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.

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.

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.

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.

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:

1. Optimization Fatigue Is Real: Tracking and optimizing every aspect of life can actually diminish well-being and life satisfaction rather than increase it.
2. Rhythm Beats Balance: Sustained high performance depends on deliberate alternation between deep engagement and meaningful renewal, not on chasing a mythical state of balance.
3. Recovery Requires Intention: Proactive, scheduled breaks—including exposure to nature and engaging in supportive social interactions—are critical for true restoration and creativity.
4. 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.
5. 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.

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.

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:

1. True safety isn’t comfort—it’s the courage to challenge, take risks, and show up authentically.
2. 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.
3. Constraints are generative, not restrictive. Boundaries and rules give creative minds something to push against, sparking deeper engagement and originality.
4. Psychological safety consistently drives team performance, innovation, and retention—not carrot-and-stick incentives or relentless productivity.
5. 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.

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.

Episode 80: Lucky By Design – Show Notes

Is luck really just random, or can we engineer it? In this episode, we explore how “luck” is often the result of preparation, pattern recognition, and a deep understanding of hidden systems that shape opportunity. Drawing from the unlikely success story of Gary Dahl’s Pet Rock and the groundbreaking research of Wharton economist Judd Kessler and his new book Lucky By Design, we dig into the ways luck is built, not found.

Judd Kessler introduces his framework of “hidden markets,” where things like tickets, jobs, and creative opportunities aren’t always allocated by price or obvious mechanisms. Instead, they’re shaped by invisible rules that govern access and advantage. We discuss the “three E’s”—efficiency, equity, and ease—as the building blocks of these markets, and examine real strategies to decode the signals and systems at play.

Along the way, we unpack how showing up prepared, making it easy for others to work with us, and understanding the actual rules of the game can help leaders and creative professionals tilt the odds in their favor. We also take on the coming wave of AI-driven speed and automation, and ask what it means for authentic signaling in a world where bots are getting faster and smarter.

Five Key Learnings from the Episode:

1. Luck favors the prepared. What looks like serendipity is often the outgrowth of discipline, awareness, and the willingness to build a “door” for opportunity to knock on.
2. Hidden markets have hidden rules. Whether it’s a ticket lottery or landing a client, outcomes are shaped by underlying systems—not just price or “fairness.” Learn the rules, and you can play the game more strategically.
3. The three E’s—Efficiency, Equity, and Ease—are metrics for opportunity. Whether trying to get noticed, land a deal, or hire the right people, balancing these three helps you become the option others choose.
4. Reducing friction creates value. In creative and business relationships, being easy to work with and removing obstacles can be a more powerful signal than raw talent alone.
5. Signals matter more than ever in the age of AI. As automation makes it cheap and easy to fake enthusiasm or speed, genuine signals—like real relationships and proven follow-through—become even more vital.

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.

How do we keep our creative edge—and ourselves—intact while navigating constant demands, distractions, and emotional turbulence? In this episode, we explore two distinct yet overlapping paths to real impact and creative resilience.

We first sit down with Robert Glazer, best-selling author of The Compass Within, who demystifies the role of core values as more than just aspirational words—they’re non-negotiable principles that serve as a compass for decision making, relationships, and leadership. We discuss how to identify actionable, clarifying values, why supposed “values” like “family” often hide deeper principles, and how lack of alignment between values and life leads to burnout and stagnation. Glazer shares his “big three” most life-defining decisions and what happens when our work, partners, or communities are out of sync with who we really are.

Next, we’re joined by Josh Pais, veteran actor and creator of Committed Impulse, whose new book Lose Your Mind offers a radical take on performance and presence. Pais reveals how reframing so-called “negative” emotions like anxiety and nervousness—as simply energy—transforms dread into creative fuel. He walks us through practical access points to presence, explains why emotion labeling sabotages creativity, and shares tools for cultivating the embodied awareness needed to consistently put ourselves on the line, whether the audience is one person or a thousand.

Together, these conversations serve up a roadmap for navigating modern creative pressures with clarity, energy, and authenticity.

Five Key Learnings from This Episode:

1. Core values aren’t beliefs—they’re actionable, non-negotiable principles that guide behavior and decisions across every area of life and work.
2. Naming surface-level values like “family” isn’t enough—clarity comes from articulating how those values show up as decisions and actions, both personally and professionally.
3. Burnout is often rooted not in workload, but in living incongruently with our core values, which drains energy and leads to fragmentation or eventual crisis.
4. Emotions like fear or nervousness are not “bad”—they’re simply sensations, or energy, that, when accepted and embodied, can be used as creative fuel rather than barriers.
5. Authenticity is grounded in presence and congruence: anchoring to core values provides direction, while welcoming our emotional experience gives us the fuel to show up bravely and perform at our best.

Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.

Mentioned in this episode:

The Brave Habit is available now

My 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.

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.

How often do our teams, family members, or collaborators end up misunderstanding each other even when we think we’re being perfectly clear? In this episode, we dive into the high cost of miscommunication and what it takes to become a “super communicator” in a noisy, divided world. We’re joined by Pulitzer Prize-winning journalist Charles Duhigg, whose new book “Supercommunicators” unlocks why our conversations so often miss the mark—and offers a toolkit for breaking through confusion and building true alignment.

Together, we explore how clarity, empathy, and attention are more crucial than ever, especially as our workplaces and lives move online. From hospital handoffs to debates with Uncle Gary, we unpack the vital art of matching the right kind of conversation, listening deeply, and decoding the signals that don’t show up in written words. If you’ve ever walked away from an exchange realizing you and your counterpart were simply talking past one another, this episode is for you.

Five Key Learnings from This Episode:

1. Assumptions are the enemy of understanding. We can’t assume others interpret our words as we intend; confirming mutual understanding is essential—even in routine exchanges.
2. There are three types of conversations—practical, emotional, and social. Misalignment around which conversation is taking place is often the root cause of frustration and disconnect.
3. “Matching” the conversation builds trust. Super communicators detect what kind of conversation someone needs and mirror it—acknowledging emotion when present, before pivoting to solutions.
4. Deep questions invite deeper connection. Asking about values, motivations, or experiences (rather than just surface details) opens the door for more meaningful dialogue.
5. Non-linguistic cues are powerful—but different channels require different strategies. Tone, posture, and facial expressions matter, but in written or digital communication, politeness, clarity, and rereading from the receiver’s perspective become the superpowers.

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.

In this episode, we explore the exhilarating—and sometimes terrifying—landscape of disruption with innovation expert Scott Anthony, author of Epic Disruptions. Together, we examine the rapid shifts happening across every industry and what it takes not just to survive, but to lead through change with courage and creativity.

We discuss why disruption is as much about human behavior as it is about technology, and highlight the critical missteps leaders make when they listen only to their best customers. Scott shares stories from history, from the early days of the printing press to the dawn of the iPhone, revealing the hidden patterns of how real innovation emerges. We also dig into the “shadow” cast by epic disruptions—the unforeseen challenges, culture clashes, and the uncomfortable process of rewriting rules in real time.

Scott explains how disruption often begins on the margins, serving unlikely customers and overlooked markets, and why innovation is a “collectively individualistic” pursuit that requires both lone sparks and community effort. Finally, we discuss practical steps for leaders to keep their organizations alert to opportunity: experiencing “tomorrow, today,” fostering playful experimentation, and nurturing cultures that let the sparks of creativity catch fire.

Five Key Learnings from This Episode:

1. Disruption is about behavior, not just technology: True innovation only matters if it changes how people act, not just what tools they use.
2. Listening to your best customers can blind you: When markets shift, incumbent leaders often miss game-changing opportunities by focusing too narrowly on current power users’ demands.
3. The “shadow” of disruption is real: Disruption isn’t universally good; it often generates resistance, unintended consequences, and a messy mid-transition period that leaders must thoughtfully navigate.
4. Innovations start at the edges: The next big thing rarely comes from the center of mainstream markets; instead, pay attention to niche users and unexpected applications.
5. Innovation is a team sport: Breakthrough ideas depend on collaboration across disciplines and generations, and thrive in environments that make experimentation fun, not fearful.

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.

Why does so much around us feel "vaguely familiar"? In this episode, we dive deep into the creative malaise of our overstimulated world—where endless scrolling, constant content, and a deluge of data make everything seem slightly derivative and uninspiring. We unpack the concept of “vague familiarity” and examine why our passion for novelty is constantly dulled by today’s information overload.

To help us cut through the noise, we’re joined by Andrew Robertson, chairman of BBDO and author of The Creative Shift. Andrew brings decades of frontline experience in fighting creative sameness at one of the world’s most successful advertising agencies. We explore the sometimes uneasy balance between operational excellence and breakthrough creativity, and how organizations can make space for real innovation without falling for surface-level quick fixes.

Along the way, we break down actionable principles for reigniting creative excitement, including finding inspiration at the "edges," practicing attentional minimalism, and prioritizing productive passion over passive consumption. Andrew shares compelling stories—including how Delta Airlines redefined the passenger experience by rethinking the real source of travel stress—and reveals what it really takes to recognize a great idea (even in risk-averse environments).

Five Key Learnings from this Episode:

1. Rediscover the Edges: Creativity flourishes at the intersections and boundaries of different disciplines and domains. Stepping outside your usual circles—whether it’s through new conversations or learning in unfamiliar fields—leads to fresh insights.
2. Practice Attentional Minimalism: With relentless digital noise, deliberate focus and margin are essential. Setting boundaries around your inputs and carving out undistracted time helps you notice what truly matters.
3. Pursue Productive Passion: Creative energy comes from making, not just consuming. Progress and intrinsic motivation fuel innovation more than passive amusement.
4. Define the Real Problem: The most effective solutions come from unwillingness to leap immediately to action. Every creative breakthrough begins by deeply diagnosing the real challenge, even if sitting with ambiguity feels uncomfortable.
5. Manage Risk—Don’t Chase Certainty: Seeking certainty kills originality. Instead, smart creative leaders evaluate the downside, manage risk, and are willing to act without guarantees—knowing that bold ideas don’t come with precedents.

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.

In this episode, we explore what it takes to sustain creative leadership—not just for the next launch, but through the marathon of a meaningful career. We sit down with serial entrepreneur and author Chris Ducker to dig deep into his philosophy from his new book, "The Long Haul Leader," where he shares battle-tested frameworks for combating burnout and resisting the relentless drive of hustle culture.

We reflect on how our culture glorifies quick wins and non-stop hustle at the expense of our health, relationships, and lasting impact. Chris opens up about his own struggle with severe burnout during the pandemic, describing the pivotal moment he realized he’d lost touch with what truly made him “him.” We discuss practical strategies that allowed him to recover, including building what he calls a Life Operating System (Life OS)—a set of rhythms and habits designed to make leadership and creative work sustainable for the long haul.

We also highlight the importance of focusing on the right “who” as leaders, and why serving the right people makes all the difference. Together, we offer a smart, honest take on how to build resilience, manage energy, and stay effectively creative without losing yourself to exhaustion.

Five Key Learnings from This Episode:

1. Sustainability beats constant hustle: Hard work matters, but treating hustle as a perpetual lifestyle leads to burnout. Purposeful sprints are powerful only when surrounded by practices that let you recover and refocus.
2. Breaking points clarify priorities: Real change often follows a crisis—those moments of total exhaustion or loss of purpose—but transformation only happens when you intentionally respond, not just notice the warning signs.
3. Design your Life OS: Just like computers have operating systems, leaders need intentional frameworks for health, learning, energizing relationships, meaningful work, and hobbies—layering small “micro moves” for a compounding impact over time.
4. Serve your real audience: Lasting fulfillment and greater impact come from identifying and serving those you’re best equipped to help, not by trying to please everyone or chasing external validation.
5. Burnout is not just part of the job: Chronic fatigue, disengagement, and emptiness are signals that something fundamental needs to change. Effective creative leadership means spotting the signals early and course-correcting—not waiting for a blow-up.

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.