Life’s Second Act: Traveling Toward Reinvention

Join Emily Bron on ‘Age of Reinvention’ as she interviews Denise and James Gordon from the Skip Town All Stars. Discover how they sold their home and possessions to embark on a travel adventure across the U.S., exploring different cities and redefining what it means to live a freedom lifestyle in midlife. Learn about their journey documenting their travels, the challenges they’ve faced, and their advice for those looking to reinvent themselves. Tune in for a conversation about personal growth, community, and the pursuit of passion and purpose in the second act of life.

TIMESTAMPS:

02:28 Meet Denise and James Gordon
01:49 The Journey Begins: Selling Everything
05:38 Adventurous Spirits and Midlife Reinvention
08:34 Challenges and Rewards of a Nomadic Lifestyle
16:50 Rediscovering America and Each Other
25:24 Favorite Destinations for Midlife Freedom
29:16 Exploring Chattanooga: Nature, Food, and Vibes
28:10 Healthcare Considerations in Different States
33:10 Rising Costs and Housing Challenges
36:58 Personal Growth and Community Involvement
47:03 Unexpected Hurdles and Social Observations
52:52 Practical Advice for a Travel Lifestyle
56:28 Conclusion and Final Thoughts

Emily Bron: Hello and welcome to Age of Reinvention, Redefine Freedom Lifestyle and Purpose at Midlife, the podcast dedicated to inspiring our listeners to find new passion. purpose and freedom in the second act of their lives. I’m your host, Emily Bron, and today we have a special treat for wanderlust spirits craving adventure and reinvention.

Prepare to be transported as we explore the lives of two incredible travelizers who’ve turned their love for travel into discovery. Into the way off life. Joining us today from the skip down all stars. It’s a name as a fearless empty nest. There’s do Denise and James Gordon, who are here to discuss redefining what it means to leave a freedom lifestyle in midlife.

Let’s embark on this journey together. Hello and welcome. Denise and James. I’m happy to see you in my studio today. Wow, that was an introduction. Thank

Denise: you,

Emily Bron: Emily.

James: I feel like we need to clean up our own introductions when we’re doing our show. Yeah, that was incredible. Thank you, Emily. It’s great to be with you today.

Emily Bron: Okay, so I’m making good work actually to reading the intro. And usually, actually, my guests are happy to start their Journey with me on this note. And is as a skip down all stars, I believe not yet known to each of possible listeners in the Internet. First, can you share the short story behind Skip Town All Stars, your podcast company from inception and what motivated you both to embark on this adventurous lifestyle.

Denise: Oh, babe, I think you should go. Oh,

James: okay. Gosh, I’m not really skilled at saying things quickly, but the summary is that in 2022, Denise and I decided to sell our house of about 20 years in Los Angeles. We had each lived there about 26 years. And we put it up for sale. And on our way out the door, we have a friend who is a fellow podcaster.

His name is Bert Kreischer and he recommended to us that we chronicle our mission, which was Denise and I did not have a plan. We did not have a hometown. picked out already. We just said we will know when we see it. And and our journey began when we dropped our youngest daughter off at college.

We scoured the country and so far upon Bert’s recommendation, we are up to about 115 episodes. And we’ve hit about probably 70 or 80 cities and towns across the United States at this point. I know we, we have, including our rental vehicles, we probably have over 100, 000 miles logged at this point, just going across the United States.

Denise: What he forgot to mention was that we sold all of our possessions also. So it wasn’t like we just sold our house and decided let’s move somewhere. We literally sold every single thing we owned, including our cars. So when we went on this new adventure, it was with nothing in the future, like we didn’t have a plan of where we were going to land, which was what was so adventurous about the idea of documenting it.

Emily Bron: I would agree that it’s pretty adventurous because usually, as I know, and Americans in this age range like people usually have plans. Yes. And usually follow no, I’m the same as you, but I know how kind of other normal people behave. But actually what pushed you So far away, like many of our listeners are curious about reinvention and midlife.

What catalyzed your decision to change the traditional settled down mindset appropriate for our age, I would say, to a more nomadic and exploratory way of living, like what was here specific personal characteristics, adventurous spirit of yours or something else?

Denise: I think it was a matter of both adventurous spirits, two adventurous spirits that actually just honestly collided.

And that’s the truth. People kept using words like, wow, you really blew up your life. Oh, you turned your life upside down and we just did not look at it that way, even though at our age, because we were both in our fifties, we are both in our fifties. This is when people decide that they’re looking at retirement.

They’re looking at their 401ks. We sold our cars and rented a car to do this. We got rid of everything. And It was just our adventurous spirit, but it started probably 10 years ago. To be honest with you we both came from different cities when we landed in Los Angeles and that’s where we met.

But I would say it started like in 2015, maybe even 2012, where we were just talking about one day. Like one day when the kids are off to college, one day and we would just send each other little snippets in the internet of cool towns that we came across or any kind of, lists that popped up on, like Southern Living or Forbes 500, cutest little city or, charming little town.

And we just started sending those to each other as in a what if one day. And then as the kids were getting older, that what if it wasn’t talk, because James and I just aren’t talkers. If we say we’re going to do something, we do it. In every facet of our lives that’s just how we are. So we knew that this wasn’t just talk.

For some people, it is. For us, we knew it would happen one day. And then that one day came in 2022. We thought, honestly, we would leave Los Angeles in maybe 2024. Our kids would all be gone. We’d have two years to ourselves. Get the house ready for a sale, get ourselves ready. And then in 2022 a client at my business just randomly said to me, didn’t know anything about my life, knew nothing about where we lived and just said she was a real estate agent had been one for many years.

That, it was the beginning of 2022 and she said, this summer rates are going to really change and home buying is going to have a different landscape. She said, right now it’s very much a seller’s market. And she gave me an example of a house that she sold in LA, which was an astronomically high price for the area.

And I drove home that night and I walked in the door and I said, we’re selling our house. And that was literally, that was how it started.

Emily Bron: She

Denise: was a really good

Emily Bron: real estate agent.

James: She was.

Denise: It

James: was. She was. And I think it’s important to mention that coming out of the pandemic, my industry and television had changed so dramatically.

I work in post production, which is a fancy way of saying everybody on my team goes out and shoots everything, but then they send it back to me to edit everything. And historically, I’d always had to go into an office or drive an hour long traffic each way in Los Angeles to work in, some edit bay somewhere.

With the pandemic that it changed entirely, so I could still keep my career and we could move somewhere else. There were just a few people who had done it before me, but when I recognized that this remote working thing in my specific category of entertainment was going to stick that’s when we really started laying the groundwork for our plan.

It was the perfect storm of a great real estate agent and a profession that was now willing finally to adapt.

Denise: And we both are risk takers, Emily. We’ve done it in our careers. Personally, we’ve done it also. So leaving wasn’t. It didn’t seem risky to us. Like we’re both really smart. We, he had already been thinking about another career in 2019, because he knew this was going to happen.

And I knew I could get a job or open up a business somewhere. So I think. You have to have that in order to do something that we’re doing.

Emily Bron: I think you both have really all characteristics of explorers and reinventors. Because, let’s be honest, it’s not for everyone. But that’s why I just defined the same characteristics.

I predicted and obviously for some people, it takes more time actually to make the step because, there is ideas which I now had sometimes for years, but there are circumstances that sometimes not giving up this opportunity. In your case, just all work together, like correct time and place, and I’m just thinking, what would be with your podcast and with you when you will visit all small, nice cities in the United States?

James: I would say we experienced a lot more gems. Then we thought we probably were going like we knew that there were some great cities but I would say we really became enamored with the small towns as we progressed through the country and setting up a podcast and in a hotel room.

Or trying to book space or trying to find a podcast booth or space. It, it was an added layer of challenge in addition to, we are legit still looking for our hometown. And we’re about two years out now. So that that, there were a lot of wrinkles to the whole thing, but it’s been a welcome challenge.

It’s been fun. Yeah, but

Emily Bron: what I mean after you start such a lifestyle and you obviously like it, it’s probably hard to stop.

Denise: It’s funny that you say that because we have listeners who have asked us, what’s going to happen when you find that perfect hometown for you? Is, are you still going to continue the show?

Are you still going to travel? And my answer has always been We’ll continue the show like we’ll pivot and the show will be something and his answer has always been. Oh, no We’re still traveling. I think honestly, I think it’s gonna be twofold Emily like I’m looking forward to finding our hometown To settle a little bit, but then he says we’re still going to travel.

So I think there’s probably some truth to that. I

Emily Bron: have an idea for you. You will take orders, a project to find the place for somebody else.

James: I think it’s a great idea. We’ve actually been like kicking that around.

Emily Bron: Okay. Remember about me when you will be successful in this direction. Of course.

You get full credit. No. I believe, now I’m serious, it’s, it will be the trend, people are relocating, people are, and I’m following, statistics from country to country, from state to state, from California to Texas, Florida, and again, this state’s already overblown, I would say, and you know probably better about pricing and people will again to relocate inside United States, looking for this small, nice cities, and all is changing.

Not anyone has the time and ability to do what you did over the last two years. Kudos to you, but it’s a wealth of experience, practical experience.

James: Yeah.

Denise: We’ve heard that from listeners, that they really appreciate that we are doing the footwork for them. Some people have called us the hip.

Trip advisors. Other people have said that we’re their go to for their future. So getting those compliments have been just incredible because we honestly just started the podcast like at the very last minute. When our friends said this to us, like we should document it because we’re doing something no one else.

has, something that people only talk about was what he said. He’s you should document it. And we did not even think about something like that. So it’s been really awesome to share this with people and then to find out that they’re actually utilizing what we’re putting out in the world.

People have gone to visit the cities. That we’ve gone to and have come back and given us reports about their thoughts on it.

Emily Bron: It’s pretty cool. I’m telling you already, you can launch a business because, and again, things are changing and your perspective is changing and probably after meeting so many different people and communicating with your followers, you have already certain profiles of people you know who might be good on this and other place and.

Another kind of question. So are you clear yourself why you didn’t find the ideal place for you? What happened with you?

Denise: I know

Emily Bron: why.

Denise: Okay, we each have our own answer. Can you go first?

James: Emily, I’m very non committal and I’m very impressionable. I’ve I’m like that kid in high school that falls in love with every girl that says hello to him, and you were just once married? Yeah, I’m just once married, yeah. But I love a lot of hometowns. And that is where my passion has been. And I will say, with every passing state, I find one or two hometowns where I’m like, this has got to be the place. This is the one. And then a month will go by and we’re in some other place and I’m saying, yeah, forget that place.

It’s this place now. And so I, you just need to stop. I know I do need to stop. I’m like a kid who has been given too much money in a candy store and I can’t choose now what to decide. So I could tell you for my own reasons, that’s probably why I haven’t. just definitively said, this is the place.

Although I will say, two years in I feel, I’m feeling pretty good. I feel like I’m zeroing in now.

Denise: I would say that the reason I haven’t found a place is a little similar to his, although I am not as impressionable. I don’t fall in love with the place the minute I land there. But I will tell you, Emily, the one thing I never anticipated is that when you have a choice, it makes that choice very difficult.

So there’s a difference between having to move to a location for work, Or having to move to a location because your parents are ill and you have to take care of them. When you truly have a choice on where you can live in the country, it’s too hard. Because then all these things start to come into play.

I want a piece of property and I want to be near an airport. Like you now, you have choices. I can honestly say for me, having those choices has made it difficult. If that makes any sense.

Emily Bron: It’s made absolute sense because one of the hard choices we have in life, it’s actually to select when we have too many choices it’s a drop that you fall into.

That is it.

James: It’s a very American problem too, because if you go to some other country and you walk down the snack aisle, you only have about three or four choices. Whereas if you go to an American grocery store, there’s an entire aisle. That stretches half of a football field filled with snacks for you to choose from so

Emily Bron: guys I wish it will be only problem one problem that america knows and we as the immigrants now i’m speaking from the different head perspective fully understand the difference between us and people who were born on this continent and Sometimes each of us we need to choose we need to select and I think Assume that probably your perspective was changing that probably over the two years that you are traveling, the more you’re learning about the places, probably you’re learning about yourselves and your relationship.

James: I would say so. I think one of the biggest things that we’ve touched upon it a little bit as we were talking and, what started out as a travel log, basically where we’re talking about where we were and what our experiences were and people were living. Whimsically and vicariously through us has now turned into more or less a responsibility.

Like we feel responsible when we go to a particular town and say, yes, go there. And like she was mentioning earlier there are listeners who will take us up on that advice. And I have to tell you. It makes us a little nervous when we find out they’re actually following our advice and going to this place because we pray and hope that they love it as much as we do.

And usually we’re right, but sometimes we’re wrong. And the biggest thing that’s come out of this is really for that I feel has changed us and eventually it will change our show as well. Is this psychology of, sort of risk taking and how that. When you’re the person telling everyone, take the risk take the risk.

You have to walk that walk a little bit. And there are times where, we’re like, have we taken too big of a risk? But I don’t know. It’s like in many ways we just keep going. That’s all we can do until we find our place. And until we identify what it is we can do for our listeners moving forward.

Denise: And to go back to your question. I think that I’ll speak for both of us, but if I’m wrong, you can obviously chime in. I do think that we have changed Emily. So to go back to that question about like, how have we changed in the past two years? First of all, we had ideas about certain parts of the country that have been completely nullified.

Like what’s the word? Demystified, like we, we had ideas about certain areas that we thought we’re never going to live there or areas. How about this? That we always thought was our place. Like we both would fantasize about the East coast. We lived on the West coast. So to us, like Cape Cod was a fantasy.

Cape Cod was a fantasy. And guess what? We went there. And we’re not interested, like, how is it for you? It is special, but you have to

James: be like at least 15 years older than we are to really, enjoy it. Everybody who lives there full time during the year is, it’s an older gang. It’s an older crowd.

It is.

Emily Bron: I’ve

James: been in this

Emily Bron: place, I’ve had the same pain.

Denise: It’s very quiet too. So there isn’t a lot going on. And if you were You know, we’re we love social activity. We like to go and have dinner out and go see live music. Cape Cod isn’t that place. If you’re there, November through April.

And it really does shut down. A place like that is a perfect example of how it was demystified. And then, like we never thought much of the South. We just didn’t like, cause we’re both, I went, I grew up in Chicago, he grew up in Ohio. And so we’re both we’re Northerners and traveling the South.

Met the best people and when they say southern hospitality, we didn’t know what that meant prior to our journey and I can tell you what that means now I can write it down on a piece of paper for you. I can serve it to you at a dinner table like southern hospitality because we’ve spent so much time in the south.

And then I think as a couple, we changed to you can’t spend 24 hours with somebody And not have some change in a relationship. You just can’t.

Emily Bron: What about years? What about 25 years? I know. No, yes, of course.

James: It’s a lot

different in Los Angeles when she’s driving one direction in town to get to her business and I’m driving the opposite.

And 10 hours go by and then we see each other at night or and obviously we’re around on weekends, but to be in a car producing a podcast and searching for a new home. And it really, in a lot of ways, it has been, an all day, every day sort of experience. That’s been great because on one hand, we’re picking up on.

All that lost time that we didn’t actually get to spend together when we were hustling and bustling and in the middle of the rat race in Los Angeles. So that’s fantastic. But then at the same time, it is a bit of an adjustment, and learning how to she tends to work at night.

I’m up at 5 a. m. every morning. So navigating, scheduling conflicts and In a hotel

Denise: room. Yeah. In a hotel room. Because in our home, He would get up early and go to his office while I was sleeping. And at night, I would be in the office working while he was in bed. But you can’t do that in a hotel room. It’s really hard because the light is going to keep someone awake.

So how do you do that? You have to go down to the business center. That’s how you do that. You go down to the cafeteria table in the hotel room. That’s how you, in the hotel, that’s how you do that.

Emily Bron: So as I’m listening to your conversation now, I’m thinking. The first, they rediscovered America, regardless if they’re Americans.

The second, they rediscovered each other and their relationship. Wonderful! Double discovery!

James: Yeah, definitely. It’s true. And the thing is You know, neither of us are the person that agreed to marry one another 25 years ago. And so now it’s Denise has had experience running her own business and I’ve always just been a freelancer, a gun for hire.

But now we’re trying to Do this podcast enterprise together. And she’s coming from one angle and I’m coming from just this totally free floating creative side. And she, her business Acumen. When there’s a synergy, it’s amazing. But when we disagree on something now, all of a sudden it’s okay, who’s going to, how would, how do we resolve this?

So that we’re both still enjoying what we’re doing, and so there are like these little sort of micro negotiations that go on on a weekly basis, several times,

Denise: and we’re still parents. So we still have that dynamic. So whatever we disagree about in the podcast. Or in our travels, like we’re still parents.

So then we have that other dynamic in our relationship. It’s really been interesting. I always laugh because he just needs time to himself. He’s always been like this and I’m very needy. So I feel so bad for him, Emily, because he has been stuck with me for the last two years, like day and night.

I’ve enjoyed every minute of it. When people ask, like, how are you guys doing? I always say, I’m doing great. You got to check with him.

James: It’s not true. It’s been, I feel so fortunate on so many levels. Because two reasons. Number one, there are a lot of people in my industry whose relationships could not withstand the demands of the career and the job got in the way of their, their families, their personal lives.

And I feel also fortunate that I am alive long enough and I’ve, and that we’ve now had this opportunity to do this together. That’s not a chance that a lot of people always get, to in so many ways I said it earlier, but it’s we feel like I feel like we are making up for lost time that I couldn’t give the marriage when I was trying to do.

Make a career for myself and feed three Children and get them through school and all this. And that opportunity has been just fortunate for me on so many levels because I know not everybody gets that shot.

Emily Bron: Absolutely agree with you that we need to be grateful. To all what we have and actually to derive our energy and plan for the future because it’s really appreciation of what we have.

It’s in all religion and all cultures, but sometimes we forget about it. And my next question you’ve covered many diverse destinations on your podcast. From your travels, which location best encapsulates the freedom lifestyle that midlifers might seek? Please throw a couple of names and why. Names of the city.

Go ahead. You first.

Denise: Okay. I love Guilford, Connecticut. It’s located in an area of Connecticut that is just a, I think an hour and a half train ride from New York. You have the water right there. It’s walkable in the downtown area. New Haven is 20 minutes away, which is the closest big city, and it’s a good sized city.

Yale is right there, so there’s a lot to do. Concerts, theater. Guilford is my favorite. The only issue we had with Guilford, it was in our top three, is that if you are looking for a home, it’s a little challenging. If you’re willing to rent an apartment, you can live there. But Guilford isn’t an area that has a lot of new builds.

It’s very historic. And they like to keep the charm and we appreciate that, but then the downside is you have to wait for someone to move for a house to become available. And we’ve been on the road for two years. We don’t want to wait like we’re ready. But I would say if you have time or you have multi million dollars, because you could easily buy a five to 15 million home there.

That is not in our budget. We’re under a million dollars. That’s where we’re looking. And although those homes are available, they come up on the market very they’re very sparse. But anything over 5 million is easily had. That for me was my number one city. And then I love Athens, Georgia.

That’s going back to the south. It’s in a college town. Very walkable again. Very affordable. It’s 90 minutes outside of Atlanta, so you have a nice big city when you want to venture for a play or a concert or the ballet. Anything like that. Food is good. It’s southern hospitality. It’s open spaces if you’re looking for open spaces.

So for the criteria that would fit somebody who has is looking to explore and live out some adventure, those two cities are quite different, but hold that adventure.

James: Yeah for me personally we have always loved Savannah and for empty nesters if you can there, okay, so there, there’s a caveat.

We, we specifically love Savannah because of the Victorian houses in the historic area. And the, she mentioned walkability in Athens, it’s times 10 in Savannah. You’ve got the river there. You have quick access across that river to Charleston, South Carolina. If you want to do a day trip, if you’re an NFL football fan, you can drive quickly down to Jacksonville in Florida and catch a game.

And so that has, and then obviously Atlanta is, within three or four hours. That city on its own, it’s like you could be elderly in that city and walk down your stoop every day and have everything right there at your fingertips from the bakery to the coffee shop, to the grocery store, to your favorite restaurants.

And then the weather is so mild, and there’s just, there’s 400 years of history there. So there are plenty of beautiful town squares, museums, you name it, I could go on and on. That said there are a lot of suburbs also around that area that make it I think ideal for people who want, who are okay with living in a subdivision.

Denise and I are not. Because we can’t exactly afford, she mentioned the 5 million homes and all that other stuff in Guilford. You can also find that in Savannah. We’re not in that income bracket. Let’s not fool ourselves. And we decided that where we want to live in the Victorian district in Savannah is out of reach for us currently as the current market prices stand.

So for that reason I would say I really do there are parts of Tennessee that I absolutely love. I do love the areas outside of Knoxville but more specifically and more recently we’ve done an episode on Chattanooga and we’ve actually been through there twice since then. And just access to nature is incredible.

The town has great restaurants. There is a downtown area. There’s a little bit of, when you say some place is a city or a downtown area, there are some things that come with that. There is a homelessness factor, all that stuff. But the town itself is really cool. It’s really hip. We are Gen Xers, but we love hanging out with Millennials and even Gen Zers.

And Chattanooga has a lot of that to offer hiking. River rafting, if you want to go whitewater rafting or just simply floating down a lazy river, all that stuff is right there for you. And again, the climate is really bearable there. So those would be my two tops.

Emily Bron: Just to get the question, I know that many Americans specifically close to retirement a little bit worried about health healthcare cost. And I’m just wondering, in different states, Is it the same, like the same rules, the same amenities, the same like access level? Did you check this important factor? In the places you wish to land?

James: I would say the one that is one thing that you have to worry about a little bit in the south because year after year, there are states where we found amazing towns, but they will rank in the bottom, like number 40. to number 50 when it comes to infant mortality rates or, people getting access to care and all that.

It’s in many, if you look at Louisiana specifically, it’s among the, Louisiana and Mississippi are, always neck and neck with New Mexico on who, what the poorest state in the nation is. And with poverty comes, relatively poor healthcare. So that’s always an issue even in sections of Alabama.

As, as great as Auburn is and Tuscaloosa and some of these other places it can be really difficult getting the health care that a person needs if they have a special condition of some sort a special affliction or disease or what have you. So it is, it does differ from state to state.

Emily Bron: Absolutely. And you check this box because it’s required part of lifestyle and planning your future.

Denise: Yeah, at our age. You really have to, if you’re 30 something and you’re perfectly healthy and you’re relocating, that might not be an issue, but we’re in our fifties and that’s a really big deal to get access to.

Top notch doctors if there is an emergency and we came from Los Angeles. We had USC UCLA Cedars Sinai, we had the best doctors in the entire world at our fingertips So we are a little jaded and knowing that we’re not gonna have the very best But we’re also smart enough to know that if you live near a college town.

Yeah. And there’s a university, there’ll be a universe. And if there’s a university hospital, then that’s probably like the best you’re going to get in that area. So we keep all of that in mind when I’m looking for healthcare, 100%. When I was in Athens, Actually, somebody we had dinner with, the first thing she said is, I’m a cancer survivor and the University Hospital is phenomenal.

You don’t have to go to Atlanta. It’s right here in your backyard. And to hear that, that just put my mind at ease. Because when we’re in a place we love, I ask two things. Where’s the hospital? Where’s the airport? Airport, I could take a Uber. But the hospital, that’s a different story.

Emily Bron: Yeah. Absolutely.

As I am as a owner of International Lifestyle Consulting always saying and in my kind of analysis what is the best place to be close to airport depending how it’s important your health and how close it will be to the next. Hospital and just the observation I’m thinking now after two years of traveling and again, the United States changed over this time. And I believe not only probably pricing.

Like cost of living in different states. And as we speak, it might change again because the process is still in progress, we will say. How you accommodate this one? And how did you find people are reacting to the changes in the country or in the world? Or position that, how it’s affect people in a small city.

James: Yeah, I would say our initial reaction is because we love Savannah so much, it’s a reaction of tears on our part because in the last five years everybody, everybody who has lived in Savannah for any length of time has said, yeah it’s at least three to four times the price to get a house here now as it was in 2018, 2019.

It’s with, great remorse that we had to cross Savannah off of our list, as I mentioned earlier, but we get a lot of reactions from people. It started for us, even before we moved in Idaho, we went to a ski resort town and people there were already mentioning, like I’ve grown up here.

I, my parents worked at the ski resort. I’ve lived here all my life. And now I can’t afford to buy a house in the hometown where my parents live. And so we were seeing this in 2018, 2019. Now, to your point, it’s everywhere. And, you do have a lot of people, our age Gen Xers, mid fifties, and, probably coming up or maybe even slightly younger this, who are now having children who have entered the workforce.

who can’t afford a home in the town that they’ve grown up in their entire lives. And so we get a lot of that commentary for sure. Hoping in the next year or two, couple years, it evens out a bit. Right now, as you mentioned, there’s not really any indication of that happening, but we’ll see.

Denise: It’s unfortunate, Emily, because there are cities that we like, actually, like Savannah being one of them.

Auburn, Alabama. I have a handful of cities I could tell you that we thought would be the place for us and then to land there and find out we’re five years too late. And we’re finding that actually not just like being five years too late. There’s towns we visited last year that the price and houses have already jumped 75, 000 to 100, 000.

And we’re only a year, like we just didn’t hop on that. It’s extremely frustrating. That’s like a whole topic into itself. And we could talk about how corporations are coming in and ruin it for modern families. And, cause corporations really have. There was a whole study about how Zillow is looking at the trend.

So if I look at a little town in Alabama and 5, 000 other people are looking at that town in Alabama, Zillow is going to go in and buy like 50 houses because all of a sudden there’s a trend. So you can’t, how can the average person outbid a corporation? We just had a guy on our podcast who’s living in Detroit.

And he’s actually moving to Amsterdam and he lives in this little area of Detroit that is, the community has come together and has like really done something with it. It’s downtown Detroit. And he just said somebody came in and brought up 25 buildings. That’s a corporation that’s doing that.

And now they’re going to hold on to that. Speculators.

James: They

Denise: see a trend. There’s a lot of artists moving to Detroit because it’s affordable. But they’re going to make it unaffordable. And you’re constantly against like big corporations. You’re against, it is so challenging. I it’s disheartening is what it is.

Oh, you need to

Emily Bron: land. Okay. Land at some place because it’s a process and it looks like it will be for, it’s a trend I would say. Yes.

James: Yeah.

Emily Bron: And can you share with us a particularly transformative experience or kind of epiphany from your last two years travels as it ties in the concept of. personal reinvention.

Denise: I’m very aggressive. I came from a city in Chicago. My father was a Chicago cop. My mom owned a bar. I lived in LA, like not in the suburbs. I lived in LA. I’ve been all over that city. I worked in music. I realized through living, like being in the South and interacting with people from the South how fast paced I am, how immediately I am to think that someone is trying to get over on me.

And they’re not, and they’re not, and so it literally I have been taught a couple of lessons. I have been taught a couple of lessons on our travels. Like when we are sitting at a gas station and they have outdoor tables and we are having lunch and somebody stops, my immediate response is, what do you want?

And their answer is, I just wanted to give your dog some water. And if that doesn’t make you feel like a jerk, nothing does.

James: Her first instincts are always city. I would say for me, it’s it’s emerging that. I know I’ve been fortunate. I’ve had a good career knock on wood. I’ve had three healthy children and we were successful in raising them, getting them all off to college and everything.

I think for me, the revelation now is that wherever we end up it’s actually incumbent upon me. It’s it’s imperative that I. As quickly as possible, join the fabric of that community and start giving back to those people that, can’t do it for themselves because I’ve been so fortunate.

So it’s really, it’s the cliche to he who much has been given, much is expected parable, but it’s true. It’s an undercurrent in me most mornings when I wake up now. And it’s actually become something that I look forward to. I don’t know what it is I can offer a given community.

I don’t know do they need television editing? Probably not. Yeah but it’s I’m pretty good with a hammer. So I could, I could figure out a way to maybe do Habitat for Humanity in my local community or something like that. It’s really something that. And I’m enjoying the thought of being able to do that.

So that’s something that I did not consider when we got on the road.

Emily Bron: I think it’s really result of personal development and now without any cliche and travel in. Almost every case, prolonged travel really catalyst of some changes because you get you live several lives in short times and it provide you different outlook to the life, yes?

Wisdoms that you might even not get if you would continue your previous life, at the same hamster wheel or whatever you had before. No, it is. It is. And I think this desire to, to share and contribute to community, it’s it’s what many people get like essentially, eventually, naturally, it’s this period of time and it’s great.

It’s real. Reinvention in the best sense. And for you, um, I think that life in a small city, it’s probably really what you need now. I even I grew up, I can tell you, I was born in a small city. And almost bus of big cities and I traveled a lot and I live kind of suburb of the big city, biggest in Canada, but more and more, I appreciate small city vibe.

Yes, I need to find it or because it’s a, it’s more humane. Would you agree with me?

Denise: That’s a great way to put it. Yes. You have the time to be more human in a big city. There’s so much hustle and bustle. I do feel like the word humane. That’s like perfect in some ways because when you’re in a small town.

You have a lot more time to be more human, I feel, and think about other people.

James: Yeah, I think when you’re in, when you’re in a larger city, it’s just easy to blend in and be a face in the crowd. When, you’re living in a town, like the town I grew up in is only 1, 500 people. When you’re there everybody knows who you are.

They know what you’re up to and that could be a bad thing, obviously. But at the same time, it means they can see you and they know you when you’re making an impact for other people in the community. So It’s important. It’s

Emily Bron: Both visibility and responsibility.

James: Yeah,

Emily Bron: absolutely. What changed your worldview?

And I believe it’s happened with you over the last two years. And how did the fact the search for the new home criteria? What about your criteria, other than price wise? Did you realize that you can compromise, say, on something, but to get something else instead?

Denise: Oh, yeah. I, we had to. I we had to compromise.

James: Yeah.

Denise: There’s been a lot of that, for sure. Do you want to go?

James: You want me to go? Yeah. So I would say between ourselves, there’s been compromised. Like Denise has actually surprised me at different times actually liking a city that I personally was not caring for. And so it’s changed my view on her.

I would also say global or nationally. There are states where we were just passing through and visiting. That, it’s a very derogatory term that, people on the coasts call these states flyover states, because we found some really tremendous people, friends, neighbors you name it in these towns that have really if you would have told me when we left Los Angeles, that I would consider moving to Laurel, Mississippi, I would have told you, you had rocks in your head.

There was no way that I would ever consider living in Mississippi. But dang it, the people are so nice there. And it’s I know politically, they may not agree with everything that I agree on, but I’d be happy to call the people in the town of Laurel, Mississippi, my neighbors, and I’ll see them.

I’ll see them on Saturdays at the street fair and all that other stuff. And I look forward to, spending time with them. So many bias has actually

Denise: disappeared 100 percent and compromises when you mentioned compromises. When those biases came into play, like these people are so nice. Then you find yourself compromising on how far the airport is.

You find yourself compromising on how big your house needs to be because that overwhelming feeling of welcome took over the distance to the airport, took over the size of your house. That’s something we did not anticipate happening. And those compromises 100 percent happened and we never thought they would.

James: It’s true. I’ll give you an example. Covington, Kentucky, we had some listeners. That implored us, like they said, you have to come check out our town and see what’s going on here. It’s just across the Ohio River from Cincinnati, Ohio. And sure enough, we went there and we were actually looking at houses.

And the whole time we were looking at houses, I said to myself, Dear Lord, these houses are closer than they were in Los Angeles. And all I said when we left Los Angeles was, I want land. And here I am touring this house that was built in 1908 thinking to myself it just needs some paint and some drywall.

And so now all of a sudden it’s because their community, they weren’t kidding. Their community is amazing. They have a lot of local events, festivals, all kind of hometown pride. And then right across the river, you have access to concerts, sporting events, huge museums, the Cincinnati Zoo, all these things.

It’s in your eye. Oh my gosh, this place is like really a little mecca of cool people. And so now all of a sudden I’m like I guess I don’t need a farm. I guess I don’t.

Emily Bron: Congratulations. You passed my test because it was exactly what I wish you would say, because I know, and you need time and probably travel and re evaluate.

Your relationship, with the surrounding. But again, it’s not for everyone. And I respect each of, personal choices. Good social life and sense of community is more important even than it is like amount of amenities and how close it’s to the airport, which obviously I need, for example, because at the end of the day, you live in some particular neighborhood and you need, you require to build your new social circle and be part of your community.

Only after then you can say, I feel at home. It’s what gives home actually meaning of home. Building, it was that you purchase meaning of home. When you feel comfortable, when you feel welcome, when you can, you know that you can have guests and you can go to other people. I believe you’re close to the target.

Denise: I think we are too, Emily. I think we are too. We were really fortunate enough. Also, I just want to throw this out there. We had a camera crew follow us around for about a week to see where we were going to land. And so that, that episode just aired on the channel A& E, if you’re familiar with that. And so they found our podcast and wanted to follow us around to see where our journey was going to take us.

James: Yeah.

Emily Bron: Oh, so you really became famous celebrities, no? I don’t

Denise: know

Emily Bron: about that.

Denise: I don’t know about that.

James: We’re not even D listers yet, Emily. But the name of the show is New House, No Debt. If anybody wants to check it out. We are episode number nine, I’m proud to say. And it was a lot of fun. Yeah,

Emily Bron: it was.

We had a heck of a

James: time.

Emily Bron: Excellent. Excellent. One project lead to other one, one idea, lead to development of different other projects and businesses. Okay. You have been very sincere about challenges and joys of traveling and your relationship. Could you discuss some of the most unexpected hurdles?

or challenges you faced during your adventures?

James: I’ll go first. I did not expect, I really thought that when our last daughter went off to school, that was it was just gonna be this sort of free spirited life, and I was going to just live every day doing whatever I wanted. And I will say that as time has gone on, I have realized I don’t consider myself a super serious person when I’m with other people.

But I will say that I am in a state right now where I am Trying to find my new why. I already raised three kids. They’re doing great. And like I said, I’m, knock on wood, they’re healthy and all that. But I really am at a place now and I think I touched on this when I said I want to pitch into a community or something like that.

And I really am in a state that for me has been a challenge because it’s the first time in my life where I never had a goal. Like I was always, like Michael Jordan or whoever in my head, I was always going after a specific thing. And now I’m like, what is my thing? What is my next thing? So that being puzzled about that has actually been a challenge for me personally.

Denise: That was a mouthful. I don’t even know, like mine. Generic now, for me, honestly, it’s been more social. I’m not going to lie, like going from city to city and state to state and seeing how people live has been difficult. That has been difficult and bringing it back to wherever we land. I think to myself, what impact can I make them to like, he has said what can you give back to the community?

But I really do feel like There are a lot of disadvantaged people and I’ve known this my whole life, but until you like really see it, and in LA, we see people sleeping on the street. So I know what disadvantage looks like, but when you’re in the South, it looks different. And that’s hard to wrap your head around or just the injustice of still the racism.

Like you see it in the South clear as day, like when you’re traveling and you see a confederate flag, that’s the size of the American flag at our state capitol, it’s alarming in 2024 or when you’re white and you don’t feel comfortable stopping in a place in the South and you’re white, it, that, that has been a hurdle mentally, like, why are we still here?

Something that like, so As a as who I am, how can I, what can I do to help that? So that’s been a hurdle because you don’t expect to see that. You just don’t. You know it exists, but to see it in your face is always, it’s alarming, it’s shocking.

Emily Bron: Absolutely, and you coming again, I think, and it’s good you have this period of time together, as you need to redefine what is for you, as of today A real freedom lifestyle, freedom that you were dreaming about years ago and how it looks in reality of 2024, at least.

And what is the purpose? How to find next purpose? Because without purpose, we are lost.

James: It’s true.

Yeah. So for that reason, I think we’re both close to zeroing in on where I think by the end of this year, we’ll know. 100 percent where we’re going to end up. And with that decision comes all the things that you’re talking about, where it’s like now we can dedicate ourselves to answering those questions in our own mind and contributing to people on another level.

Emily Bron: And you’re different people now, and the concept of home changes when you’re off and on the move. And you already changed a lot of hotels, I believe, and B& Bs, I don’t know, other rental facilities and options. How do you define home? Now, and how has this definition evolved throughout your travels?

Home for you.

Denise: Oh, I think I probably answered it in my other question, which is, it’s now a community. It was when I started off, the space. The size of the house, the size of the land. But now, it’s a feel I get for the people in the new town we’ve landed. How welcoming they are. How opening are they?

You get a feel right away, Emily, when you visit local businesses, when you talk to shop owners, even the man on the street. So that’s really where I am right now. The home will feel, the people will make me feel, whether or not it’s going to be home for me. And that’s just the truth.

James: Yeah. And I would say currently until we have that place we are fortunate enough to be able to see our daughters at least a few times each per year.

They’re all living in a different state, by the way, they’ve totally taken our lead and ran with it. We have one in Colorado, we have one in Utah, we have another one in Connecticut. And but we are fortunate enough to see them and I would say when we are with our kids it doesn’t matter where that location is that’s home and so we’re it’s that’s always like that gives us a little extra energy to go on that next adventure or handle the next job or whatever we’re in the middle of.

Denise: He’s definitely the better parent. He literally is the better parent. I didn’t

Emily Bron: tell him. No it’s, I like, it’s sincere. It’s open. It’s honest. All the conversation and our values are changing and even like your husband told something, I’m sure it’s in your heart, but you just cannot speak together at the same time, yes?

And finally, for those of our listeners who inspired and I believe there will be many listening to our chat and who might want to skip town like you, what practical advice do you have for someone actually looking to pivot their life towards a travel lifestyle and actually towards exploration and reinvention and midlife?

What would you say?

Denise: I’ll go first, because this is going to go back to something you said. You said something about the steps that it takes to make something like this happen. And I’m just going to be really practical. When we started off on this adventure, somebody actually stopped me and said, I need to know the first step in doing this.

I’m going to be very practical in saying, if you want to do this and you have a partner that you want to do something like this with, you have to make sure the partner is a good travel partner. I told this woman, I said, Have you ever been on a road trip with your husband? And she said no. I said, take a weekend, make sure that he is a road trip person.

It’s something simple, but you have this fantasy in your head because you saw another couple do it. And you’re like, I can do this with my husband. No, not everyone can. Does he, is he respectful in the car to not turn down your music that you’re listening to? Does he make loud sounds when he’s chewing?

Do you annoy him? So the first step is, take a long road trip with him. Do a weekend. And then find out, is your job transferable? Could you do it? These are just practical things. Are you willing to change jobs if you can’t work remotely? And then, when we talk about philosophy of it, or the idea of it, if you have a feeling, try something.

Just one thing to make you feel like you’re taking a move in that direction. Even if that means hopping on the computer to look at what other jobs you can do elsewhere. If you are a teacher, just hop on the computer and see what a job, and if you’ve always dreamed of Tennessee, what a job in Tennessee is paying.

You may not actually do what we’re doing, but that may just be the right step in that direction to give you the motivation to take the second step.

James: Yeah, and I would say piggybacking off of that, there are plenty of towns in the United States that actually offer financial incentives for people who are educators or healthcare professionals.

A lot of tech. Towns are have popped up where, they give incentives to remote workers. So that’s definitely worth a look. And then going back to her thought process on the bigger picture. I think it’s important for everyone listening to realize that, the surveys that come out about people near their end of life and their regrets and the things they wish they had done actually amount more, at least two thirds, to being questions of boldness when they were younger.

And it comes down to not what they did, probably for most normal people who haven’t committed crimes or, haven’t lived a certain lifestyle. It comes down to the things they did not do. And if you’re feeling as you’re getting up every Monday morning and going about your week, if you’re feeling like there’s probably something better out there for you.

My advice would be, you’re exactly right. And it’s your challenge to go find it for yourself. Because now, especially post pandemic, after 2020, those opportunities are out there for everyone.

Emily Bron: Thank you very much.

James: Thank you.

Emily Bron: And as we end our voyage today with Denise and James Gordon, I’d like to thank them for sharing their remarkable stories and insights.

that remind us that it’s never too late to pursue a path less traveled. For our listeners, today’s conversation has sparked your curiosity and planted the seed of reinvention in your own lives. Check out Denise and James adventures on the Skip Town All Stars website. It will be provided later. And follow their social media channels to stay inspired.

If today’s stories resonate with you, remember that your next chapter is just an uncharted map away. Thank you for tuning. Into the age of reinvention, where we believe in reinventing life on our terms. I’m Emily Bron, and until next time, keep seeking your own lifestyle of freedom. And remember, life’s second act is yours to scrape. Safe travels.

Denise and James Gordon

Hosts of Skiptown All-Stars Travel Podcast

Denise and James Gordon are the adventurous duo behind the Skiptown All-Stars Travel Podcast, where they share their journey of reinventing life after 50. When their youngest child left for college, they sold their house, ditched the daily grind, and hit the road in search of a new hometown—turning their empty nest into an adventure-filled road trip.

Through their podcast, they explore towns across the U.S. and beyond, uncovering hidden gems, vibrant communities, and the best places to call home. With humor, curiosity, and a #FullTank mentality, Denise and James prove that midlife is the perfect time for new beginnings.

Welcome to the Age of Reinvention, where we redefine freedom, lifestyle, and purpose in midlife. As we navigate through various life stages, there comes a time when we seek new passions and a sense of freedom that seems elusive in our daily routines. This blog post takes inspiration from a podcast episode hosted by Emily Bron, featuring Denise and James Gordon—two fearless wanderlust souls who have chosen a path off the beaten track. Here, we explore Denise and James’s incredible journey into transforming their lives through travel and adventure.

Finding Freedom: The Adventure Begins

The Gordons’ story is not just about travel; it’s about reinvention. In 2022, they decided to sell their Los Angeles home and most of their possessions, embarking on an open-ended journey across the United States. Motivated by a blend of adventurous spirits and pivotal career realizations, they set off without a predetermined destination, trusting they would know home when they saw it.

Inspiration from the Journey: Discovering the Untapped Potential

Denise and James’s narrative goes beyond novelty; it illustrates the profound journey of discovery. Exploring over 70 cities, they recorded their experiences and shared insights on the Skip Town All Stars podcast. Beyond the miles logged Denise realizes how preconceived notions of certain regions have dissipated. James underscores the power of embracing new environments and communities that challenge our comfort zones and biases.

Lessons Learned: The Transformative Power of Travel

Travel often acts as a catalyst for personal growth, as evidenced by the Gordons’ experiences. By embracing roles outside their comfort zones, they discovered untapped potential within themselves and each other. Denise learned to soften her city-bred wariness, while James found a sense of more profound community responsibility.

Choosing a Home: The Art of Compromise

The pair redefined what “home” meant to them as they continued their quest for the ideal hometown. Though initially centred on tangible aspects like land size and location, their criteria eventually prioritized community vibes and inclusivity over material attributes. This realization reflects a broader truth: the essence of home is more about the people and spirit of the place than its physical structure.

Practical Advice for Aspiring Adventurers

The couple offers invaluable practical advice for those inspired by the Gordons’ story. They recommend starting with small travel experiences to gauge compatibility with your partner in a nomadic lifestyle. Additionally, they emphasize the importance of exploring remote work opportunities or locations offering incentives for newcomers.

Conclusion

Denise and James’s journey reminds us of the beauty and excitement of life’s second act. Their story encourages us to venture beyond our comfort zones and reinvent ourselves unexpectedly. As you contemplate your own path of reinvention, let the Gordons’ story be a beacon of inspiration. Remember, your next chapter is just an uncharted map away.

For more on their journey and insights, check out Denise and James on the Skip Town All Stars website and follow their social media channels. They’re open to new adventures and might even help you find your perfect spot. Until then, keep seeking your freedom lifestyle and embrace the notion that life’s second act is yours to write. Safe travels!