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BRAVE • FOCUSED • BRILLIANT Embracing "Safe Danger" Ben Swire and Cas Holman believe that we don't play enough. And, that it's not only bad for culture, but negatively affects our work as well.

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What if the future of your team depended on tipping the shopping cart over... on purpose?

This week on Daily Creative, I sat down with Ben Swire, author of Safe Danger and former design lead at IDEO, and Cas Holman, designer, play advocate, and author of Playful, to explore a radical idea: what looks like play might actually be the smartest path to innovation and trust.

Here are some key ideas that stood out, plus a challenge for you to bring into your week:

Real safety isn’t comfort; it’s courageous connection.

Most leaders think safety means smiles and comfort, but Ben Swire argues that’s just surface-level. True psychological safety is when people feel brave enough to question, challenge, and step outside their comfort zones without fearing consequences. Building that kind of environment demands trust, vulnerability, and a willingness to let conflict emerge, rather than always keeping things agreeable.

Do people on your team feel free to challenge the status quo, or do they just agree to keep the peace? How do you respond when someone on your team voices tension or disagreement? Do you resolve it quickly, or let it surface and transform?

Play is not the opposite of work; it’s the engine of it.

We often treat play as an escape from work, but it’s actually one of the best training grounds for risk-taking and creative leaps. Play lowers the stakes, giving people the psychological space to experiment, improvise, and stretch without fear of failure. When work feels playful, people are less risk-averse and more likely to try new things—often leading to the results the team needs most.
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​How might you introduce playful experimentation into your team's routine, even when the deadlines are tight?

Constraints fuel creativity, not the other way around.

Cas Holman flips the myth that creatives want "no boundaries." In reality, the blank page is overwhelming; constraints are liberating. Thoughtful parameters give us something to push against, channeling energy, sparking ingenuity, and making play possible. Arbitrary boundaries—like limiting your tools or materials—force new approaches and fresh solutions.

Where in your current project can you impose a new (even arbitrary) constraint, just to see what emerges?

Friction and challenge are where growth begins.

It’s seductive to optimize for ease and avoid hard things. Yet, Cas Holman reminds us: easy is boring. Whether designing for kids or leading adults, the learning and growth happen at the edges of discomfort and challenge. Friction isn’t the enemy—it’s the ingredient that makes creativity thrive. When you linger in unfamiliar territory, you rediscover play and new strengths.

What’s one area of your work that feels too comfortable right now, and how might you deliberately introduce healthy friction?

Slow down to speed up—psychological safety multiplies performance.

We’re conditioned by scarcity: move fast, cram more in, focus on output. But study after study shows that teams with psychological safety out-perform, out-innovate, and outlast those with a grind mentality. Slowing down to build trust and connection makes teams not only happier, but more effective, more resilient, and ultimately more successful. The paradox: investing in safety and play unlocks a powerful velocity most leaders never expect.

When you feel pressed for time, are you tempted to push harder—or would investing in team connection deliver better results in the long run?

Trust the power of your boundaries, lean into healthy friction, and find one small moment to ask "What if?"—whether that means playing with a new idea, reframing a challenge, or just letting yourself tip the proverbial cart on purpose.

The serious work of play might be exactly where your next breakthrough—and your team’s best work—will begin.

Leading talented people is hard. Don't do it alone. Creative Leader Roundtable is a one of a kind program for leaders of small and mid-sized creative teams. Discover practical strategies for unleashing your team’s brilliance and discuss real-time issues you’re facing with others who “get it”. ​ Learn More

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​ Todd Henry teaches leaders and teams how to be brave, focused, and brilliant. He is the author of seven books, and speaks internationally on creativity, leadership, and passion for work. ​TODDHENRY.COM​ ​​​​​

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