Instead, we got a full blueprint for how to turn design volunteerism into actual impact—plus karaoke stories, human pyramids, and someone skipping the White Stripes to read Harry Potter alone in a hotel room.

This conversation hit hard—in the good way. Here’s what stuck with me:

At her first retreat, Jenn made herself ask a question out loud. Not to be impressive. Just to get over the fear.

Justin noticed. That one moment kicked off a connection that led to decades of collaboration, national board service, family vacations, and a whole lot of design-for-good work.

I love this reminder: sometimes your job is just to say one thing. That’s how people find you.

These retreats weren’t passive conferences. You had to earn your way there by actually doing the work—board meetings, student events, sponsor calls.

Then once you got there? No sleep. Pizza costumes. Karaoke with Debbie Millman. Jenn projected a pyramid photo of me in front of 200 people. Justin had to sing Baby Got Back. Someone always cried at breakfast.

This wasn’t “thought leadership.” It was actual leadership. Messy, funny, deeply human.

What hit me hardest is how much they took with them.

Jenn became a department chair, then associate dean. Justin built a B‑Corp, launched global water projects, mentored hundreds of designers. They didn’t get that from a course or a boss—they got it from figuring out how to run a chapter, plan an initiative, and make it to the next meeting with your dignity mostly intact.

Everything they learned at the local level—about values, momentum, collaboration, delegation—became the scaffolding for the rest of their work.

We also talked about what’s missing now: the hallway conversations, the feeling of “these are my people,” the access to design heroes who were just there in the room with you.

Not everything scales well. But some things—trust, community, accountability—only scale because they start small.

If you’ve ever wondered why people used to cry at retreats (and also build human pyramids), this one’s for you.

→ [Listen to the episode]

And yes—if someone invites you to see a band at your first retreat? Go. Even if you brought a book. It might be the White Stripes.

Want to hear more stories like Jenn’s and Justin’s? Subscribe to Cheers & Tiers on Apple Podcasts, Spotify, or wherever you get your podcasts. We’ll have more episodes featuring your friends and your favorite design leaders, sharing their journeys, challenges, and triumphs.

Please subscribe, rate, and review Cheers & Tiers: Design Leadership Tales Retold wherever you get your podcasts.