In this episode, we take a step back from our typical interview format to reflect on something many creative leaders are feeling right now: a subtle but persistent sense of drift amidst uncertainty. Drawing from recent conversations with leaders worldwide, Todd Henry digs into the changing dynamics of organizations, shifting marketplaces, and the unique challenges and numbness that come with these times.

Instead of providing easy answers, Todd shares five uncomfortable—but essential—questions designed to provoke deep reflection for anyone with influence, whether you lead a team, guide clients, or simply shape decisions in your organization. He explores how apparent success can mask underlying misalignment, the dangers of leading from within an echo chamber, the paralyzing fear of looking foolish, the temptation of ego-driven systems, and the fine line between creating stability and fostering complacency in teams.

This episode is an invitation to wrestle with the deeper work of leadership, sense-check our motives, and create environments where honest conversations and breakthrough ideas can flourish.

Five Key Learnings:

1. Success Can Be a Trap: Achieving goals and hitting metrics doesn’t always equate to true progress if we lose sight of our original purpose. We must vigilantly check what we’re really optimizing for.
2. Truth-Telling is Essential: Leadership naturally creates distance. If we don’t intentionally invite honest feedback (even if it stings), we risk operating in a false sense of alignment.
3. Risking Embarrassment Fosters Innovation: Many great ideas die because we’re afraid to look foolish. Innovation demands courage, and that courage is strengthened by sharing bold ideas in safe, trusted circles.
4. Ego vs. Mission: It’s easy to unconsciously build systems that feed our ego under the guise of excellence or mission. The real test: Would we do the work if nobody noticed?
5. Stability Isn’t Safety: Teams crave both challenge and stability, but protecting them too much can lead to complacency. The goal is to create security so that bold, meaningful risks—and growth—are possible.

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The Brave Habit is available now

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Apply for Creative Leader Roundtable

 Leading creative people is rewarding, but it can also feel isolating. That's why I've started Creative Leader Roundtable, a private community where leaders like you connect monthly to get practical insights, honest feedback, and real encouragement. You'll leave every round table with fresh perspective and tactical ideas. You can apply right away. So if you lead a team of talented people, go check us out at CreativeLeader.net, because creative work deserves brave leadership.

In this episode, we explore the unconventional story of Yvon Chouinard, the “dirtbag” climber who became the founder of Patagonia and ultimately gave away his billion-dollar company to protect its mission. In conversation with David Gelles—New York Times journalist and author of Dirtbag Billionaire—we dig into the paradoxes of success, the power of awareness, and the ongoing tension between principle and profit. We discuss how Chouinard’s love for the outdoors led him to create climbing gear out of necessity, and how his refusal to ignore the negative impact of his products shaped Patagonia’s legacy of environmental stewardship and values-driven leadership.

We reflect on how meaningful work often reveals itself not through grand visions, but through paying attention to the patterns and tensions within our everyday actions. The episode challenges leaders and creatives to reconsider what it means to act with integrity and to recognize the marks—both good and bad—we leave through our work. Chouinard’s story offers a blueprint for leading with conviction, making hard calls in service of a greater purpose, and understanding that values build momentum over time.

Five Key Learnings from the Episode:

1. Calling is Revealed, Not Found: Purpose often unfolds through the work we’re already doing, showing itself in the problems we care about and the frustrations we can’t ignore.
2. Principle Over Profit: True leadership is measured not by stated values, but by the sacrifices made when those values clash with financial incentives—as shown when Patagonia prioritized environmental impact over sales.
3. Awareness Precedes Change: Staying attentive to the second- and third-order effects of our decisions is essential for creating lasting positive impact and avoiding unintended harm.
4. Success Requires Restraint: Responsible growth means not chasing expansion at all costs, but deliberately throttling progress to ensure alignment with core mission and sustainable practices.
5. Legacy is Built Through Consistent Integrity: Values-driven decisions compound over time, creating an enduring legacy that outlasts individual achievements or wealth.

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Apply for Creative Leader Roundtable

 Leading creative people is rewarding, but it can also feel isolating. That's why I've started Creative Leader Roundtable, a private community where leaders like you connect monthly to get practical insights, honest feedback, and real encouragement. You'll leave every round table with fresh perspective and tactical ideas. You can apply right away. So if you lead a team of talented people, go check us out at CreativeLeader.net, because creative work deserves brave leadership.

For decades, we've been told that high performance is about gathering the brightest stars—the so-called “super chickens”—onto one team and watching the magic happen. But what if this approach is exactly what’s holding us back? In this episode, we challenge the myth of the lone genius and superstar culture, inspired by the research of evolutionary biologist William Muir and our guest, Jon Levy, author of Team Intelligence.

We dig into why the true driver of organizational excellence isn’t the brilliance of any one leader or individual, but the collective effectiveness of the team. Jon shares surprising findings from research on team dynamics, showing that stellar individual credentials often don’t correlate with high-performing teams—and sometimes even torpedo them. Together, we explore what makes teams “intelligent,” the concept of bursty communication, and the underappreciated power of “glue players”—team members who multiply the effectiveness of everyone around them, often quietly and behind the scenes.

If you’ve ever found yourself thinking, “We have the right people, so why aren’t we clicking?”, this conversation gives you an entirely new framework for team effectiveness. It’s not about outshining one another; it’s about amplifying each other.

Five Key Learnings:

1. The Super Chicken Fallacy: Prioritizing only high-performing individuals can lead to toxic rivalry and stifle collaboration, ultimately reducing the team’s overall output.
2. Fluid Leadership: Effective teams allow leadership to flow based on expertise, not title—leadership shifts to those best suited to solve the problem at hand.
3. Emotional Intelligence Matters Most: The best predictor for team effectiveness is the group’s collective emotional intelligence, not the average or highest IQ.
4. Glue Players Are Multipliers: Certain team members—rarely the stars—can significantly raise the performance of those around them by prioritizing team success, facilitating communication, and demonstrating forward-thinking.
5. Aligned Incentives Create Real Teamwork: Misaligned incentives that reward only individual performance sow competition; when incentives support team outcomes, collective intelligence and output flourish.

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Apply for Creative Leader Roundtable

 What if you had a space every month to sharpen your leadership edge without the fluff? The Creative Leader Roundtable is where smart, driven, creative leaders gather to exchange ideas, solve real challenges, and grow together. So if you lead a team of thinkers, makers, or dreamers, this is your lab. We're launching soon with a new group of leaders. So, if you're interested, check it out and apply at CreativeLeader.net.