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Breaking Up With My Boss

Our collegial relationship started off strongly, but when it soured, I knew I had to make a change

By Kelly K. James

I'd been freelancing full-time for more than 20 years when I decided to look for a full-time job. I'd gotten divorced and the cost of my health insurance kept climbing, so I was willing to consider an in-house position.

An older adult working from home, frustrated with his boss and working late. Next Avenue
Credit: Getty

A few days after I applied for a writing position with a small company, I interviewed with the man who would become my boss. "Michael" was about my age, about my height, dressed in a crewneck cable knit sweater and khaki pants. His hair was cut close to his scalp, and he appeared confident and comfortable with himself, traits I appreciate.

The interview wasn't that different from a date. He told me a little about himself, or rather, about the job, and I told him a little, or rather, a lot, about myself. I was upfront about being divorced, that I had two kids at home, and that I'd been self-employed for more than 20 years. About being over 50.

"I've probably covered everything you legally can't ask me in an interview," I said with a laugh.

While the salary was less than I wanted, the health insurance coverage was excellent. I started the job excited about tackling a new adventure.

A Good Start

The first few weeks, I introduced myself to whoever I met and used the company's seating chart for the open-concept office to get people's names down. I learned how to navigate around the company's server, respond to messages on the content marketing system we used, and eavesdropped on the sales team that I sat next to.

I listened and offered my feedback, feeling flattered that he was so interested in what I thought.

I started to master the style preferences of my new employer, brought brown-bag lunches every day, and posted a few favorite photos of my kids and boyfriend on my cubicle wall.

Michael called occasional meetings with me as I onboarded. He didn't like to discuss any work-related topics on the floor of the office, preferring to meet in one of the rooms provided for that purpose. We'd sit in the small conference windowless room with the door closed, and he'd go through a checklist of topics, neatly crossing them off as we covered them. I listened and offered my feedback, feeling flattered that he was so interested in what I thought.  

He was smart, sarcastic and funny, and we joked back and forth via email, trying to stump each other with movie quotes and bantering over grammar rules. He was more of a traditionalist when it came to grammar, but English is a fluid, evolving language and so are its rules. I occasionally start sentences with "and" or "but," which he pointed out isn't technically grammatically correct.

I replied:  "But I like starting sentences with 'and' and 'but.' And I'm going to keep doing it."

His reply: "But I don't like it. And it annoys me."

I cackled and plowed merrily on, enjoying the growing confidence I was developing in my work and in my relationship with him. I enjoyed our conversational volleys, and the fact that he seemed impressed with not only the amount of work I could produce, but its quality.

I started coming up with ideas I thought could improve our department's productivity, gunning for a much-needed raise. When he rejected one promising one, I stewed over it a few days. Then I took it over his head to one of the partners who told me he'd consider it.


I didn't realize I'd misstepped until I mentioned it to Michael during one of our meetings. I explained that I was trying to prove my value but wound up apologizing for refusing to take "no" for an answer.

A Change in the Workplace Dynamic

I'd been self-employed for too long. As a freelancer, I was used to thinking creatively, to figuring out ways to work more efficiently, for creating value for clients. Now I had to ask permission to stray outside my fairly narrow job description and it began to rankle.

The dynamic between us had changed. There was no more easy banter via email or in our meetings, the number of which dropped off abruptly.

"You know, this is the room that the company always used to fire employees," he remarked one morning during a meeting. The threat was so subtle I almost missed it.

Remote work because of COVID only accelerated the disconnect. I met all of my deadlines, taking on more responsibilities as I continued to prove myself. But I wasn't perfect. I spelled a client's name wrong. I forgot to attach an email. Michael would send a terse email pointing out my mistake.

Other times he would send a group email to our team, listing our shortcomings as a department without identifying who had committed the crimes. Before I would have laughed it off, but now I cringed every time I received an email. A couple of the other writers and I would text each other, trying to determine just who had screwed up this time.

"It's the pandemic!" I wanted to email him back. "We're all under stress. Mistakes will happen!" Instead, I would apologize, again, and promise to do better.

I still wanted to please him. I wanted him to like me again. For our relationship to go back to where it had been when I had started work, where I felt like I was working with a colleague, not a taskmaster.

Beginning to Feel Trapped

I'd started the job feeling confident, capable, self-assured. Now I was so afraid of stepping wrong that I reread my work two, three, four times before turning it in. I woke up every weekday morning with a sense of dread. The more overwhelmed I felt, the more trapped I became.

As a freelancer, I had valued and fostered relationships. If I didn't get along with an editor or client, or if the client was too demanding or didn't treat me well, I finished the project and chose not to work with the person again. As an employee, however, I was trapped in a dead-end relationship. One that had started out promising, but had turned sour.

"I already know you hate your job," she said. "I see your face every day when I get home from school."

Should I stay? Should I quit? Should I look for another job? I felt trapped, immobilized, even though I knew that having a bad or unsupportive boss is one of the top three reasons for leaving a job.

One afternoon while working remotely, I realized I'd forgotten to attach a file. I swore, and frantically pounded my keyboard to rectify my mistake before I received another nasty note. I hadn't realized my 11-year-old daughter was in the room.

"I forgot to attach a document," I said to her, hearing aloud how ridiculous I sounded. I shook my head. "I'm sorry. I hate my job."

She rolled her preteen eyes. "I already know you hate your job," she said. "I see your face every day when I get home from school."

That stopped me. What was I teaching her? To put up with a man who didn't respect her? To live, if not in fear, in low-level dread? To try to please someone who would never be satisfied?

For months, the good girl in me had been trying to fix the relationship, to do better, to be better. The woman in me finally realized that there was no fixing it.

It was time to break up with my boss.

[Kelly James left her old boss and old job for a new position at another company.]

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