Turn It Over

This week on the show: Aaron Draplin, founder of Draplin Design Co., on origin stories, junk stores, and the kind of generosity that never makes it into a design portfolio.

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When Aaron Draplin was about ten, his dad snuck him through a fence into Detroit’s Olympia Stadium, the old home of the Red Wings, a few weeks before the building was demolished. They found their way into the locker room and his dad got down on his hands and knees and started ripping up the carpet. Draplin asked what he was doing.

“Aaron, this could be the carpet that Gordie Howe’s balls dripped on.”

They hauled out armloads of carpet, cut it into squares, and loaded a couple hundred loose bricks into the back of a minivan. For years afterward, his dad handed the pieces out to Red Wings fans like sacred relics. Draplin still has his.

That’s the kind of household Draplin grew up in. His dad pulled moldings out of Detroit houses before they were torn down, chased garage sale signs down dirt roads on the promise that this one could be the one, and once talked his way out of a hardware store with a pocket of things nobody had rung up. Decades later, Draplin still can’t walk past an estate sale without lifting one small thing into his own pocket, just to keep the tradition going.

He’s now one of the most recognizable names in American graphic design: the founder of Draplin Design Co., the guy behind Field Notes, a run of Nike and Ford work, and a U.S. postage stamp. We pulled three things out of this conversation that go beyond “cool logo guy.” How he thinks about identity. How he actually built his design education. What he thinks he owes the people around him now that he’s made it.

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1. He never ignored where he’s from

Most creative people, at some point, decide their origin story is something to outrun. Draplin didn’t. During his junior review at art school, a panel dressed him down for wanting to do “pedestrian” commercial work, like designing catalogs for a company such as Cabela’s, instead of chasing the high-concept polish that was fashionable in 1998. He didn’t take the hint. “I wanted to go into function,” he said. “You had to go make Cabela’s catalog for guys to buy big elephant guns. And that’s a vital job.”

What he’d actually grown up around wasn’t polish. It was hardware store aisles sorted into little bins of nails and screws. Garage sale tables covered in baby clothes and rusted signage. An extra refrigerator in the garage that his dad kept stocked with beer, joking, “Wisconsin might get tired of the jokes. If they ever invade over Lake Michigan, at least I have enough beer to get us through.” Salvaged Victorian oak furniture, scavenged lead type, Coca-Cola signs pried off buildings on their way to the wrecking ball. That was Draplin’s visual diet, and instead of trading it in for something with more art-school pedigree, he kept it.

“I didn’t need to detach from something to get to the next better thing.”

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Hi folks! Aarron and I are taking a short summer break, so we’re rewinding to one of our favorite episodes from the end of last year with Aarron Draplin. Enjoy the episode, and we’ll see you next week with a new episode!

A larger than life figure in the creative world, Aaron Draplin has been designing everything from logos to posters since 1995. Few designers are as prolific as Aaron. He’s the founder of Draplin Design Co. (DDC). Priding himself on craftsmanship and quality, the DDC has made stuff for Field Notes, Esquire, Nike, Red Wing, Burton Snowboards, Ford, and he’s even designed a US stamp.

We caught up with Aaron in person at The James Brand studio in Portland, Oregon, where he walked us through an origin story that begins with a meteor in Navajo country and winds through the skate parks of Michigan in the 80s, the snowboard culture of the 90s, and eventually to one of the most recognizable voices in American graphic design.

But this isn’t just a conversation about making cool stuff—though there’s plenty of that. Aaron opens up about the work ethic he learned from his parents, and why being prolific isn’t about perfection—it’s about experimentation, and loving your work enough to show up every single day.

We talk about collecting, organizing thousands of ideas, and what it means to run a design practice where you can still work on your own terms. And throughout it all, Aaron brings the humor, the heart, and the hard-won wisdom of someone who’s never forgotten what it’s like to work a crappy job—and who reminds himself every day just how cool a life in graphic design really is.

Bio

Aaron Draplin was born in Detroit in 1973 and raised in the small village of Central Lake in Northern Michigan—population 800. After a brief stint at Northwestern Michigan Community College, he moved west to Bend, Oregon at 19 to chase the snowboarding life, and started designing graphics for Solid Snowboards. To fund his winters, he worked summers as everything from a traveling fair pizza wagon cook, to a dishwasher in Anchorage, Alaska.

He eventually returned to the Midwest to finish his design degree at Minneapolis College of Art and Design, before heading back west to become art director of Snowboarder Magazine in Southern California. In 2002, he moved to Portland to work as a senior designer at Cinco Design, where he worked on brands like Gravis, Helly Hansen, and Nixon.

In 2004, Aaron founded Draplin Design Co., working with clients ranging from Nike and Patagonia to Sub Pop Records and the Obama Administration. In 2009, he co-founded Field Notes with Jim Coudal and Coudal Partners—a collaboration that would become one of the most successful and beloved stationery brands in America. That same year, he gave his first public talk, which spiraled into a speaking career that’s now reached over 580 engagements worldwide.

His book Pretty Much Everything was published by Abrams in 2016 and is now in its 13th printing. At 51, Aaron continues to run his fiercely independent design practice from a backyard shop in Portland, Oregon.

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Years ago, two friends in Philadelphia went looking for a parking lot. They’d been staring at the same six words on the back of their favorite jazz records for years — recorded by Van Gelder in Hackensack, and one Saturday they drove out to find it. They tracked the address down in a 1955 phone book. They pulled up expecting something. What they found was a parking lot for Hackensack Sports Stadium. No sign. No plaque. Nothing to mark that Rudy Van Gelder had turned his parents’ living room into a recording studio and quietly helped capture some of the most important American music of the century.

Chris Entwisle and Mark Havens had a quiet ride back down the turnpike. It’s also the reason WAIL: The Visual Language of Prestige Records exists. Unlike Blue Note, Prestige never got its design mythology — despite cover art that’s just as striking and just as durable. Entwisle and Havens spent two decades tracking down original pressings and interviewing designers before that history disappeared for good, and what they found was a label that ran, in one historian’s words, “like a mom-and-pop store” with no budget, no briefs, no marketing department and somehow produced a visual identity coherent enough to still echo through design today.

If you find yourself wanting for a fresh approach to your work, the Prestige record catalogue is a treasure trove of inspiration on how to use color, typography, and imagery in innovative ways.

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Chris Entwisle and Mark Havens: Spotify, Apple Podcasts, Substack

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Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain — see the lineup and reserve your spot.

1. Nobody was hired to be a graphic designer

Let’s start with who these designers/artists actually were, because none of them set out to make album covers. Reid Miles trained at Chouinard and wanted to be an art director. Tom Hannan studied under Hans Hofmann and considered himself an abstract expressionist painter first. David X Young came to New York from Cape Cod to paint alongside Franz Kline and Willem de Kooning at the Cedar Tavern. Esmond Edwards was a freelance news photographer who talked his way into a session by offering to drive the musicians out to New Jersey.

Bob Weinstock, the label’s founder, didn’t have an art director because he didn’t have a staff to spare one. His hiring process was a portfolio and a hunch. “Tom Hannan just knocked one day and said, ‘Hi, I’m an art director,’” Weinstock remembered. “Bob Parent was a jazz photographer who was always hanging around. Whenever you needed a picture, you’d go to him.” There was no brief, no comp, no client approval — Weinstock vetted everything the same way, whether it was the music or the cover art. “I viewed it all as art,” he said, “the music and the covers.”

Prestige had none of that scaffolding, and it produced Esmond Edwards — a self-taught photographer who became, in Entwisle and Havens’s words, the label’s de facto creative director simply because he kept showing up and getting better.

“I viewed it all as art—the music and the covers.”

—Bob Parent

That freedom produced work that never even got the label’s blessing. David X Young — a Cedar Tavern painter who ran a jazz loft in the Flower District before he ever touched a record cover — designed this portrait of Lester Young for a rival label, Clef Records, using cut paper and a single word. It was rejected. Entwisle and Havens tracked down the original artwork decades later; it had never been printed.

The absence of a house style wasn’t a failure of management. It was the whole point. Each designer’s background — painter, photographer, sign-maker’s son — shows up directly in the work, because nobody was hired to execute someone else’s system. They were hired to have a point of view.

2. Limitations created opportunities

Reid Miles wasn’t even a jazz fan and he said so himself. What he loved was the blank 12-by-12 canvas and the fact that Prestige couldn’t afford to pay for art. “I only had type to work with,” he said, “and being a good designer, I guess I took advantage of the opportunity.” The result was the Thelonious Monk Quintets cover: the word MONK, split across two lines, filling the entire square in black type so large it reads as pure shape before it reads as language.

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Years ago, two friends in Philadelphia — both designers, both obsessed with jazz — kept noticing the same notation on the back of their favorite records: “recorded by Van Gelder in Hackensack.” So one Saturday they drove out to find it. They tracked down the address in a 1955 phone book, pulled up — and found a parking lot. No sign, no plaque, nothing to mark that Rudy Van Gelder had once turned his parents’ living room into a recording studio there, capturing some of the most important American music of the century.

That quiet drive home planted the seed for a twenty-year project. Mark Havens and Chris Entwisle are the authors of WAIL: The Visual Language of Prestige Records — the first real look at the design history of a label that, unlike Blue Note, never got its design mythology, despite cover art that’s just as striking and durable. They tracked down original pressings, interviewed the designers before that history disappeared for good, and uncovered how a label run, in one historian’s words, “like a mom and pop store” — no budget, no briefs, no marketing department — produced a visual identity coherent enough to still echo through design today.

Buy the book

What we love about this conversation is how much of it comes down to constraints driving creativity. Reid Miles couldn’t afford imagery, so he made typography the art. Tom Hannon had no budget for stock photography, so he shot the musicians himself. Designers got an album title and nothing else, and turned that absence of direction into creative freedom — because Bob Weinstock “viewed it all as art,” the music and the covers alike. This is a conversation about jazz, but it’s also about what happens to creative work when nobody’s watching too closely, and why limitations so often produce things that last.

Bios

Chris Entwisle is an artist and illustrator. For over thirty years, he has used his passion for both jazz and postwar graphic design in his illustration work. Entwisle has a BA in graphic design from Rutgers University. He and his wife live in the Philadelphia area.

Mark Havens is an artist and educator with a dual background in graphic and industrial design. His work has been exhibited internationally and is held in both public and private collections. Out of Season, his first major monograph, was described by the New York Times as “a decade-long elegy.” Havens is a professor of industrial design at Thomas Jefferson University.

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Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

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The Design Better summer reading list

As you head out on holiday this summer, it’s always nice to have a couple good reads tucked in a bag to pass the time. Our reading list this summer has nothing that would pass as homework. While you may not want to read books that take you back into work mode, these titles will get your wheels turning in new ways that just might make you look at design and technology with fresh eyes.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain — see the lineup and reserve your spot.

Aarron’s summer book recommendations

Frankenstein by Mary Shelley

Hollywood has done this book a disservice. The monster of film and Halloween costume is not the creature Shelley actually wrote: he is articulate, heartbroken, abandoned by his creator, and adrift in a world that refuses to see him. The real horror isn’t the monster. It’s Dr. Frankenstein’s hubris — his willingness to wield the power of technology without once pausing to consider what he’d set loose.

Two hundred years after its publication, that question feels newly urgent. The dialogue alone is worth the read. And it’s hard not to be a little awestruck knowing Shelley wrote it at 18, during the Napoleonic Wars, in an era when publishing was nearly impossible for women.

It’s a classic for a reason.

Zen and the Art of Motorcycle Maintenance, by Robert Persig

On the surface, this is a book about a father and son riding motorcycles across the American Northwest. Underneath, it’s one of the most serious attempts anyone has made to answer the question: what is quality, and why does it matter?

Pirsig’s narrator is obsessed in the best way with the relationship between a person and the thing they’re caring for. A motorcycle maintained with genuine understanding runs differently than one maintained by the manual. The difference isn’t mechanical. It’s philosophical. When you truly know something, you stop working on it and start working with it.

He calls this “gumption”, the psychic fuel that keeps a craftsperson going when the work gets hard. It’s not enthusiasm. It’s the willingness to stay present with a problem until it opens up.

That idea feels worth examining right now. As more creative work gets handed off to tools that can approximate quality without understanding it, there’s something clarifying about a book that insists expertise is not just useful, it’s a form of care, a discipline, and maybe even a moral obligation.

The Three Body Problem, by Cixin Liu

It’s easy, lately, to lose faith in us. The news does not help. And yet.

Liu Cixin’s novel — the first in a trilogy that became a global phenomenon — opens during China’s Cultural Revolution and builds toward one of the most unsettling premises in science fiction: an alien civilization has spotted Earth, and they’re on their way. They’ll arrive in four centuries. Humanity has until then to prepare.

What follows is a profound argument about what we actually are. The alien threat is assumed to be technologically insurmountable. Certain humans, confronted with this, decide the species isn’t worth saving anyway. It’s a seductive kind of despair, the feeling that our failures are too deep, too structural, too human to overcome.

The book demolishes that conclusion.

What makes us formidable turns out not to be our tools. It’s the way we think, our capacity to reason under pressure, to cooperate across impossible distances, to refuse the obvious answer when something in us insists there’s another one. Curiosity. Stubbornness. The willingness to stay in the problem.

A great summer read, and a useful corrective for anyone who’s been spending too much time doom scrolling.

Eli’s summer book recommendations

Endymion by Dan Simmons

This was a recommendation from DB guest Paul Dichter (Stranger Things writer). It’s part of Simmons’ Hyperion series, which I loved as a teenager. I’d revisited some of the earlier books in the series, but this is my first time re-reading Endymion, which explores themes that seem very relevant right now. It’s set in the far future, and explores what forms AGI might take, and what happens when technologies have their own motivations, and what happens when some are taken away from us.

Make Something Wonderful by Steve Jobs

A physical copy of this book was gifted to our graduating class of design students at Stanford this year. Hard copies can be hard to come by (though you can find them on eBay) but you can find the whole thing online for free too. As a kid who grew up playing games like Karateka, Lode Runner, and others on the Apple II, it was a nostalgic journey to read the oral history, emails, and other communications that his archive collected for this book. As a designer, it was interesting to see how much he cared about the design of his products from the very beginning (this quote is from a talk he gave at the Aspen design conference in 1983): We have a chance to make these things beautiful, and we have a chance to communicate something through the design of the objects themselves.

Rumpole on Trial by John Mortimer

This one is a bit far afield from the design and tech world, but sometimes we need a break from such things, and summer seems like a good time.

I'm not typically a fan of legal dramas, but I am a fan of British humor, and the poetry-quoting, “Chateau Thames Embankment” drinking barrister Rumpole is so entertaining that he makes even the inherently dry legal system in the UK entertaining.

“The main aim of education should be to send children out into the world with a reasonably sized anthology in their heads so that, while seated on the lavatory, waiting in doctor's surgeries, on stationary trains or watching interviews with politicians, they have something interesting to think about.”
—John Mortimer

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Niyati Gupta describes her career as one long experiment — deliberately putting herself in uncomfortable, ambiguous situations and treating every move as a personal learning loop. That instinct took her from a bachelor’s in design inside one of India’s most prestigious engineering colleges, where almost nobody understood what design was, to a research role at Carnegie Mellon where she studied health info needs for low-literacy users in rural India, to Autodesk’s bio-nano innovation lab building molecular visualization tools for scientists — and eventually to Google, where she joined the Next Billion Users team.

That team’s mission was to ask an open question: where would the next wave of users come from, what did they need, and what products didn’t exist yet to serve them? Niyati ran immersion sprints in the Philippines, India, Indonesia, and Mexico — shadowing users, building prototypes in the field, testing them in the wild, and bringing those insights back to a team that was building products like Camera Go and Google Files from the ground up. And she’ll tell you that the swim lanes between designer, engineer, and PM felt just as artificial out there in the field as they do today with AI accelerating everything.

These days she’s a senior product designer at Netflix, working on commerce and partnerships — which means thinking hard about discovery, about fandom, about how you help someone decide what to watch on a Friday night without making them feel like the choosing is harder than the watching. It also means designing across a ten-foot TV screen, a phone, and every device in between, and trying to make all of it feel like one seamless experience.

In this conversation, we get into what the Next Billion Users work taught her about designing for people who aren’t like you, how she thinks about influence as a designer — and why she’s convinced the title was never where the influence actually lived — and what Netflix’s design culture looks like from the inside, including how they run crits and how they think about A/B testing.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

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Normally, I don’t write The Roundup while sitting in the middle of the Big Sur River, on one of the Adirondack chairs that The River Inn places on its property. But this week is different.

My father passed away after a long illness last Saturday, and as painful as that was, I was grateful to be there for his final moments, along with my brothers and mom. I took some time off today to surf at the Big Sur river-mouth, and now I’m here, sitting in the river, writing this.

Normally, I don’t write The Roundup in VS Code either, but one of the blessings of this place is its lack of cell service. So here I am, instead of writing directly on Substack, using a tool that doesn’t require an internet connection. A side benefit of this constraint is that I’m not tempted to lean on AI too early in the writing process. I’ll use it later to help with research, but it’s no surprise that using it too early leads to very average writing at best. Stay Human, as the hat I’m wearing reminds me.

Though my father was a physician, he had a diverse array of interests: poetry (he wrote under the pen name Jamie Irons), mathematics, biology. One of the books he left me was Wonderful Life: The Burgess Shale and the Nature of History, by the paleontologist and evolutionary biologist Stephen Jay Gould.

Among other things, the book discusses what is popularly known—among us nerds at least—as the Cambrian Explosion, a point in the evolutionary history of life where life explored a dizzying array of different forms in a geologically short time period. Roughly 540 million years ago, the fossil record lights up with a diversity of body plans. Creatures with five eyes. Animals with no clear descendants. Arthropods in shapes evolution would never try again. The burst of experimentation was spectacular, and sometimes spectacularly strange (see a rendering of the aptly named Hallucigenia below).

Scott Belsky, chief strategy officer at Adobe, used the Cambrian Explosion as metaphor when we spoke with him last year to describe what generative AI is doing to software.

“So now we’re in this Cambrian Explosion of sorts where there are just so many new models and capabilities and apps and all these things. And I feel like every few weeks, orientation changes about what’s the best this and what’s the best that. And it’s hard to keep up with…

In some ways, you could argue that empathy outperforms passion when it comes to product design. And sometimes as technologists, we’re like, oh, if the technology can do that, we’re just going to apply it. But people may not be ready for some of these things, especially with the ramp of capability right now.” — Scott Belsky, Chief Strategist at Adobe

We are watching an explosion of new tools, new workflows, new categories of creative possibility, in real time. It’s exciting. It is also, as Gould would remind us, mostly going to fail.

While the actual Cambrian Explosion is relatively well known, one fact about it isn’t. Of the many arthropod groups that emerged, only four survived past that period. Three persist today: the Uniramia (insects, millipedes), the Chelicerata (spiders, scorpions), and the Crustacea (crabs, shrimp, lobsters). The fourth, the Trilobata, lasted another 270 million years before going extinct. The rest were filtered out by evolution.

As for the software explosion, every week brings new tools, new features, new categories. The Cambrian seabed of 2026 is thick with strange creatures, most of which will not make it to 2030.

Gould’s deeper argument was that the Cambrian Explosion was not random. The survivors were not simply the strongest or the fastest. They were the ones whose body plans were most adaptable, most capable of being elaborated over time into something the environment could use. I think the same logic applies to what we are living through now. And when I look back across the conversations we have had over the past few years, three ways of working keep surfacing, like body plans that might actually survive the filter.

AI x Influence Workshop

Bobby Hughes and I have a few spaces left in our upcoming AI x Influence for Design Researchers workshop happening next week over two days (Tuesday the 23rd and Friday the 26th).

We’re happy to offer two 50% off tickets for Design Better listeners.

September Work(shop) Leadership Excursion

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain — see the lineup and reserve your spot.

1. Specificity of intent

Eric Snowden, head of Adobe Design, said something in our conversation that I’ve thought about many times since:

“Most AI out there today is very good at making something generically beautiful, but not very good at making a specific idea you have in your head a reality.” — Eric Snowden

On one side are tools that produce output on demand, a slot machine you pull and something comes out. On the other side are tools that amplify our human abilities.

The tools that survive will be the ones that help us amplify our humanity, and the specificity of our creations. The singer and songwriter Bishop Briggs told us she wanted to throw her phone across the room when Suno wrote a song that sounded exactly like her work. Not because it was bad, but because it felt like her work, and it had cost her nothing:

I kind of wanted to throw the phone away, it was so terrifying…it’s [like] seeing all the answers for your homework and you don’t have to put in any of the work.

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Typography is often treated as a detail — the thing you finalize after the real design decisions are made. But for our next guest, it’s closer to the foundation everything else rests on. He’s spent two decades in editorial design at some of the most iconic American magazines — Men’s Health, Esquire, Popular Science, Entertainment Weekly — and he’s now the Creative Director of Fast Company, where he recently led a redesign that does something pretty unusual: the magazine gets a completely new typeface every single issue. His name is Mike Schnaidt.

Mike’s also a professor, a runner, and the author of Creative Endurance — a book that maps the principles of physical and mental endurance onto the creative life. It’s built around 56 rules for sustaining a career in design, drawn from interviews with ultra-marathoners, astronauts, and designers who’ve pushed way past the limits most people set for themselves. And as you’ll hear, he’s already working on book two.

We chat about the nuts and bolts of typography (utilitarian vs. expressive, food metaphors, Fast Company's per-issue typeface system), the philosophy underneath it all (design as service, authorship, hospitality). We dig into his book — and his counterintuitive take on burnout: the cure isn't rest, it's picking up something creatively different.

Bio

Mike Schnaidt is the creative director of Fast Company. He’s also the host of the Webby-awarded video series It’s All in the Typeface, a professor of illustration at the School of Visual Arts, and the former president of the Society of Publication Designers. One of the coolest moments in his life was when Paula Scher said his first book, Creative Endurance, was “beautifully designed.” His second book arrives in 2028.

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This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

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Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

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Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

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— Eli & Aarron

Creativity is a discipline in optimism

When Tina Roth Eisenberg moved to New York from Switzerland in 1999, she kept asking herself one question: where are my people? Eighteen years ago she answered it by starting Creative Mornings — a free monthly breakfast lecture series that has since grown into 252 cities, 70 countries, and roughly 25,000 people gathering every month. She calls it “church for creativity.”

The scale of Creative mornings is astounding, but even more impressive is how little of it she built by controlling anything. Creative Mornings, the Swiss Miss blog she’s kept for 21 years, the Friends Work Here co-working community, Tattly — none of it ran on a growth plan. It ran on trust, friendship, and a stubborn belief that there’s a better way.

That belief turns out to be the through-line. Late in the conversation Tina said the thing this whole issue is really about: creativity is a discipline in optimism. You can’t make something better unless you first believe better is possible. Here’s what that looks like in practice.

Listen to the episode and join the conversation

Tina Roth Eisenberg: Spotify, Apple Podcasts, Substack

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Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain — see the lineup and reserve your spot.

1. The metric is friendship

Most communities die because their organizers measure the wrong things — headcount, engagement, reach. Tina measures one thing, and it’s a joke that turned out to be the strategy.

“The only thing I measure is ROF — return on friendship.”

She told us about a night last year when Timothy Goodman spoke at Parsons to 475 people. She ran a live, in-the-room data visualization: stand up if you’ve ever made a friend at a Creative Mornings event. Out of 475, about 450 stood up. That’s the whole business model. Not attendance — belonging.

It tracks with something Bill Burnett told us about what he calls a formative community: “a group of people who get together to help each other become better people… deeply interested in each other’s journey.” The opposite of a networking room, where everyone’s performing their résumé. If you’re building a community — and a lot of you are, internally or otherwise — the design question isn’t how to get people in the door. It’s whether anyone leaves with a friend.

2. Communities scale on trust, not control

When the first stranger knocked on Tina’s door asking to bring Creative Mornings to their city, her instinct was to clamp down. Will they keep it safe? Will they translate the values? What she did instead is the most transferable lesson in the conversation: she wrote down the non-negotiables, and then handed away everything else.

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Vestaboard is the vision of Dorrian Porter, and has its origin story in a Parisian train station. A few years ago, we had Dorrian Porter on the show to tell us about Vestaboard, and since then, we’ve become even bigger fans of the product. We keep spotting them in the wild, from coffee shops in Savannah to airport storefronts in Minneapolis.

Dorrian is back to tell us about the Vestaboard Note, a smaller, more affordable, and more versatile version of the original that went from basic prototype to Red Dot Award winner in about a year — a story that starts, believe it or not, with tariffs.

In the video above, Dorrian shares a touching story about giving his mom one of the new Vestaboard Notes

We talk about what it’s like to build a hardware company through supply chain disruptions and trade wars, why Dorrian keeps betting on the consumer market when the easier path might be B2B, and how Vestaboard is finding its way into classrooms, baseball stadiums, and a bar in Northern California born out of a community recovering from wildfire.

We also dig into the tension between nostalgia and innovation — Dorrian’s honest about the fact that split-flap displays attract people who love vintage and transportation, but his ambition goes further than retro. He wants to build products that pull meaningful content out of our phones and into the physical spaces where we actually live together.

This is a special sponsored episode of Design Better, and we’re happy to share it because Vestaboard is a brand we truly love. Their mission to inspire and connect people resonates with us, and we think it will with you, too.

There’s currently a waitlist for the Vestaboard Note. But as a Design Better listener, you can head over to vestaboard.com/designbetter to skip the waitlist and receive a special offer.

Claim your special offer

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When Tina Roth Eisenberg moved to New York in 1999 as a new designer, she kept asking herself the same question: where are my people? Eighteen years ago, she answered it by starting Creative Mornings—a free breakfast lecture series that has since grown into what she describes as the world’s largest face-to-face creative community: 252 cities, 70 countries, and more than a thousand volunteers gathering with around 25,000 people every month. Or, as she puts it, “church for creativity.”

But Creative Mornings is just one thread in Tina’s story. She’s the voice behind Swissmiss, the beloved design blog she’s kept up for 21 years; the founder of FRIENDS, a creative coworking community in Brooklyn; and the creator of Tattly, the designer temporary tattoo company that started as a joke and turned into a business.

In our conversation, Tina shares what she’s learned about building communities that scale on trust rather than control, why she measures success in “return on friendship,” and how playful side projects increase “the surface area for luck to find you.” We also talk about commitment as a creative practice, raising creative kids, and why she believes the future isn’t lonely—it’s hyperlocal.

Bio

Tina Roth Eisenberg is a Swiss-born, Brooklyn-based designer and serial founder—though many know her simply as "swissmiss," after the design blog she started in 2005 as a personal visual archive, which grew into a popular design journal drawing an average of a million unique visitors a month. Raised in Speicher, Switzerland, and shaped by Swiss design (and, as she puts it, a lot of fresh mountain air), she completed her design studies in Geneva and Munich before moving to New York in 1999. She is the founder of CreativeMornings, the world's largest face-to-face creative community, with monthly talks in 252 cities across 70 countries; the founder of Tattly, the designy temporary tattoo company; co-creator of the to-do app TeuxDeux; and founder of FRIENDS, a creative coworking space in Brooklyn. She lives in beautiful Fort Greene, Brooklyn, with her two children, Ella and Tilo, who teach her about current memes and TikTok.

Books & Links mentioned:

• CreativeMornings.com

• Creative Quests, Sam Furness

• Dark Forest,Yancey Strickler

• Nanowrimo

• Swissmiss

• Yancey Strickler: Creative Mornings talk from May 2025

• Vacation With An Artist

• Creative Mornings Field Trips

• Creative Morning Clubs

• The Serviceberry: Abundance and Reciprocity in the Natural World

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And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

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“Being a parent is like being a psychic who is constantly correct, but always ignored.” – Jim Gaffigan

The comedian Jim Gaffigan has a funny bit about being a parent. It’s familiar to many of us who have raised kids from toddlers through the teenage years: “It’s cold outside, grab a jacket,” we say, or, at a different time of year, “put sunscreen on. You’ll get a sunburn.”

Inevitably, the mandate/directive/advice is ignored, and the child comes back: “Can I use your jacket?” or “Dad, my skin hurts!”

As parents, much like the Greek priestess Cassandra, we can predict the results of ignoring our sage advice, but it doesn’t matter. Our kids need to learn through direct experience that their mistakes, despite our best efforts to protect them, have consequences.

Which brings us to our guest this week, Paul Ford — writer, developer, entrepreneur, and co-founder of the software agency Aboard. Paul describes himself as a “fun Cassandra”: someone who makes predictions, sometimes gets them right, and has learned to deliver the news with grace and humor. When Claude Code dropped in November, Paul saw immediately that something had fundamentally shifted. The people around him, not so much.

In this conversation, Paul walks us through what’s actually changing, and what’s stayed the same, inside a software agency that has gone all-in on AI. Why ideation gets faster but building stays slow. Why transparency about AI use is becoming a competitive advantage. Why taste and judgment are becoming more valuable, not less. And why the liberal arts kid who can parse ambiguity and connect disconnected ideas might end up being the most important person in the room.

Here are four things we learned from Paul in our conversation.

Listen to the episode and join the conversation

Paul Ford: Spotify, Apple Podcasts, Substack

The acceleration paradox

If you’ve spent any time vibe coding or prompting your way through a project lately, you’ve probably felt it: the beginning is exhilarating. Ideas materialize, prototypes appear, whole interfaces snap into existence. It feels like a superpower. And then, somewhere around the point where the thing actually has to work — really work, for real users, with real data — the pace drops back down to earth.

Paul has been living this dynamic inside Aboard:

“The coding is really fast, but the thinking is actually not that much faster. It’s maybe a little bit faster, or possibly a little bit slower, because there’s so much more product to work through. Once people get that taste of the incredible acceleration, they’re like, well, now it’s always going to be like this. But I actually don’t see product going away. Everything kind of still needs to be there.”

The bottleneck, it turns out, was always the thinking. Prototypes are important of course, but so is the research, the iterations and testing, and the shared understanding that has to get built before anything real can ship. AI hasn’t changed that. If anything, by making the early stages so fast, it’s thrown the slowness of the rest into sharper relief.

Taste is the new technical skill

One of the most useful reframes in the conversation is Paul’s argument that as AI commoditizes execution, the ability to recognize quality becomes the scarcer, more valuable thing. Not just having taste, but being able to articulate it, defend it, and use it to pull the work back when the machine goes in the wrong direction.

He illustrates it with a telling detail about LLM-generated prose:

Read more

Read more

Paul Ford likes to call himself a “fun Cassandra” — someone who, like the priestess in Greek mythology, sees trouble coming, but unlike her tries to make the warning as entertaining as possible. He’s the writer, developer, and co-founder of the tech agency Aboard who saw Claude Code drop last November and immediately understood it was going to change everything — while finding, to his surprise, that most people around him simply weren’t seeing it that way.

That same instinct is what drew him into AI early. Where others hedged, Paul dove in — vibe coding nonstop, running full enterprise subscriptions for his entire team, and building in earnest. But he’s not a fanboy. He’s a critical optimist who believes something important is happening, while holding equal concern about the companies pushing it, the students expected to learn from it, and the decades of hard-won knowledge that might be quietly evaporating in the rush.

Paul is also an English major who sold an agency, a developer who thinks in prose, and a father of 14-year-old twins — one of the most multi-disciplinary thinkers we’ve had on the show. He won the National Magazine Award for writing an entire issue of Bloomberg Businessweek dedicated to explaining programming to a mass audience — a 38,000-word essay called “What Is Code?” A regular contributor to Wired and published in The New Yorker and MIT Technology Review, he’s one of the rare writers who can make the inner workings of software feel urgent and human.

We chat with Paul about the strange paradox of AI that makes ideation blindingly fast but leaves the hard work of product thinking as slow as it ever was, why the best thing you can bring to this moment might be taste rather than technical skill, and what it actually means to build a company around tools that didn't exist two years ago.

He’s exactly the kind of thinker this moment needs: someone who can write code and read the room, and who cares about quality as much as velocity. He can also make you laugh while explaining why you should probably be a little worried.

Bio

One of the world’s leading technology thinkers, Paul Ford has written about the way that software works for dozens of publications like Wired, Businessweek, and the New York Times, including his National Magazine Award–winning Bloomberg cover story “What Is Code?” After years of writing about technology, Paul decided to do something about it, co-founding Postlight and Aboard to help deliver quality products to the people who need them.

Books & Links mentioned:

• Gamer Gate

• Ftrain

• Jeff Koons

• Marcel Duchamp’s urinal

• To Own the Future, Read Shakespeare

• What Is Code?

• Strudel.cc

• Firewalla

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

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In this issue of The Brief:

1. Observations on designing a personal portfolio

2. Things to watch, read, and explore

3. Job openings

Join Portfolio Club Wednesdays 10AM PT/1PM ET

Join us every Wednesday through the end of July to talk through the best practices of portfolio design. A new industry expert joins us each week to critique portfolios and talk about what they look for when hiring. Build a portfolio you’re proud to share!

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Observations on designing a personal portfolio

by Aarron Walter

I have always struggled to design my own portfolio. It’s an exercise in showing off, and that has never sat comfortably with me. But recently, I did the impossible. I launched my new website.

When designing for a client, I can be objective and curious. But when I design for myself, subjectivity clouds my judgment. Finding the right style and concept to represent my own personality, without overthinking every choice, is hard. I spin my wheels trying to satisfy my worst critic: myself.

Tooling has become another big hurdle. Though I spent years teaching coding, building large-scale products, and served on The Web Standards Project and the W3C, the modern web stack has grown so complex that it trips up my ideas.

For a long time I leaned on Squarespace to make the design process easier. It worked fine, but at times I felt pinned in by it, not really able to design what I wanted. By using a WYSIWYG editor, I felt I’d lost a piece of my identity as someone who prided himself on hand-building websites.

But no longer able to tolerate my old, cringy website, I resolved to get something new started. Something. Anything!

To break the ice, I brought in a collaborator.

AI can be an icebreaker

Sometimes tiny steps open the creative floodgates. That’s what happened for me in April, when I began describing to Claude Code the ideas in my head for my new website.

I started designing not in Figma, but in a Google Doc where I outlined my goals, site structure, the colors and typography I pictured, the feeling I was chasing. I gathered a few images that captured my imagination. The album cover for Joy Division’s Unknown Pleasures. Broken Bells’ debut record with its geometric sphere. Hans Zimmer’s music for Dune. Star Wars: A New Hope. The future and the past colliding into a kind of aspirational nostalgia.

Claude served as a partner to push off of, instead of getting lost in my own ruminations. I described what I was searching for, and it came back with a version of my vision that carried new things for me to consider. Eventually I realized I wanted data from space and Earth, real signals from pulsars, seismographs, the oceans, and the climate, turned into visualizations that describe a feeling without spelling it out. I wouldn’t have attempted that without an AI collaborator as I would have considered it to be too much work. But with Claude, I felt some of the limitations I’d placed on my creative process lift.

At no point did I feel like Claude was the lead designer on this project. The ideas were mine, and I was able to stay focused on concepts, whereas in my many failed attempts at redesigning my portfolio in the past, I’d get lost in execution. It was liberating.

I chronicled the whole backstory on my site, in the colophon.

What our first Portfolio Club critique taught us

Building my own portfolio is what inspired us to start Portfolio Club, a community support group where Design Better members learn from one another, get honest feedback, and build a portfolio they’re proud to share. For our first session, Matt D. Smith (MDS, of Shift Nudge) joined Eli and me to critique real portfolios live. His advice was so good I want to pass the best of it along.

Make the work the hero

Matt’s first principle is the one most of us get wrong. Your work should fill the project page, roughly 80% of it. Explaining your process matters, but in the end people want to see what you made.

I want to see big, beautiful images of your work. Show me 50 images you’ve handcrafted for one case study. Eighty percent images, maybe 10 to 20 percent text. I need to see the work. Less text, less text.

Matt D. Smith, Portfolio Club

Show the work, show it well, and present it in a consistent, easy-to-see format. Matt keeps a “soft mini design system” in his head for this: every image the same width, set in the same frame, displayed the same way, so the whole thing is easy to take in.

Read more

This week on the show, Aarron and Eli talked with Jessie McGuire, managing partner of Thought Matter, the New York studio whose decade of civic, neighborhood, and cultural work just earned the 2026 National Design Award for Communication Design from Cooper Hewitt, Smithsonian Design Museum. An important question kept surfacing in the conversation: how does a studio committed to doing work that's good for the world actually keep the lights on? Jessie makes the case below , in her own words, that this is the wrong question. And then she tells us what the right one is.

Plus, at the end we share some amazing job opportunities for designers.

Listen to the episode and join the conversation

Jessie McGuire: Spotify, Apple Podcasts, Substack

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Join the conversation about this interview in our chat room. →

Who funds the future?

by Jessie McGuire

There’s an assumption buried inside one of the questions I get asked most often: that design for the public good and design that pays are fundamentally in tension. That civic work is charity. That community-centered projects are a tax you levy on your profitable clients.

I’ve come to think this framing gets almost everything backwards.

Running Thought Matter for the past decade — making payroll, supporting a team, finding the right clients — I’ve found that the most meaningful projects don’t exist despite funding constraints. They exist because someone, or more often several someones, decided to put money behind something before its full value was obvious. That’s not charity. That’s how culture gets made.

What it means to show up

In the fall of 2016, like a lot of designers in New York, we were shaken by the election results. Our founder, a journalist before he became an agency owner, pushed us: if you don’t like what’s happening, you go into the streets. You figure out where your values are and you show up.

So we made posters. We did a Kickstarter for the Women’s March in Washington in January 2017, which turned out to be one of the largest demonstrations in American history, though we didn’t know that yet, raised tens of thousands of dollars, and printed 15,000 posters. Designers contributing visual communication on behalf of something they believed in.

That project lit something. We came off it asking: what else can we do?

The question that launched the Constitution project

A few months later, in the spring of 2017, the headlines were full of variations on the same question: has the new president even read the Constitution? We were sitting around the conference room table — we do that every week, looking at newspaper clippings, talking about what we want to see in the world — and someone asked: well, have we read it?

We ordered 25 copies. They all arrived at the studio looking identical. Small type. No imagery. Poor paper. Dense, utilitarian, forgettable. As designers, we knew we could do better. And we knew it mattered.

A Kickstarter raised enough to design, print, and donate 3,000 redesigned copies to New York City public schools. Buy one, we donate one. A paper company contributed materials. Our team contributed their time. We used a Risograph press and thought carefully about every detail — paper stock, typography, a fold-out insert for the Bill of Rights — to give the document the physical presence it deserved.

The design question we kept coming back to: how do you make something that people actually want to touch and find out more about? Not a political statement, not a rebrand — just a document that invites participation. We wanted a 13-year-old to open it and feel like it had something to do with him.

“Design is how we shape who feels invited. It’s how we think about who’s informed.”

Then we asked twelve designers we most admired — Milton Glaser, Seymour Chwast, Jessica Hische, Adele Rodriguez, and others — to each create a poster for one of the amendments in the Bill of Rights. Every single one said yes. The show ran at Cooper Union during Constitution Week in September 2017.

No institution owned that project. It lived because a community decided it mattered enough to show up.

What “shareholders” actually means

The studio has also worked with Business Improvement Districts, the Long Island City Partnership, the Times Square Alliance, the Union Square Partnership, as well as commercial brands, cultural institutions, and advocacy groups. That mix is intentional.

When I talk to potential clients and one of them says the work needs to be guaranteed not to upset their shareholders, I’ve learned to hear that as a signal. What they’re telling me is that they’re not actually committed to anything yet.

When I push on the shareholder question, though, something shifts. Working with cultural institutions, neighborhood organizations, civic groups — the shareholders aren’t a board. The shareholders are the community. They’re the people being affected by whatever the work is doing. That’s who I want to be designing for.

This is also what I mean when I say I want to do the work we want to talk about. Over the years, clients would hear about our civic projects and say: so you just want to do activist work. I’ve been sitting with that framing. We need a new word for it — because design that helps communities see themselves more clearly, that makes civic life more legible and more participatory, shouldn’t require a separate category. It should just be design.

The question behind the question

The most meaningful ideas that have shaped society were usually funded before their return was obvious. Patrons supported artists. Foundations funded journalism. Universities invested in research that didn’t have an application yet. Design belongs in that lineage.

The work that helps people see themselves as citizens rarely happens at the speed of a campaign cycle or a social media reaction. It happens over time, through schools, libraries, museums, neighborhood organizations, public spaces, and the people willing to invest in them before the outcome is easy to measure.

What would it mean to fund the future before it’s profitable? Because by the time something is proven, it’s no longer the future. It’s already the system.

We don’t have to wait to be the organizations willing to invest that way. We can choose to be them right now.

Jessie McGuire is the managing partner of Thought Matter in New York City. She also teaches entrepreneurship at Pratt Institute.

New jobs posted on Design Better Careers

View all job openings →

UX/UI Designer at Archetype AI
Full-time · San Mateo, CA

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Full-time · Remote, USA · Remote OK · $198,700 – $275,000

Sr. Product Designer, Growth at Life360
Full-time · Remote, USA · Remote OK · $129,000 – $190,000

Senior UX Researcher at GitLab
Full-time · Remote · Remote OK · $130,000 – $145,000

Art Director (Product Design) at Hello Heart
Full-time · Tel Aviv, Israel

Designer, Marketing & Custom Content at Vox Media
Contract · New York, NY · $40/hour

Product Design Program Manager at OpenAI
Full-time · San Francisco, CA · $216,000 – $240,000

Product Designer at Substack
Full-time · San Francisco, CA · Remote OK · $150,000 – $215,000

Product Designer at brand.ai
Full-time · Remote · Remote OK

VP, Product at brand.ai
Full-time · Remote · Remote OK

Designer, Web & Brand at Linear
Full-time · North America · Remote OK · Competitive salary + equity

Principal Product Designer at Linear
Full-time · Europe · Remote OK · Competitive salary + equity

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Full-time · San Francisco, CA · Remote OK · $146,000 – $222,000

Product Design Manager at Figma
Full-time · Remote, US · Remote OK · https://boards.greenhouse.io/figma/jobs/5790585004?gh_jid=5790585004

Product Designer, Design, Dev, & AI Tools at Figma
Full-time · Remote, US · Remote OK

Product Designer, Growth & Monetization at Figma
Full-time · Remote, US · Remote OK