I was asked recently about the worst job I ever had.


I knew immediately which job earned that label in my life.

It wasn’t the data entry job on the ancient software that took 20 seconds to register each entry.

Though I nearly died from boredom.

And it wasn’t the research assistant job at a hospital, which turned out to be another boring data entry job in disguise. (I quit after 3 days).


It also wasn’t teaching nursery school when I was 23, even though I caught every single bug the kids brought in, and was sick more than I was well the entire year.

They were pretty awful in their own way, but none of those compares with the retail job I had right after graduating high school.

Dealing with rude, privileged customers in the high-end shopping mall was its own brand of hell.

But the real reason this job was the worst boils down to one thing: my manager, Karen.

My gut still clenches when I think about how it felt to walk into work each day, wondering what kind of mood I would find her in.

Going to work with her was like playing a game of emotional Russian Roulette.

Sometimes she was perfectly friendly…

Other times, she seemed to take great pleasure in shaming me and making me suffer.

Was she cranky because of something going on in her life?

She was probably about the age I am now, so perhaps she resented me my youth?

Whatever the reason for her nastiness, I remember sweat dripping down my back as she firehosed me with the complexities of the register exactly ONCE before quizzing me.

“Um… Is this right?” I asked, my gut clenching with anxiety.

Contempt seemed to drip from her stony glare. She raised her eyebrows and blinked at me, waiting me out.

She blinked again, then let out a long, eye-rolling “Nooooooo….”

The kind of “no” you’d say to an idiot.

Which, of course, only made me more nervous. My brain completely froze up.

Finally, she rolled her eyes, heaved a big sigh, and showed me again, but her tone made it very clear that this whole endeavor was beneath her.

That I was beneath her.

This was just one example of many in which Karen did her best to shame me.

No wonder I dreaded going to work.

Looking back, I’m amazed I stayed at that job at all, but I was too young and inexperienced to know better.

I was so happy on the days when the assistant manager, Penny, was in charge, and Karen wasn’t there. I felt like I could breathe.

Penny was kind, and fun.

Where Karen was a powder keg, waiting to go off in a shame explosion, Penny was a sanctuary.

Karen tied my stomach up in knots. Penny made me feel safe.

If I didn’t understand something, she didn’t shame me for it. She’d happily explain it again, because she wanted to help me learn.

That horrible job was a learning experience, though.

I learned from Karen the kind of leader I NEVER wanted to be.

A leader who tears you down, shames you, or undermines you, in order to make herself look or feel better is a toxic leader.

Penny, on the other hand, was always doing her best to make others look good.

Many years after my experiences working retail, I would learn that “Make your partner look amazing” is a foundational principle in the world of improv.

This makes so much sense if you think about it: improv performers have to work together to create something brand new on the spur of the moment in a high stakes situation to please an audience.

If anyone on the team is just out for themselves, things could get stalled or ugly really fast.

But if everyone is focused on supporting each other, and making each other look amazing, it means each person can take risks, trusting that they’ll be supported by their teammates.

And THAT is the ultimate in teamwork.

So let me ask YOU: Which kind of leader to you see more of in your workplace — Karen, or Penny?

And even more important, what does your team do to make each other look amazing? Do your leaders do their best to make others look good?

If you don’t have clear answers to those questions, let’s chat about how I can help, so your employees don’t tell their own stories about the “Karens” in your organization.

I love using play to help people-first teams and organizations strengthen connection, communication, collaboration, clarity, and creativity. If you or your team could use help increasing your impact, and getting there faster and more joyfully…

click here to reach me via my contact form and let’s schedule a 10-minute clarity call, so I can learn more about you/your team.

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