Starting Over at 55: How Solo Travel Helped Diane Rebuild Her Life After Divorce

In this episode of Roam Alone, Theresa speaks with Diane about navigating one of life’s biggest transitions and choosing solo travel as a path toward personal renewal.

After divorce, selling her business, and entering an empty-nest chapter, Diane set out alone to reconnect with herself — volunteering at resorts around the world and rebuilding confidence, purpose, and identity along the way.

We discuss:

•  Why major life transitions often spark solo travel 
•  Traveling alone after divorce 
•  How volunteering abroad makes long-term travel affordable 
•  Letting go of other people’s expectations 
•  The emotional reality of starting over at midlife 
•  How solo travel helps you hear your own voice again 
•  Reinvention after 50 
•  Practical tips for women considering their first solo journey 

✨ This episode is for anyone standing at a crossroads wondering: Who am I now?

https://helpx.net/

Pueblo Ingles

Nomadic Matt - Travel on $75 a Day

Roam Alone is hosted by Theresa Stephens.

Instagram: @theresaannstephens

Facebook: /theresastephens

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Transcript

SPEAKER_00 0:00

Welcome to Roam Alone, the podcast about the transformative power of solo travel. Today's guest Diane reached a moment many people quietly fear and secretly dream about. At 55, her marriage ended. She sold the business she had built. Her children were grown, and suddenly the life that had defined her was gone. Instead of rebuilding the same life, Diane did something radical. She left alone. Over the next year and a half, she volunteered at resorts across Italy and Spain. She went to Costa Rica, traveling solo, not to escape her life, but to rediscover who she was without anyone else's expectations. This is a story about reinvention, courage, and what happens when you finally hear your own voice again. I'm Teresa Stevens, and this is Rome Alone. So my guest today is Diane D'Amico. Welcome to the show, Diane. Hi, great to be here. Thank you. Thanks so much for coming on. So Diane and I met, I think it was last December, December 25, on a pickleball court. And we got to talking, and I don't even know how it came up that we started talking about this podcast. You mentioned spending several months at resorts, and they were several different resorts. And you did this as a solo traveler, correct? Yes, it's right. So how did you get into this? And what made you even think to try something like this?

SPEAKER_01 1:44

Well, I had been going through um a rough part, not a rough part, I should say a transition in my life where just getting separated from my husband. I sold my small company. The last two of my three kids were launching, and I wanted to know more about me and what I thought about things and where I was going to go in my next, I want to say my next level of life because I knew things were changing. And what I really needed was not so much an adventure, but more of quiet and clarity. And solo travel was not something that I had done. I did not do a lot of traveling at all. Yeah. But it was maybe in thinking about it now, it might have been a fight or flight response to everything going on. But I knew that I needed to get down to my core more of what I believed without all the external influences.

SPEAKER_00 2:50

Oh, that's perfectly, perfectly said because I've been there quite a few times in my life. And I know that idea of just I need to get away, I need everything to calm down, I need some clarity and some quiet. Yes. And I totally, totally get that. Take us through the process of deciding to do this as far as working at a resort. Why that, as opposed to just, I don't know, traveling or just vacationing.

SPEAKER_01 3:18

Well, a friend of mine told me about a place that she went to, and now it's called Pueblo Inglesis. Not really a place. They have four or five resorts. And what it is is that there's English-speaking volunteers that go there and they have Spaniards or Germans, because that's where the resorts are, adults that want to be immersed in English. Okay. So it's a volunteer program. Teens or adults can do it. And it was a way to get myself to Europe because I had never done it before.

SPEAKER_00 4:00

That's a huge leap. Not only you'd never solo traveled, didn't travel much, but to go to Europe of all places, completely foreign, completely away from everything that you're familiar with. How did you handle those first few weeks, being away?

SPEAKER_01 4:16

Well, really, I should step back and say how this all began. Yes, please. So I was living in central Indiana, and I decided to do this travel. I found a book from I actually pulled out my old copy.

unknown 4:32

Oh, good.

SPEAKER_01 4:33

This guy named Nomadic Matt. He was writing, somehow I got on his his website and he was writing about budget travel. And his book at the time is called How to Travel the World on $50 a day. Oh wow. I looked at it last night and is now called How to Travel on $75 a day. Makes sense. Tagline is travel cheaper, longer, and smarter. And so I did do some research before I I left. But the first thing I did was I went to AAA office and I said, I need to get to a beach. What would be the fastest way to get to the ocean? And they said, uh, you should go straight out east to Delaware. So I did. I got in my car and trip to Delaware. Oh wow. And I said, Oh, I could do this. But I gotta tell you, Teresa, I did not know what to expect because I had an Airbnb in my house, but had never used Airbnb.

SPEAKER_00 5:38

Oh, you've only just hosted, you've never been a guest.

SPEAKER_01 5:42

Right. And I hosted also on Couch Surfers. I think that might still be a thing. Like if we just stay free at somebody's house. Oh well. So I did I like that name a lot. Right. So then I did that for people, mostly middle-aged women, that were coming to Purdue to see one of their kids, and they just would crash at my house. And so anyway, I got in my car, I went to Delaware, and I got there and I got out of the car. I had an Airbnb ready and got to the beach first. And I don't know why, but when I got to the beach, and it was March, and I just started to sob and cry and watch the ocean. And I said, wow, I didn't know I had all this going on.

SPEAKER_00 6:29

Right. Because probably so much was going on. Your mind was cluttered, everything was happening physically around you. And then now you had nothing but yourself to sit with.

SPEAKER_01 6:41

And I sat.

SPEAKER_00 6:42

Yeah.

SPEAKER_01 6:43

And I watched the ocean. And like I said, there was nobody around. And then I said to myself, well, good thing no one overreacted.

SPEAKER_00 6:55

And sometimes you do have to laugh at yourself.

SPEAKER_01 7:00

So I spent like a week there. And then that's where I started actually researching, like, huh, maybe I should do this some more and wonder how I could do this. Went back home and just started taking all these little smaller trips and went to see friends in different states, always with my trusty trius, not real happy about flying. I'm not afraid of it. I just feel like it's, you know, inconvenience. Did all this research while I was in Delaware and then decided when I got back, I'm just gonna go and take off. And so I did that, and it became more and more an adventure and less and less of a ride or flight thing.

SPEAKER_00 7:40

Right. Yeah. Yeah, I get that. You know, I interviewed someone just last week who said solo travel for her has been a practice, like a yoga practice. Like you don't do it right the first time, or you don't do it the same way every time it's a learning experience, and you get more and more comfortable the more you do it, and more settled into your decision making, your belief, and your ability to handle pretty much everything that comes your way on your own. And so I can see that uh for you as well. The more you did it, the more you got comfortable with it.

SPEAKER_01 8:18

And the more risk I was willing to take. I think that people tend to think of things as more risky than they are. And so if you take these smaller steps and maybe just go visit a friend in St. Louis or you know, and just keep going, it's like these are not very risky things after you get used to that. Absolutely. I decided, like, oh, now I want to go a little further. And that's when a friend of mine told me about Pueblo Inglesis, which is a program where you go and you stay at a resort and you just speak to people in English, and they just take care of everything. All I had to do was fly to Madrid, and then they picked us up and took us to this really nice resort in Salamenca, Spain, and I think was there maybe eight days, and it was a blast. One thing that was surprising too was that in my mind I thought of all English speakers, I guess, as American. I was one of the few Americans there. There were people from the EK and from Australia, and so I did that for a while, and I had planned to build this European vacation around that. I was spending three months in Europe, and so that was the first stop. The second was that I had connected with a resort in Italy that was right on the cusp of Tuscany. That region where let's just say it's gorgeous. I found that by a website called HelpEx. It's h-elpx.net. Okay. Most of the opportunities are in farming or animal care or something like that. But I only wanted to do hospitality.

unknown 10:14

Yeah.

SPEAKER_01 10:15

So I went to Umbria and stayed there for about 10 days. When it first arrived, it's small. They only had 12 rooms, but they were a wedding destination place. Oh, perfect. Wow, they had this. I don't know what I'm trying to think. It used to be a nunnery or something.

unknown 10:34

Oh wow.

SPEAKER_01 10:34

So they had this really beautiful chapel in a different building. It was another safe landing where I got there and there was things that I was supposed to do for them. And for that, you get a room and your food, just like the other place. What an incredible trade-off. I mean, it's the best of both worlds. It was kind of funny because when I got there, our first job, there was another much a younger woman there who was doing the same thing. The first day, I think we were pulling weeds out of the driveway. Gotcha. Okay. Because that was my question is like, what are they asking you to do? I eventually was doing some bartending at the reception. So there were the rooms to take care of, there was wedding guests to take care of. And they were very good hosts. They liked the help of different people coming in. They didn't have to pay us. We were volunteers living high on the hog.

SPEAKER_00 11:26

Do you think what you got in return for what you gave was like in equal measure? Oh, I was getting a lot more than I was giving, you know.

SPEAKER_01 11:35

Because even the jobs they had to do. I mean, whereas one day I was ironing sheets out in the sun, and it was just so peaceful and quiet, and everything smelled beautiful. And the thing that struck me about at least that part of Italy where I was, it looked like the sun had a different look to it. It was kind of glittery. And I realized like the Renaissance paints, there's a lot of that glow to it.

SPEAKER_00 12:04

I think that's why.

SPEAKER_01 12:05

I think it was the sunshine there, just looked different. Wow, that's incredible. I would have never known that, you know, gone. I was getting a lot out of it. So from there, the woman that I met there, the young woman that was traveling a lot, Catherine, she and I decided just to go to Greece. And so we went to Greece, and that was just a vacation. But it was hostile prices where I'd never stayed in a hostel before. And it's a different idea, but it looked a lot like our motels, but bigger. And they had all the amenities, and you know, we had a pool and then had the beach. Sort of a spring break area. So I was surrounded by a lot of uzo drinking, crazy. But they even at one point had a toga party. So oh my. So I went from the peaceful quiet of having, you know, coffee in the morning with my my Italian cookies to like, whoa, let's go. So by that time, after Spain, Italy, and Greece, I was planning on going to Portugal. And Catherine said, Well, how long have you been here? And I said, uh, 88 days. And she said, You better get back. You can only do 90 days. And I'm like, What are you talking about? He explained it to me. I had no idea. She was like, How did you not know that? I go, Really?

SPEAKER_00 13:31

Who would have told me? And this is the Schengen In N Out 9180 days. Yes. What year was this that you did this? Uh, this was 10 years ago. So you had to literally you had two days to get out.

SPEAKER_01 13:43

I had I couldn't go to Portugal. I had to go home. Oh dang it. But I was like, oh, I didn't do all my research. Details. Yeah. It's like, which you know, and think about this for all kinds of things, not just travel, but you're not born knowing any of it. Nobody tells you, or you didn't come across that information somehow. It's like, oh what? Well, exactly.

SPEAKER_00 14:04

Yeah. Do you mind if I ask how old were you when you did these three months? Uh, I was 55. Wow. Yeah. I mean, do you think you could have done this in your 20s and 30s, or did you need to go through all that you went through with the marriage and the family and the raising of the family and having a business? Did all that lead you to be able to do this? I mean, even though you went through an extremely difficult time.

SPEAKER_01 14:32

I think I needed it then, and I could do it then, the empty nesting and everything else. Although I would not say after I met so many people doing the same thing, it seemed like most were in some kind of transition period. Even if they were the young people that they were going to go to college or they just finished college. It seemed like for them, it wasn't such an adult thing like mine, like, oh gosh, I now my kids are grown. And so I don't think I could have done it in my twenties. No.

SPEAKER_00 15:07

Yeah.

SPEAKER_01 15:08

I think my my life just kept going old really fast. You know, as it does. And that's why I said I think I just needed to sit and see like what my opinions now were.

SPEAKER_00 15:22

Right, exactly. Find yourself as an individual again after being part of a family. And it does sound cliche, but go travel by yourself and and meet yourself more than you would with other people. Absolutely. And that that would be my next question is how would all of the those three months been different had someone tagged along with you, had you brought a girlfriend along?

SPEAKER_01 15:48

Well, first I should say that I actually did this for about a year and a half.

SPEAKER_00 15:53

Oh, wow.

SPEAKER_01 15:53

So, because after after I got back from Europe, then I decided Nova Scotia, Costa Rica. And, you know, if you spend more time in a place, you can get down into like what is the place really like? But I I think going back to your question, as far as going with someone else, you know, I just needed to hear my own voice for a while and make solo decisions, whether they were gonna be good or bad, because you know, usually you're making decisions about how it affects everybody around you, too. So it's like, well, you know, in your business, it's like how's it gonna affect my customers, my employee? You know, you're just with a family, you're just making all these decisions. Like, what do I want to do? Different. So even with a friend, I still wanted to be around people, but I didn't want to have too much influence from outside what people wanted to do. You know, everything from like what's your daily timeline gonna be to you know, what country are you gonna go to next? Or sure, you could have somebody very compatible, but there's still that discussion about what where do you want to go eat? I probably did things that other people would think were too risky, right?

SPEAKER_00 17:11

And then they would not want to do it, and then you would compromise and you would have missed out on incredible opportunities. Right.

SPEAKER_01 17:18

And like I said, it could have been good or bad decisions on my part, but I made them. My mom, she and I sort of think and talk in headline sometimes. It's like I'll give you an example. One of the resorts I worked in was in Costa Rica. I went there to Costa Rica to stay at a yoga retreat. It was a listen on Airbnb, and it was fabulous. It was like a week-long meditation, yoga. It was very eat prelug, as far as I can tell. Down the road, there was a resort that had everything that I would want. It had a great restaurant, it had dance parties, it was like completely different from the meditation center. I would do the meditation center during the day and then go down the street. I was sitting at the bar and the woman next to me was telling me that her brother owned the place and that she had just come down from New York to help him run it. I said, Well, I can help you out here if you want to trade for a room. Would you? I said, Yeah. And I told her what I did in Europe and I said, Yeah, well, what kind of things are you working on? And so we talked about it at the bar. And then I said, I can come back Monday. And she said, Great. So I get back Monday and she said, You're here. And I'm like, I he said, You got a will that I'm gonna do things. Let's do it. And so she said, This is so great. So she, you know, showed me around a little bit. Her and her brother were both Americans. He had been down there running, you know, owning this place for 10 years or something. She said, Okay, this is fabulous because I have a wedding to go to, and now you can, you know, be here and do this and that. And I was like, Okay, great. I said, Where's the wedding? And she said, Mexico. She took off.

unknown 19:07

Oh my gosh.

SPEAKER_01 19:09

But before she did that night, her brother said, Hey, let's walk over to my house for dinner. And so she's walking in front of me, he's walking behind me and walking through a jungle. Wow, hey, it's black. Oh my gosh. And I'm thinking about my mom reading a headline, woman found dead in a jungle, going to dinner. Like, that's how you know you're doing something crazy. You're like, if people read that story, they'll be like, why is she in the jungle? Where are these people? Where is she going?

SPEAKER_00 19:43

I mean, look at you. Look at you from sitting on that beach, balling your eyes out, yeah, to walking through the jungle in pitch black at night. Yeah. I mean, look how far you went.

SPEAKER_01 19:54

And I'm like, sure, let's go to dinner. One of the things my mom said when I told her I was going, she's like, I don't get sold into the sex trade. Is the mom, I don't think I'm the target market for that. I think we're good. We came to this clearing and it's a beautiful house, and he had these huge windows where you could see all the people inside having this little party. And it was such a like cool moment. Like, okay, I escaped death and I'm gonna have a nice time. Well, if I was with somebody else, they might have said, Who are these people? You know, they might be like, you know, the voice of reason.

SPEAKER_00 20:33

Right, exactly.

SPEAKER_01 20:35

Which I really didn't want. You know, I don't want the voice of reason at this moment.

SPEAKER_00 20:38

So yeah, absolutely. It's like I want to make these decisions for myself, and if I want to do something risky, I'm gonna do it. Yeah, yeah. So, from that person who sat on the beach in Delaware to a year and a half later of all these travels and and volunteer opportunities and learning all these different cultures, how did you change over that time, over that year and a half time?

SPEAKER_01 21:07

Well, well, I think really I got back more to myself, who I am. I know there would change it, like there was immediate changes. When I came back, everybody was thriving without me. It wasn't like I had to carry the world. The kids would, they're young adults, but they were young adults, and um, they were doing all right. And the business that I sold, I had a non-compete, so I couldn't have been there anyway. But she had had some questions, but she's she's fine, my friends were all fine, everybody's good. You know, I had been heavily involved in my community. All those organizations were going about the business. You would think that would make you sad or like, Well, I wasn't important enough, but it didn't, it made me feel free.

SPEAKER_00 21:58

Wow.

SPEAKER_01 21:58

That I could still You know, just be a little bit more thoughtful about how I want to spend my time and not give up so much of it to others and other issues. Absolutely. I don't know. People I'm avoiding using the word selfish because it's got a negative connotation, but getting back to self, I think is what's really happened.

SPEAKER_00 22:25

Oh, absolutely. And it's not selfish. And I think that as women in particular, we are, and I was talking about this in another episode just recently. It's like we're by design, give all of ourselves to everybody. And to put ourselves first feels selfish, and it's not. It makes us better people for others.

SPEAKER_01 22:47

You know, I agree. I think another change in me, though, was that I was a little more skeptical about what I would hear or believe because the host in Italy one day we were talking, so maybe this is going to date when I went, because the Iraq war was going on. And he was under the impression that all Americans were a little bloodthirsty and were wanting to go into that war. And I said, no, a lot of us, you know, there were a lot of protests and there was a lot of pushback, and it was a very hard decision for the government to get into that, as far as what the people that I was aware of. He got that impression because where he was in Italy, because he was Welsh. Like he would listen to English language Russian news. Oh wow. So he was getting a different impression of Americans. And everywhere I went, people had impressions of Americans. So I realized that I have impressions of other people. Right. And we're getting, especially nowadays, we understand more that we are getting our news filtered by what we listen to and but also but what's put out there. Absolutely. And so now that we have all these multiple uh ways of getting information, I have to be skeptical about and on a one-to-one basis, who I'm talking to someone, so what they're hearing that I'm not hearing. It didn't make me like people less, it just made me understand that there's opinions formed that it's not our choice, really. Because, like I said earlier, you're not born knowing anything. You have to get that research where you have to get the experience to, you know, know what's going on personally in your life, right?

SPEAKER_00 24:43

Absolutely. I always go back to that Mark Twain quote about travel is fatal to prejudice and bigotry because you know you make impressions of places and of people, and it's influenced by a number of things. And until you're actually in a place meeting those people, you really don't know. And so to travel and to see them and for them to see you as an American and you changing what they perceive as who Americans are is hugely important worldwide. Right.

SPEAKER_01 25:20

And if we don't, if we don't get an opportunity to travel and to talk to each other, even within our own country or within our own city, we don't get those opinions or information. We're just basing it on what I would say. The third thing was going back to risk, because my motto, I guess, has been risk on the side of people and fun. You know, life is gonna be risky, and people will say, Hey, do you want to go to this or you wanna, you know, try that? And to me, everything you try new as a risk that you might be bored, could be a waste of my time, could be I meet somebody I don't like. But if you risk on the idea that it might help some people, or you might have a good time, there's that risk.

SPEAKER_00 26:07

And had had you not taken those trips over that year and a half time, you may not have responded in the same way. But all of that led you to where you are now, and you know, a risk taker, which is absolutely amazing.

SPEAKER_01 26:22

Little baby risks nowadays, I think. I have a part of my yard that is really sunny, and I don't have time right now to do any vegetable gardening, but I want a vegetable garden. So I put the word out and said, Hey, does anybody want to use this? I met this woman last week, and her and her uh teenage kids want to put in a vegetable garden. Her yard got too shaded and she couldn't do it. So people are like, Oh, you're gonna let people come in your yard and do your thing. I said, Yeah, I gave them a code for the garage, they can use the tour, they could do whatever. No. Wow. And so they're thinking it's a risk. And I'm thinking, it's a risk that I could get some vegetables, you know. They came in the first day, and I can't tell you what a great job they did. They tilled it up, they put new plants in, they put a little greenhouse on the plot. Oh, to me, there was not a big risk. Yeah, I don't know. Look at that. I was worrying about somebody hitting you in the back of the head in the jungle. I mean, this is my backyard, I'm good. Different level of risk for sure. And you had asked about safety issues, and I could only think of a few. One was if you're traveling by car, you should probably always keep your gas tank pretty full, at least halfway, you know. And the other thing I thought about was I walked up to a hotel check-in one time, and the woman said, Okay, uh, room 103, party of one, and handed me the key with all these people around. And I said to her later, when I came down, I said, I would not have liked people to know I was traveling solo. Yes. So now I always ask for two keys, no matter what.

SPEAKER_00 28:09

That's very smart. That's another very good tip. Yeah. I'm putting that on my list.

SPEAKER_01 28:14

And as far as healing comfortable, I would say at a restaurant, I always would sit at the bar. You get a lot more information from who's ever attending bar than you would by sitting at a table by yourself. Although a couple of times I did this thing where I saw in the movies and I asked my server, I said, Will you ask that young man? Tell him I'm not hitting on him, but if he'd like to join my table at lunch, I would appreciate the company. Oh, that's awesome. I know. I met a couple of people that way where we didn't keep in touch or anything, but it was just like, I want to have lunch with that that guy right there.

SPEAKER_00 28:52

I love that. Good for you. Good for you if you're putting yourself out there like that. Diane, you have just been an absolute pleasure to talk to. And everything that I've done these shows about, you've incorporated it into one thing. It's like we were talking before, it's not just just the destinations and how to do these things, but what you take from it and who you become because of it. And who you are now is probably somebody you might not have been had you not taken the risk to go overseas several times over that year and a half. That's amazing. Yeah. Thank you so much for coming on today. Well, thanks for the chat. I really liked it. I'm Teresa Stevens, and this has been Roam Alone.