Why "Should" Is a Jerk

And what to do when your writing sticks out

Read time: 5 minutes

Welcome new subscribers!

I’m grateful you’re here, and hope you like story—because that’s the star I’m drifting toward after two decades writing.

Oddly, not fiction. Not the fantasy I grew up reading, that’s still home.

I feel like I should write those things, having read them forever, but as a writer they don’t pull me—and it’s important to be real with ourselves about “should.”

Because “should” is a jerk.

It’s just another way of judging yourself. Your writing, your creative endeavors. You don’t pursue what you could do because should gets in the way.

It’s a theme this week if you look closely.

  • Photo inspiration

  • What to do when your writing has a bit that sticks out

  • Book Stop: Station Eleven

  • A story (sort of) about beer, theatre, and football: How a Bud Light Commercial Reconnected Me With Courage

We spend a lot of time running from one thing to the next. Don’t forget to create space for stories to happen.

Next week, I’ll share an idea called “Homework For Life” that’s made a huge difference for me.

Bringing you a bit more Austin Kleon this week. I have to, after his latest newsletter.

Back in college, my writing professor, Cathy Smith Bowers, told us about a poem she tried to write once. How she fought like heck with it.

The problem was that her father wouldn’t stay out of it.

No matter what she did, he crab-walked back in. Eventually, she realized the poem was about him, and that her resistance to the problem was the actual problem.

It was a funny story then. Twenty-some years and lots of writing later, it’s funnier. Austin Kleon wraps the idea in his visual genius below.

Lesson: sometimes the writing knows what it’s about better than you do.

Do you have any books you re-read? Stories you dive back into after years, that never wear out?

Station Eleven is like that, for me.

Its action is subdued: it’s a post-pandemic world (the book came out years before COVID) and much of the conflict happens in the past. But there’s a poetry to the language, and a surrealism in how the plot comes together that grabs me every time.

Pay attention to the use of a list here—it’s a device often used in poetry that works wonders to tally up the losses of an ended world. And line length: that long list, followed by a shorter sentence, and then a closer of just three words. Just masterful stuff.

Note: Station Eleven was adapted by HBO to a mini-series which, unusually, is not only a bit different to the book but wonderful in its own right.

No more internet. No more social media, no more scrolling through litanies of dreams and nervous hopes and photographs of lunches, cries for help and expressions of contentment and relationship-status updates with heart icons whole or broken, plans to meet up later, please, complaints, desires, pictures of babies dressed as bears or peppers for Halloween. No more reading and commenting on the lives of others, and in so doing, feeling slightly less alone in the room. No more avatars.

Emily St. John Mandel, Station Eleven

We think only the things other people write are capital-S Story. That the things we can offer the world are lesser, somehow.

It’s so easy to look just at the good we see in others—and forget to be the good we already are.

This is a story about that feeling.

How a Bud Light Commercial Reconnected Me With Courage

I time-traveled twenty years and back once, on a bright October Saturday.

It was shorts weather and the sun was generous and warm — you could almost have believed it was spring.

I could almost have believed I was still 17. It felt so close.

Reunion day

It was my 20th high school reunion and we had an afternoon school tour planned, followed by an expensive, late-evening group dinner. I didn’t care a thing for the dinner and didn’t go — too much expense, too much “group.”

The tour was the magic, for me.

See, I loved high school. I know that’s unusual. But I did, and my memories of the place sometimes feel more alive than my memories of the people. I’m aware this could sound antisocial (warning, introvert ahead!).

But people are slippery to remember. Places mostly stay put.

At the school, there was so much familiar: the painted mascot mural, the lockers, the lunchrooms, the science building with the classroom where I could still hear Mr. Holder’s corny chemistry puns.

That yardstick he’d slap on a lab desk to keep us awake.

Damned thing sounded like a firecracker.

The whiffs of tempera paint and gesso in the art room where Mr. Baucom gave me and my poor painting the advice that “everything goes through a vomit stage.”

The gym. Its echoes. Our shoes on the basketball court.

The locker room, still smelling like practice and rivalries.

The Auditorium

Our last stop was the auditorium. There, too, were still-familiar things: folding wooden seats, heavy red doors, stage patina. Inside it still smelled like old playbills.

I was never a theatre kid, but my friends who were sat on the edge of the stage together, recalling memories and names. John Hoogenakker’s name was one of them. I remembered John, who’d been two years ahead of us.

My abiding memories from high school include sitting in exactly that auditorium, in exactly one of those curved wooden seats, watching him perform in a student production. I think it might have been “Runaways.” There in the dark, I looked up at the stage and felt inspired — and envious.

Because even in the minefield of adolescence, he’d been so clearly in his element. He’d had passion.

He’d known what he wanted to do and was up there, doing it. Sharing it.

After the reunion I got curious about him and turned to Google, to find out he was still acting — and successful. Seeing that made me feel happy; age wears away some of envy’s sharp edges.


Weeks after the reunion, on another weekend afternoon, I was reading while the Dallas Cowboys were on TV when the sound of medieval music got my attention. It’s not a staple of NFL halftimes, you know.

And I don’t make football a habit. It’s nice in the background, or to watch the big games on occasion. The playoffs, for example.

Ah. Beer commercial, I thought, looking up at the screen. But in a castle?


It was a part of Bud Light’s “Dilly, Dilly” campaign. I hadn’t seen the ad before and as a non-beer-drinker, the quirkiness hooked me. But then the camera cut to the king and queen, and I saw him.

The Dilly Dilly King. It was John Hoogenakker. Amazing.


I couldn’t stop thinking about it . . .

Finish reading HERE

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