Bad bosses this baby boomer has known

I recently saw an ad for a 2011 movie entitled “Horrible Bosses.” The plot centers on three friends who decide to murder their respective overbearing, abusive bosses.

While I’ve never felt compelled to take action quite that drastic, I have to admit that, over the years, I’ve had some—shall we say—challenging bosses. For example:

  • A female boss was involved with a married man and spent a good portion of each day talking to him on the phone. She and I shared a tiny office, so I could hear every word she uttered (although I had to pretend not to). Since it was part of my job to answer the phone, my small rebellion was to always ask Mr. Married Man “Who’s calling, please?” even though I knew darn well who it was. Take that, you philandering d*ck.
  • One summer during college I worked at the front desk of a motel in my hometown. A friend gave me a ride to work one day and when I arrived, the motel owner looked at me and said, “Do you have a comb?” Nonplussed, I replied, “Um, yes,” whereupon he haughtily said, “Well, then use it.” Evidently my hair was too windblown for his taste. His tone was too condescending for mine and, fortunately, the summer (and that job) was almost over.
  • A married male boss and I attended a swanky bash at New York City’s Tavern on the Green celebrating a milestone anniversary of the big-league PR firm that represented the institution we worked for. Boss and I took the shuttle from Boston to NYC and back the same day. Tired and a bit buzzed after all the festivities. Boss drove me from the airport back to my car at our office and, as I was about to exit his car, he lunged and kissed me, sticking his tongue in my mouth. I don’t remember what I said, just that I hightailed it out of there. At work the next day—and thereafter—things were decidedly awkward between us, and he wouldn’t look me in the eye. I gave my notice a couple of months later.
  • At a quasi-governmental municipal agency where I once worked, I was told by a superior that he’d be letting me know what percentage of my salary I was expected to contribute to the mayor’s reelection campaign since, according him, my job existed because said mayor was in office. I opted to return to working in the private sector forthwith.
  • At another job where I was director of marketing, I was responsible for producing six different versions of a quarterly newsletter. The CEO of the company, to whom I reported, reviewed the copy prior to publication (an indication of his tendency toward micromanagement). After the newsletters were printed, however, I found copies in my mailbox marked up in red ink, indicating where he thought commas should have gone. I saw red all right—along with the handwriting on the wall, and accepted another job offer before a year was up.
  • My final corporate job was at a company where the CEO liked to drink his lunch, and he’d spend afternoons sleeping it off behind the closed door of his office. You quickly learned that if you wanted to schedule a meeting and/or have any top-level decisions made, you had to make it happen before noon.

Today I look back on these situations and say, “If only I knew then what I know now.” Such as how to speak up for myself. How to address inappropriate behavior in a direct, unapologetic way. How to know that I had legal recourse in certain situations, if I chose to take that route. How to speak truth to power, as in “WTF are you thinking?” (Well, that last one probably wouldn’t have worked too well, but a girl can dream.)

Instead, my strategy was invariably to find a different job—kind of a variation on “living well is the best revenge.” Frankly, given my experiences, that really was probably the best strategy, because I gained the expertise, motivation and connections to ultimately became my own boss. And that’s been a much better fit for 21 years now.

Because another thing I’ve learned at this age is that you really can’t change other people or make them act a certain way—in the workplace or in our personal relationships. You can set boundaries, you can refuse to be insulted or harassed, you can express how you feel about someone’s behavior, and you can ask for what you want and need. But despite our best efforts, sometimes it’s all for naught: the other person can’t or won’t change, and you just have to walk away—inspiring this haiku:

We teach people how
to treat us, but some of them
just aren’t trainable.

What about you? Got some bad-boss stories to share? I’m listening…



Roxanne Jones

About Roxanne Jones

By day, Roxanne Jones is an award-winning freelance copywriter specializing in health and medicine. She launched Boomer Haiku, a humorous blog about life as a baby boomer, in 2015, and a Boomer Haiku greeting card line in 2016 (available at 6 Maine stores; visit to learn more). Born and raised in Brunswick, she left Maine after high school (Class of 1971) and, after living in Massachusetts and California, came screaming back to her home state in 2006. She enjoys chardonnay, laughing at the foibles and frustrations of getting older, and contemplates plastic surgery to get rid of the wattle on her neck.