The co-founder of Refinery29 makes the case for playfulness

The airport is chaos. Lines snake beyond the designated barriers and out the doors as frazzled travelers tug their luggage and scowl at their phones, their grimaced faces even more dramatic in the harsh lighting.

I stand in the security queue, sensing the stress emanating from everyone around me like swarms of buzzing flies. A man behind me huffs with dramatic indignation, a couple ahead bickers in hissed whispers “we should have left earlier!”, and someone’s roller bag keeps thwacking my heels.

My fists clench as irritation winds me tighter. The security checkpoint seems miles away and my flight is in an hour. I feel myself being sucked into the collective vortex of misery.

Then, as we make our first zig in the queue, I catch my partner’s eye and make a split-second decision. I raise my hand for a high five.

“Yes!” I exclaim with exaggerated enthusiasm. “One turn closer!”

My partner looks momentarily confused, then a half grin lights up his face as he slaps my raised palm. A few people nearby glance over, some with bemused smiles.

When we reach the next turn, we were ready. “Turn number TWO!” We announce together, high-fiving with gusto. A woman behind us lets out a chuckle that seems to surprise even herself.

By the third turn, a family with a toddler holds up their hands for high fives before we can even offer ours. “We’re on a roll now!” the dad says, grinning.

With each zigzag, our celebration grows a little as others join our absurd celebration of incremental progress. Soon, a pocket of genuine laughter has formed in our section of the line, rippling outward like a skipped rock as others catch on to our game.

Pressured vs. playful

In that moment of travel chaos, we made a choice: instead of facing the frustrating situation with tense resentment (what I now call “The Pressured Way”) we decide to transform it through levity and connection (“The Playful Way”).

This simple shift doesn’t change our situation. We are still in the same painfully slow airport security queue. We are still at risk of missing our flight. But it changes what the situation feels like—from stress to humor, from isolation to community, storm cloud to sun break.

This choice between The Pressured Way and The Playful Way appears constantly in our lives: during technology crashes, tricky conversations, power struggles, or canceled plans. When challenges arise, we can clench our jaws and white-knuckle our way through—or we can bring imagination, inquiry, and openness to the situation. This choice isn’t just about boosting fun (thought that’s a welcome bonus), it’s about accessing new solutions, deeper camaraderie, and a richer experience of everyday life.

Playfulness isn’t one size fits all. While our airport moment involved a social game, you might express your playful side by finding beauty in the terminal architecture, creating backstories for fellow travelers, or scoring the scene with a film soundtrack—turning a mundane wait into the opening of your personal heist movie or Broadway musical.

The Pressured Way tightens our vision like horse blinders, while The Playful Way opens our peripheral sight to possibilities we’d otherwise miss entirely.

A transformative mindset

When I talk about playfulness in adulthood, I’m often met with puzzled looks. “You mean sports?” people ask. Or “Board games with friends?”. “Oh, like, work hard/play hard… partying?”

But playfulness runs deeper than scheduled recreation (though that is important). It’s not a leisure activity reserved for weekends or vacations—it’s a mindset that transforms how we experience everything.

Playfulness is:

— Finding humor and lightness even in tense moments
— Navigating situations with genuine questions instead of assumptions
— Staying open to possibilities rather than fixating on one “right” way
— Experimenting rather than seeking perfection
— Bringing an ethos of adventure to difficulties
— Reimagining the mundane through reframes and games
— Being willing to collaborate rather than control

When we move through the world playfully, we remain pliable, ready to adapt, change, and work with whatever comes our way: to navigate obstacles nimbly and alchemize even the most mundane tasks into micro adventures.

Playfulness is often dismissed as frivolous — a charming but dispensable quality best left in childhood alongside stuffies and imaginary friends.

But watch any child transform a cardboard box into a spaceship or a pile of sticks into a fairy house and — beyond the cute façade — you are witnessing them exercising some of humanity’s most valuable capacities: imagination, adaptation, and ingenuity.

The good news? Playfulness is part of us all — it’s standard issue for the human species. Even if you’ve left it in the drawer gathering dust, you can pick up your playfulness again and relearn to use it.

I haven’t always been able to find the high-five moments in life’s security lines. There was a time when I was deeply lost in what I now recognize as “The Pressured Way.”

Beyond burnout

During a particularly intense period building my first company, I found myself alone late one night, pen in hand, making a list titled “Ways I’m Failing RN.” It contained eleven meticulously detailed items—work projects falling behind, leadership shortcomings, fertility struggles, neglected friendships and family relationships—each one a knife twist of self-criticism. At the bottom, almost as an afterthought, I’d written: “Stressing myself out with my stress and inability to emotionally regulate.”

I was beyond burnout — overworked and under-played. Night after night, I’d come home, collapse on my apartment floor, and sob until I was empty, unable to see any of the success around me. The brilliantly colored, creative world I’d built felt like it was happening to someone else entirely. The weight of my perfectionism had become so crushing that I couldn’t imagine a way forward.

What moved me through this period wasn’t working harder or being more disciplined. It was remembering The Playful Way of life I’d learned as a child, sitting around our kitchen table in Maine with my family, brainstorming wild ideas over dinner.

Our kitchen was the beating heart of my childhood home, with its cheerful painted tiles, bright green countertops, and wall jam-packed with family photos. After my brother and I helped our parents serve dinner, the fun began. My words would tumble out in excitement: “Hey, what if we started a kids’ karaoke club?” My parents would exchange a conspiratorial glance. “Now there’s an idea!” Mom would reply, leaning forward. “What would that look like? Where would we host it?”

Between bites of penne, my brother would chime in: “We could have themed nights — Disney songs one week, pop hits the next!” My dad would smile, his laughter-creased eyes twinkling. “I love it! Now what would we name it?” Before anyone could answer, his fork was in the air, face lit up with enthusiasm. “Ooh! Ooh! Ooh! I know! Kiddieoke!”

These kitchen table sessions were boisterously loud, as we built upon each other’s ideas. No idea was too outrageous to explore. We were elementary schoolers doing business brainstorms—and our parents took us seriously and egged us on.

Eventually, we’d have to clear the table, do our homework, and return to our daily responsibilities. But in these moments, I learned that any endeavor could be handled with an inquisitive attitude and a spirit of adventure.

I was fortunate to have parents who showed me that wonder and whimsy could be woven into all aspects of life. My mom—a social worker, artist, gardener—and my dad—an entrepreneur, engineer, inventor—modeled what it looks like for adults to be playful while simultaneously building businesses, dealing with illness and loss, and nurturing families and communities.

My voyage of questioning took a new turn at age 15 when I found my heart fluttering like butterfly wings whenever I was around my best girl friend and realized I wasn’t just attracted to one gender. Growing up Catholic, I learned that boundaries were fixed—lines drawn between right and wrong, holy and profane, approved and forbidden forms of love. But my bisexual heart didn’t fit into hard pews or rigid boxes, it spilled out like vivid stained glass light. Luckily my mom told me that some rules were for bending so I turned to playfulness, curiously exploring and embracing the expansiveness of being queer, rather than fearing it.

Carving out play space

This current of exploration carried me to New York City, where I co-founded and built Refinery29 from a small style website into one of the most influential digital media brands for women, reaching millions with its distinctive mix of fashion, culture, and boundary-pushing storytelling.

Even in boardrooms, I carved out spaces for play—like my apricot-colored office dubbed “The Peach Pit” with its round table that became our magic circle for brainstorms. All the players around the table now were adults, so I had to take some extra measures to get the ideas flowing including doing physical shake breaks and having a lovingly bedazzled Taboo! game buzzer on hand for when anyone got into excessively “serious mode.”

Our playful approach led us to create innovative experiences like 29Rooms—a funhouse of culture that reimagined vacant warehouses into kaleidoscopic, artist-made wonderlands where 100,000 adults came through to frolic and fall down imagination rabbit holes in cities across the US.

A new chapter

In 2021, I found myself ready to begin a new chapter. But leaving the company I’d built over fifteen years was like moving out of a home you’ve loved — even when you’re ready to go, there’s still a bittersweet ache. Add to that the wild adventure of new motherhood and a global pandemic, and I was navigating multiple identity shifts at once. Daunting questions loomed: Who was I beyond the role I was most known for? What kind of parent would I become? What did I want to create next?

As I faced these huge transitions, my spirit whispered an answer: experiment! Instead of rushing to figure it all out, I turned my life into a play laboratory. I led cathartic dance parties on Zoom, created public art experiences connecting strangers in parks, took classes in improv and storytelling, and said “yes” to pretty much any foray that sparked curiosity. I dove deep into researching the power of play for our health and happiness, and piles of books stacked up on my desk.

My calendar filled up with what I lovingly called “play dates with possibility,” and something magical happened: as I led thousands of people in unlocking their vibrant spirits, I discovered my next chapter — creating spaces for playful, creative practice and shared joy.

Playfulness is my power tool and my life preserver across all aspects of my life from parenting to self care to career. It’s how I’ve come up with innovative solutions at work, built meaningful relationships, found purpose during transitions, and made memories in mundane moments. My relationship with playfulness isn’t just about joy—it’s been essential medicine for navigating life with depression, anxiety, and ADHD.