She Went Solo — and It Changed Everything

What happens when you stop waiting for someone else and just go? In this episode, Jennie Blackwood sits down with Charlotte Lilly, founder of The Retreat Co, who turned a spontaneous solo yoga retreat in Cuba into a thriving business creating transformative travel experiences for women. Charlotte shares how that one trip gave her a confidence she didn't know she needed, why the scariest part is always saying yes, and what she sees happen when women finally stop waiting to feel ready. Whether you're dreaming about starting a business, booking a solo adventure, or just taking that first scary step — this episode is your sign. Just go.

Guest: Charlotte Lily, Founder of The Retreat Co 

Website: theretreat.company 

Instagram: @_theretreatcompany

Transcript

SPEAKER_01 0:00

I'm Jenny Blackwood, a small town mom of four who refused to settle for a life that didn't like me at. When everything felt uncertain, I didn't run back to a nine-to-five. I bet on myself. I took a simple idea and turned it into an almost seven-figure business my first year, all while being a mom first. Now I'm here to help you trust your own power. Chase the dream that keeps tapping your shoulder and build a life that feels like you. This is Girl Why Not You. Hello, hello, everybody. Welcome back to Girl Why Not You. I am your host, Jenny Blackwood, and today's episode is for the woman who has been waiting, waiting for the right time, waiting for the right person, waiting to feel ready before she finally does the thing she knows she wants to do. Because what if the thing that's actually holding you back isn't fear? It's waiting for someone else to come with you. And what I love about today's guest is that her story started with a moment like that, a solo retreat, a decision to go anyway. And what she discovered in that experience completely changed the trajectory of her life. Today I am joined by Charlotte Lilly, founder of The Retreat Co., a business creating transformative travel experiences for women, many of whom show up completely solo. What started as a side hustle alongside a full-time tech career is now a growing movement helping women build confidence, connection, and a whole new sense of what's possible. Charlotte, my friend, I am so excited to have you here today. Welcome to Girl, Why Not You? Thank you. Love it. I'm so excited to dive in. I for some reason to me, retreats are like a fascinating thing. One, because they're fabulous. And oh my gosh, like, should we all go on a retreat this year? Make sure you put that on your list, everybody. But it's like transformative. It's all the things to the person attending. But behind the scenes, putting a retreat together is a lot of work. It's probably an understatement, right? But I want to go back with you for a moment because I think that's where everything really started for you, where this kind of seed became planted. So let's go back. Take me to that solo retreat. Okay. Give us a little insider information on that. What was happening internally for you in that moment? What's the story?

SPEAKER_00 2:18

Okay. That was in 2016. And like many of these things, there was a transformation in my life. I was going through a breakup. And so I was like, I want to do something for myself, you know? Um, and I was like, I've never been on a solo trip. I'd never been to Cuba. Oh Cuba. Yeah. And, you know, at the time it was you needed to go on some educational journey to be able to enter the country. And so this yoga retreat somehow was able to do that. Yeah. So I got to go on this um this trip. And it was so empowering to go on a trip by myself. You know, I showed up at the airport and I was like, okay, I guess I'll look for the leader. Um what am I doing? What am I doing? I guess I'll just show up and meet all these people. And, you know, not only did I meet awesome people on the trip, I also got to do an experience that I never had done before. Yeah. Right. And so, especially the solo element, you know, it was so empowering to be like, yeah, I went on this trip by myself and telling people that, you know. But then it opened up the doors for me to go on more solo trips by myself. So it just gave me kind of a confidence that I didn't really know I needed, but um, I went on it anyway and had a great time. And that's actually what inspired what I do now.

SPEAKER_01 3:38

That is so cool. Truly fascinating, actually. I'm finding it like the weirdest thing since I had babies and I'm 41. Because I never have alone time anymore, even simple things like going to grab coffee alone, right? It almost makes me uncomfortable to be alone. And it's weird. So I really give you some kudos for not only going on a retreat solo, but also to Cuba. I mean, that is like a big decision there. But you, like you said, you were going through a breakup. You were looking for some like life-changing transformation. And and so was it worth it? Are you glad you went? Oh, hands down, yeah. 10 times over. I love so what about that experience like hit differently for you compared to maybe other things you had tried in the past?

SPEAKER_00 4:22

Most of my other trips, I'd travel with friends or a something like that. And so you have a built-in buddy, you have a built-in plan, you have somebody to share those memories with that you know, you know, and that you can like kind of bond with over time. But I don't know, on this trip, you kind of just wing it. You go in, you say, I'm gonna trust it. It's way different than like, you know, planning your own trip. Like, I'm a spreadsheet, like every day I have a spread, you know, planned out. Like, not only was it all planned for me, which is amazing, but also was like, you know, just winging it and seeing what happened. And I think the best things in life happen that way. You know, we plan so much, we work backwards from goals, we plan everything out. But like, how often do we just go for it? We don't get the opportunity as much. So it felt really great to be able to do.

SPEAKER_01 5:12

That is so cool. And it sounds like it really inspired this big aha moment for you. You know, you you're pushing your boundaries, you're getting uncomfortable. My favorite saying, which by the way, everybody, I'm making swag that says get uncomfortable. Um, because that's really where transformation happens. And so here you are. You're in a foreign country, you know nobody, you're like, I think this is gonna be amazing. But at this point, there's a lot of unknowns, right? So when do you think that it hit you? Like you're there, you're loving it, it's starting to feel life-changing. When did you decide I think I want to create this type of experience for other women?

SPEAKER_00 5:44

Actually, it was like looking at the trip leader and saying, How do I get her life? Yeah. Going to all these awesome places. She's bringing together people who are making connections. She gets to lead the show, right? So she gets to decide where she wants to go and what she wants to do. And I always wanted to be a founder, but I didn't really know what I would do or how I'd go about it. But when I saw that, I was like, okay, this is interesting. Um, I love yoga, but I don't want to be a yoga teacher. But meanwhile, I was like planning ski trips left and right, like for friends, for my work. So it was something I was already doing. And so it kind of just dawned on me, like, oh, I guess I could do this around skiing. You know, I could take people, I could take people I don't know skiing because I do the same thing where I go skiing with friends that I know. It's a built-in trip, like, you know, all the same things as what you experience when you're going on a retreat or something like that. So totally. Yeah. It was kind of that moment where I was like, oh, I could, you know, I could do this. I could ski for my job.

SPEAKER_01 6:49

I think that's amazing. So you're taking what I'm getting from this is you're taking something that you already love. You know that about yourself. I am passionate about this. I'm already kind of dabbling in this with just friends. And then all of a sudden you're like, wait a minute, why couldn't I make something out of this? Why couldn't this be something that I actually did seriously that I could build a business upon, but I actually get to like what I do? I think that's where a lot of women get stuck is that they may have those aha moments, but a lot of people are struggling to find the momentum to actually act upon it. So for you, you know, what type of beliefs do you think are actually holding people back that in those moments where they're like, this could be truly something I love, life-changing, all the things, but they decide to wait instead of actually act.

SPEAKER_00 7:35

Yeah, I think there's a lot of reasons for that. I mean, if I look at myself, it would be is it something people are actually gonna like? Like I like this, do other people like this? Or I don't have the time or bandwidth or energy. You know, I think that's a really big one. Um, like when I was starting this, there were a lot of tears because it was holding full time and I was doing this, but I was like, I want to do it, but it's so stressful. But um, you know, there's a lot of stories we tell ourselves as people, yeah, and especially women. And um, you know, there's that confidence piece around, can I do this? I've never done it before. Uh, you know, do I have the skills? The answer is yes to all of these things. It's just, you know, actually doing it. Um then, you know, it morphs over time. It's kind of like that just start, just do something, yeah, and then see how it goes. It doesn't have to be perfect because guess what? In like three years, five years, one year, it's not even gonna look how you thought it was gonna look anymore.

SPEAKER_01 8:33

Yeah. So maybe even three months from now, it's not gonna look how you thought it was. Yeah, that's that's very um, that's very spot on, like from what I see all the time, you know. And I talk to so many different types of entrepreneurs, but a big fundamental thing is actually taking action. You know, it's like we can all have the best thoughts, but our thoughts are nothing if they only live in here, right? They only live in your head. Your thoughts have to have action behind them to actually get somewhere. So for you, you know, you look you're loving the retreat world. You're like, hey, I could really do this. You're on a retreat. What do you think retreats do for people? Like, versus like when they come in to the retreat and then who they are after they leave a retreat. What do you see?

SPEAKER_00 9:16

You know, it's funny too, is that's what my only retreat that I've gone on that I didn't plan. So I've only gone on one limit. And I'm like, I think I need to go on more, you know, just as like market research. Market research, right? Expense, but also to just learn and see what other people are doing. But I think, you know, sometimes it's better to just do what you know is best instead of trying to see what other people do. For sure. Your own flavor to it. But for women, you know, for the our guests who go on these trips, they have a lot of pre-conceived beliefs, um, similar to what we were talking about before. But instead of starting a business, it's more like, can I go on this trip? So for my retreats, you know, it's like, oh, I'm not really outdoorsy, or I'm not a good skier, or I've never been camping before. The big ones that I hear is like, I don't know if I'm gonna fit in. You know, what if for some reason everybody else is super excited and confident, but I'm the only one who's nervous, you know? Yeah, yeah. Everybody's the same, everybody has the same fears is kind of like the funny thing that I've discovered. But afterwards, you know, what people really discover is like, oh, I can do hard things. Yeah. Oh, I'm actually capable of doing this stuff, or oh, I can just show up and figure it out, you know. Or and I'm not the only one who feels nervous, or I don't have to wait for somebody else, you know, to go with me. I can go on my own. Yes. Yes. You know, there's a big difference between the pre-trip and the post-trip from what I see with the guests.

SPEAKER_01 10:52

Yeah, there's a lot of transformation that can be had, but you're right. I I feel like I've I've seen that too. And I think that makes what you do so powerful. You know, I what would you say the transformation actually looks like for women who come on your retreats? Like, what are you seeing from they walk in the door? Maybe they're super excited, but also like, what am I gonna get out of this? You know, what do you see in the transition with your retreats specifically?

SPEAKER_00 11:18

With ours, yeah, it's kind of some of the things I just mentioned, but I um so one I've talked to almost all my guests about what did you think before? Or you know, how did you find us? What did you think in terms of should I book this or not? When you booked it, then how did you feel? I really asked them those questions, like for the full journey, because yeah, I need to know. And I like to do stories and testimonials with them. So I mean, a lot of times they actually think it's spam. You know, they're like in this day and age, I just don't know. You know, you don't know if these trips are legitimate or not. Right. Which, you know, I totally understand. And I've gotten on the phone with many a guest ahead of right, they say, Hey, can I just chat with you? One just called me on FaceTime out of the blue, maybe trying to like catch me or something. I want to make sure you're real. Yeah. And I'm like in my pajamas. I'm like, hi. Um so I will chat with them, you know, and they have a lot of those kind of like fears, like, oh, is it gonna be okay? I don't have my own gear, or, you know, I'm gonna share a bathroom. Like, what's that like? You know, I'm I'm scared I'm gonna be the only one who XYZ, or I don't want to like drive by myself, or is there anyone I can carpal with? You know, all these options. Um, but like they usually tell me on day one, once they arrive, there's just a tone that's set that's like very welcoming, everybody's open. Because if you are going on a trip solo, you have to have at least a like a little bit of openness, vulnerability, adventurous spirit. So already these women have something in common, right? Yeah. They all have that baseline.

SPEAKER_01 12:58

Yeah.

SPEAKER_00 12:58

Otherwise, you're usually pretty different, which is kind of cool. But, you know, we also do a few things to like break the ice when they first get there that night. Um, I'm kind of like a deep cuts person. It's like we have three days together. So we're gonna get to know each other.

SPEAKER_01 13:13

We're gonna get to know each other quickly, ladies. Yeah.

SPEAKER_00 13:16

Yeah. And then, you know, throughout the trip, we do a lot of intentional activities that really help create a bond between the ladies that can create memories, funny moments, um, things that they, you know, can get to know each other well off of. So, you know, that really helps throughout just the few days we're together. Yeah. And then yeah, it's like after, you know, the last day, there have been tears, right? Like, oh my gosh, like this has been so amazing. It's just what I needed. Oh, it needs to feel good to hear that. Oh my gosh, that's when I'm like, this is why I'm doing what I'm doing. Yeah, it keeps growing. Why am I doing this?

SPEAKER_01 13:52

I know, because it is a lot of work getting into it. You know, you're mentioning right now, you're talking about connection that happens in these environments. And, you know, it's it's a it's a different type of environment than many people are used to. Like you just said, you're thrown into a group of people, maybe you know one, maybe you know none, right? But what would you say kind of creates that connection that can happen so quickly? You know, you're doing these different exercises and whatnot. But do you think that people out there are like, like you said, they leave and they're saying, Oh, I really needed this. What do you think that they're finding like a tribe of women that are like all in a place of needing something, but they don't know what it is? If that makes sense.

SPEAKER_00 14:35

Yeah, I know. And it's so hard to like tangibly say what that is. But yes, if we had to boil it down to one word, it's connection. Because what I hear before these trips is I don't have anybody to go with. It's hard for me to find other women to go with. You know, my friends don't camp, they don't ski. My partner doesn't camp, they don't ski. I used to go with my kids, but they don't want to go with me anymore. Like instantly, these are the things that I hear. And so yeah, I mean, they come and they meet women who have similar interests at baseline, you know, the like anchor point, the skiing or the camping or whatever.

SPEAKER_01 15:10

Yeah.

SPEAKER_00 15:11

Then from there, I mean, yeah, many of them have like, you know, hooked up on their own and gone on their own trips. Oh, cool. Like a WhatsApp group that stays alive and people are sharing, you know, what they're doing and things that we chatted about on the trip, you know, come back up. And I it really is that connection piece. We do a survey at the end of each trip. And this season, 90% of them said that they made lasting friendships. Yeah. Oh, I love that. Isn't that amazing? And like 10% were like, yeah, my skiing got better. You know, it's definitely more about that connection piece than it is about the activity itself. The activity is just like our excuse to get together, but it's like, you know, it's that connection piece for sure.

SPEAKER_01 15:56

There's got to be a lot of confidence built at these things too. You know, for people who are feeling like they're lacking confidence in certain areas, and maybe that is like, you know, weirdo me that's like, I'm too scared to even go to the coffee shop by myself anymore. It's like, you know, when you push your boundaries, you get growth there, even if it's personal development. Yeah. So maybe a lot of people come out of there even feeling more confident from the things that they learn in those relationships that they're building with you and the other people who are there. Sometimes we just need to get with like-minded people who are also, sorry, my French, going through some shit because it just helps us to heal, knowing that there's power in numbers, right? Like sometimes we get so tunnel visioned. We have all these things happen in our life and it's just running us over. But when you realize that there's kind of like a sisterhood out there of other people have shit going on too. And you can kind of like almost, I hate to say commiserate together, but you can kind of like heal together and and just find like comfort in knowing that you're not alone. So I think that that is a massive thing from a retreat. I have a friend, her name is Lindsay. Maybe she's listening to this. Um, I don't know. But she is like a major retreat lover. She's like a Sedona person. She's she's not a skiing person, but she's a Sedona person. But it's like she comes back and she'll be like, My entire life is changed. I am a new person. She even went on one with her husband and she's like, we've never been more connected, we've never been better. And I'm like, wow, you know, it's like in such a short amount of time, you can have such a magnitude of growth and really transformation. So I love that you are doing this. This is so cool. So I feel like I think this is really like the message, probably underneath everything that you do. Um, what would you say to someone who's waiting to feel ready to start something? You know, what would be your advice to them?

SPEAKER_00 17:39

I asked that to the guests after their trip. And it's some combination of just do it. Yes. You know, because it's like, you know, one thing coming from me, it's easy for me to say, I obviously created this and I'm the type of person who would go on it. But like, what would they say, right? And 100% of them had said something very just straight, like, why, why wait? Why wait? Just do it, just do something like this, you know, because it depends on your, you know, the way you think about life. But, you know, if you think about it in the way of like, you know, you only live once, now is the time, tomorrow you don't know what it brings, you know, those types of things, which I very much subscribe to. I'm like, just if you think about it, you know, I get that there's fears involved with stuff like that, but I think that we only grow when we face those fears. And then you realize usually anything that you're scared of, once you do it, you're like, oh, that wasn't that bad. Yep. Yeah. So I Time and time again, right? Yeah. Yeah. And I do think to your point earlier, the confidence piece is really big. Like, not only do you gain confidence through what we do on the retreat and the experience, but like even just saying yes to something does grow confidence. You know, we have our trips are all ages. Um we have, but we have quite a few like more mature people who come. So, like, you know, 70s, early 70s. Many of them have never been on a solo trip before ever. Oh. And so a lot of their fears are like, am I too old for this or am I gonna hold everyone back? You know, the typical woman like way we think. It's like, I don't want to hold anyone back. Yeah, yeah. But they, you know, have a they gain this like amazing confidence that is so, and this is anyone at all ages, but it's so awesome to watch someone, you know, where you understand what they're feeling beforehand, but then they come on the trip and you see afterwards like blossom and you know, just feel more confident, which is really cool.

SPEAKER_01 19:43

I think anytime that we're in a position where we're doing something we love that we can truly see that the fruits of our labor are helping other people, it's the best feeling ever. It's like for you to walk away every retreat and go, oh my gosh, like this person is forever changed because of this moment that happened or this experience and or this person that they met or whatnot. I mean, that feels good at the end of the day. So that's probably, you know, this is like a passion project for you that you love doing. And I think it's really cool that the way that it started, you never would have thought that that one split decision that you made was going to transform your life in the way that it has. And I think that that's a really valuable like underlayer of all of this that you guys can resonate with is like think of Charlotte. All she thought she was doing was going on a yoga trip to Cuba and it completely changed everything. So you never know. Like you can try to prepare for everything that happens in your life. You can try to control everything, but things are gonna happen when you least expect it. I know we all get so annoyed hearing that, especially when it comes to like men, you know, oh, you'll meet someone when you least expect it. Like, shut up, people, right? But no, seriously, in this situation, all situations in life, you just never know when the things that are meant to be a part of your life are gonna strike. So just always be ready. Never shut down an idea. Never refuse to take action on something that feels like it's right. You know, if you have that nudge, if you have that feeling inside of you and you're like, hey, what's the worst that could come from me actually taking steps to see if this becomes something? What's the worst thing that's gonna happen? Right. So if someone's listening and they're waiting on something, waiting for somebody else to go with them, what is their first step?

SPEAKER_00 21:24

I think that they already have some idea in the back of their mind about what they want to be doing. Whether it's taking a trip, whether it's starting a company, like it comes from somewhere, right? And for me, I think it was already in there. And then I went on that trip and I was like, oh, okay. It got me thinking a little bit more. I think for me, listening to other people's stories is like 100% hands down the thing that inspires me the most. Like I listen to different podcasts of women who started their businesses. I listen to um other interviews, I read books, you know, I am like all about it. Yeah. And, you know, sometimes like we have our in charge. inspiration within us, but also it's nice to kind of like hear other people's stories. Like for me, I was in a corporate tech career. And it was a big choice to leave that a year and a half ago. And one of my one of the podcasts I listened to like talks about the transition from your first life to your second life of going from a corporate job to your own business. And specifically I would listen when did they do it and why and how? Yes. You know, the answer is it's different for everybody, you know, because like your financial situation can be different. Like, you know, taking this risk involves so many different pieces. So you know what was it for me? Um, you know, was is different than other people. But yeah, I really feel like listening and being inspired by other people is one way to be positively influenced and to like have it bring you like one step forward, one step forward, one step forward.

SPEAKER_01 22:57

Sure. Yeah. No, I I couldn't agree with you more. Listen to those words, everybody. Listen to this podcast. Listen to this podcast, dang it. Okay. We will inspire you. So guys, here's the thing. If this episode hits you, if you've kind of started to feel that pull while you're listening to this, I just want this to be your reminder today and every day. You don't need somebody else. You do not need perfect timing. You do not need to feel ready. Most people who end up successful still don't feel ready, okay? You just need to go. You need to take action. And if you've been waiting, I ask you today and every day, girl, why not you? Charlotte, thank you so much for being here today. If somebody was listening and they feel really seen by this and they're looking for their best next steps, if they want to attend a Charlotte Lilly retreat, what's the best thing that they can do?

SPEAKER_00 23:51

They can go on our website theretreat.company. They can go on Instagram at underscore the retreat company and they can sign up for our newsletter to see the things first. So I think those are the best ways.

SPEAKER_01 24:04

Oh my gosh. I hope that everybody listening to this is excited thinking about a retreat. If you love skiing Charlotte is from Lake Tahoe who doesn't want to go spend some retreat time with Charlotte. She is a lovely human. I highly recommend that you check out her website. I'm going to make sure every piece of that information is in the show notes so that you can look into this further. But guys, this is just another beautiful example of somebody who took a chance even when they weren't sure she started messy, but she started and wow what you have built Charlotte congratulations on your business. Thank you so much for being here with us today. Thank you. Okay everybody you have a fabulous rest of your week thank you so much for tuning in and I can't wait to catch up with you next week. See you later everybody in this episode made you sit up a little straighter or dream a little bigger don't ignore it. That's your future nudging you I'm living proof that you can start messy, start scared, start in the worst timing, and still create something beautiful. Thank you for listening to Girl Why Not You now go take one small step towards the life you've been craving. Hit subscribe leave a review if you feel called and share this with someone who's ready for more