We recently connected with Charlotte Lilley and have shared our conversation below.
Charlotte, thanks for joining us, excited to have you contributing your stories and insights. One of the things we most admire about small businesses is their ability to diverge from the corporate/industry standard. Is there something that you or your brand do that differs from the industry standard? We’d love to hear about it as well as any stories you might have that illustrate how or why this difference matters.
The Ski Retreat sets itself apart from the traditional ski industry by creating an experience that is thoughtfully designed for women, prioritizing community, confidence-building, and adventure without the hassle of planning. Some ski/board trips often feel intimidating or male-dominated, The Ski Retreat fosters a supportive and inclusive atmosphere where women encourage each other both on and off the mountain. One guest shared this feedback with us after a trip, “It’s scary to learn how to ski as an adult. But this group was so compassionate and helped me challenge myself in ways that wouldn’t be possible if I didn’t come on this trip.”
The fun and unique thing about The Ski Retreat is most women come solo, so it’s a really wonderful place to find other women who also want to hit the mountain. One women who signed up told us, “…I’ve skied alone far too many times in my adult life and it’s great but it’s not the same as being with others, especially other women!”
The Ski Retreat is also a no hassle, seamless and curated experience! By nature, ski/board trips require extensive planning—booking accommodations, securing lift tickets, coordinating transportation, and organizing meals. The Ski Retreat removes that burden by handling all logistics, allowing guests to fully immerse themselves in the experience.
Also, unlike many ski experiences that revolve around après culture and heavy drinking, The Ski Retreat takes a wellness-first approach. While après is part of the fun, the retreat ensures that non-alcoholic options are available and incorporates elements of self-care such as yoga, nutrition, and mental wellness. The goal is to create a balanced, health-conscious atmosphere that welcomes all women, regardless of whether they drink.
Perhaps one of the biggest differences with the Ski Retreat is it goes beyond just the skiing/boarding, it’s a holistic experience. The Ski Retreat integrates elements like fireside chats with female founders, foodie experiences, art classes, private yoga classes, a private chef and other fun surprises including a lovely gift bag with goodies from our wonderful partners. One of our guests shared this lovely feedback with us after a trip, “The whole trip was wonderful! So many details were carefully crafted. I loved all the activities and felt so empowered by being around other supportive women.”
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I’m Charlotte Lilley, the founder of The Ski Retreat, an adventure organization for women who can’t sit still. My journey into this space has been a little circuitous as I spent over 15 years working in corporate tech, building a career in sales and marketing at SaaS startups. But while I was navigating the world of software, my true passion was always outside—skiing, hiking, camping.
I grew up in the California foothills, just a couple of hours from Lake Tahoe, and started skiing when I was two years old. After attending Cal Poly SLO and embracing a beachside lifestyle (I thought I’d become a surfer and didn’t surf once!), I moved to San Francisco and fell into the startup world. That’s when I started organizing ski/ride trips left and right—for my girlfriends, for my mixed guy/girl groups and I’d also plan an annual ski/ride trip at the different companies I worked for. I brought a lot of girlfriends into the sport or reignited their passion for it and quickly realized how hard it was for women to find other women to ski/ride with—so many were either learning from male partners, struggling to find ski/ride buddies at their level, or just feeling intimidated by the scene. That’s when the idea for The Ski Retreat was born and I launched the first retreat in 2018. For six years, I ran The Ski Retreat alongside my full-time tech job, however in September 2024, I took the leap (!!) and committed to running the business full-time—and it’s been a whirlwind ever since.
The Ski Retreat redefines the traditional ski/board trip experience by creating a women-focused, community-driven adventure that removes the stress of planning while fostering confidence, connection, and growth. It’s a place where women come to challenge themselves, build confidence on the mountain, and leave with lifelong friendships. It’s not just about skiing/riding; it’s about adventure, community, and growth. Our retreats are carefully curated experiences that combine incredible food (think: private chefs, tailgate breakfasts, and après-ski done right with charcuter-skis) as well as female founder guest speakers, art instruction, sound baths, private yoga classes and a supportive, encouraging atmosphere where women feel empowered—both on and off the slopes. Prioritizing wellness over party culture (while still fully enjoying the aprés scene), the retreat incorporates self-care elements to make it an experience that nurtures both body and mind. The weekends are truly magical and they also truly are for those who ‘can’t sit still.’ The Ski Retreat is more than just a trip—it’s a movement empowering women through adventure, camaraderie, and personal growth.
This 24/25 season has been an incredible journey as we expanded The Ski Retreat beyond Lake Tahoe and Breckenridge, bringing more women together for unforgettable ski adventures. Each retreat was filled with confidence-building moments, deep belly laughs, and the kind of connections that last well beyond the slopes. Now, with just one retreat left in Sun Valley, Idaho, on March 20th, we’re gearing up for an epic finale. This last retreat is held at the same time as aprt of the Stifel World Cup Finals, so this last retreat is a dream opportunity for women to experience world-class skiing/riding, the energy of a major event, and the camaraderie that makes The Ski Retreat so special—all without the hassle of planning it themselves. It’s the perfect way to close out an incredible season!
I’m incredibly proud of the partnerships I’ve built this year—including collaborations with brands like Coalition Snow, Spiritless, Flylow, and Siblings Candles—all of whom align with our mission of empowerment, sustainability, and adventure. I’ve also had the honor of seeing The Ski Retreat featured in Outside Magazine and local Tahoe media, which has been a full-circle moment for me as someone who has always admired adventure journalism.
Beyond our multi-day retreats, we’ve also hosted one-day community events like free Community Shred Days and Wine & Wax nights, making it even easier for women to connect, ski, and build community in a fun, supportive environment. Our next Free Community Shred Day is coming up at Palisades Resort on Friday, April 25th—a chance for women to come together for a casual, no-pressure day on the mountain.
At the core of everything I do is this belief: The more you fall, the more you learn. It’s something my parents instilled in me while skiing as a kid, and it’s become a guiding lesson in my work, relationships, and the way I’ve built The Ski Retreat. It’s also the theme of our guest speaker fireside chats! I want women to walk away from these retreats feeling proud of themselves, supported by an incredible community, and inspired to take on whatever’s next—on or off the mountain.
Looking ahead, The Ski Retreat isn’t stopping when the snow melts. We’re planning summer events that bring women together in the great outdoors through camping, hiking, and stand-up paddling—because we know adventure and community don’t have to be seasonal.
We’re also introducing corporate retreats—designed for women in middle management who are navigating the challenges of managing up and down, being a player-coach, and ultimately, trying to avoid burnout. I’ve been there. I know what it’s like to feel stretched thin, constantly problem-solving for a company while trying to maintain your own energy and balance. That’s why I want to create retreats specifically for these women—to give them the space, tools, and community they need to reset.
These retreats will offer a mix of structured workshops and outdoor activities like hiking, stand-up paddling, skiing/boarding, and yoga—all designed to help women process challenges, connect with others, and take a much-needed break from the grind. We know that nature is the best cure for feeling overwhelmed, and these retreats will be the reset that so many women need—helping companies ensure their female employees feel valued, supported, and empowered to thrive.
Exciting things are ahead, and I can’t wait to continue building this community, both on and off the mountain!
We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
One lesson I had to unlearn the idea that success means following a traditional career path. I spent years in tech before realizing that my passion didn’t need to be just a side project, but something I could actually pursue as my full-time job.
I never consciously chose tech—it just unfolded that way. Looking back, I think the real influence was that my dad was in tech and lived in the Bay Area and so when it came time to choose my path, I unconsciously chose something that I was familiar with and if I’m honest, something I thought my parents would be proud of. Growing up, I actually wanted a farmer—something hands-on, connected to nature, and full of purpose and cute animals. I’m still not a farmer but I’m at least closer to nature – ha! Maybe that’s next.
Instead, I found myself in the corporate world, surrounded by smart, ambitious people, solving complex problems, and benefiting from financial stability. It was intellectually stimulating, I learned invaluable business skills, I was given opportunities to build and lead, it was exciting to be on the edge of innovation and world changing tech, and I made lifelong friends. I feel lucky that I had the opportunities that tech afforded me. In so many ways, I am extremely grateful for the experience.
For six years, I built The Ski Retreat alongside my corporate job, believing that I needed to stay the course with stability, career progression, and financial security and keep The Ski Retreat on the side. Who would give that up!? But when I finally walked away from the predictability of tech and took the leap into entrepreneurship, I realized that success could look completely different. It could mean taking risks, forging my own path, and building something that actually lit me up inside.
Quitting the familiar didn’t just mean leaving a job—it also meant diverging from what so many of my friends and community were doing. Most of them are staying the course, climbing the corporate ladder, getting promotions, and securing some very significant financial milestones. It’s been a mental exercise not to compare their salaries, bonuses, and titles to my new reality where there’s no structured path, no clear validation, and, for now, no real income. But they say when one door closes, another opens.
Since stepping into this new world, I’ve met so many incredible female founders doing things their own way – creating from the heart, building businesses that are deeply meaningful, and proving that success doesn’t have to come from a traditional structure. One of the biggest things I’ve had to relearn is creativity. In corporate, I became an operational machine – executing, optimizing, and managing. My ability to dream big, think freely, and trust my gut had faded a bit. Now that I’m running The Ski Retreat full-time, I’ve been to rebuilding that muscle. I’ve had to trust myself again, to make decisions based on instinct rather than structure.
And yet, this is still very much the beginning of this journey. I haven’t been out of corporate for that long, and I still have moments where I struggle, where I wonder if I made the right decision and sort of keeping toe in in case I decide to go back. There are days when the uncertainty feels overwhelming, when I catch myself longing for the stability I left behind. But deep down, I know I made the right choice. At least for now. Even in the hard moments, there’s something undeniable about following my own path. It might not come with a clear roadmap, but it comes with possibility, growth, and a kind of fulfillment you can only find when you build something yourself.
Leaving tech wasn’t just about quitting a job. It was about reclaiming my own way of thinking, my own creativity, and my own definition of success. And I’m enjoying the journey!
Contact Info:
- Website: www.theskiretreat.co
- Instagram: https://www.instagram.com/theskiretreat/?hl=en
- Linkedin: https://www.linkedin.com/in/charlottelilley/
Image Credits
Photo credits to Kristin Addis (@bemytravelmuse) and Kari Humphrey photography