Charlotte Lilley is the founder of The Retreat Co an adventure organization designed for women who can’t sit still. Growing up in the California foothills, just a couple of hours from Lake Tahoe, she developed a deep love for the mountains and started skiing at age two. Before launching The Retreat Co full-time, she spent over 15 years in sales and marketing at SaaS startups.
Beyond her professional career, Charlotte is passionate about fostering strong networks and support systems for women. For over a year, she has been organizing women’s networking events in the Lake Tahoe region, providing a space for local women to connect, collaborate, and uplift one another.
In her free time, she’s downhill skiing, learning how to XC and skate ski, getting back into dance, planning get togethers, attempting to maintain a yoga practice, and enjoying van trips with her two dogs, Oink and Brandi, and her husband, Scott.
What is your typical day, and how do you make it productive?
As an entrepreneur, my days vary significantly. I don’t have a set start time, nor do I have anywhere to go but my kitchen table for my day-to-day computer work. I usually wake up around 7 a.m., ideally after getting a solid 8-9 hours of sleep. My morning starts with a hot lemon honey water while I check my phone for any urgent messages. I intentionally keep my phone in the living room at night to create separation from work. After that, I feed my dogs and tackle a few emails before making a high-protein breakfast which is something I’ve learned is crucial, especially since most women don’t get enough protein!
My workday often involves several calls with potential partners, other female entrepreneurs, and prospective The Retreat Co guests. The nature of my business is seasonal, which means my focus shifts throughout the year. Summer is all about planning and logistics: finding destinations, securing houses, and researching vendors and partners. Fall is launch season: bookings launch and promotion is in full swing. Winter into spring is the busiest time, as I’m fully immersed in hosting and executing the retreats. On any given day, I typically have one or two bigger “rocks” I’m working on—things like email campaigns, business growth strategies, or PR research—alongside the daily tasks that keep the business moving, such as social media, calls, and press pitching.
Productivity-wise, I rely heavily on my to-do list and calendar. Everything goes into my calendar, from personal appointments like the dentist to all my calls, errands, and dedicated work blocks. I also use AI for brainstorming, which is a lifesaver when working solo. It’s like having someone in the room to bounce ideas off of! I try to structure my work in focused chunks rather than multitasking, which is way easier said than done! I learned a habit or two about how to focus from my corporate startup career. With so many tasks competing for attention, the most effective approach is to focus on one thing at a time, check it off, and move on.
Taking breaks is pretty essential for my productivity, even though I don’t always do it. Some days are easier than others to get outside but some days I find I barely go outside. That said, always feel sharper if I step away from my screen, whether it’s a short dog walk, a workout, or a couple of hours skiing (both downhill and cross-country). One of the challenges of working from home in a rural area is the lack of nearby cafés or coworking spaces to switch up my environment. I thrive on a change of scenery and a bit of hustle bustle, so that’s something I’m still figuring out.
I take my nighttime routine seriously—my bed is my temple, and sleep is sacred (can you tell I love my sleep?). I always shower before bed as a way to “wash away the day,” which helps me mentally reset. A solid wind-down routine ensures I can start fresh the next morning, ready to tackle whatever’s ahead.
How do you bring ideas to life?
I bring ideas to life by starting before I’m ready and staying open to how things evolve. I’ve learned from years in startups that done is better than perfect, so when I have an idea, I tend to just start it and build while I’m going. “Building the plane while flying it” and “fail fast” are very common terms in startups and have always resonated with me. I like to treat ideas experiments. If they stick, great. If they flop, I’ve learned something. That test-and-iterate mindset has been key to growing The Retreat Co.
For example, this year at The Retreat Co we brought on brand partners. That was an idea I had and just started reaching out cold to brands that I love to see if they wanted to partner. Of course I had ideas of what we could do but I was throwing it out there and seeing who it resonated with. When a brand did respond, I’d share my thoughts, we’d chat about what would be best for their audience and come up with a plan from there. Not every ‘pitch’ landed with some brands but the ones that did turned into real value for the guests!
Most of all, I stay in motion. Creativity and clarity come from doing—not just thinking. I love trying different things, having new experiences, meeting new people. I say ‘just get started’ to a lot of people if they ask for advice on how I did it and what they should do.
What’s one trend that excites you?
It might not come as a huge surprise, but I love seeing more women carving out space in the outdoors. There’s this growing movement of women getting into skiing, snowboarding, mountain biking, and all kinds of outdoor adventures, not necessarily to be the best or most hardcore, but to enjoy it, connect with others, and push their own limits in a way that feels good.
It’s not about keeping up with the guys or fitting into some idea of what an “outdoorsy” person looks like. It’s about showing up, trying something new, and building community. I’m more immersed in the outdoors world than I ever was before and I’m getting to see it all over in women-led events, brands designing gear specifically for women, and nonprofits making the outdoors more inclusive. It’s exactly what we’re all about at The Retreat Co and it’s so fun and we’re proud to be part of this shift.
What is one habit that helps you be productive?
Now that I’m in this new chapter of entrepreneurship, having more control over my calendar has been a game-changer. I’m no longer stuck in all day meetings or someone else’s schedule. Of course there are meetings I need to take or places I need to be that aren’t dictated 100 percent by me, but it feels good to actually design my days around what works for me more than I ever have before.
I’m also working on being more in tune to ride the wave of whatever energy I’m feeling. It’s weirdly challenging to not do what you think you’re supposed to do or what you’ve been used to. So I’m trying to notice if I need a slower morning or a midday walk to reset. I would like productivity to be less about being ‘busy’ and more about and making space for the work that actually moves the needle.
Also, a random productivity hack for me: cleaning my house is both a procrastination task but once it’s done I feel I can be more productive in a clean and neat environment. I don’t think I’m alone on this one!
What advice would you give your younger self?
Besides chill out, I would say to pay very close attention to what genuinely excites you-the moments when you feel energized, lit up, or totally in flow. That’s not random. It’s your gut telling you you’re on the right track. Follow that feeling, even if the path doesn’t look traditional or obvious.
Tell us something you believe almost nobody agrees with you.
I actually genuinely like change. I know most people find it uncomfortable or avoid it, but I crave it. I get restless when things stay the same for too long, whether it’s in my work, environment, routines, or hobbies. I think change keeps things interesting and keeps me learning. I don’t want to wake up in 10 years and regret something I didn’t do that I could have. That’s one of my biggest fears.
What is the one thing you repeatedly do and recommend everyone else do?
Eat good, high-quality food that’s ideally organic and locally sourced when you can. I’m a big believer that what you put into your body affects everything—your energy, your mood, your ability to focus and show up fully. When I eat well, it almost feels like everything else falls into line. I believe prioritizing quality ingredients (and supporting local farmers or producers when possible) is one of the simplest and most powerful forms of self-care
It’s something I live by personally and bring into The Retreat Co experience—whether it’s our private chef dinners, breakfast tailgates, or surprise foodie moments sprinkled throughout the weekend.
Food, access to good food, food education – all of it – is a cause I’m passionate about.
When you feel overwhelmed or unfocused, what do you do?
It’s easy to feel overwhelmed or unfocused when you’re the only person doing everything, so on any given day I’ll need to take a moment. Often times in winter I’ll just lay down on the couch and look outside giving my eyes and brain a rest when it’s hard to get out. Otherwise, I try to get outside, usually using the opportunity to take the dogs for a walk. Inevitably stepping away gives me more pep in my step, I come up with a bunch of ideas and get out of the funk I was in.
What is one strategy that has helped you grow your business or advance in your career?
Building real relationships. Whether it was in my corporate career or now with The Retreat Co, creating genuine connections has been the joy and the basis of my work. I really enjoy connecting with people, hearing their stories, and finding ways to support or collaborate.
In my tech career, that approach helped me grow communities, build customer advocacy programs, and open doors to some awesome experiences and people. With The Retreat Co, it’s led to some amazing partnerships, media features, and loyal attendees!
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
As cliché as it sounds, one failure I’ve experienced throughout my career is letting imposter syndrome get in the way of fully stepping into my potential. It isn’t always abundantly obvious either – sometimes it’s quiet, like staying in my comfort zone too long, second-guessing myself, or talking myself out of big ideas because I didn’t feel “ready.” Even now, as I run The Retreat Cofull time after seven seasons of doing it on the side, I still feel it. There are moments when I’m super confident or I have a win that puts some wind in my sails and then other times where I question everything and feel like I’m not doing enough or there’s a better way.
In the “failure moments” I’ve realized it’s simply not trusting myself and holding back when I know I’m capable of more. Over time, though, what I’ve learned is that imposter syndrome isn’t something you defeat once and for all – it’s something you learn to live with and move through. It shows up when you’re growing, which can be frustrating, but honestly growth, for me, is the ultimate goal.
What is one business idea you’re willing to give away to our readers?
I was just talking about this on my last retreat! I would love to see a seasonal gear-sharing platform just for women. Think Rent the Runway meets outdoor adventure where women can borrow or lend high-quality gear (like ski clothes, hiking packs, snowshoes, mountain bikes, etc.) for short trips, retreats, or trying out a new sport before committing.
It solves a real problem: outdoor gear is expensive and it can feel intimidating to buy for the first time (or even for someone with gear) and it’s often only used seasonally so it sits around for a good portion of the year taking up space in our homes.
I’m sure someone has thought through this before, and maybe there are a million reasons it’s not a viable business… but what if it was?!? Someone please build this. I’ll send customers your way!
What is one piece of software that helps you be productive? How do you use it?
This is actually an area I’d love to improve—using software more intentionally to scale my work and make things more efficient.
That said, if I have to choose, Canva has been a really great tool. I use it for everything: social posts, email graphics, pitch decks, packing lists, partnership proposals, etc. As a solo founder wearing all the hats, it helps me keep things looking polished and professional, even when I’m building something last-minute and even though I am not a designer.
What is the best $100 you recently spent?
This is more on a personal note and it was actually a little more than $100, but the most meaningful money I’ve spent lately was the deposit to start IVF in the coming months. My husband and I are beginning the next phase of our family planning journey, and taking that first step (both financially and emotionally) was a big moment for us.
It’s given me a stark reminder to focus on health, balance, and taking care of myself in a deeper way. As someone who’s always in motion (literally and figuratively) and building things, I’m trying to shift some of that energy inward. There’s so much that’s unknown in this process, but choosing to move forward with hope and intention feels like the best investment I could make right now.
Do you have a favorite book or podcast from which you’ve received much value?
I love the Second Life podcast with Hillary Kerr. I’ve recommended it to so many women. Hearing stories from women who’ve taken the leap in their careers has been so inspiring. I like to listen to the episodes of the “regular people” who weren’t already famous and put everything on the line (finances, living situations, draining their bank accounts, etc) before launching their business as that resonates more with me. I can honestly say that after listening to these stories for years, it helped me make the decision to leave my stable career in tech to build The Retreat Co full-time.
What’s a movie or series you recently enjoyed and why?
“Apple Cider Vinegar” on Netflix totally pulled me in and brought out some big feelings. The show is based on the true story of Belle Gibson, a woman who faked a cancer diagnosis and became a “wellness influencer” around healing herself naturally. As someone who’s passionate about wellness and food, I found the show both fascinating and completely disturbing.
What really struck me was how the show navigated the complicated balance between what (and who) we trust when it comes to our health, and how critical it is to advocate for ourselves.
It also made me think a lot about the tension between traditional healthcare and holistic approaches. I genuinely believe both have a place, but it can be dangerous when misinformation is presented as truth. It’s just a really good reminder to do your own research, know that healthcare and general health is complex and what we see on social media is not the only place we should get our information.
Key learnings:
- Follow what excites you. I’ve learned to pay close attention to what genuinely excites me as those moments when I feel in flow are usually pointing me in the right direction even though it’s hard to recognize sometimes.
- Say yes before you feel ready. Saying yes to the scary things has helped me grow more than most of the play it safe choices I’ve made.
- Change is a strength, not a weakness. Change keeps me evolving and helps me avoid stagnancy, both in life and in business.
- Community is everything. Building real relationships has been one of the most powerful ways I’ve grown The Retreat Co and also built community in Lake Tahoe.
- Health and balance are the foundation. Doing my best to prioritize my health (mental and physical) has reminded me that finding balance helps every other area of my life.