and think about what she wanted the rest of her life to look like. It actually turned out this way, and I couldn’t be more grateful for a boss who made the hard decisions that helped me get where I needed to be. 

*names changed because duh!