Design Better

Design Better

The Roundup: Creative teams need skeptics, sitting with the note you hate, and knowing when to break the rules

Things we learned from Stranger Things writer Paul Dichter

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Eli Woolery
Apr 24, 2026
∙ Paid

Yes, I’m a Stranger Things nerd. As I mentioned in our recent interview with Stranger Things writer Paul Dichter, I watched the series myself, and then with my daughter when she was old enough, and most recently with my son. If you need any further evidence, just check out the birthday card my son created for my 50th birthday this year, which features a demogorgon and mind flayer, two of the shows iconic creatures.

The birthday card my son made me…and on the inside, among other nice things, it says “you look young for 50” 😅

And if you can get past our nerd factor, Aarron and I learned quite a few things from our interview with Paul, that apply not only to film and television writing, but to the collaborative efforts of any design or creative team out there.


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Every Creative Team Needs Its Skeptics

Paul spent a decade in a small, tight-knit writers’ room — rarely more than six people around a table, in rented houses, with whiteboards and snacks. What strikes him most, looking back, is how clearly different roles emerged, and how essential each one was.

“I think inevitably in this process, you do end up feeling like you’ve got different camps — and one camp is the people that you have to convince, the skeptics. And another camp is the enthusiasts who want to make everything work. I’m definitely an enthusiast. Someone has an amazing idea and you just become obsessed with it... And then you have kind of the big-picture, macro, vision-of-the-whole-board brain, which is able to look at that and be that “Kill Your Darlings” fearless voice of, yes, it is an amazing idea, an amazing character, an amazing moment, but it doesn’t belong here because it slows the story down too much.”

This maps almost exactly onto how strong design teams function. The enthusiast generates energy and possibility. The skeptic prevents the team from falling in love with their own ideas. The big-picture thinker holds the vision steady when the details get chaotic. The mistake many creative teams make is trying to homogenize these roles — to turn everyone into a collaborator who agreeably builds on every idea. The Stranger Things room worked, Paul suggests, because the tension between these roles was embraced rather than managed away.

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