The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving

610: Cas Holman on Play, Creativity, and the Future of Work

Dec 15, 2025

Cas Holman, founder of Heroes Will Rise and former designer for LEGO and Disney Imagineering, advocates for the power of play in creativity and resilience. She emphasizes that play is essential for innovation and coping with uncertainty, not a distraction from productivity. Cas discusses how adults often suppress play due to societal norms, yet free play can enhance flexibility and communication. She also warns against fully outsourcing creativity to AI, urging listeners to embrace curiosity and reframe success to unlock deeper connections.

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INSIGHT

Play Improves Mental Agility

Adults often dismiss play as unproductive, but it reduces anxiety and improves problem solving.
Playful approaches make people more adaptable in both work and everyday life.

ANECDOTE

Learning By Breaking The Studio

Cass describes fixing broken systems at her studio to learn plumbing, electrical, and solar systems.
Breaking and repairing things taught her how systems actually work and increased her curiosity.

ADVICE

Reframe Success To Preserve Play

Reframe success: make the shared outcome the goal rather than perfect conditions.
When plans fail, invent new games or approaches to achieve the underlying purpose.

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When was the last time you played, really played?

For Cas Holman, founder and chief designer of Heroes Will Rise and star of Netflix's Abstract: The Art of Design, play isn't childish. It's the foundation of human creativity, resilience, and connection. She worked with LEGO, Disney Imagineering, and the LEGO Foundation and on a mission to help adults rediscover what children know instinctively: that play is how we learn, adapt, and feel alive.

"Play isn't what happens after work," Cas explains. "It's how we manage uncertainty. It's how we cope, experiment, and find our way through the unknown."

In this conversation, Cas reframes play not as a distraction from productivity but as the engine of it. She explains why play is essential for innovation, executive presence, and emotional agility, and how suppressing it has drained creativity from our professional lives.

"Playful thinking lets us reframe success," she says. "It makes us flexible enough to keep moving when things don't go according to plan."

We discuss:

Why free play (activities that are intrinsically motivated, freely chosen, and personally directed) is the most powerful form of creative renewal.
How reframing success turns frustration into discovery: "You came to play basketball, the ball's flat, the court's full, so what? Invent a new game."
Why curiosity and uncertainty are not threats to be managed, but conditions for growth.
How "breaking" systems or routines can reveal how they actually work.
And how adults can learn to release judgment, the internal critic that says "I should know the answer" instead of "let's find out."

Cas's insights are strikingly relevant to the age of AI. As technology automates more of what we do, she reminds us that what matters most is how we create, not how efficiently we delegate creation.

"We're outsourcing the wrong things," she says. "Creativity wasn't the problem that needed fixing. It's what makes us feel alive."

Get Cas' book, Playful, here: https://shorturl.at/jxR4O

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