Daily Creative with Todd Henry

• 5 Questions Every Creative Pro Should Be Asking

  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: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.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.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.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?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.Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.Mentioned in this episode:The Brave Habit is available nowMy new book will help you make bravery a habit in your life, your leadership, and your work. Discover how to develop the two qualities that lead to brave action: Optimistic Vision and Agency. Buy The Brave Habit wherever books are sold, or learn more at TheBraveHabit.com.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.

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• Dirtbag Billionaire: Why Calling Isn't "Found", It's Uncovered

  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: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.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.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.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.Legacy is Built Through Consistent Integrity: Values-driven decisions compound over time, creating an enduring legacy that outlasts individual achievements or wealth.Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.Mentioned in this episode: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.

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• Super Chickens vs. Super Coops: The Power of Team Intelligence

  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:The Super Chicken Fallacy: Prioritizing only high-performing individuals can lead to toxic rivalry and stifle collaboration, ultimately reducing the team’s overall output.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.Emotional Intelligence Matters Most: The best predictor for team effectiveness is the group’s collective emotional intelligence, not the average or highest IQ.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.Aligned Incentives Create Real Teamwork: Misaligned incentives that reward only individual performance sow competition; when incentives support team outcomes, collective intelligence and output flourish.Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.Mentioned in this episode: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.

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• Slow Down To Go Fast (Why Optimizing Isn't the Answer)

  In this episode, we dive deep into what it truly means to sustain high performance—without losing ourselves along the way. We explore why the relentless pursuit of optimization can leave us exhausted, disconnected, and ultimately unsatisfied, even as our productivity dashboards look more impressive than ever.We sit down with Dr. James Hewitt, a human performance scientist and author of Regenerative Performance, who challenges the contemporary obsession with “optimization.” Instead, he offers a fresh perspective: success is about rhythm, not balance. We discuss how alternating between periods of intense focus and intentional renewal is not just effective, but necessary.Also joining us is Jim Murphy, author of Inner Excellence, whose coaching of elite athletes and leaders centers on training not just the mind, but the heart. Jim’s journey—including a literal desert retreat—led him to believe that excellence is grown from within, through the cultivation of peace, confidence, and love, especially under pressure.Together, we examine why greatness isn’t something you manufacture through sheer effort. It’s something that arises when you let go, reconnect, and cultivate an inner life that is in sync with your values and goals.Five Key Learnings from the Episode:Optimization Fatigue Is Real: Tracking and optimizing every aspect of life can actually diminish well-being and life satisfaction rather than increase it.Rhythm Beats Balance: Sustained high performance depends on deliberate alternation between deep engagement and meaningful renewal, not on chasing a mythical state of balance.Recovery Requires Intention: Proactive, scheduled breaks—including exposure to nature and engaging in supportive social interactions—are critical for true restoration and creativity.Excellence Comes from the Heart: Training your heart—clarifying your life purpose, embracing vulnerability, and mastering the ego—is more impactful than simply mastering skills.Self-Centeredness Is the Core Obstacle: Overcoming the default setting of self-focus opens the door to authentic creativity and connection, but it requires the courage to face discomfort and uncertainty.Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.Mentioned in this episode: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.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.

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• Safe Danger: Why Play Is Serious Business

  In this episode, we dive deep into the paradoxical space where creativity thrives: the intersection of safety and danger. Drawing inspiration from IDEO’s iconic reinvention of the shopping cart, we explore how play, risk, and psychological safety fuel real innovation. We’re joined by Ben Swire—author of “Safe Danger” and former IDEO design lead—and Cas Holman, designer and author of “Playful,” to rethink the role of play and trust in work, leadership, and life.Ben shares why “safe danger” is the sweet spot creative teams need: an environment where people feel secure enough to step outside their comfort zones, challenge the norm, and speak candidly. We unpack why “comfort” is often mistaken for true safety—and why suppressing tension or chasing certainty kills innovation. Through real-world anecdotes, Ben reveals how play isn’t just childish fun; it’s a training ground for courage, trust, curiosity, and honest collaboration.Cas invites us to rediscover the lost art of playful exploration in adulthood. She challenges the myth that creative people crave boundless freedom—showing instead how constraints and a bit of friction spark our best ideas. We discuss how reframing success and experimenting with “what if” moments in daily life cultivates the resilience and curiosity critical for growth. The real challenge? Overcoming our aversion to looking foolish, letting go of performative pressures, and making the unknown a place of opportunity rather than fear.Five Key Learnings:True safety isn’t comfort—it’s the courage to challenge, take risks, and show up authentically.Play is not an escape from work; it’s the work. The most innovative teams use play as a safe way to experiment and lower the perceived risk of failure.Constraints are generative, not restrictive. Boundaries and rules give creative minds something to push against, sparking deeper engagement and originality.Psychological safety consistently drives team performance, innovation, and retention—not carrot-and-stick incentives or relentless productivity.Embracing challenge, reframing success, and maintaining curiosity in the face of uncertainty build resilience, satisfaction, and lasting creative growth.Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.Mentioned in this episode:Apply for Creative Leader Roundtable Every creative team needs a leader who's brave, focused, and brilliant, but none of us get there alone. The Creative Leader Roundtable is your place to connect with peers, sharpen your leadership craft, and stay inspired for the long haul. We're about to launch with a brand new group of leaders. So, if you're interested, visit CreativeLeader.net to learn more and to apply. Great leadership is a practice, not an accident. 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.

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