| Aug 17, 2022

Open Letter to Fun Bosses: Your Fun May Not Be Our Fun

There’s a right way to do fun, and then there’s what usually happens.

Dear Bosses,

Being a boss is tough. At least, it seems like it would be tough. I have never been a boss, but as a longtime boss-haver, I appreciate what you are trying to do. Your bosshood gives you power, which you must exercise carefully. That’s a delicate balancing act!

One strategy I have seen bosses turn to repeatedly — especially when they need to drop beans on the “morale” side of the scale — is encouraging and instigating fun. Sometimes it works like a charm. 

Other times, not so much.

I have never voluntarily notified my bosses when it’s not working, but as an observant worker bee, I have some valuable insights. Let me tell you three short stories about fun at work, some of them true.

Blindsided by Richmeister

I’m standing at the copy machine in the break room at a new job. The boss walks in. He considers himself a fun boss. The copy machine hums and shucks rhythmically. The boss smirks.

“Make-in cop-eeez,” he sing-song drones in the Rob Schneider “Richmeister” voice.

I freeze. Oh no. Oh, please, no.

I make eye contact. He repeats himself, nodding with the cadence of the catchphrase. 

Despite recognizing the reference (it’s from a “Saturday Night Live” sketch that aired when I was five but I caught during a rerun), blindsiding me with Rob Schneider in the break room is somehow not funny to me. 

I smile and mumble something slick like, “Yeah, the copy guy.” An unconvincing performance, I’m sure.

The moral of the story? Your fun may not be their fun.

Sometimes it’s just a matter of taste. 

Other times, the boss-worker power imbalance kills our fun. A boss can assess me, reprimand me, or ruin my life on a whim. I need to trust a person like that before I can loosen up and have any genuine fun around them. Richmeister and I did not have that trust, yet.

Aunt Polly’s Fence

This did not happen. I’m paraphrasing chapter 2 of Mark Twain’s The Adventures of Tom Sawyer.

It’s the 1840s, summertime in Missouri. Tom steps up to Aunt Polly’s fence, dirt and rocks of the road hot to the touch under his leathery feet. He’s holding a pail of whitewash and a brush. Against his will, Tom starts brushing. And sweating. The fence is long. 

But then, in a moment of inspiration, he pretends to have fun.

The neighborhood boys see Tom “enjoying” himself, appearing to take great artistic satisfaction in the work. Tom lies about how gratifying it is to whitewash a fence. They want to try it for themselves. Tom sells them the opportunity to do so. They pay him in boyhood treasures: An apple, a tin soldier, a dead rat, and a string to swing it with.

Tom retires to the shade to supervise.

Twain’s narrator expresses the moral of this story: 

“If [Tom] had been a great and wise philosopher, like the writer of this book, he would now have comprehended that Work consists of whatever a body is obliged to do, and that Play consists of whatever a body is not obliged to do. And this would help him to understand why constructing artificial flowers or performing on a treadmill is work, while rolling ten-pins or climbing Mont Blanc is only amusement.”

He’s right.

For us, this means that otherwise fun activities may become work when the boss gets involved. When I have to laugh at a joke because my boss wants me to, that’s work. When I have to go to a picnic because my boss wants me to, that’s work.

When a fun boss — big guy, college football player — notices that I’m finished with a task in the conference room, and smirking, holds the door closed so that I can’t get out, and I have to decide how I am supposed to play this “game,” that’s work.

I’m not saying that work is never fun. But work is, famously, less fun than play. That’s OK. I don’t come to work for the fun of it, anyway.

Patty’s Eucharist

Let’s begin with the moral this time. You don’t have to initiate fun to cultivate joy.

Here’s the scene: I’m a Master’s student in a university English department. If you have ever been involved with a graduate school, you know that labor practices in that setting are often bad.

Lucky me, at least I had a great boss.

We will call her “Patty” because that’s her name. Patty is the professor who oversees the English composition program, which puts her in charge of dozens of graduate students and untenured faculty members who teach those classes.

Patty constantly strives to give us the tools we need to do our best work. She fights for us. She’s honest. Most remarkably, she trusts us. We respect and adore Patty.

But I wouldn’t call Patty fun.

In part because of Patty’s leadership, I enjoy my job. I enjoy it so much that I decide to go for a PhD. (This turns out to be a huge mistake, but that’s not Patty’s fault.)

My girlfriend and I (we’re married now!) have both worked for Patty for several years. After we successfully apply to PhD programs, she invites us out for a farewell dinner. We have no obligation to go, so it’s not work.

We meet at a dimly lit, independently owned restaurant. After dinner, Patty orders herself a digestif. I, a bumpkin, have no idea what a digestif is. Patty offers to share it with the rest of us. To this day, I still don’t know whether this was intended as a performative joke, but if it was, hats off to you, Patty. 

We pass the itty bitty cup around the table and take turns tasting the ounce of sweet liquor, sipping like hummingbirds except without the tongue. I feel a little silly. But it’s good.

What a fun evening.

Dale Grauman

Opinion Contributor, Strixus

Dale is a writer and student living outside Chicago. Once an English teacher, he has recently begun a new journey in natural resources and environmental science. view profile


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