We worship productivity. We optimize for efficiency. We schedule meetings about meetings, set OKRs nobody reads in Q3, and perform seriousness like it's a competitive sport. But somewhere in this relentless push to be serious about serious work, we forgot something crucial: the leaders who actually change things — they play.
Not games. Not ping-pong tables strategically placed near the cold brew. I mean play as a cognitive state — an open, curious, low-stakes mode of thinking where creativity happens not because we force it, but because we finally stop trying to control it. When children play, they don't ask permission to be imaginative. They just are. The question is: when did we unlearn that?
I've keynoted for Fortune 500 leadership teams, startup founders fresh off a Series B, and educators rethinking what school even is. And the pattern is always the same: the people driving the most unexpected, the most genuinely interesting outcomes — they bring an element of play into how they think, how they lead, and especially how they recover from failure.
Here's what nobody tells you: play isn't soft. It's not the opposite of discipline or ambition. It's the engine underneath them. Playful leaders ask better questions because they're not afraid of looking foolish. They experiment faster because failure feels like a level to retry, not a verdict. They build the kind of psychological safety that makes teams perform at levels no slide deck can manufacture.
I've sat in boardrooms where the atmosphere was so heavy with seriousness that nobody dared say the obvious thing out loud. And I've been in scrappy team workshops where someone made a dumb joke that cracked open exactly the right conversation. Guess which room produced better strategy.
So if your leadership team feels stuck, heavy, overly cautious, or allergic to new ideas — I have a question. Not about your roadmap or your North Star metric. Just this: when did you last play with an idea? Not execute it. Not justify it to your board. Not stress-test it into oblivion. Just play with it. Because the most underrated leadership skill isn't resilience or executive presence or strategic thinking. It's the willingness to be playful — and the courage to call that serious business.
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I write about play, leadership, Women in Tech, and building things that matter. More posts below — or reach out if you want to talk.