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. 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.

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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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.

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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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. Buy The Brave Habit wherever books are sold, or learn more at TheBraveHabit.com.

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