A Love Letter to All of my Horrible Bosses

So I’m sitting at my desk typing up a memo, when all of a sudden I hear my boss’s office door swing open behind me. As I turn around to see what’s going on, I instinctively duck to avoid the object flying at my head. A box of pens hits the wall above my desk and breaks open, spraying 12 brand new blue Papermate medium ballpoints in all directions.

My boss had just thrown a box of pens at me.

“What the hell?” I exclaimed.

My boss picks up one of the scattered pens from my desk and shoves it in my face.

“What does this say?” she asks.


“No, next to that, you idiot.”

“Medium point.”

“And what kind of pen do I use?”

“Fine point.”

“So, if I always use a fine point pen, then why the hell am I standing here holding a medium point?”

“Because the office supplies guy must have sent up the wrong ones…”

“I don’t want to hear any of your excuses. You always have an excuse for everything. Just pick up all of these pens, put them back in the box, and exchange them for the right ones. If you can’t even handle something as simple as ordering a box of pens, maybe you better start looking for another job!”

Office door slams. End of scene. And cut.

No, that was not a scene from a movie. That was a scene from early in my career.

And while it happened a long time ago and I can laugh about it now, the pain and humiliation of working for a horrible boss like that still lingers after all these years.

I was working as an administrative assistant at the time for one of the major TV networks out in Hollywood. I won’t say which one, but it had a “C,” a “B,” and an “S” in its name. And my boss was an absolutely insane lunatic. Condescending, sarcastic, abusive, overly emotional, always in panic mode, and, in some ways worst of all, completely incompetent. Add it all up and that’s a deadly combination.

Getting a box of pens thrown at my head was just the tip of the iceberg when thinking back on the most obnoxious things she did to me. Looking back now at the “Abuse Log” I kept at the time (I’m not kidding, I still have it), it’s unbelievable how much I put up with while working for her. The greatest hits include:

  • Referring to me as her “boy,” as in (and I quote), “I’ll have my boy deliver a copy of that script to you.” Bear in mind that I was 29 years old at the time, and 6’4” tall.
  • Frisbee-ing a copy of a script at the back of my knees while I was walking out the door of her office, saying, “Hey, throw this out for me,” even though she has a nice, blue paper recycling bin right next to her desk.
  • Making me stay til 5pm on a Friday of a three-day holiday weekend when everyone else – by official company memo – was allowed to leave at 1:00pm, with their manager’s approval. As you can guess, she didn’t approve. I had to stay the whole time “in case any important calls came in.” None did. And did I mention that she left at one? She did.

Allow me to go ahead and answer some of the questions you probably have after reading these tales of horror:

Q: Why did you put up with all of this?

A: Because my career dream was to someday work for a TV network and I finally made it in! I didn’t quite expect it to be like that. And always hoped it would get better. It didn’t.

Q: How did you allow yourself to be treated that way for almost a year? Didn’t you have any self-confidence, self-respect, or self-esteem?

A: I did when I first got there. But my boss quickly started chipping away at it one day at a time until there wasn’t much left.

Q: Did you ever just try sitting down and talking with her about it?

A: Yes, I did. I finally got up the courage and calmly went into her office one day and said, “I feel like you are always yelling at me and that whatever I do is wrong. I want to do a good job and I’m happy to do things however you want them done. So if you just take the time to explain things a little more clearly and talk to me a little more calmly, I’ll do a better job and we’ll both be happier.”

Q: That sounded great! So what did she say?

A: She said, “Listen. I spent many years being treated like crap before I got this job. Now it’s your turn. And if you don’t like it, I can call down to HR right now and have them find a replacement for you by tomorrow. Now get back to work.”

Q: She reminds me a little of Kevin Spacey in “Swimming With Sharks.”

A: You mean in the classic “Sweet and Low” scene?

Q: Yeah, but even more in the…

A: “…My Pencils are More Important Than You” scene”!

Q: That’s the one! Was she the only horrible manager you’ve ever had, or were there others?

A: Unfortunately, there were others. Way too many others. There are a lot of them out there. They’re called Bossholes.

Q: That’s a good one. So many people have Bosshole managers. Is there anything you can do if you have a boss like that?

A: You can anonymously leave a copy of this book on their desk and hope they can take a hint. And that they don’t figure out who left it there.

Q: Will that really work?

A: Probably not. Unfortunately, many of the ones who are Bossholes think they’re not. And the others actually enjoy it. I’ve learned the hard way that there is no cure for this condition, except leaving it.

Q: As bad as it was to work for all these awful jerks, were there any benefits?

A: Actually, yes – definitely! Working for some of the worst bosses to ever set foot on this planet taught me more about management and leadership than any business book or MBA ever could. They taught me by showing me how NOT to manage people. And for that I thank them. The key is to take note of everything they did wrong and do the exact opposite!

Q: Lastly, if you were to send a Valentine’s Day card to all of the horrible bosses you’ve had, what would you write?

A: I’d say:

Dear Horrible Boss:

Thank you for teaching me how NOT to manage and lead people. Thank you for showing me how to destroy people’s morale and confidence. Thank you for showing me how to demotivate and un-inspire. Working for awful bosses like you left me with so many great horror stories to tell, and motivated me to go out and learn more about management and leadership, ultimately leading me to discover my true calling as a management consultant, trainer, and executive coach. I knew there had to be a better way, and I found it. Were it not for you, I would not be doing what I do for a living today. And I would not have made my personal mission: “Helping to make the world a better place, one manager at a time.”

So, for that I thank you and wish you a happy Valentine’s Day.

Yours truly,


EXTRA: Speaking of Valentine’s Day and bad bosses, here’s my short list of non-romantic Valentine’s Day movie suggestions for you to watch in celebration of bad bosses everywhere:

  • Office Space (see Gary Cole)
  • Swimming With Sharks (see Kevin Spacey)
  • Horrible Bosses (yes, Kevin Spacey again…along with Jennifer Aniston & Colin Farrell)
  • Glengarry Glen Ross (see Alec Baldwin)
  • Wall Street (see Michael Douglas)
  • The Devil Wears Prada (see Meryl Streep)
  • Working Girl (see Sigourney Weaver)
  • The 40-Year-Old Virgin (see Jane Lynch)

P.S. There’s a lot more where these came from! So tell us: who are some of YOUR favorite bad movie bosses of all-time?

About this Gun

Todd Cherches

Todd Cherches

is the co-founder and CEO of BigBlueGumball, an NYC-based management and leadership consulting, training, and executive coaching firm. With their motto "We make training entertaining" as their foundation, Todd and his brother Steve are on a mission to make the world a better place by ridding the planet of bad bosses -- and painful PowerPoint -- through their cutting-edge, visual thinking-based approach. Follow @toddcherches.