What happens when the chase is over and the dream is finally caught? In this episode, we sit down with Lionel Cartwright—whose career soared to the top of the country music charts—to explore the rarely discussed crossroads of success. After years of relentless pursuit, Lionel achieved all the milestones he’d imagined: record deals, number one hits, and recognition. Yet, in those quiet moments away from the spotlight, he was confronted with the unexpected question: Is this it?

We follow Lionel’s journey from cover band beginnings and publishing deals, to Nashville stardom and the unexpected tug to redesign his life. Along the way, we unpack the paradox of ambition, the need for alignment over applause, and the courage required to leave "success" behind for something more sustainable.

Together, we challenge leaders and creative pros to pause, reassess whether momentum is driving their choices, and listen for the subtle signs that realignment might be overdue.

Five Key Learnings from the Episode:

1. Chasing the Dream Isn’t the Finish Line: Pursuing success provides meaning and adrenaline, but catching it brings new questions about fulfillment and sustainability.
2. Beware of Momentum’s Seduction: Success often leads to expectations and obligations that can detach us from what truly sustains us.
3. Alignment Beats Applause: True creative bravery lies in pursuing work that fits who we are, rather than playing roles imposed by past ambitions or industry pressures.
4. Listen to Your Inner Voice: Quiet whispers of misalignment are worth investigating, no matter how much time or energy you’ve invested in the chase.
5. Redirection Isn’t Failure: Leaving a high-profile path to redesign your work around life—rather than vice versa—is one of the bravest moves a creative professional can make.

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Listen to Todd's interview on Lionel's podcast Off The Charts: Spotify - Apple Podcasts

This week, we celebrate a major milestone... 20 years of the podcast! The first episode of The Accidental Creative launched in December 2005. While this is episode 88 of the re-branded version, Daily Creative, this is something like episode 1,398 of the podcast.

We take a reflective journey back to where it all began, unpacking the origin story of the show and the creative work that continues to shape everything we do.

Todd shares the challenges of being a young creative director attempting to help a team thrive under relentless pressure, while also confronting his own ambitions and the ever-present risk of burnout. He digs into the early days of creative community-building (over coffee in Cincinnati), the revelation that healthy, productive creativity was possible, and the pivotal experiments that inspired him to share our ideas through the newly emerging medium of podcasting.

We revisit the genesis of “The Accidental Creative,” recounting the surprise of discovering a growing audience, and how the podcast became a launching pad—not just for a community, but for books, company invitations, and interviews with creativity legends.

Todd also breaks down crucial moments behind his most influential books, including how a single candid conversation with a publisher unlocked the process for Die Empty, and why Louder Than Words remains a favorite despite modest sales. Through it all, Todd highlights the non-obvious lessons that define a creative career: trusting the work, letting your audience find you, and embracing friction as an ally rather than an obstacle.

To the listeners, supporters, and creative pros who have joined us week after week—thank you. Here’s to the past 20 years, and the decades to come.

Five Key Learnings from This Episode:

1. Success Is Layered, Not Linear: The “big deal”—whether it’s a book contract or viral moment—is only the true starting line. Real creative progress builds in stages and unexpected iterations.
2. Experimentation Unlocks Opportunity: Sharing what we were learning (even when unsure or new) was the secret to resonance and growth. Community comes from honest experimentation.
3. Outside Perspective Is Essential: Creative pros often get stuck in their own heads. Inviting editors, mentors, or collaborators can break patterns and unlock genuine progress.
4. Let the Work Find Its Audience: Not every project will land where we expect, and that’s okay. Sometimes our work will deeply impact people we never predicted—and that’s its own success.
5. Friction Fuels Growth: Instead of removing all obstacles, thoughtful creators learn to leverage friction—slow down, synthesize, and let intuition do its work.

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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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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.

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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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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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 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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 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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 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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