Last night’s Chicago Literary Salon pop-up with Piera Gelardi at the Wicker Park Inn felt a little different from our usual evenings—in the best possible way. There were no candlelit tables or formal dinner courses this time, just a small gathering in a cozy room, the hum of the L train outside the window, and the kind of easy intimacy that invites people to exhale and be themselves.
This evening also came together thanks to Kit Graham of The Kittchen, who so thoughtfully pulled the event together and invited me and the Chicago Literary Salon to be part of it. Kit has such a gift for creating warm, welcoming spaces, and this night felt like a perfect reflection of that—collaborative, relaxed, and full of genuine connection. It was a joy to bring the Chicago Literary Salon into that environment and see how beautifully the spirit of the salon translated in a new, more informal setting.
Photo by Erika Lowerr of EEBauer Photography
In conversation around her new book, The Playful Way, Piera shared stories from her own life about reclaiming play as an adult—not as something frivolous, but as something essential. She spoke about growing up with parents who infused playfulness into everyday life, then losing touch with that spirit as work became more serious and success more demanding. At one point in her career, she realized that in trying so hard to be taken seriously, she had packed away the very qualities that made her resilient, creative, and alive. That realization ultimately led her back to play, and eventually to this book.
What made the evening so special was how quickly it became a shared conversation rather than a traditional author talk. Piera invited guests to reflect on their own relationship to play, and the stories that followed were funny, touching, and unexpectedly vulnerable. Women shared memories of dance parties with their children, imaginative games played in libraries, rituals invented to make school drop-off or tooth brushing easier, and the small ways they bring levity into ordinary days. Others shared more tender stories—about humor carrying them through grief, movement helping them through anxiety, and the way laughter can create just enough space to survive hard things.
Again and again, the conversation returned to one of the evening’s most resonant ideas: that play does not remove difficulty, but it can change how we move through it. A security line at the airport still stretches endlessly, a child still resists brushing her teeth, grief still arrives—but a playful gesture can soften the edges, create connection, and remind us we are still alive inside the moment.
Photo by Erika Lowerr of EEBauer Photography
There was something especially fitting about hosting this conversation at the Wicker Park Inn. The setting felt relaxed and personal, more like gathering in someone’s home than attending a formal event, which made it all the easier for guests to jump in with their own stories. By the end of the night, the room was full of laughter, knowing nods, and that unmistakable feeling that can happen when strangers become a little less strange to one another.
Piera closed the evening with a story about finding a literal message in a bottle while searching for a sign that this new chapter of her work mattered—a story so perfect it almost felt invented, except of course it wasn’t. It was a reminder of the very thing she had been talking about all night: that when we choose the playful way, we create ripples. We don’t always know where they will lead, but they matter.
And that, in many ways, is exactly what this pop-up felt like too: a small, joyful ripple in the middle of a Monday night in Chicago.
Photo by Erika Lowerr of EEBauer Photography
We’re so grateful to Erika Lowerr of EEBauer Photography for so beautifully capturing the spirit of the evening. Erika has a remarkable ability to document not just how an event looks, but how it feels—the laughter mid-story, the quiet moments of reflection, the warmth between strangers becoming something more. These are the kinds of moments that define the Chicago Literary Salon, and it’s such a gift to have them preserved with so much care and intention.
About The Playful Way:
Playfulness can help you navigate life with more creativity, resilience, and joy—entrepreneur Piera Gelardi offers simple practices and radical permission to shift from the Pressured Way to the Playful Way.
Somewhere along the way to adulthood, we learned that play is frivolous. Childish. Something to outgrow. We treat it like a reward we have to earn, separate from our "real" lives. But denying our playfulness has a cost—it leaves us feeling drained and disconnected. We rely on pressure and perfectionism, trying to force outcomes, wondering why nothing feels fun anymore.
There's another way.
In The Playful Way, creative entrepreneur Piera Gelardi shows how to shift from the Pressured Way—clenching, forcing, white-knuckling through life—to the Playful Way, where you move through the world with fluidity, curiosity, and aliveness. For Gelardi—who has built iconic brands, created daring experiences, and consistently put herself out there in bold, creative ways—play has never been frivolous. It was how she made sense of the world. As an adult, she realized that what she'd called burnout or creative block was really a disconnection from play—and that returning to it helped her feel alive again.
Through intimate stories, research, and accessible practices, you'll discover how to:
quiet the inner critics that restrict your playfulness
unlock the Eight Powers of Play
embrace a mindset that transforms how you navigate challenges, deepen connections, and find joy in everyday moments
The Playful Way is your guide to living with more whimsy, wonder, and possibility—through both the light moments and the tough ones. Because when you embrace playfulness, you don't have to go play. Play comes with you everywhere.