We caught up with the brilliant and insightful Charlotte Lilley a few weeks ago and have shared our conversation below.
Charlotte, thank you so much for taking the time to share your lessons learned with us and we’re sure your wisdom will help many. So, one question that comes up often and that we’re hoping you can shed some light on is keeping creativity alive over long stretches – how do you keep your creativity alive?
Creativity, or more specifically my long-lost creativity, is something I’ve been yearning for and something I used to have in abundance. As a kid, I lived in my imagination. Art, fashion, gift wrapping, rock stacking, playing with my imaginary dog (only child things!) – all of it! I loved making things with my hands, wandering outside, talking to animals, getting lost in colors and ideas. Creativity was effortless back then and was a natural extension of how I played and saw the world.
Then came grownup life. College was great and I still was able to be my creative self. Where I started to feel a big difference was after a couple of years in corporate life. My creativity found itself neatly contained within work-approved boundaries. Outside of my job, I sought outlets, like when I took up indigo-dyeing paper during COVID. But honestly there wasn’t much time for outside hobbies. Inside the office, I became an operational machine. And an impressive one at that. I could shut out an open office’s chaos, focus intensely, and churn through tasks with relentless efficiency. I made lists. Lists of lists. And I checked them off like nobody’s business.
Now, having left the corporate world, I’m excited to tap back into my creativity in a way that feels limitless again. I know it’s still in there and I can feel it wanting to flow out, but it feels a little overwhelming because it all wants to flow out at once. Entrepreneurship is allowing me to flex that creative muscle, whether it’s experimenting with social media, carving out time to doodle, or just letting myself dream a little more. But it’s a work in progress! I still feel that pressure to always be executing, always crossing something off a list. I’m learning that entrepreneurship is this strange, chaotic balance of flexibility and having a million things to do at all times.
To keep my creativity alive, I’ve been practicing following what feels right instead of what I should be doing. Honestly I’m practicing noticing when something strikes my interest and paying attention to that. I’m reading more magazines, going down internet rabbit holes to explore an idea deeper, doing puzzles, letting myself just be curious again. My latest obsession is an in-person cardio dance class, but that’s led me to online hip-hop dance classes! I used to love performing and learning routines, but as an adult, those opportunities are few and far between. It’s been wildly fun and super challenging (I’m very rusty at dancing to steps!) to revisit that part of myself.
When it comes to The Ski Retreat, I’m channeling creativity into partnerships and how I promote the business. I’m connecting with other entrepreneurs, diving into new tools, and constantly learning from other businesses. I feel like I’m making up for lost time, dabbling in everything, trying to rediscover what truly lights me up.
It’s a journey as I know I could be better at carving out dedicated creative time rather than just squeezing it into the spaces between my productivity sprints. I thrive when I work in new environments like cafés or coworking spaces, but the convenience of my kitchen table makes it hard to leave the house. I also run a nonprofit, furtHER, that connects local women to collaborate and create together, and meeting those women is always inspiring and sparks my creativity.
Right now, I’m still in the middle of getting my creativity back. But I know it’s there, waiting. And I trust that the more I lean into it, the more it will come alive.
Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?
I’m Charlotte Lilley, the founder of The Ski Retreat, an adventure organization built for women who crave movement, challenge, and connection. My path to this work wasn’t exactly linear as I spent years in the corporate tech world, climbing the ladder in sales and marketing roles at SaaS startups.
I grew up in the California foothills, just a few hours from Lake Tahoe, and was lucky enough to start skiing at age three. After college at Cal Poly SLO, I moved to San Francisco and immersed myself in the startup scene. Still, I kept organizing ski trips for friends, and one thing became clear: it was hard for women to find other women to ski with. Most were learning from male partners, unsure of their ability, or simply didn’t know where to start. I saw the gap and thought it would be fun to plan trips for women I don’t know and that’s when the idea for The Ski Retreat was born!
For six years, I ran The Ski Retreat on the side while working full-time in tech. But in September 2024, I made the leap and went all in and it’s been an interesting ride with ups and downs, but it’s been very rewarding and fun to try out things that I’ve been thinking about for years that I now have the time to do. What makes this work truly special isn’t just the skiing—it’s the way it brings women together in an uplifting, empowering environment where they can challenge themselves, build confidence, and walk away with real, lasting friendships.
This 24/25 winter was one for the books. We hosted 5 retreats in different destinations: Lake Tahoe, Breckenridge, and we wrapped up the season in Sun Valley, Idaho, during the Stifel World Cup Finals, which was a fun and unique experience overall.
In addition to our signature multi-day retreats, we’ve been growing our lineup of one-day community events, like free Community Shred Days and Wine & Wax nights, which offer more casual, low-pressure ways for women to meet and connect. Our last free Community Shred Day is happening Friday, April 25th at Palisades Resort, and it’s open to all women who want to get outside, make new friends, and have fun on the mountain.
Looking forward, we’re expanding into summer experiences like camping, hiking, and stand-up paddling to keep the momentum going all year long. And we’re also introducing corporate retreats—something I feel especially passionate about. As someone who spent years in middle management, managing up and down while trying to keep everything together, I know how easy it is for high-performing women to burn out. These retreats will be tailored for women in those roles offering outdoor wellness, workshops, and space to connect with others facing similar challenges. And because we believe fun and friendship also deserve celebrating (why not?!), we’re now exploring concierge-style custom retreats for groups like bachelorettes, birthdays, and girls’ trips who want to experience a destination getaway that’s personalized, and curated without any of the planning stress. We bring the food, the activities, the logistics, you just show up and make memories.
Through these new offerings, my goal is to help women gain confidence and enjoy the outdoors. For corporate offering it’s about supporting companies to better support their women leaders—and give those women the chance to step back, gain perspective, and return stronger. With activities like yoga, hiking, skiing, cooking, and paddling, and built-in time to rest, reflect, and recharge, these retreats will offer the reset so many of us need.
At the heart of it all, I’m all about creating spaces where women feel seen, strong, supported, and free to be themselves.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
1. Working at startups. Most of my corporate journey was working in tech startups, from where I can attribute most of my business skills. I’ve worked at a company that had 5 people total (before folding), I worked at a company that was 30 people when I joined and grew to 2,000 and had an IPO before I left and pretty much everything in between. There was never a dull moment and that culture jives with me. Through that experience, I learned how businesses work, I got to wear many hats, I learned how to move very quickly and be extremely productive (even in a loud open office environment). Some of the most poignant lessons I learned are to fail fast and ownership over full areas of work. Now, I operate as a one woman startup with all those skills I learned: scrappy, experimenting and letting go of what doesn’t work, and moving quickly.
2. Saying yes to scary things. One quality that’s served me really well is saying yes to the things that completely terrify me. Over the years, that’s looked like public speaking, selling all my belongings and leaving San Francisco after 11 years, starting to mountain bike and dirt bike, getting back into dance, showing up solo to events where I didn’t know a soul, and recently, quitting my corporate career to go all-in on The Ski Retreat. I say yes because I’ve learned that something good always comes from it, whether it’s confidence, clarity, new connections, and it’s always nice to challenge yourself in those ways to be sure you’re pushing your boundaries. We’re all capable, we just need to do the scary things. Next up, cold plunging (maybe) ;).
3. Understanding how to build and connect a community. Building community and connecting people comes naturally to me and over time, I’ve realized it’s not just a strength, but more of a passion. Throughout my corporate career, I was an pioneer in the world of Customer Marketing—an area of marketing that focuses on the human side of business. I helped create programs that highlighted customer stories, brought people together through events, and turned happy customers into true advocates. It was always about the relationships and the sense of belonging. Funnily enough, that same philosophy is at the heart of The Ski Retreat! I’m bringing together women, most of whom don’t know each other, and creating a space where real connection happens, even if it’s just for a weekend.
Okay, so before we go we always love to ask if you are looking for folks to partner or collaborate with?
We would absolutely love to partner with some amazing people out there. The Ski Retreat was built on connection, and I’m always looking to collaborate with people and brands who align with our mission: bringing women together for adventure, wellness, and community. Whether you’re a wellness brand, outdoor gear company, female founder, nonprofit, chef, or just someone who wants to have some fun in the mountains, I’d love to connect!
Some of my dream collaborators include incredible female-founded brands like Kari Traa, Wild Rye, Skida, and Halfdays—companies I personally look up to for how they show up in the outdoor space. I also deeply respect nonprofits like SheJumps, B4BC, Women of Winter, and 1000 Hours Outside for the work they’re doing to expand access, visibility, and joy in the outdoors.
And of course, I’d love to team up with female athletes, especially local Tahoe legends like Amie Engerbretson, Michelle Parker, and Julia Mancuso (just to name a few). There are so many women out there doing rad things, and it would be an honor to collab in a way that inspires and uplifts more women to get outside and try something new!
All of our partnerships have start with a conversation, so if you’re reading this and something clicks, please reach out! You can connect with me directly via [email protected] or our IG @theskiretreat.
Contact Info:
- Website: https://www.theskiretreat.co
- Instagram: @theskiretreat
- Linkedin: https://www.linkedin.com/in/charlottelilley/
Image Credits
Kristin Addis (Be My Travel Muse) and Kari Humphrey Photography
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