Writer’s Workshop: The Boss from Hell
by Jenners • 06/16/2010 • Life, Writers Workshop • 35 Comments
It’s Writer’s Workshop time again!Join the fun over at Mama’s Losin’ It
Back before I landed the high-paying, do-nothing job of Stay-At-Home Mom (heavy sarcasm here), I worked professionally for 15 years. During that time, I was often privileged (more sarcasm) to work for some very unique individuals. Let me tell you a bit about one of them today. I call him “The Boss From Hell.”
First a little back story. At one point in my career, I toyed with the idea of running a business of my own. So I accepted a job working for the owner of a small marketing firm–thinking it would be a good opportunity to see what went into the running of a small business and hoping to learn some valuable lessons. (This firm was so small that the only employees were him and me.) I learned quite a bit during my time there; unfortunately, it had nothing to do with marketing or successful management of a small business. Rather, I learned about fraud, theft, and what self-delusion looks like up close. Here are some highlights of my time spent there.
- My very first day of work, I was handed a shoebox overflowing with bills, checks, receipts, and bank statements and told to get the company’s accounts in order. Apparently, this “shove it in a shoebox” method had been the company’s accounting system since the previous employee had quit 4 months before. Once I finally sorted everything out, I discovered that the firm had a total of $145 in the bank. With a sinking feeling in my stomach, I gave my report to my boss, who blithely said: “Don’t worry about it, I’ll move some stuff around. You’ll get paid.” To his credit, none of my paychecks ever bounced, but I never fully understood how he pulled it off. After a while, I didn’t want to know.
- One day, my boss was complaining about his camera equipment and how he wanted to upgrade his lenses and base camera. Coincidentally, the very next week, the office was burglarized and his camera equipment was stolen. The (very neat and tidy) burglars had carefully broken a window to gain entrance (a window that would be replaced by the company from whom my boss leased the office) and moved things askew … leaving almost everything important behind … except for the camera equipment, which was “stolen” from my boss’s office. Naturally, the camera equipment was covered by insurance, and my boss was able to replace it with the very same equipment he had talked about wanting the previous week! “How fortuitous,” I thought, “And very, very, very suspicious.”
- This guy was a crank of the highest order. He was forever dictating epic letters of complaint to the myriad of people who “crossed” him in his everyday life. One time he had a bad burger at Burger King. Not content to complain at the counter or just throw it in the trash and move on (like a NORMAL person), this guy spent WEEKS dictating increasingly angry letters to the CEO of the Burger King Corporation. Whenever someone crossed him–and it didn’t take much–I would gird myself for weeks of angry letters that would steadily grow longer and angrier … until they were dropped to begin another campaign against a new enemy.
- It didn’t take me long to realize the guy was a master bullsh*t artist. Whenever a new client would come in, I felt like slipping them a note and telling them to run for the hills. My boss was a master of seeming like he knew what he was doing, but he was a huckster and a liar. He once got a client who wanted some marketing research conducted for a new business and wanted help picking a location. There was this new, very expensive software that my boss sold the client on … software that would permit the user to assess various business locations relative to competitors, traffic flow and so forth. My boss convinced the client that this software was the key to his future success, along with my boss’s “years” of marketing expertise to analyze the data. The only catch was that my boss didn’t actually own this software … nor had he ever used it. Once he got the contract, I was told to get a trial version of the software for 30 days, learn how to use it, generate the information the client needed, and return the software before the trial period was up. This was the company’s typical modus operandi the whole time I was there.
- One of my boss’s hobbies was playing in a Grateful Dead cover band. I spent countless hours printing out postcards promoting the shows and designing tie-dye t-shirts they could sell at their (infrequent) shows. During my time at the company, Jerry Garcia passed away, and–I kid you not–my boss sent a letter to the manager of the band offering his services to replace Mr. Garcia. It was at that moment I knew he was truly off his rocker and began contemplating my exit.
Believe it or not, I worked for this guy for a year!!! Part of the reason I stayed so long was that I really needed the job and wasn’t in a good place personally to quit. Another part of the reason was that working there was like watching a car accident … I couldn’t turn away. It finally dawned on me that this guy had some serious mental issues, and when I finally decided to leave, I felt like I had to get out of there RIGHT NOW. Being professional, I gave him two weeks notice … and left without having found another job. Once I decided to leave, it was even more unbearable than ever to work there. When I left, I could barely look at him or speak to him. The day I walked out of that office for the last time, I felt a huge weight lift off my shoulders and I could breathe easily for the first time in a year. Personally, I’m amazed I didn’t develop an ulcer during my time there.
For about 7 years afterwards, he would occasionally find me and call me and beg me to come back. My standard response was always: “I would never ever in a million years work for you again. I would rather go hungry than work for you.” To this day, I’m amazed I never got an angry letter from him.
Still regretting my brief sojourn in Crazyville Marketing Firm*,
* Not the actual name of the firm … but it might as well have been.


Awesome. How did I not know about this?
LOL! I'm amazed you stayed so long! Amazing! And even more amazing that you never received a letter, lol. I worked for a lawyer who seemed much like this, lol.
Wow, I thought I had a boss from hell! It's amazing that you lasted a year in that job. I did however had a male supervisor whose coffee mug had a picture of a naked couple in a compromising position. He loved drinking it in front of me, I was so naive back then- I should have reported him to HR.
Wow. My boss just stole my ideas and took credit for them. I feel sorta lucky. Maybe I'll send him a "You're a great boss" card next boss's day.
I told my ex-boss that I would rather go hungry than work for him again – and then I proved myself right. Thanks for this great post.
All the best, Boonsong
Glad that you survived that job. Amazing to think that he could keep any kind of business running with that attitude and personality!
Wow and I thought it was bad when I worked for the Greek mafia.. At least then I only got hit on and offered money by a lot of old guys.
Oh. WOW. I thought I had the crazy boss from hell in the past. You definitely win in this category.
Wow. I can't believe how this guy could have kept his business running the way it did! That's just crazy!
ha! he sounds like quite a character….
I absolutely loved that he tried to replace Jerry Garcia. A little full of himself, no? what a nightmare. bless your heart for lasting a whole year. i would have made it about a month, tops.
I wonder what ever happened to that guy, if he's still in business or what?
Oh God, the stories I could tell about having worked for the Devil herself. But because I worked there as recently as two years ago, I can't yet. But suffice it to say that one of my coworkers sued her and the company we worked for shortly after I left…and he won. I'm just glad I made it outta there before the physical violence began. Thanks for the laugh Jenners!
My bosses aren't mean or crazy…but I do relate to the shoebox way of handling things. They to this day would like me to literally put paperwork in a cut up falling apart old cardboard box that has been there for 23+ years….and when I arrived…2 years ago…I had 2 years of back taxes to deal with. Ugh!! Because they didn't realize the secretary before wasn't doing them???
Oh Lord! And I thought my old boss was the evil hahaha. Oh btw, I only lasted 3 months in my last job because I will never sell my soul to satan hahaha. Great writing btw!
That monkey story is taking some bizarre twists!
As for that job, good experience to look back on, but terrible while undergoing it.
A Grateful Dead cover band? Classy. Just think if he had replaced Jerry you could have been his personal assistant.
I have found that the two-man operations are the most likely environments for this kind of shenanigans.
He sounds like a real tool.
Stopping by from Mama Kat's.
I'm seriously learning that the crazy is more pervasive than the normal.
OMG! Totally sounds like you worked at Crazy-Town. Big time. Thanks for the laugh, tho. Just what I needed for a tired me who has been up too early this AM!
That guy sounds like all kinds of crazy! I think after the "robbery" I would have made an anonymous phone call to the insurance company!!! Found you through Mama Kats!
wow what a boss from Hell and you only worked there for a year..it must have been a vert long year for you. Glad that you got paid.LOL
I can't believer that guy never went to jail! What a wack job!
Gee, sounds like my ex. Was he short, Bi-polar, compulsive liar with a Napolean complex??
YIKES It's a good thing you got out of there, I'm amazed he hasn't been either shot or jailed!
And I almost fell over with laughter about the Grateful Dead…I had a friend who almost lost her mind when Jerry died.
Glad you got out while you could. Does it make you think twice whenever you want to write a complaint letter?
I'm really shocked that you never got a letter. What a whack!
Holy Crap!
That is all I can really say.
Sounds like a terrible job and a very suspicious company indeed. I'm surprised you lasted there a year.
I'm doing the happy reunion prompt tomorrow.
What a freakin' nut! The part about him contacting the Grateful Dead manager is just the kicker. Wow! I wonder if he was even talented at all.
Wow. That is some serious crazy right there. I'm glad you got out SAFELY!
And I'm writing about the same prompt tomorrow, but it a TOTALLY different vein.
It is only when nightmare part of your life is finally over that you can look back and marvel at how you survived it for so long. A terrible experience but at the same time you learnt a lot from it – about how NOT to run your own business
I think I worked for the same guy…….except he was a big fat Vet who farted, belched and sang Sinatra during dog circumcisions……..
I worked for someone like that one time. I didn't realize how awful that job was until I left it.
Holy crapola!
I cannot believe you lasted a year. And you didn't even get an ucler? Major kudos.
Sounds like one scary year to me.
I think I must have been the one that replaced you….