In Praise of My Worst Boss.

I’m no cactus expert, but I’ve worked for my share of pricks. I credit one such prick named…oh, why not, let’s just go ahead and assassinate the man’s character directly…Russell Son of Jeffer, for being a main impetus of my FIRE. If I hadn’t suffered through three years and eight months and seventeen days of his supervision, I’d still be working.

Before I launch into story mode, let’s get the trite and self-obvious moralizing out of the way. Working for a bad manager teaches you how to recognize & avoid such in the future, but it also teaches you a few lessons about how not to be a bad manager yourself. Yes?


So how did I come to have Russell Son of Jeffer for my boss?

When I was twenty-three and in MBA school I kept myself fed & watered by working in commercial and college radio. Morning zoo, live remotes from bars, hanging out backstage at concerts, and such. Heady.

But being also the son of a white-collar worker, I’d been programmed since birth to believe that having a “good corporate job” meant you’d “made it.” Can you identify? So promptly upon graduation I split the music industry, moved across the state, and started working in a cube farm under Russell Son of Jeffer’s oversight.

As the man once said: people remember life in phases, but they live it from day-to-day. Looking back through my journals from those years I find far too many entries where I focused on whatever the latest Russell-screwed-me-over story was. There were also all sorts of good things that happened to me during that time, of course, but sad to say that I spent 3.5 years under a shadow and I wrote nowhere near as much about those good things as I should’ve.

Such is the power of a bad boss.

But here’s an entry from my third year/second month that I’ll always prize. My contempt for Russell Son of Jeffer will obviously shine through, but I’d earned the right to be contemptuous. His department had fourteen people and the bulk of us felt the same way. I hope you find it valuable, or if not valuable, at least entertaining.


Four ten-hour days including last Saturday working on that PowerPoint bullshit for R’s Board of Directors presentation on the public utility commission situation. Constant frigging revisions telling me to do one thing and then deciding he didn’t like it and throwing it out and sending me off to do something else because (he said) I didn’t give him what he wanted the first time. Chewing me out for not delivering fast enough. Then changing the entire thing after I finally did deliver it. And of course he slapped his name all over it. “By R.” with no mention of anybody else. I guess a co-credit was out of the question, but you’d think he’d at least mention the department by name.

But then he gets up in front of the board Monday, must’ve been three hundred people in the auditorium, and he gets thirty pages through the thing. Pure R. A ten-minute fifty-page presentation for the Board of Directors on a subject they’re only including on the agenda to fondle the genitalia of the regulatory people. Everybody pretending to listen.

So on the thirty-first slide, I checked it, he leaves out the L in PUBLIC DATA. Swear to God, the heading now reads PUBIC DATA in San Serif Streptococcus or whatever. One of those mistakes a spell-checker won’t catch. Wasn’t my slide. He must’ve added it on Sunday.

Audience NOW paying attention. Galloway chews his lip and Sestin takes a sip of water and Williams smiles and scribbles something on his notepad.1

R. goes absolutely Tartan Plaid in the face. All that sucking up and brown-nosing and he’ll forever after be the guy who gave the board of directors PUBIC DATA. He managed to finish the presentation with actually some dignity and thanked the board and there were four seconds of polite applause and that was that.

He was out Tuesday. On Wednesday AM he calls me into his office and gets bent about “your mistake” and did I do it on purpose to embarrass him?

Told him it wasn’t my slide. “Look at the time stamp on the change. Sunday. You were the only one here.”

Says that won’t cut it. I was supposed to proofread it. But I did on Saturday, I wasn’t there Sunday, and Monday AM he said he’d finished it.

R. sat there and steamed and then said he wanted me to take the blame and he’d make it right later. But just then his phone rang and he looked at the call-in number and told me to get out.

When, WHEN O Lord, is my parole hearing? Shall I beat him about the head and shoulders with a tire iron, fire his ass from a trebuchet, or what? Give me a Sign.

And so endeth the Tale of Russell Son of Jeffer.2 I was pretty far along in my FIRE modeling by then, and amassing some savings, and this was just one more of the many small incidents that motivated me to keep going.

So here’s where the requisite humblebrag starts, but truly, I wince a little when I tell it. Self-aggrandizement, and even the appearance of it, is an ugly thing.

Roughly thirty-six months later, after I’d already jumped ship and was making what let’s call “real money” in my new “real job,” I was managing a staff of six people. My God, did I try to be Russell Son of Jeffer’s opposite. Tried as best I could to train them right and to give them what they needed to get the job done and to get out of their way and to let them see and be seen.

And then this happened.

I worked downtown and there happened to be one of those corporate-type fitness centers around the corner. Several of us used to go there after work to lift. On this particular evening I was there with a direct-report and a my friend from another department. After working out I didn’t bother showering and changing afterwards; just wore my workout clothes home.

As I’m leaving, though, they’re in the showers and I overhear my direct-report say to my friend, “You know, that guy’s the best boss I ever had.” And my friend says, “Yeah, he’s a good guy.”

I don’t *think* they knew I was walking by. It wasn’t a gang shower; you had individual stalls you pulled a curtain across. I think they were being sincere. I hope so, anyway.

And if so, I guess I have Russell to thank for that.

So Russell, if you’re reading this…[author grins, readies trebuchet.]

As a guy who’s passionate about helping people escape corporate toxicity, I’d be grateful if you’d support my work by visiting my sponsors via the sidebar. Thanks!



  1. Those were likewise the real names of the three board members…which I’ve therefore changed.
  2. Some of you having read it will now say, “Well, you obviously had a bad attitude so it’s your fault, not his.” Fine. Believe what you like. You didn’t have to work for him.

Author: ER Dude

Sick of your job? After a thirteen-year career, Early Retirement Dude fled corporate America for good. You can do it too! Visit or email

21 thoughts

  1. Dude, you just made my day 🙂 After an acquisition, I am experiencing more and more of the essence of that cubicle farm job as they try to standardize us. It is good to know that there is light at the end of the tunnel. Looking forward to using this mistake in the future 🙂

  2. Ha, great story. Ironically enough my worst boss ever was during the exact same time period – 1995 – 1997. Mine never really got mad or yelled at us, he was just an immensely incompetent buffoon. You’d go in his office to ask a question and he’d be sleeping, with a bit of drool on his shirt.

    He definitely showed me what not to become in life.

  3. I had something so opposite of that I have to tell it. Early in my career I ran an engineering department at a chemical complex. We had both full time engineers and often paid intern engineering students. A couple of weeks ago one of the former interns who now lives out of state was in our town and she looked me up, 15 years later. She is at the stage of her career where she now leads an engineering department just like the one I ran. She said her goal was to do that exactly the way I did because she said everyone had so much fun working in that group and there was so much laughter and affection among the team. Wow, that made me feel so good about my 9 to 5 career, now behind me.

    1. That had to make not only your day, but your whole month. I know a couple of schoolteachers who tell stories like that one, and they always grin big-time and maybe get a little misty-eyed.

  4. Thanks for posting this ER Dude. Its been a really dark couple days at the office, I have to remind myself to be the leader I want and who to be the exact opposite of!

    I had a tandem boss I’ll forever refer to as Dumb and Dumber. Dumb was slick and incompetent, evil to the core. Dumber was genuinely a good soldier, but has now been verified to say “My job is to do exactly what Dumb tells me to do”

    I forever learned that 10s hire 10s, but 9s hire 7s who are adequate but don’t threaten their job. 7s hire 2s.

    1. > Dumb and Dumber.

      That sounds terrible. I can put up with a dumb boss as long as he/she stays out of the way, but slick, evil incompetent one…ugh. I don’t envy you that experience.

  5. We’ve all had those bosses….

    That’s why I never understood how people can say with a straight-face, that they want to work at their jobs forever. Even with a good boss, they eventually move on to other things OR that boss became a bit of a jerk due pressures from up top or a down-trending business cycles. Work environment can change fairly quickly just from a small personnel change.

    Makes me want to share my own tale of working for county government – where motivation goes to die and the staff rather spend more time to avoid work, than actually do it. I can’t wait to be FI, so that I can call out people/employer out by name like you did, without jeopardizing my current livelihood.

    1. > I can’t wait to be FI, so that I can call out people/employer out by name like you did, without jeopardizing my current livelihood.

      Keep it up, it’ll happen. 🙂

      But yeah, there’s a certain beauty to having F-U money. Funny thing is, though, that I googled him a couple of days ago and discovered that he’s still middle management at that same miserable company. I can’t imagine justice that’s any more poetic.

  6. Great story.
    It’s good to be able to grow from bad experiences. Some say you can grow more from bad experiences than good ones. My current job I have regular opportunities to grow.

  7. “Believe what you like. You didn’t have to work for him.”

    I generally nod along in agreement at your wisdom, but not this time because —Neither did you. You clearly made the decision to suck it up and take whatever this jerk dished out. You were not an indentured servant. Quitting was always an option. Perhaps not a convenient option. Perhaps it made more sense to stay there and put up with it. Or perhaps your 23-year-old self was too afraid of the unknown or felt some misplaced sense of loyalty or duty or was too invested in climbing the corporate ladder. The point is, on some level, you did a cost/benefit analysis and chose to put up with it for 3.5 years despite the cost to your physical/mental health and relationships. I am not judging you, but it seems to me that this post says more about you (or your younger self) than it does about him. I wish that formal education addressed things like “learning to manage difficult people who are in a position to make your life miserable,” but sadly we all have to figure that out on our own. Cheers.

    1. Yeah, I totally take your point. Nobody was holding a gun to my head.


      Being older and more self-aware than I was, I want to share with you that a good big whack of the reason why I put up with the situation for so long was that my parents had always put a great deal of pressure on me to take a corporate job and be successful in it. I could armchair-shrink their reasons for doing so, but set that aside for now. Subject for another column, maybe.

      It wasn’t until I was twenty-six and pretty far gone in this miserable shit that it dawned on me that I was a grown man and responsible for making my own decisions, and consequently it was long since time for me to quit living even a last vestige of my life according to their expectations. If I wanted to pursue happiness instead of $$$, then I was entitled to. So I went to them and told them how I felt about all that pressure, and I told them I wanted them to explicitly release me from any such obligation to please them…and, get this…to do so in writing. (All that corporate law I’d studied, I guess.)

      Well, they were extremely surprised to hear I felt that way. The pressure they put on me was very real, but I don’t think they considered it inappropriate or capable of causing pain. Wanting your kids to be as successful as possible is an element of love, right? But that puts a heavy slant on the definition of “success.”

      Anyway, they both wrote me extremely sweet and supportive and loving letters that I still have and treasure.

      Tough to get into that kind of thing in a tongue-in-cheek post. The more I think about it, the more I feel like I ought to write a serious and analytical post about it.

      Edit: yeah, I admit that getting them to write letters may in retrospect seem strange. At the time it was what I needed to feel healthy.

      1. Thanks for the thoughtful response. The reason that I read your blog is because much of what you write about eerily hits home with me — same expectations to be in “respectable” white collar job after much formal schooling (i.e., college, law school). Never mind that most lawyers are miserable pushing paper around and fighting over arcane minutiae. It’s a “good” job, right? I left that profession for a good 10 years to do something very grounded and alternative which I loved. My parents never conveyed any disappointment, but other people felt free to tell me that I was wasting my intelligence. Nearing 40, with no $ and no stability, I went back, but to a congenial, stable environment in a low pressure part of the country that is as good as it gets if one still has to practice law. But if I hadn’t been “encouraged” to go into a white collar profession, I would have been far happier doing something simpler. All of those years forcing myself to sit at a desk, study, take exams, work in an office, etc., when I would rather have been outside and/or doing something that actually meant something to me, took their toll. Now that I am older, I am finally at peace with working in an office environment, but when I was younger, it was torture.
        I totally get the “formal release” and letter writing thing too — my parents write me letters to convey how they feel about things. Some things just have to be put in writing to give them finality and accord them the proper gravitas.
        After I posted my first response, I thought — so now he understands the #Me Too movement. At its essence — so many angry women who felt powerless to deal with a jerk boss or similar power figure when they were younger. You didn’t suffer sexual abuse from your former boss (hopefully), but you were in the same kind of situation. When I was a young woman in my 20s and 30s, me and other women my age, just had to deal with sexual abuse and not complain because we didn’t want to appear that we couldn’t handle the job. The leering boss or the client who sat too close or the colleague who made inappropriate comments were just accepted and dealt with as best as possible. Now it’s all out in the open. Maybe this will lead to a closer examination of all types of “boss abuse.”

        1. >now he understands the #Me Too movement

          Wow. Honest to God, that thought hadn’t occurred to me. No, I didn’t suffer sexual abuse from Russell, and in fact I never have from any boss at all. Russell’s “punishment” for being a jerk was that his reputation got so bad that he started getting passed over for promotion and his underlings got promoted around him. They, of course, had long memories. Shortly after I wrote this article I looked him up and found that he’s STILL stuck in middle management in that company. One more guy in a grey job holding out for his pension.

          But at any rate, the managers you dealt with didn’t get the comeuppance they deserved. I’m guessing they never did/will. One more indicator that sexism in the workplace still isn’t dead.

          Is this a reason you’re so interested in FIRE?

          1. No. I am not interested in FIRE for myself. Very happy working for another 20 years in my current position to support, ahem, certain $ hobbies. Great boss and very little sexism. Actually quite peaceful work environment. Retiring early would make me very, very nervous. Although I would have no trouble filling my days, if I ran out of $, I would never be able to find a job with this much flexibility at this salary.

            Interesting post recently on Rockstar Finance describing one person’s take on 3 levels of FIRE — 2 of which I recall were marked by insecurity and worry about running out of money and/or requiring a spouse to continue to work or scaling back to stay within budget. No thanks. I read your blog because I am always interested in maximizing my $ and enjoy your take on certain social issues, but I don’t intend to retire early. That said, amassing enough F-U money (Collins) is a brilliant goal whether or not the need arises to actually use it.

            I’m done commenting on this post. 🙂

  8. Man this makes me wish I had journaled more regularly throughout my life. Great read btw. Working for the government is so different, on both good and bad ways.

        1. That and just being able to have the memories to look back on. As I get older I know that I don’t remember nearly as much as my childhood as I thought I would and I am afraid it will only get worse 🤔

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