In December 2025, we celebrate something special—twenty years of this podcast, which first launched as Accidental Creative in December 2005. We reflect on how starting, even with imperfect beginnings, is an essential part of a creative journey. In this episode, we draw insights from the book Daily Creative, sharing a series of thought-provoking essays designed for creative professionals navigating the end of the year.

We explore themes from balance and priorities (Rubber and Glass Balls), beginner’s mindset (Just One Song), the power of working from what’s known (The Edge Pieces), and the importance of knowing what “actual work” is (When You’re Working). Each essay comes with a practical application question to help leaders and creative pros pause, reflect, and reset for the coming year.

If you’re looking for a ritual or rhythm to keep your creative juices flowing and your mindset sharp, this episode is packed with reminders and prompts to help you refocus and get ready for fresh challenges ahead.

Five Key Learnings:

1. Starting Imperfectly Is Essential: Early creative work will rarely be polished, but the act of beginning is what opens the door to growth and excellence.
2. Protect the Fragile Elements of Life: Not everything rebounds after a setback; relationships, health, friendships, and spirit deserve proactive care and attention.
3. Approach Work Like a Beginner: Tackling each project with fresh enthusiasm and curiosity ignites new insights, regardless of past experience.
4. Solve Problems Starting With What You Know: Like edge pieces in a puzzle, letting your certainties frame the unknowns brings clarity to complex creative challenges.
5. Distinguish Busyness from True Work: Knowing which activities actually create value helps redirect energy away from distraction and toward your core genius.

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In this episode of Daily Creative, Todd Henry explores the subtle ways in which we avoid true commitment to our creative and professional ambitions. Todd discusses the concept of "escape hatches"—the backup plans, excuses, and rationalizations that prevent us from risking real vulnerability and discovering what we’re truly capable of. Drawing from personal stories and practical frameworks, we unpack three common escape hatches that undermine creative and leadership excellence: procrastination and last-minute work, dilution and divided attention, and backward rationalization of success.

Todd also digs into actionable strategies to help you spot these patterns in your work, close escape hatches, and move forward with greater intentionality. Whether you lead teams, dream of launching a business, or simply want your creative efforts to have more impact, this episode offers practical, non-obvious guidance for getting braver, more focused, and brilliant every day.

Five Key Learnings from the Episode:

1. Escape hatches often feel like wisdom, but are usually just disguised fear. We tend to rationalize delay or avoid commitment under the guise of being "prudent," when in reality it is keeping us from meaningful progress.
2. Procrastination and last-minute work protect us from knowing what our best effort truly looks like. Setting step goals and using time blocking can counter the urge to push everything to the last minute and drive more consistent creative output.
3. Dilution and divided attention dilute impact. By focusing on your "Big Three" priorities and carving out protected space to pursue them, you ensure that your energy is devoted to what matters most—and can actually achieve excellence.
4. Backward rationalization undermines growth. Defining what success looks like in advance and creating external accountability removes the temptation to justify poor outcomes, fostering honest self-assessment and improvement.
5. Real creative progress requires closing escape hatches, even though they seem safe. The real safety comes from confidence in your ability to adapt, not from having endless backup plans.

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 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 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

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.

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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 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.

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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.

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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.

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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.

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 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.

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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.

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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.