50 Thoughts: A Labor Day Salute to Bad Bosses Everywhere

What better time to offer up an ode to my cross-cross applesauce of a career path than Labor Day weekend?

I touched on it here — and no lie, I’ve enjoyed the trip from college to content marketing. But I don’t know that I’ve given proper due to some of my past bosses and the lessons I learned from those experiences.

I’ve worked for, probably, an equal number of men and women. And there were good and bad experiences with both. I’ve had #metoo moments and empowering opportunities as well. Each and every one has left a mark one way or another.

Now that I half-joke about being on the back nine when it comes to the course of my career’s journey, here’s what I can tell people just starting out:

The grass isn’t necessarily greener, anywhere: The first time I learned this, I was too young to take it to heart. I left a fast food job where the boss was just kind of gross, making realllllly inappropriate comments about my body, to a telemarketing job selling globes. Yes, you read that right. I sold globes over the phone. For four hours a night, I had to hound people into buying a globe (but it lights up!) without actually seeing it.

This is where I also learned that I can take no for an answer, I am not meant for sales, and there was no way I was going to meet my quota. When asked to quit or be fired, I tucked my tail between my legs and went back to the fast food job after a month, despite the skeevy boss. Because at least there I had friends and didn’t have to push a plastic ball-shaped map on anyone.

Being a smart-ass never pays: I don’t harbor many regrets, but I have tripped over myself occasionally, and have always felt worse for it. In one particular instance, I left a job for a better-paying, smarter position in a corporate environment. I was young and pretty full of myself when, in a move meant as a joke for one of my past colleagues, I sent her a note that derided my old boss, forgetting the boss opened all the mail. Wow, that was dumb. So much for looking smarter.

Being humble is different than being humiliated: While the previous lesson served to knock me down a peg or two, deservedly, there’s nothing worse than working for someone that does not value your worth. I’ve had a number of bosses over the years, there’s only been a handful that I would aptly describe as just awful. You know it when you are in it. I’m not talking about being a teenager and upset because the pool manager won’t let you take a day off to go to Lollapalooza. I’m talking about the type that offer up general disdain toward those that don’t represent their aesthetic, openly accuse you of taking kickbacks (writers can get kickbacks?), verbally abuse you in front of others, make insane demands not just of you but the entire staff and, generally, are just batshit crazy. You can be humble all you want, at some point, you need to understand it is perfectly OK to walk away from toxic situations. Which leads me back to ...

No, really, the grass isn’t always greener: Don‘t do what I did, which was to jump from one toxic ship to another, where the “family” business really meant “No, we just want the profit tor the family. The rest of y’all can suck it.” Thankfully, older and wiser, it was easier to see when a situation wasn’t going to improve.

Don’t ever doubt there is a good fit for you somewhere: There are several places I have worked that I felt valued, empowered and appreciated — all things that I think are critical for a great career experience. And even as I am driving the beverage cart down the back nine of my career, I can still be grateful that I have a team I work with now that supports each other and offers new opportunities to learn all the time.

A sense of humor will get you everywhere: This, and all of this, every day. Work is work — if it wasn’t, it would be called something else. There are going to be days that kick your ass, and mistakes you make that’ll have you in fetal position on your living room floor at the end of the day, sucking off a bottle of Chardonnay. I’ve accidentally linked co-workers to cheesy porn sites. (The one and only time I bawled at work and my very nice boss told me anyone could have made that mistake and I couldn’t sleep until IT fixed it.) I’ve had typos in names and given people devil’s horns on the cover of a magazine. But the ability to laugh at yourself and with others in the face of defeat is the perfect balm for a broken spirit. And when you and your coworkers can catch one of your bad bosses coming to work without pants on (true story),I guarantee you and those coworkers will laugh for decades to come.

 

Day 1: 50 Days, 50 Thoughts, 50 Books. Book recommendation: The Bitch is Back

Day 2: There Aren’t Any Do-Overs, Are There? Book Recommendation: A Place for Us

Day 3: Is Pop Culture Circling the Drain? Book recommendation: Live from New York

Day 4: Perimenopause in the Age of Trump Book Recommendation: Where'd You Go, Bernadette

Day 5: Take A Knee at the Altar of Common Sense Book Recommendation: How Not to Be a Dick

Day 6: Perspective is the Gift That Keeps on Giving Book Recommendation: A Fine Balance

Day 7: The Accidental Editor Book Recommendation: Theft by Finding: Diaries (1977 - 2002)

Day 8: The First Last of the Firsts Book Recommendation: The Little Book of Hygge

Day 9: All Kinds of Tired Book Recommendation: Believer

Day 10: Overthinking is Anxiety's Bitchy Best Friend Book Recommendation: Let's Pretend This Never Happened

Day 11: Where Would You go with a Wayback Machine? Book Recommendation: A Little Life

Day 12: Fall in my Favorite Chicago

Day 13: On Having It All Book Recommendation: Lean In

Day 14: Where Were You When ... Book Recommendation:The Nix

Day 15: 5 Things to Purge Before you Turn 50 Book Recommendation: The Art of Tidying Up

Today's recommendation: Steve Jobs. Such a complicated man.

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