10 Ways My Boss Has Made My Life A Living Hell


If you’re lucky, you work for someone you can admire. My dad tells me stories of a boss who took him under his wing, taught him the ropes, and enabled his success through being tough, but fair, and cordial, yet still professional. To this day, they’re still terrific friends. Me? Well, there’s a decent chance my boss has been attempting to give me Stockholm Syndrome.

Throughout the past year, I have dealt with the most irrational, passive aggressive, jealous, insecure, and incompetent person I have ever encountered in a professional environment. Worse yet, he has a certain affinity for “hitting me because he loves me,” criticizing me to unnecessary levels only to tell me how special I am and how much he wants “us” to work. As this comes to a head, almost everyone at my office sees the situation for exactly what it is, which is reassuring to say the least, but still the conflict remains.

You see, my boss isn’t a manager, but he has thrust himself into a manager’s role. While he can, and still does, produce, he can’t manage to save his life. Still, he believes in his own greatness at least, so I decided to make a tribute to it. If your boss sucks as bad as mine does, I’m sure you can relate.

1. My boss is great at misplacing blame.

As odd as it sounds, my boss and I first came to blows when a friend and coworker left my company for another job in a larger market. My boss was incensed, ranting to me, not him, about the disloyalty of my generation and, in fact, my own disloyalty, for an act I was not even a part of. After my friend left, my effort began to be questioned with no real benchmarks as proof and even my interest in the industry was maligned without evidence or motivation. I hadn’t done a thing wrong, yet I was taking the heat.

2. My boss is great at downplaying success.

Until the point that my friend left for that new job, I had been a rising star. My writing and client-facing skills were lauded, I had personally prospected what would be the largest account in my firm’s history before I had even moved into the front office, and I was the head of an entire department. Now, I get nothing but shit, but it isn’t just me. Former employees, fellow coworkers, and even his other partners do not escape his disrespect and derision.

3. My boss is great at demotivation.

Perhaps some people respond to demeaning, shaming, mood swings, and ego trips in a positive light, but my response is almost always the “fuck you” death stare. Instead of inspiring me to “do better” or “work harder,” the result is the complete opposite. Nothing makes you care less than someone ignoring your successes while overplaying created flaws. If he doesn’t land an account he’s going after, it’s obviously because I didn’t work hard enough. If he doesn’t know something, it’s obviously my fault for not telling him.

4. My boss is great at pointless dick-measuring contests.

He’ll point out how much better he is at prospecting that I am, as if his 25 years are comparable to my one. He’ll claim to understand how to use the analytic software better than I, an assertion not only blatantly false, as he can barely operate Excel, but also completely pointless. He will turn anything and everything into a way to “one up” me, whether it is partying on the weekends, eating food, knowing a submarket, or anything else that may apply or not apply to work.

5. My boss is great at lecturing, not mentoring.

Even if he truly was “better than” me at all of these things he claims, or even if you just took that things that he, by experience and expertise, is actually superior in, the fact remains that instead of lecturing me about them he should be mentoring. It is in both his and the company’s interest for me to become a more effective employee and producer, but neither have any concept of how employee improvement or retention is accomplished. There is a reason I’m the fourth person to hold my position in eight years.

6. My boss is great at being jealous.

Perhaps most frustrating is that while there are four principals at my firm, I am stuck working for the awful one that I do. I was never hired to work solely under him – he simply claimed me. I was always told I would be able to work under each until I discovered what I was best at – it never happened. One time I took matters into my own right and simply asked if I could voluntarily attend another principal’s strategy meeting, before work hours even. I was then torn apart for not being “loyal” and a “good team member,” as if it wasn’t all the same company. If I even mention a different industry sector or type, still within my company, I am guaranteed to catch heat. There is a reason I’m applying for new jobs.

7. My boss is great at setting a bad example.

There was a time I came in early and left late. There was a time I went above and beyond on everything I did. There was a time I pulled all-nighters to prove myself and spent my minimal free time absorbing all of the information I could. Then I realized that my boss does none of this. He comes in late. He is detached from the work but doesn’t spend his time prospecting or overseeing. He takes personal calls and appointments regularly. He leaves early. This morning, he fumbled through a conference call, completely unable to function without our regular VP present.

8. My boss is great at being emotionally unstable.

Like other abusive relationships, my boss doesn’t stop at jealousy and also plays me hot and cold. Throughout one day, I can easily and expectedly be told how amazing I am, how awful I am, how incredibly my skillset is, and how much of a letdown my application of those skills has been. Neither is usually fully inspired from reality, and after each insult followed by an awkward high five or “pal around” session I couldn’t be more exhausted.

9. My boss is great at pretending like he’s helping me out when he’s screwing me over.

I have a “prestigious career in finance” for one of the “top three companies in the world” for what I do, and yet, unlike the bankers on Wall Street, I make about as much as I would if I was an assistant manager at McDonald’s. My boss continues to talk about my paltry income as some sort of gallant opportunity, attempting in vain to impart a sense of pride in “paying my dues” as if they weren’t simply ripping me off. I commute two hours every day because I can’t afford to live any closer. As other people waltz in late, I get chastised for not coming in early.

10. My boss is great at being delusional.

As accounts continue to not be won, employees continue to leave, and frustrations mount, my boss will always have an excuse or rationale that is barely recognizable from the truth. Instead of looking inward and readjusting or re-examining, my boss points fingers, makes excuses, and changes nothing. My company is in the undisputed top three of what we do, but there is a reason we’re not number one, and my boss is as much of a part of that as anyone.

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I used to write for TFM and PGP when they were funny.

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