Permission to Be Silly: A Modest Case for Strategic Foolishness

A person laughing freely with their head back, warm sunlight, feeling light and unburdened

Let me tell you something I wish someone had told me ten years ago: you're taking this way too seriously.

And by "this" I mean everything, your job, your relationships, your side hustle, your fitness journey, your Instagram aesthetic, the way you frame every conversation like it's a negotiation. You've turned your life into a strategic plan and somewhere along the way you forgot that living is supposed to be part of it.

I know because I've been there. Twenty-plus years as an email marketing professional, crafting messages by the thousands, obsessing over subject lines and open rates and conversion, trying to make every single send the right one. Then five years as an improv coach and still counting, which is really just a different kind of communication except this time you can't unsend anything, the audience is right there, and there's no spell-check for a bad choice. And the thing nobody tells you about that level of seriousness is that it doesn't make you better, it makes you brittle. You start second-guessing every choice, running every conversation through a mental filter, and by the time you decide what to do the moment's gone.

Improv gave me the antidote and it's embarrassingly simple.

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The scene that changed how I think about this

I'm on stage, two minutes into a scene that's going fine, not great, not terrible, just fine. I'm playing a character who's supposed to be serious, a doctor or a CEO or whatever authority figure I grabbed, and I'm doing my job, I'm committed, I'm grounded. I'm also, I realize in real time, deeply boring.

My scene partner looks at me, and without breaking character, says four words: "But are you having fun?"

Two people on a wooden stage under warm theater lights, one laughing and one in a serious pose

The audience laughed. I laughed. And in that laugh the whole scene unlocked. I dropped the posture, I started playing, and suddenly we weren't doing a competent forgettable scene anymore, we were doing something alive.

That's the thing about seriousness, it's a mask, and masks keep people at a distance. They keep you at a distance from yourself.

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I think we get scared that if we stop being serious we'll stop being taken seriously, that people will think we're immature or unserious or unreliable, that somehow the permission to enjoy ourselves is the same thing as permission to fail.

But here's the counterintuitive truth I've watched play out a hundred times on stage and in life: the people who are best at what they do are also the ones who know how to have fun doing it. They're not tense about being perfect, they're loose, they play, they make mistakes in real time and laugh them off because they know the next moment is a new offer.

The best scene partners I've ever had weren't the most technically skilled improvisers. They were the ones who showed up ready to be surprised and delighted, the ones who didn't have their next three moves planned, the ones who were present and playful and trusted that the fun would carry them through.

And it does, every single time.

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So here's the permission slip

Pick one thing today, one conversation or meeting or creative project or interaction with a stranger, and decide that your primary goal is not to nail it. Your primary goal is to enjoy it.

Say the wrong thing and see what happens. Make a joke that might not land. Take the weird offer instead of the safe one. If you find yourself in a situation that feels heavy, ask yourself: "What would this look like if it were fun?"

Not irresponsible, not reckless, just lighter.

I do this before every show. The lights are up, the audience is right there, and I could feel the weight of wanting to be good, but instead I take a breath and remind myself: this is play, I've been playing since I was a kid and I'm still good at it, the weight is optional.

—

There's a thing in improv called "caring less to care more." It sounds like a paradox until you feel it. When you stop gripping so tight, when you stop trying to force the scene to be great, you open up to what's actually there, and what's actually there is usually better than whatever you were going to manufacture.

A handwritten permission slip on a wooden table reading Permission to Be Silly, with a coffee cup and flower

That goes for life too. You don't have to lower your standards, you just have to raise your tolerance for messy, surprising, imperfect moments, because those are the ones that actually matter.

I've had people tell me after shows, "I wish I could be that free." And my honest answer is: you can. The only thing standing between you and that freedom is the belief that you shouldn't be having this much fun.

So go find something ridiculous today. Take it seriously enough to do it well and not seriously enough to forget why you're doing it. Laugh at yourself before someone else does. Say yes to the weird offer. Play.

The scene's waiting, you just have to show up and enjoy it.

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As always, your move: what's one thing you've been overthinking that you could just enjoy today?