women who can't not: the east coast girl who sent it west

When Elaine first called me, many times, just to make sure The Ski Retreat wasn’t a scam I knew she was my kind of person. At 22, she booked a solo ski trip across the country, leaving behind East Coast ice for California powder and a group of women she’d never met.

She also bravely opens up about having persistent depressive disorder and how you can do things for yourself, like travel, to make yourself feel better. basically elaine is the best and she embodies everything Women Who Can’t Not stands for: brave, adventurous, and carving her own path. Enjoy the conversation!

Charlotte: First things first, can you introduce yourself? Share your name, where you live, and where you like to ski or snowboard.

Elaine: My name’s Elaine. I mostly ski in Vermont at Sugarbush. I love going to Jay Peak, but it’s two hours away from me, so it’s kind of a trek. I also go to Bolton Valley and Mad River Glen—basically anywhere that’s not Stowe or Smuggs because I don’t have a pass there.

Charlotte: Nice! Okay, so let’s talk about the lead-up to the Ski Retreat. What was your first experience learning about it, and what made you excited to join?

Elaine: I was looking for a trip because skiing is basically the only thing I want to do in the winter. I don’t have a ton of friends who want to spend money on skiing or who like it as much as I do, so I was trying to find a group of people to go with. I was also really excited to ski out West since I usually only get East Coast ice.

The Ski Retreat popped up on my Instagram feed, and I thought it looked great. It didn’t seem that expensive, everything was included, and I didn’t really have to think about anything—so I kind of just full-sent and hit “book.” I also called you, like, four or five times to make sure it wasn’t a scam. I was like, “I’m young. I don’t know things. I will spend money on literally anything—especially if skiing is involved.”

Charlotte: Love that! So it felt pretty turnkey. But were there any hurdles standing between you and actually going on the retreat?

Elaine: I do a lot of things on my own, but I was still nervous to meet new people. I’m 22, so I figured most of the group would be older. I was expecting that—like, what 22-year-old flies across the country solo for a ski trip?

And honestly, I had no plan for getting to the ski resort after I landed. I dropped a message in the group chat like, “Hey, I’m stranded.” But one of the other girls picked me up at a gas station. That was super helpful—because, you know, I didn’t get kidnapped. Small chance, but getting dropped at a gas station in a state you’ve never been to isn’t ideal.

Charlotte: Definitely not. Did you ever think, “I probably can’t pull this off,” and if so, what kept you going?

Elaine: Not really. I was pretty committed. I had just come back from studying abroad for four months, and we did whatever over there—like, we almost got kidnapped in Morocco. So my stress threshold around logistics was lower than it probably should’ve been. I know I can handle myself and have good instincts. Worst-case scenario, I figured I’d just take an expensive Uber to the resort.

Charlotte: Side note—can’t wait to hear more about that Morocco story later. So you mentioned cost might’ve been a potential hurdle. How did you think about the financial side of it?

Elaine: The fact that I didn’t have to worry about food or housing made the price feel worth it. Really, I just had to pay for my flight and some Ubers. My mindset is kind of: if it’s an experience I think I’ll enjoy, I can’t really put a price tag on it.

I’ve worked since I was 16 and haven’t spent much of my money, so I have a bit more cushion than some people my age. And honestly, I think experiences like this are good for you. They shake things up in a healthy way.

Charlotte: Very wise. Have you ever done anything like this for yourself before?

Elaine: Not solo. For bigger trips, I usually rely on other people—whether it’s splitting Airbnbs or just not wanting to go alone. But I really liked doing this by myself. I got to be in my own space and meet a bunch of new people. I always forget that meeting people is good for me and that I’m not that awkward. It usually goes okay.

Charlotte: You were amazing to be around that weekend. I hope you do more things like this.

Elaine: Thanks! It helps when I’m doing something I love. I tend to overthink less. And we were pretty busy the whole time, which I liked. I enjoy having a schedule.

Charlotte: Do you think you lived up to our name—“The Ski Retreat: For Women Who Can’t Sit Still”?

Elaine: Oh, 100%. We were moving from 6:30 in the morning until the evening.

Charlotte: Did you tell anyone you were planning to go on the trip? What did they say?

Elaine: Yeah. My mom thought I was a little crazy. She was like, “You’re going where? With who? Nobody?” She told me to be careful. My friends weren’t surprised—I do a lot of “weird” things like going into the woods for 24 hours with no plan. So they were like, “Classic Elaine.”

Charlotte: Was there a moment during the retreat when it really hit you—like, “This was so worth it”?

Elaine: Yes! The second day, skiing at Alpine Meadows. Everyone was just as excited as I was to ski for eight hours straight. It was refreshing to be around people who wanted to ski all day, not just two hours. That made it feel totally worth it.

Charlotte: Was there anything that surprised you about the experience?

Elaine: How easy it was to get along with everyone. Skiing with guys is often competitive—they’re all trying to go fast or hit big jumps. This was different. Everyone just wanted to have fun. It was validating to be in that kind of environment.

Charlotte: Did the group support or uplift you in any specific way?

Elaine: Definitely. On the first day, I skied with Viet, and she said, “You can rip!” I’d told her I was nervous and only had three years of skiing under my belt, but I was flying down the mountain. It was so confidence-boosting. Everyone was super impressed that I came solo at 22. That felt good.

Charlotte: What were you most proud of during the retreat?

Elaine: Skiing my first bowl—and actually carving and skiing technically well. Being at Palisades helped me improve so much. When I got back to the East Coast, I could really ski. It was confidence-inspiring.

Charlotte: Was it the snow? The terrain?

Elaine: I think it was skiing with people at my level—not feeling like I had to keep up with guys who wouldn’t wait for me at the bottom. I could take my time and focus on skiing well instead of fast.

Charlotte: Totally relatable. Anything else about the trip you want to mention?

Elaine: I loved having activities planned—candle making was fun. The food was amazing. It was so nice to come back from skiing and have meals ready. I always say, if I were rich, I’d hire a private chef.

Yoga was... a bit of a struggle. I’m not flexible, and I was laughing the whole time with Viet. Probably not ideal during a quiet yoga session, but it was still fun.

Charlotte: Everyone can do yoga! But yes, laughter is definitely welcome. Looking back, what does it mean to you that you came on this trip, despite the challenges?

Elaine: It was affirming. I feel very adult and responsible. Just because something is scary doesn’t mean you shouldn’t do it. I didn’t know where I was going or who I’d meet, but I made it happen. It’s a cheesy takeaway, but it made me feel like I can do anything.

Charlotte: What would you say to someone who’s holding back—because of fear, distance, or money?

Elaine: YOLO. Seriously. You only live once. Obviously, financial situations vary, but money comes back if you’re working. Experiences and people don’t.

Charlotte: You mentioned it came at a good time in your life. Would you be open to sharing more about that?

Elaine: Sure. I was going through a depressive episode. I have something called persistent depressive disorder—basically, my emotional baseline is lower than average. When things go wrong, I can sink pretty low.

Getting on that plane and doing something I love was probably the best thing I could’ve done for myself. It reminded me that even when life feels heavy, I can still do things that make me feel alive. Skiing in the sun in California made me feel like I was living. And that helps me carry that feeling into daily life.

Charlotte: Thank you for sharing that. It’s so powerful to hear—and so helpful to others who might be in a similar place.

Elaine: Yeah. I wasn’t planning on the timing aligning like that, but I’m really glad it did.

Charlotte: Okay, a few quick rapid-fire questions! What’s one word you’d use to describe The Ski Retreat?

Elaine: Fun. I had a blast.

Charlotte: What would you tell someone who’s thinking about joining?

Elaine: Do it. It’ll be worth it. You’ll meet cool people. I still talk to some of the girls—Alena texted me when she was in Vermont. I wasn’t around, but I wished I was!

Charlotte: What’s your ski alter ego name?

Elaine: I forgot to think of one! But we did that icebreaker at the start, so let’s go with “Enthusiastic Elaine.”

Charlotte: Will I see you next year?

Elaine: Hopefully! I’m getting an Ikon Pass, so I want the flexibility. I’m also open to hosting something on the East Coast—I don’t know what that looks like yet, but I’m open to it.

Charlotte: Love that. Let’s stay in touch.

Elaine: Definitely. And congrats to you too—I saw your LinkedIn post! It was really nice to read about your success.

Charlotte: Thank you!

we promise you’ll love joining a retreat. Don’t take it from us, take it from elaine: