OK, who here has a terrible boss?

Today, I want to talk about them, because if you have one, you think about them every single day you go to work.

What makes a bad boss?

Maybe they’re overbearing and rude. Maybe they dismiss every idea you have.

Or maybe they’re the spineless boss that meekly says, “Sorry, I can’t give you a raise…that’s all the wiggle room I have…” If he can’t stand up for himself, how will he ever stand up for you?

Just try to imagine the look on someone’s face on a Sunday afternoon as they think about going back to work for their boss the next day. I can see them in my mind, drinking at a Sunday brunch and complaining about something their boss did. Their friends, who’ve heard this 50 times, roll their eyes and try to change the subject. It’s hilarious…as long as it’s someone else. That last line is also my life philosophy.

A bad boss means that every day — for 8+ hours/day, 2,000+ hours/year — some of us are walking around on pins and needles, dreading seeing our boss. It’s like walking around with a 50lb weight on your shoulders that you can’t take off…because it’s also secretly keeping you alive (aka giving you a paycheck).

Now here’s the interesting part.

Of all the people who have bad bosses, how many leave to find another job? Maybe 1 in 100? Why does everyone else stay? You’re not a slave. You can leave whenever you want.

There’s a lot of boo-hoo, woe-is-me, waa-the-economy-is-so-bad. Actually, no, it’s not. Top performers can get a job in days in this economy. (In fact, we’re hiring for lots of positions.)

If you have a bad boss, it’s not your fault — but it is your responsibility to do something about it. Once you’ve admitted that your boss is bad and you want out, you have 3 options:

  1. Try to change your boss (unlikely)
  2. Find another job (hmm, if only there were some way to find your Dream Job)
  3. Do nothing and complain (I’ll see you in hell)

It’s just like being in a bad relationship. You can blame it on them all you want…but ultimately, it’s your decision to stay or leave.

One of the skills that few people talk about is knowing when to quit. Seth Godin writes about this in The Dip, where he says:

“…What really sets superstars apart from everyone else is the ability to escape dead ends quickly, while staying focused and motivated when it really counts.

Winners quit fast, quit often, and quit without guilt — until they commit to beating the right Dip for the right reasons.”

For all the people who complain about a bad boss, how many of them spotted the telltale signs — years ago? And did nothing?

Ultimately, it comes down to this: You don’t have to accept a bad boss. It’s not “normal” or part of paying your dues. Nobody should have to sigh and say, “Another Monday…back to the grind.”

I actually think a lot of us are in this situation — a lot more than we want to admit. So I want open up the conversation around this.

What’s your boss horror story?

Do you have a bad boss? Did you finally escape? I want you to share your boss horror stories in the comments.

Beyond pure curiosity, I want to start a conversation about this. What made them so bad? And as you write this, notice how it makes you feel.

Share your boss horror story in the comments below. Don’t worry about naming any names or revealing yourself. You can keep it completely anonymous.

This isn’t just for employees, either. If you’ve been a boss, flip it. What’s your employee horror story?

I’m excited to read yours.

P.S. It’s fun to commiserate about horrible bosses. But I’m more interested in understanding what we can do about it.

Recently, I heard one of the most fascinating boss horror stories of all time. It came from a guest in my Brain Trust program, Kevin Hillstrom. Today, Kevin is the CEO of a successful business, MineThatData (and an amazing strategist). But early in his career, he was an awkward junior analyst — with ZERO communication and business skills.

One day, he was sitting in his cubicle and overheard his boss saying horrible things about him behind closed doors.

Instead of complaining about how bad his boss was, he took a totally different perspective — one that changed his entire career.

Check out Kevin’s story here:


The full interview is available to members of my Brain Trust community. If you’d like to learn more about it, simply enter your name and email below and I’ll give you exclusive updates the next time the program opens.

Join the waitlist and learn more about Brain Trust

P.P.S. I’m flying my entire company to Portland, OR, next week for our annual company meetup. If you’ll be in the Portland area on Friday, February 12, we’re hosting a casual, happy hour event with my team and the IWT Community. Space will be limited — click here for details and to reserve your spot.

Dealing with a bad boss: Nutty horror stories is a post from: I Will Teach You To Be Rich.