The More You Fall, The More You Learn: Fireside Chats with Inspiring Female Founders

At The Ski Retreat, we believe that the lessons we learn on the slopes extend far beyond skiing and boarding. One motto that has stayed with me since childhood and shaped so much of my life is "the more you fall, the more you learn." Growing up, our parents would remind us of this every time we did a full yard sale. Falling wasn’t something to fear—it was a sign we were pushing ourselves, trying new things, and ultimately getting better.

I’ve carried that lesson into every part of my life—work, relationships, and especially in building The Ski Retreat. It’s become a guiding ethos for everything we do, which is why we bring in local female founders to share their stories during our retreats. These women are not just entrepreneurs; they are trailblazers in our community, running their own businesses and inspiring others along the way. Their stories show us that falling, failing, and learning are essential parts of the journey to success.

Each fireside chat is much more than a formal Q&A. It’s an intimate, cozy conversation where I ask our guest founder about her journey—what lessons she’s learned, the challenges she’s faced, and the advice she has for our group. There are always plenty of laughs as we exchange stories, sharing not only the struggles but the moments of humor that come with taking risks. Often, these conversations become heartfelt and meandering, as we relax around the fire, sipping warm drinks, and connecting over shared experiences. The best part? Our speaker stays and joins us for dinner, where the conversation continues around the table, creating even deeper connections and allowing everyone to engage in a more personal way. Breaking bread together is one of the oldest and most powerful forms of connection, turning strangers into friends and fostering a sense of community that lasts long after the retreat ends.

Our goal with these fireside chats is simple: to inspire and empower the women attending to follow their dreams, whatever those dreams might be. You don’t need to be starting a business or facing a huge life transition to feel inspired. Sometimes, it’s about finding the courage to make a small but meaningful change or simply to double down on what’s already going well.

The laughter and shared experiences in these moments create a special bond. Women leave feeling connected and empowered to take the plunge—whether that means making a bold decision, trying something new, or simply embracing where they are right now. And if they stumble along the way? They’ll know that every fall is a step toward growth, with a community of women cheering them on.

Because at The Ski Retreat, we know that the more you fall, the more you learn—and the more you learn, the stronger and more resilient you become.