Women Who Can’t Not: The Repeat Guest Who Found Her Girl Gang

Sometimes one retreat becomes more than one weekend. It becomes proof that you can keep finding new versions of yourself, new ski friends, and new reasons to say yes.

Jessica first joined The Retreat Company for a Sun Valley ski retreat after her original travel plans changed. She came for the World Cup Finals, shared lodging, and a group of women who loved skiing as much as she did. Three retreats later, she has found local friends, unforgettable mountain memories, and a deeper appreciation for what happens when women choose collaboration over competition.

What made you decide to join your first ski retreat?

Charlotte: What is your name, where do you live, and where do you like to ski?

Jessica: I’m Jessica Star. I live in Southern Orange County, California, and I love to ski all over the place.

I’m lucky that my home mountain now is Mammoth.

Charlotte: You’ve been on a couple of retreats. Thinking back to the first one, what were your thoughts about joining a women’s trip solo, not knowing anyone?

Jessica: It was interesting because I love alpine ski racing, and I really wanted to go to the World Cup Finals in Sun Valley in 2025.

A friend of mine was supposed to come with me, but she couldn’t because of her son’s ski racing obligations that weekend.

I think I found you on Instagram, or the ski retreat algorithm found me, and I saw the coinciding trip.

I thought, “This might be a cool opportunity to take in the races, but also have like minded people to socialize with and share lodging with while I’m there.”

What made you nervous before going solo?

Charlotte: Were there any obstacles or hesitations around joining?

Jessica: Anytime you’re traveling solo, there are logistical questions.

How far away is the airport? Do I need to rent a car? Can I Uber? Do I rent gear or bring my own?

I usually bring my own boots and helmet, and a lot of times my skis because I love my equipment.

The idea of staying in a house was attractive to me. It’s nice to have a kitchen, even if you’re only making coffee and toast in the morning.

I was a little reserved about staying with a bunch of people I didn’t know.

I signed up late because I had been waiting on my friend, so I ended up in the group room situation.

You wonder, is someone going to talk a lot? Snore? Am I going to trip over someone in the middle of the night? What’s the bathroom situation?

But it came down to taking a leap. If this is terrible, it’s three days. If it’s awesome, it’s three days. So I decided to go for it.

Charlotte: Before that first Sun Valley trip, had you ever joined a group trip solo before?

Jessica: Not really.

I had traveled by myself before, and sometimes I would put myself in a group ski lesson so I wasn’t skiing alone.

But this was truly the first time I immersed myself in a group of women.

That is always a little intimidating.

Women have big personalities. We have different lifestyles, goals, and priorities.

I was concerned about whether I would connect with someone, whether I would fit in, and all of those social concerns we all have.

What was it like once you arrived?

Charlotte: Once you arrived and experienced it, what was it like?

Jessica: That first Sun Valley retreat was very cohesive, even though now that I’ve been on three retreats, I’d say it was maybe the least cohesive of the three.

There were different skill levels, different ages, and women from all over the country.

If I felt any trepidation, it was partly my own fault because I had bought ski race tickets and spent Saturday watching the races while a lot of the group activities were happening.

But we checked in Thursday night and skied with the group on Friday.

By the afternoon, I had met a few people and thought, “This is really cool. I’m glad I’m with this group of women.”

There was a girl from New York I ended up skiing and hanging out with.

We all did fondue, which is always fun at Sun Valley.

Then we had the chef dinner, and it was just a really fun group dinner and an amazing experience.

Why did you decide to come back again?

Charlotte: Tell me about your decision to come back again, and then again.

Jessica: I was in a big transition last year.

In the middle of summer, I decided to move across the country.

When I went on your first retreat, I lived in Georgia. I had lived there for 11 years and had been at the same job for 18 and a half years.

I was burnt out and made the decision that I needed to move.

That’s when I got the job in Southern California.

There were financial challenges involved. I still had my condo in Atlanta, and it was slow to sell. I had moving expenses and unexpected costs from moving into a new space.

I really thought I wasn’t going to have the financial flexibility to do much skiing other than driving to Mammoth.

Then I saw the trip returning to Sun Valley and thought, “Oh man, that was really fun. I’d love to do that again and really participate this time.”

The first time, I took myself out of some things because of the ski racing.

When my condo went under contract, it became a bit of a “why not” situation.

I love skiing. It makes me happy.

This was something I could give myself after all these months of feeling like a stranger in a strange land.

I reached out about Jackson Hole because I had never been there, but that trip was full.

You told me there were spots for Sun Valley, so I thought, “Well, I’ve been to Sun Valley, but I’ll go back.”

I’m so glad I did. The house was very cool. The women were unbelievable.

We had the most dynamic group. We all skied and snowboarded together all weekend.

There were different phases of life, different career backgrounds, different family situations, and everyone got along fabulously.

Everyone cheered each other on and was really welcoming.

Living in Southern California and not really having friends yet, I met Mel (another guest on the Jackson Hole Ski Retreat) on that trip.

We are now friends in real life.

We work in the same office park, strangely enough, so we’ve had lunch and have plans to go to Mammoth.

I truly made a local friend through those trips.

What surprised you most about the experience?

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

Jessica: I’m not a big picture taker.

I’m not a selfie person or someone who wants to take group photos or try Instagram tricks.

You brought a photographer to the experience, and I was fine hanging in the background.

Then before fondue at Sun Valley, you had us take individual photos on this beautiful deck.

I was dreading it.

But at the end of my little photo shoot, you all made me laugh.

There’s this really fun picture of me laughing, and when I look at it, I just see joy.

I was having a really fun time.

I forgot the camera was there.

It’s just a neat picture of me laughing.

Charlotte: A lot of women who come on these trips are going through some kind of transition. Does that make sense to you?

Jessica: I think so.

For most people, it’s a step out of your comfort zone.

For some people, it’s a huge step because they’ve never done anything like it.

Now that I’ve done it three times, I see it as a baby step in the grand scheme of things.

It might feel like a crazy large step beforehand, but once you make the arrangements and step into the environment, there is comfort there.

There are people with no kids, young kids, empty nesters, people getting out of relationships, people dealing with sick relatives, work challenges, and other life changes.

You don’t have to have the same experiences as everyone else.

There is value in listening. You can learn a lot even if it’s not your situation.

There doesn’t need to be a cookie cutter version of what your life has looked like in order to be accepted, welcomed, or comforted by the group.

That has been my experience across all three retreats. The group never looks the same.

What does women supporting women mean to you?

Charlotte: Your Super Bowl team was playing during one of the retreats, right?

Jessica: Yes.

I have a major league sports obsession.

I grew up in Massachusetts and spent the first 30 years of my life in Massachusetts.

When you grow up around Boston and New England sports, you get indoctrinated into fandom.

The weekend of Jackson Hole, my team was in the Super Bowl.

I had already extended my trip by one night to stay Sunday night because I wanted to watch it.

Mel and I were in the Jackson Hole retail store at the bottom of the mountain, looking at sweaters, and I looked across the room and locked eyes with a friend I hadn’t seen in a year since we were in Switzerland.

He yelled, “What are you doing here?”

And I said, “What are you doing here?”

He was there with his wife and grown daughters.

They invited me to their Super Bowl party, and then I skied with them and their instructor on Monday.

It ended up being a wild weekend of emotions and amazing experiences, but also a heavy heart because I had lost my uncle, who I had been close to my whole life.

I was lucky to have amazing people around me, even coincidentally.

Charlotte: What does women supporting women mean to you?

Jessica: In the professional environments I’ve worked in, they tend to be boys clubs.

It’s really disappointing when you see women who are impactful in an organization, and instead of banding together, there’s a tendency for them to cut each other down.

When women are encouraging, supportive, giving, and just there for someone, I think that’s so important.

It’s a reminder that we need to be a girl gang.

Especially in this day and age, it’s important to look out for one another and feel empowered to do that.

Charlotte: What shifts when there is collaboration over competition?

Jessica: There’s a chance to have such different experiences than you would on a trip with friends you’ve known forever or on a mixed gender trip with couples.

You can be your best, most confident self because you know the group isn’t judging you.

Everyone is there to support one another, get to know one another, and have a great time.

There’s this sense of collaboration and creativity.

When we did the tote bag art project in Sun Valley, everyone’s bag was so different.

Everyone was encouraging each other and sharing pointers while we were carving stamps.

One side of my bag has everybody’s stamps on it, and it’s really special.

We can have such a better experience and go so much further supporting each other instead of competing.

What would you tell someone thinking about joining?

Charlotte: What is one word you would use to describe the ski retreat?

Jessica: Fun.

Charlotte: What would you tell someone who is thinking about joining the ski retreat?

Jessica: Come. Join in. As long as you come in with an adventurous spirit and a willingness to participate, you’re going to have a great time.

That might look like enjoying the yoga and relaxing all weekend.

It might look like going out and being social.

You can make it your own experience in a lot of ways.

Charlotte: What is your ski alter ego name?

Jessica: Bryce Kellogg.

Charlotte: Where should the ski retreat go next?

Jessica: I was in Telluride last weekend, and I love Telluride. The town is so cool. I’d also really like to go back to Jackson Hole.

Charlotte: Anything else you want to add about your experience or the retreat?

Jessica: Having been on three of these experiences now, getting to know Charlotte and the programs she puts together, there is so much thoughtfulness behind them.

You’re meeting cool women creators and women entrepreneurs.

You’re having chef driven dinners with women who are amazing in the culinary field.

Charlotte is really thoughtful about bringing women into those experiences and living what she’s promoting, which is women’s empowerment.

I think that is really special.

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Whether you’re joining solo, moving through a life transition, or looking for ski friends who understand why the mountain matters, our retreats are designed to help you make the leap and find your people.

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