Midlife Reinvention: Moving Alone to Costa Rica

What happens when the life you built no longer feels like the life you want?

In this episode of Roam Alone, Theresa sits down with Jen Rulon, who made a bold decision at age 50: she left her marriage, her career, and the United States to start over alone in Costa Rica.

Jen opens up about the fear that came with such a massive transition — and how stepping into the unknown ultimately allowed her to rediscover herself.

Today, Jen is thriving. She has built a successful business as a midlife reinvention coach, cultivated a strong community in her new hometown, and found love again — proof that reinvention isn’t reserved for the young or the fearless.

This conversation explores what it really means to choose yourself, especially in midlife, and why starting over can become the most empowering chapter yet.

In This Episode, We Talk About:

•  Leaving a marriage and long-term career later in life 
•  Moving abroad alone at 50
•  Navigating fear, doubt, and identity loss during major transitions 
•  Building community from scratch in a new country 
•  Reinventing your career after midlife 
•  Why reinvention requires courage — not certainty 
•  Finding love and belonging after starting over 

Key Takeaway

You don’t have to feel ready to change your life. Sometimes courage simply means taking the next step while you’re still afraid.

About Jen Rulon

Jen Rulon is a midlife reinvention coach helping women redesign their lives with purpose, confidence, and authenticity after major life transitions. After relocating solo to Costa Rica at age 55, she now supports others navigating reinvention, identity shifts, and bold new beginnings.

Connect with Jen

jenrulon.com

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Roam Alone is hosted by Theresa Stephens.

Instagram: @theresaannstephens

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Transcript

SPEAKER_00 0:03

Hello everyone, and welcome back to Roam Alone, the podcast about what happens when we choose ourselves, even when it feels terrifying. I'm your host, Teresa Stevens. Today's episode is about reinvention, the kind that doesn't come neatly packaged or perfectly timed. My guest, Jen Roulon, made a decision many people only dream about, and just as many fear. At 50 years old, she left her marriage, stepped away from her career, and walked away from the life she had built in the U.S. to move alone to Costa Rica. She didn't move because she had everything figured out. She moved while she was scared. In this conversation, Jen shares what it really felt like to dismantle a familiar life, how she navigated uncertainty, and how that leap led her to reinvent herself as a midlife reinvention coach, building a thriving business, a deep community, and a loving new relationship in the process. If you've ever wondered whether it's too late to start over, this episode is for you. Let's dive in. Welcome to the show, Jen.

SPEAKER_01 1:16

Thanks for having me, Teresa.

SPEAKER_00 1:18

I was looking over your Threads account, which by the way is my latest favorite obsession. I love that social media more than any other. And what stood out to me initially was when you said I moved alone to Costa Rica at 50. So I got to hear all about it. What was going on in your life leading up to that point that made this huge decision? Huge decision.

SPEAKER_01 1:44

So I lived in Texas for 25 years. I'm a U.S. citizen. I was born in Detroit, all that thing. But to be honest with you, I was going through a major life change. And it was, I was going through a divorce. And I I recognized when my ex and I were going through therapy, and we were in Florida in 2020, it made me really realize that I need water constantly. I need I'm a beach baby. And so I really needed that. And I remember like sitting at the beach doing a meditation, and I walked in and I said, Hey, I need to talk to you. Like I have recognized that, like for me, I need to be on a beach. And that's not just a once every three months down to Puerto Rancas, Texas. It's you know, it's it's something that I have to have continuously. And he's like, That's a crazy decision. And in like two minutes, like on the beach in Florida and Panama City Beach, I'm like, no, no, no, you don't understand. Like my whole life was around water. Um, you know, from the very you know, I was born in Michigan, uh moved over to Wisconsin, but I was um my other job was working with marine mammals. So I was in the water, and then I was a traffic for years, right? So I always had water, and then all of a sudden I retired from the sport, I retired from working with marine mammals, and then it's like all of a sudden I had no water.

SPEAKER_00 3:12

I get that. I live on the Ohio here in Kentucky, and I can't imagine life without water somewhere in my close vicinity for sure.

SPEAKER_01 3:22

Agreed.

SPEAKER_00 3:23

Agreed.

SPEAKER_01 3:23

I asked for the divorce. I said to myself, okay, there's gonna be three places that you want to live Hawaii, California, or Costa Rica. Well, Costa Rica won. Yeah.

SPEAKER_00 3:36

So why? How Costa Rica? What made it stand out?

SPEAKER_01 3:40

Sure. So I visited Costa Rica in 2019 for the very first time. It was after I retired from the sport of trathlons. And I needed to go somewhere. I didn't want Wi-Fi. I just needed to sit on a beach and just sort of like disconnect myself from the world because for 30 years I was chasing the dream to get to the Iron Man World Championship in Hawaii. And so I said I was going to do that when I was 17 years old. And so my whole life was always like really building up to that. Did I make it to Iron Man Hawaii? Yes, I did. In 2017, amazing is when I qualified. Thank you, qualified, participated. And then 2019 is when I retired from the sports. So here I was. I did my last Iron Man in 2019 at Panama City Beach, Florida. It was my 15th Iron Man. And here I was like coaching trahes. It was all consuming for me for over 20 years. And so I was like, all right, I need to go to a beach. And my ex was like, okay, well, where are you going to go? To Port Arrances, uh, Miami? I'm like, no, I'm going to Costa Rica. And he's like, wait, what? You know? And at that point, I was supposed to go with one of my best friends and she couldn't pull it off because she just started a job. So I'm like, all right, I'm going to go by myself. Wow. And so I came down by myself and just sort of like sat at this hotel and just walked the beach and really like, really just cried and just sort of like just released so much. Absolutely. So that was the first time I've been to Costa Rica. And then 2020 happened. I was supposed to go on a retreat with a woman, Bella, who Bella and I are still dear friends. We've gone on many other trips together, but she was going to put on a woman's retreat in April of 2020. Well, we know that didn't happen. So we have some plans winter rye that year for sure. Yes. And so then at that point, like Bella and I just stayed in touch. And she was like, Hey, if you're interested, you know, me and a few friends are going down to Costa Rica in December. Do you want to join us? I'm like, absolutely. You know, I asked my ex if he wanted to come. He's like, no, I'm good. Just go have fun. So I was like, okay, sure. You know, so I went down there and then went down again in 2021 during the separation, and then went down again in June because I was invited as an influencer to go do a yoga retreat. And so they needed to fill a spot. So he asked me to come. He's like, I got your room and board. He's like, Can you get here? I'm like, absolutely. Yeah. And so that that moment at the retreat was when I knew I was ready to ask for the divorce. So yeah. You know when you know, for sure. You know when you know. And I think I knew for quite some time, I just couldn't use the voice to use it.

SPEAKER_00 6:44

Absolutely. So you're going through this huge transition. You narrow down your choices for what's next. Costa Rica wins out. What are the steps that you took going from Costa Rica's the place to actually moving there and moving there alone?

SPEAKER_01 7:03

Well, uh, you know, I think the biggest thing, you know, somebody asked me this on threads about like making like the move to Costa Rica. And they go, Were you scared? Like, what was your chance? Or they said, What were your challenges? And I said, you know, the challenges were not the logistics of behind everything, it was more about trusting what I wanted to do and not what everybody thought I should do. Right. Right. That's a huge difference. And so I'm a big advocate of higher power universe, God, whatever your beliefs are, right? But I gave it to God and just said, you know what? I'm going to reach out and connect with people on Facebook. I'm going to read the room. I'm going to visualize. I'm going to see things. So, like all of a sudden, I am, you know, sitting on Facebook and I see an apartment pop up. And I was like, okay, that's the town that I want to stay in. It's on the other side of where I visited before. But let me, you know, let me reach out to them. So I reached out to Corinne and I said, Hi, Corinne, my name's Jen Roulon. I saw that you had availability on your apartment. Are you, you know, do you have any availability after January? And she's like, not right now, we don't, but if I do, I'll let you know. And I was like, great. And that was probably in October of 2021. And so I was like, all right, you know, and so, like in my mind, I'm like, I move into Costa Rica at the end of December of 2021. I don't know how, I don't know why, I don't know when, but I'm gonna make it happen. And so I did. And so then all of a sudden, like a month later, I'm getting my nails done with my girlfriends. I open up my phone, I open up my WhatsApp, and crin's like, Jen, you won't believe it, but our apartment opened up at the end of January. Would you be interested? And I said, Yep. I go, what do you need? She's like, I need a deposit. I'm like, done. I'll send it to you in PayPal. Like, I didn't even think about it. I just went with it, right? I didn't overthink about it and just be like, oh, I don't know. I don't know what I should do. So one is to trust on why you want to do why you want to go solo. I think that's the number one thing is trust it. Number two, stop listening to people who want to hold you back.

SPEAKER_00 9:39

Absolutely. A thousand percent. Nine times out of ten, they're wanting that because of whatever's going on in their own lives. And it doesn't even have anything to do with you.

SPEAKER_01 9:50

Absolutely. And it's their fears that they're bringing on to you or to yourself. I think really putting those boundaries up and being adamant, like, no, this is what I want to do, and this is what I'm going to do, right? So, and then I think I think number three, which did help me is that I did connect with some people in my little town in Samara because I kept going down in 2019. I went down in 2020, but I didn't really stay in Samara. I went down in 2021 a couple of times. And so I met this local family. And then I would go to these yoga classes and started meeting people through yoga, through Instagram. It's all of a sudden I started meeting these people, and I'm like, you know what? But I do sort of have people that I can connect with, you know. You know, one was a local family. There's a partner, Renee and Andrew. There's some of my best friends, and Renee's a local, and Andrew's from Ireland. We just connected, and it's like, I have a community. So I think having a little community is really helpful as well.

SPEAKER_00 11:02

Absolutely. So you completely reinvented yourself in midlife, and now you're a midlife reinvention coach. So tell us what that is and what's involved in that. Yeah.

SPEAKER_01 11:14

For my whole life, I've been that fitness coach. And I still do the fitness aspects of things because if you can't, you got to take care of your body, you know, the physical, the movement. And then what I see with a lot of my ladies is once I get them stronger on the outside, then they have that confidence to speak up authentically, wherever that might be, whether that they want to leave a job or leave a relationship or like speak up because they want to raise something like that. So with my coaching, I have four pillars. Pillars are movement, metabolism, mindset, and meaning. So movement, you name it. Strength training is key, especially for women over 35 and up. Like strength training at least three times a week is what I ask for a lot of my ladies. And then obviously, if you like to dance, walk, run, swim, surf, by all means, please do so. Um, another thing is the biggest thing for me also is uh metabolism. So it's not just like counting the macros, carbohydrates, fats, and proteins, but it's really looking at resetting your nervous system, like looking at your stress levels. Like, why am I stressed? Oh, I have a very high stress level because of, you know, my job or whatever that might be. So, like, I have to teach my women how to reset that nervous system. And it's not just through nutrition, it's through learning other habits such as journaling, meditation, that type of thing. The other pillar is mindset, and mindset is really learning about how to take care of your mind and stop listening to those naysayers and those people that want to bring you down and and really learning how to put up boundaries with other people too.

SPEAKER_00 13:00

Absolutely. It's hugely important. Yeah, I find that with women, it's so difficult for them to set those boundaries because they want to be there for everybody else. And they put everybody else before themselves and they think, oh, I'm being selfish if I don't. And it's not the case.

SPEAKER_01 13:18

I share with a lot of my ladies, like if you're gonna sit there and give, give, give, who's giving to you? Like you have to take care of you. And that's not self-ish, that's self-love. Absolutely. And meaning, yeah. And meaning is, you know, it's going back to that the TEDx talk by Simon Sinek, is really finding your why. And if you haven't seen that TEDx talk, I highly recommend it. It's probably one of the best TEDx talks that I've seen in a long time, other than my own, right? But um, I I gotta plug it in, right? It's been like 10 years, but it's like, oh my gosh. Anyways, but yeah, it was really finding your why. It's like, well, why am I moving to Costa Rica? Why am I move moving farther away from my family? My mom's in Florida, my brother's in Michigan, Texas no longer serves me. But then I thought, well, if I move to California or Hawaii, I'm still gonna be farther away from my family, you know. Well, that's true, exactly. And just because I'm in another country doesn't mean I'm farther away from my family. I think people have like, uh-oh, you're you're crossing a border, but it's if I was in Hawaii, I would be whatever, is it like six, seven hours apart? Or you know, that's crazy.

SPEAKER_00 14:32

And Costa Rica is very actually very close. You could literally drive to Costa Rica if you needed to.

SPEAKER_01 14:38

You could, but I wouldn't, I have a friend doing that currently. I was like, girl, like I'm impressed. And she you probably need to interview her too. So yeah, she's a woman traveling solo. Yeah. Wow, I'd love, yeah.

SPEAKER_00 14:53

I'd love to hear more about that. So when I started the podcast, the one thing that struck me is traveling alone is more than just the logistics of it. Like you were saying before, it's it's how it makes you feel when you accomplish something like this on your own, the empowerment that you feel. So, how does that fit into what you're coaching as a midlife reinvention coach? How did those two things go together? The the what you get from from the solo travel to what you're teaching your clients.

SPEAKER_01 15:29

You know, and this I think this is one of our the questions that you have about a retreat. But last year I did my very first Rise with the Tides retreat, and I had one of my clients, and she's like, I'm really interested in your retreat, but you know, I've never traveled alone. I go, what do you mean? She's like, Well, I've been married for 20 plus years, and my husband's like encouraging me to go. And so, like, I had to break everything down for her, like to travel from Minneapolis to, I think she had a layover in Dallas and then Dallas to Liberia, Costa Rica. So, like, I had to break everything down. I'm like, this is what you need, you know, and we talked everything out. Like one phone call was like, all right, this is what you're gonna do. You're gonna get up at four o'clock, you're gonna leave by this time, you're gonna do this, this, and this. Like, you're gonna walk into Liberia, you're gonna go downstairs. Like, I had to break everything down for her. And she was like, Oh my god, I never would have thought I could have done this on my own. And she did. I mean, talk about powerful. And so she's graduated. I shouldn't say we broke up, but she's graduated from my program. And she's like, you know, but thanks to you, I'm able to speak up. I'm like, no, thanks to you, because you trusted in yourself for figuring out how to travel by yourself. It's you did rely on your husband for 20 plus years, you know, you did it all on your own.

SPEAKER_00 16:55

That's true. And that's and that is the thing. It's those steps of how how do I book a flight? How do I choose if nobody is helping me, if I'm if I'm the decision maker? But then you you break it down and you make those tiny decisions that lead to your first solo trip, you know, by yourself, and you realize that hey, I I can do this, I am capable. And that was the one thing I wanted to teach my son as he was growing up is to look at me as somebody who is capable of doing anything that I set my mind to. So let me ask you this question. Had you gone to Costa Rica post COVID 2021, and you had gone with someone, how do you think that would have been different than you going all by yourself?

SPEAKER_01 17:47

I think the dynamics would have changed. Yeah. You know, I think I think when you travel with people, and there are there are friends that you can travel with, and there are friends that you should not travel with. And I know that about some of my friends. Like one of like one of my best friends, love her to death. But I think I would, I think her uh her and I traveling would drive me crazy. Cause like I would I would go run or whatever. I mean, even my mom, my mom and I traveled, and she's like, Do you want to go check out like church or like castle number five? I'm like, no, I just want to go for a run. Or you just want to go down and have a cup of coffee and a uh and a cookie, you know, like exactly when your travel styles are very different with other people, it could be a problem for sure. Yeah, and I think and I've seen people who have traveled together not be as close as they used to be because of their travel styles. Like if somebody's like OCD, it's like, all right, here's our schedule. This is what we got to do. So I think I do think if I would have went, let's say, for example, I would have came down with Melissa in 2019 that we were originally supposed to do, I think we would have had fun and not really, I wouldn't have addressed maybe what I needed to address about the whole trathlon space. Or if I was with somebody in 2021, you know, I would have had, like, let's say I was with my girlfriend, like or like a friend. If they were there, I would be talking to them about my issues with my ex. I am sure like she would have given me feedback and given me ideas and advice, but I actually had to figure it out myself because it was just me in the room alone at night.

SPEAKER_00 19:30

Yeah. Yes, exactly. I interviewed a woman last week, her name is Diane, and she started volunteering at resorts. And she did this over a period of like a year and a half, all by herself after a divorce. And I believe she was in her mid-50s. And she initially went to Delaware and sat on the beach, and she did it all by herself because she didn't want any noise. Yes. She needed to sit with herself and feel the things that she was feeling without the influence or advice or just anything that anybody else had to say. And I get that deep down, I feel that.

SPEAKER_01 20:09

And and I'll share with you. I mean, that's exactly what 2019 was all about. I went down to Samara, where uh like I live south of there now, but I remember I didn't want anybody after Melissa said she couldn't go. My ex is like, can I come? I said no. And he's like, What? I'm like, no, because I've known this trathlon space for 30 years. I'm saying goodbye to it. This is like my business and my and my who I thought I was. But the great thing is, is when I was running on the beach that that time in 2019, I realized that Iron Man trathlons doesn't define who I am as a person.

SPEAKER_00 20:53

That takes a lot to see that separation. Yeah. And you needed that, obviously, to see that for yourself. Yeah.

SPEAKER_01 21:00

Because if I was there with him, I would have been sitting there talking it out. And he would have been like, oh, but you're fine. Like you could, you know, you could do another Iron Man. It's like, well, what's the point? I've done everything. If he would have been there, it would have been just me talking it out. And I needed that for myself.

SPEAKER_00 21:17

Absolutely. So you had mentioned Rise with the Tides retreat. You've got another one coming up at the end of this year. You want to talk about that? I do. I, yes, I am super excited.

SPEAKER_01 21:28

I last year, you know, the first, the first retreat, I think is always going to be like the most like special to your heart, right? And I mean, it's like your first kiss, your first hug, your first like connection with somebody, right? Like my first Iron Man. It's something like I always remember, right? But I'm super excited. The second one will be coming up. I've already have two people who are coming, like they're already booked the rooms or whatever. But so what this is all about, it's a mix of strength training. Because of course I'm all about the movement. Last year I did a I did like a lecture about metabolism. And all my girls were like, but you talk about that every time we talk, you know. So I realized going into this next year's, I'm not really gonna do like any workshops, but it's just gonna be more about a natural like conversations that we had. I also am gonna have yoga. So we'll have a strength training like three to four times, three to four times a week. We'll do some body weight stuff, we'll do something at the beach, and then we'll go to the gym. We're gonna do yoga twice twice a day. Or not twice a day. No, I would go crazy if I did yoga twice a day. We're gonna do yoga twice a week during that week. And what rise with the tide is all about is really teaching women how to one, I think speak up, two really find themselves and who they are, and then three, disconnecting from the devices. And I'm picking it up, and I know we're we're not uh we're audio, but you know, really teaching the ladies to reset their nervous system and not be sitting on your dang phone when the sun goes down. Nope, you're leaving your phones in your room, we're gonna go out and watch the sunset. This is how you reset your nervous system. Showing women how to take care of themselves in Costa Rica, but then able to take that back to their home.

SPEAKER_00 23:36

And that's the one thing that I usually end an interview with, which is how you felt traveling solo and how you bring that back into your real life, quote quote real life. Because it is, it's not just feeling that empowerment and that strength when you're out there. It's how do I translate that back into my daily life and keep that powerful feeling within me. And that's huge. And it's and to to bring it up during a retreat and to really focus on that so that they're aware of how they feel right then, and then translate that to their home life. I think that's I think that's huge. So Jen at 50 leaving for Costa Rica. Now Jen at 55, five years later. Compare the two.

SPEAKER_01 24:29

Oh no, I get an emotional thing about it because the girl at 50 was scared as all as F. Oh, I was so scared, y'all. I was so scared. I was I wasn't I wasn't confused because I knew I wanted to go to Costa Rica. I wasn't confused, but I was scared. I was nervous. I was like, I even second guessed myself, what am I doing? Why am I leaving the States? And now I have to laugh because the timing was impeccable. I was scared, so scared, but I knew I needed to trust my heart. The 55-year-old woman, or almost well, let me rephrase that 54. I'll be 55 in October. So I still got a few months, right? That girl is thriving. Oh, she's thriving. My business has exploded. My conversations with the women that I talk with are real. And don't get me wrong, I mean, I've coached translates for most of my career. And then when I I shifted, when I shifted, I realized my business was shifting too. So I think I've been building my business of working with women since COVID, since 2020. Since I said goodbye to transolence. Now I am oh, I'm happy. I I pinched myself. My boyfriend and I are actually um in a different town. He's on his vacation for the week. And so we came up to playa Avayanes in uh Costa Rica, and it's a surf town. And so we've been surfing every morning. I come back, we get breakfast, I do a couple calls, I have a podcast with you, and then after we get off of here, we're gonna go back out and we're we're probably gonna go watch the sunset, you know. But it's like, and all during this time, I'm still coaching. I'm I still have spots open for my clients to jump on. It's like the girl at 50, scared as all get out. The girl I am today, I'm happy as I'll get out, and I'm thriving. Oh, that's amazing.

SPEAKER_00 26:48

And you look it too. You just look like you're glowing and just full of joy. I love to see that. I love to see that. Jen, thank you so, so much. I can't tell you how much I appreciate talking to you and being inspired by everything that you've said. I really appreciate you moving on. Thank you for having me.

SPEAKER_01 27:04

I appreciate it.

SPEAKER_00 27:08

Thanks for listening to Rome Alone. If today's story resonated with you, I hope it reminds you that you don't have to have everything figured out to begin again. Sometimes the most powerful journey start with a single decision to trust yourself. If you enjoyed this episode, make sure you're following the podcast so you never miss a story of courage, reinvention, and solo adventure. And if you know someone standing at the edge of a big life change, share this episode with them. You never know who might need the reminder that it's not too late to start over. Until next time, go somewhere new. Try something that stretches you, and remember, you are allowed to choose your own path. I'm Teresa Stevens, and this is Roam Alone.