Can Leaders Afford Play When Deadlines Loom?

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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