That’s what happened when I talked to Debbie Millman and Michael Bierut.

Two people who are absolute design royalty—the kind of people where you practice what you’re going to say to them in the shower—spent an hour talking about feeling like outsiders. About thinking the cool kids were somewhere else. About getting kicked out of groups and feeling like they were on melting icebergs watching their careers drown.

And the whole thing started because Michael typed a letter on Pentagram stationery in 1998 asking Debbie if she wanted to come by for lunch and talk about rap music.

I’m still processing this.

Erik couldn’t make this podcast recording, which honestly might have been for the best because what unfolded was this quiet, intimate thing where Debbie and Michael just... remembered. I almost felt like I wasn’t even there—just lucky enough to witness it.

We thought they met in Baltimore in 1999. Wrong. Debbie pulls out this letter—PULLS OUT THE ACTUAL LETTER—dated April 27, 1998. “Dear Debbie, it was nice to meet you face to face in Chicago...”

Chicago. 1998. They were seated next to each other at an AIGA dinner. Michael had just done the Rock and Roll Hall of Fame. Debbie had just repositioned Hot 97, the world’s first hip-hop radio station. They bonded over being “white suburban rap music fans” (Michael’s words) which is both hilarious and perfectly them.

The Knicks were in the playoffs that night. Debbie kept calling her dad for score updates because smartphones didn’t exist yet. And Michael, watching her do play-by-play at this fancy AIGA dinner, said something that made her feel seen in a way she hadn’t before.

Debbie told me she felt out of place that night. That AIGA felt elitist. That she wasn’t part of that world. But Michael’s warmth in that conversation changed how she felt in that moment.

One dinner. One letter about rap music. And now, decades later, both of them say they wouldn’t have their careers without AIGA.

How many dinners have we sat through thinking we don’t belong? How many times have we missed the Michael Bierut sitting right next to us?

Michael said something that I keep replaying: “Every movie star thinks that someone else is getting the good parts.”

He was working for Massimo Vignelli—MASSIMO VIGNELLI—literally learning from a legend. But he was convinced the real action was happening on the West Coast with the Emigre crowd. They seemed cool. They seemed relevant. And he could tell they thought people like Vignelli were dinosaurs with their heads up their asses.

There’s this story he tells about Massimo's garbage can that I won’t spoil, but let’s just say even when you’re working for a master, you’re still fishing around for validation elsewhere.

Meanwhile, Debbie got kicked out of AIGA’s brand experience group for being “too commercial.”

Too commercial. Debbie Millman. Let that sink in.

Both of them thought they were on the wrong side of some invisible line. Both of them felt like they were failing at being the “right” kind of designer. And both of them kept showing up anyway.

And you know what Michael said about that whole elite vs. commercial divide? “You just have to stop the scorekeeping and embrace the marvel of the diversity of practice.”

But here’s what I didn’t know: that tension was there from the very beginning. Michael remembered Milton Glaser at that first leadership retreat in 1988, warning that AIGA’s new democratic chapter structure would fundamentally change what the organization stood for. It wouldn’t be an “arbiter of excellence” anymore—but would it stop being an elite gatekeeper?

That’s the tension we’re still navigating. Who gets to decide what “good design” is? Who gets a seat at the table?

The scorekeeping. That’s what we’re all doing, right? And it’s exhausting and it’s bullshit and apparently even Michael Bierut felt it.

Okay, so Debbie redesigned Tropicana in the late ‘90s/early 2000s. Then somebody else redesigned it. That redesign failed spectacularly—they pulled it after six weeks and went back to Debbie’s version.

Debbie was gleeful. Her design “won.” Validation! Vindication!

And then she had dinner with Paula Scher.

Paula told her it was terrible that it happened. Not because the new design was bad—because of what it meant for ALL of us. Every time designers cave to public pressure, every time we pull something back because people don’t like it, we’re teaching everyone that they don’t have to trust us. That change is only okay if it’s comfortable.

“And she was absolutely right,” Debbie said, “because then what happened for the next two decades, anytime there was a logo that didn’t do well and was retracted, people are like, they did a Tropicana.”

We turned it into a verb. A cautionary tale. And in doing so, we made everyone more afraid to be brave.

Paula’s lesson: if we’re supposed to be change makers, we have to be okay with change being uncomfortable. BUT—and this is crucial—we also have to explain it in a way people can actually understand. Not with “crazy cosmic” explanations, but with strategy. With empathy. With the parts of behavioral psychology and cultural anthropology that actually matter to real humans buying orange juice.

I think about this all the time now. How many times have I pulled back on something because I was afraid of being “the next Tropicana”? How many of us are designing scared?

Here’s what got me. Both of them—BOTH of them—said unequivocally: they wouldn’t have the careers they have without AIGA.

For Michael, it started with making a mixtape for an AIGA opening party in the mid-‘80s. That’s how he met Paula Scher and Woody Pirtle. Eventually, those people became his partners at Pentagram for four decades.

“There was no other medium through which I could meet these people,” he said.

For Debbie, it was exposure. She graduated in 1983 but didn’t get involved until the late ‘90s—fifteen years into her career. And when she finally did, everything changed.

She didn’t know. For fifteen years, she didn’t know any of this existed.

When she became president, she visited all 66 chapters because she remembered feeling excluded. Michael made a commitment to visit any chapter that asked, and another commitment he STILL keeps today about responding to emails.

“When you reach out to someone and you don't even get an acknowledgement, that makes you feel even more invisible,” he said. “It’s so easy to acknowledge that someone shares this earth with you.”

I had to pause after that one.

When I asked what advice they’d give current chapter leaders, they both landed on the same thing: say yes.

Say yes to partnership. Say yes to who you’re willing to let in. Say yes to making the tent bigger.

Michael told a story about a recent Pentagram book launch—standing room only, the kind of crowd any AIGA chapter would dream of. The executive director of AIGA New York was there as an attendee, not competition.

“The design community is the design community,” he said. “The more broadly you can define it, the more healthy it is.”

And then they both shared how they still practice this. The chapters they still visit. The emails they still answer. The commitments they made decades ago that they keep today.

Because here’s the thing: all those chapter leaders out there right now trying to rebuild post-COVID, trying to prove relevance, trying to compete with every online community? These two people who’ve been doing this for 40+ years are saying: stop keeping score. Make the tent bigger. Just say yes.

You never know who’s sitting next to you.

Debbie said something near the end that I keep replaying: “As difficult as it was sort of onboarding into the AIGA world, that's also part of my history and experience.”

She didn’t have an easy path in. She felt like an outsider. She got kicked out of groups. But she stayed. She kept showing up. And eventually she became president and visited 66 chapters to make sure no one else felt how she felt.

That’s not a success story. That’s a love story.

Michael talked about how AIGA used to be “the sole analog channel” before the internet. How people wondered if it would survive digital culture. Whether face-to-face would matter anymore.

But then he said: “If by some miracle you go to something and you’re sat down next to someone and you connect with them... it’s still electrifying.”

Even if they’re not a movie star. Even if they’re just someone you follow on Instagram. That moment when the parasocial becomes real? That’s still magic.

“There’s a good case for going out and sitting next to people at dinner, if you can possibly swing it,” he said.

And I thought: yeah. Yeah, there is.

Because sometimes you sit next to Michael Bierut and he asks if you want to talk about rap music. Sometimes you sit next to Debbie Millman and she’s doing basketball play-by-play with her dad on the phone. Sometimes you sit next to someone who changes your whole life and you don’t even know it yet.

But you have to show up to the dinner first.

Want to hear the full story about Michael’s New York City mixtape? Or see Debbie literally pull out a 26-year-old letter on camera? Or hear more about what Paula Scher said that changed how Debbie thinks about risk? Listen to the full episode wherever you get your podcasts.

And if you’re a chapter leader feeling like an outsider right now—like you’re on the wrong side of some invisible line—please know that Debbie and Michael felt that way too. They kept showing up anyway. So should you.