In Episode 2 of Being Playful, therapist and songwriter Bill O’Hanlon offered a deceptively simple insight:
“I always master the structure. Then I play.”
At first glance, it sounds familiar. A cousin of “learn the rules before you break them.” But for leaders navigating pressure, complexity, or ambiguity, this principle is something far more strategic—and more generous.
Because what Bill is pointing to isn’t just permission to loosen up once you’ve earned it. It’s a call to reimagine playfulness itself: not as a luxury or a break from the work, but as a state that emerges from structure. Specifically, from the right-sized structure. The minimal viable structure.
This is an idea that has real bite for senior leaders. Because too often, when we talk about creativity, innovation, or psychological safety, we imagine a tension between structure and spontaneity. Between planning and play. And so we either over-engineer—killing all the air in the room—or we under-structure, hoping something magical will emerge from chaos. But playfulness doesn’t thrive in either of those extremes. It doesn’t live in rigidity. But it doesn’t survive long in a vacuum either.
The trick is to give yourself and your team just enough of a framework—a rhythm, a container, a starting shape—so that something more human and creative can unfold inside it. That’s the minimal viable structure.
Bill talks about preparing his talks with this principle in mind. He learns the shape, the key transitions, the opening and close. He doesn’t script every word. He gives himself a container. That container becomes the confidence, and the confidence becomes the freedom. Once it’s in place, he can improvise. Make a joke. Shift tone. Respond to the room. Not because he’s winging it—but because he’s held by something that allows him to let go.
This matters for teams too. So many of us say we want more spontaneity, more openness, more innovation. But in moments of stress—high stakes meetings, product sprints, sensitive strategy conversations—our nervous systems don’t crave freedom. They crave clarity. Not rigidity, but something to lean on. Something to trust. A shared sense of rhythm. If you skip the structure, people spin. If you lock it down too tightly, they shut down. The sweet spot? A structure just strong enough to hold the room, and just light enough to invite something unexpected.
This is where the PPM Method—Pause, Play, Move—earns its keep. The pause is the structure. The pattern interrupt. The breath. The move gives direction. But the play in the middle? That’s where possibility lives. And it only works when it’s cradled on either side.
This principle shows up in everything from agile project design to therapy, from music to public speaking. Jazz musicians don’t wait until they’re experts to improvise—they improvise within chord structures. Kids don’t need total freedom to play—they use rules to create worlds. And in leadership? The best strategic offsites, the best feedback sessions, the best pivots in crisis—they don’t happen because someone said “let’s be playful.” They happen because someone created the conditions where playfulness could emerge. And often, that means starting with a minimal viable structure.
Importantly, this doesn’t mean you need to have everything figured out before you begin. You don’t need to master the whole system before you’re allowed to be creative. That’s just perfectionism in disguise. What it does mean is that playfulness is rarely chaotic. It’s often incredibly well-held. Invisible scaffolding is doing its job so well, you barely notice it. But it’s there.
For leaders, this is a shift in how we see our role. Instead of asking “how do I control this?” or even “how do I lead this?”, we might ask: What’s the lightest structure I can offer that makes play possible?
Sometimes that’s a thoughtful agenda with one open space. Sometimes it’s a brainstorm with a clearly framed prompt. Sometimes it’s just showing up with your own state regulated enough to let the team settle into their best.
Bill’s insight is deceptively simple, but it runs deep. He’s not just saying “prepare first, then relax.” He’s saying: if you want to do your best work, or help others do theirs, stop trying to choose between structure and spontaneity. You need both. The structure is the kindness. The play is the gift. One makes the other possible.
So the next time you’re writing, creating, coaching, designing—or leading a room—ask not what you need to add to make it more playful. Ask instead: what’s the minimal viable structure that will let playfulness find its way through?
Because when you get that part right, the rest often takes care of itself.