Ep 103 Leadership: Why creating organization and cultural change is so hard

Show notes

Welcome to Episode 103 of The Crazy One Podcast. I’m your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design—and everything else that empowers creative people.

You can always find past episodes, show notes, and more at thecrazyone.com, or watch videos, tutorials, and keynotes on YouTube. Follow me on Twitter or Instagram for updates, or follow the show on LinkedIn or Facebook.

Returning to the Classic Format

This episode marks a return to the more traditional format of The Crazy One. But before we dive in, I want to talk about the Share the Mic Now series and give you an update.

Over the past couple of months, I’ve thought a lot about what to do next—how to transition back, what these episodes mean, and how they’ll continue. Truth is, they aren’t ending. They’re becoming a permanent part of the show. Because these conversations matter. They need to happen. And too often, when problems arise, we focus on them briefly and then move on. Real, sustainable change gets lost.

Huge thanks to Maurice Cherry, Delby Millman, and Sylvia Baffour for kicking off those episodes so powerfully. Sylvia recently asked me, “When are those episodes going to end?” My answer: they’re not. We need to keep these conversations going.

If you’re Black, Brown, Indigenous, or part of the LGBTQ+ community and have a story to share, please reach out. I’d love to talk and see how we can help amplify your voice on the show.

Why I Nearly Quit the Show

The last few months have been emotional. On one hand, working with Maurice, Delby, and Sylvia was profoundly inspiring. On the other, the silence from the design community—especially white creatives—was deafening. And honestly, it pushed me to the edge. I questioned whether I should even continue this podcast.

In two months, I heard from 20–30 white supremacists. I heard from zero white design leaders. No one asked about the movement. No one joined. Some reached out privately, worried about my career—asking if speaking out would hurt my chances of getting hired. But no one asked: “How can I help?”

To those people, I asked: Why are you worried about people remembering what I did? You should be more afraid of people remembering what you didn’t do.

I was heartbroken. I give so much to this industry—years of time and energy—and when it mattered most, the silence from “leaders” was louder than words.

The Power and Pain of Silence

People will remember this moment.

They’ll remember who showed up. And who didn’t.

To the trolls and cowards who were quick to criticize but vanished when action was needed—where are you now?

To the so-called influencers, podcasters, and creative “leaders” who went quiet: You were never really leading.

To those who told me not to care as much, just say feel-good stuff, and grow my following—no. I’m not interested in building a career on silence or fake optimism.

The Heart of the Problem: Willful Ignorance

What this moment exposed is something bigger. I realized that a lot of our systemic issues—racism, sexism, ageism, creative burnout, toxic leadership—are perpetuated not because people are evil, but because they choose not to care unless it affects them.

• Men mostly don’t care about sexism—because it doesn’t affect them.

• White people mostly don’t care about racism—because it doesn’t affect them.

• Young people don’t care about ageism—because it doesn’t affect them.

• Executives don’t care about company-wide problems—because they’re not impacted.

That’s what’s at the root of so many issues: willful ignorance. Choosing to stay blind to the pain of others. Choosing comfort over change.

Language That Masks the Truth

We also need to talk about the language that hides discrimination behind buzzwords:

• “Gamification,” “stickiness”—these sanitize unethical design goals.

• “Cultural fit”—often used as a disguise for discrimination.

Too many companies use culture as an excuse for exclusion: “If they don’t act like us, they don’t belong.” That’s not culture. That’s bias.

Why Change Fails

Whether it’s in society or your company, change fails when:

• People only care until it affects them.

• Leaders protect comfort over integrity.

• There’s no accountability, no risk, no vulnerability, and no courage.

What We Need More Of: 4 Words

To create real change—personally, professionally, and culturally—we need more of four things:

1. Courage – Speak up. Take a stand. Listen to opposing views.

2. Vulnerability – Admit when you’re wrong. Share your truth. Be open.

3. Risk – Put something on the line. Stop waiting for it to be easy.

4. Accountability – Don’t just say the right things—follow through.

This isn’t about perfection. It’s about progress. No one says the right thing every time. But staying silent? That’s a choice.

Where Do We Go From Here?

I’m still figuring that out. I’ll keep making episodes. I want to do more Share the Mic Now conversations. Maybe start a new interview series. But more than anything, I want this show—and this community—to be about real, sustainable change.

If you’ve been feeling this too, if you’re outraged, heartbroken, or just tired—reach out. Let’s talk.

You can always find me on Twitter and Instagram. The show is on LinkedIn and Facebook.

Final Thoughts

We can’t just be passively outraged. We can’t keep choosing comfort over action. We need to be better. All of us.

And yeah, I’m angry. But I’m not quitting. Because even if I’m the only one still speaking up—one voice is better than none.

Thanks for spending your time with me. Stay safe. Stay bold.

And as always—stay crazy.

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