I Had The Worst Boss Ever! But You Won’t Believe How She Changed My Life

The Worst Boss of All Time

Back in 2008 I got the best job I’d ever had. The only problem is that it also came with the worst boss I’d ever had. She was unreasonable, critical, and heavy handed, just like most bad bosses.

But there was one trait she had that made her bad bossness so epic that it had a lasting impact on my life. This week I was lucky enough to share my story of dealing with a truly bad boss at cool story telling event called SuperThank: An Airing of grievances.

Normally at SuperThank events people tell stories of gratitude to people who have helped them but this event was all about stories of woe with gratitude at their core. So today instead of just writing a post about how you might change your life, I’m excited to share a story about one bad boss that truly changed mine.

I Had The Worst Boss Ever, But You Won’t Believe How She Changed My Life

Transcript of the story:

Tonight I’m here to tell a story about the worst boss of all time. And I know that’s a grandiose claim but I have context. You see before the time I was 28 years old I held 28 different jobs. I did everything from being a rock band roadie for the Gin Blossoms, to working in an adult book store selling sex toys, to running a sumo chicken boxing ring where rednecks paid to put on chicken costumes and oversized boxing gloves and hit each other. But I didn’t care I made money.

All of this is to say I’ve seen a lot of bosses good and bad. But this boss was truly epic.

I had her at the 2nd job I got when I moved to Portland. My first job was working as a ski instructor up, but after that I got a part time job working at this cool new music venue. Then after I’d been working there a month the manager of the venue suddenly quit, so they offered me the job and I took it with tons of gratitude.

And at first everything was awesome. I was running this cool venue, I got to work with amazing local artists, and it was amazing. It wasn’t until I’d been there a couple of weeks before I realized that I might have a truly epically bad boss.

The first hint came when one day my boss brought in a vintage lamp that she wanted to use for decoration behind this stage and she asked me to get a light bulb for it. And at first I figured sure no problem, because in my mind this was at most a 30 min task.

So I go down to the light bulb store and get a light bulb, bring it back, screw it in, and go back to my office. Then a few mins later she walks in and says, “Sam!” (I went by Sam back then) Anyway she said “Sam come here!” And led me into the venue. Then she asked me “What do you see?” And at first I was confused. Because I saw a lamp behind the stage with a light bulb and so I said “Um… I don’t know?”

She looked at me and replied, “Well the lamp is lighting up the back of the stage area and it doesn’t look very good.” “Oh ok,” I replied” I’ll go ahead an fix that. “

And so I did what most anyone would do in this situation. I went back to the store and bought a dimmer light bulb a 45 Watter. Then I came back, screwed in the light bulb, and went back to my office.

Then not 10 mins later she comes back into my office. “Sam come here!” “What do you see?” In mind I’m like, I don’t know a dimmer light bulb? But I knew I’d did something wrong and so I just say “Um I don’t know?”

“Well Sam, now you can’t see the lamp!” And then it hits me. What this woman is asking me to do is get a light bulb that lights up the lamp with out lighting up anything around it. Which is of course crazy! I mean I can do a lot of things, but I absolutely cannot control the way light interacts with other surfaces.

Anyway 6 hours and 4 trips to the light bulb shop later I finally find a light bulb that has a special cap on it that doesn’t shoot light up, but only out to the sides. To which I get very little gratitude and a well it shouldn’t have take you so long smirk. Suffice it to say that it was a very frustrating experience.

The next big indication I got that my boss was epically bad came when I had my first performance review. My boss asked to meet me during the day in the bar of the club, which to be honest is a bit creepy. Bars are supposed to be filled with people, and during the day they seem empty and sticky.

So we sit down and she’s making the Mr. Burn Teepee power hands. She looks across at me and says, “Sam we’re worried about you because you just don’t seem to be getting it.” And to be honest I was surprised. I thought I’d been doing a pretty good job all around. And so I asked her, “What kind of stuff am I not getting? What could I be doing better?”

“Well for one, you don’t turn the lights down in the bar at the right time” Now I have no idea what the deal was with this woman and lights, but apparently they are very important. And so I ask what any reasonable person would ask. I say, “Oh ok well what time should I turn the light down and what’s a good level for them to be at?”

Which is when she looks and me a says, “Oh I can’t teach you this stuff, you just have to know it.” I swear to god, that’s what she said. And then she looks at me and says, “Oh and another thing, we’re worried that you seem really stressed out.”

In my mind I’m like ‘of course I’m stressed out! You keep complaining about lights and giving me unclear instructions.’ Then she says, “Well maybe you could try being less stressed out?”

At which point I almost lost it, but then somehow it got worse, because this is when she said the piece de résistance. She said, “ You know Sam, you just got to find your Zen” For the life of me, to this day I don’t know what that means?!?

Do you want me to get a rock garden? Do you want me to take a vow of Silence? What does find my Zen mean???!!!???

But anyway of course this is just standard boss stuff. It wasn’t until the last instance that I knew he badness was truly epic.

One night one of my favorite artists came into the venue. It was this guy named M. Doughty, he was the lead singer of Soul Coughing for a while and I had been a fan for years. And it was really cool because when you get to host an artist like this it’s super cool because you get to interact with them, not like a fan, but like an equal. And he was really nice and played a great show.

Then after the show my boss came up and wanted to look over the closing sheet for the show, which is how we paid the bands. And so she looks over the sheet, says it looks good, prints it out, and leaves.

But then as I’m sitting there and looking at the numbers I realize that something isn’t right. I realize that while she was ‘looking at the numbers’ what she had really done was change the number of tickets sold on the sheet so that we were going to underpay this guy but like five hundred dollars.

And while I wish I could stand here and tell you that I put on my armor and did battle with the dragon, I was scared. My boss was one of the most powerful women in the music business in Portland and I didn’t know what to do. And so I swallowed my pride, and when he came up to get paid I looked him in the eye and stole five hundred dollars from him. Which sucked! But don’t convict me yet.

Because this decision haunted me and so two days later I went to her house and I confronted her. I told her that what we had done was wrong. To which I got a lot of excuses and justifications and there, there, dear this is how the music business is really run.

To which I replied, “I don’t care if that’s how you do business, that’s not how I do business.” “And if you ever do that again I’ll walk out the venue right then!”

To which she then started crying, and in my head I was like “Bulllllllshit!” They were crocodile tears if I’ve ever seen them. But I’m a guy and weak when women cry and so I comforted her and left it at that.

Of course, I’m sure it will come to no surprise to anyone that about a month later I was fired for, ‘not having enough booking experience.’ And for a long time I was bitter about this.

Here I had done the right thing, stood up for honesty, and still I had lost my job. But looking back on it now I’m very grateful to this woman. Because you see I’d been living my life in a moral gray area for a long time. And I’d been giving up my integrity in small ways. But when I was confronted with someone with so little integrity it made me realize what I didn’t want to become.

And so I ended up leaving the music business and moving in to a Zen monastery and now I help people live lives that are aligned with there values and what’s truly important to them. And in some ways it’s all thanks to this woman.

Which is why I’d like to say, Thank You, for being a crappy boss, and so dishonest, because now I can look at my self in the mirror and be proud of the man I am, because you showed me who I didn’t want to become.


2 thoughts on “I Had The Worst Boss Ever! But You Won’t Believe How She Changed My Life

  1. Such a great story and fantastic job telling it Toku!
    The lightbulb bit reminded me of Elaine on Seinfeld trying to buy the right socks for Mr. Pitt.

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