Emma’s Note: Emma Walsh here, managing editor of the Diary.

Regular readers will be familiar with Bill’s colleague Tom Dyson’s story. A couple of years ago, battling depression, he gave up everything – including his job and his apartment – and traveled the world with his ex-wife, Kate, and their three children.

Back in America since earlier this year, he’s currently four months into a nomadic road trip across the U.S. with Kate and the kids. Living in a small trailer tent, they’re exploring as much of the country as they can before winter. So far, they’ve passed through 19 states.

A few weeks back, they visited Bonner-Denning Letter coauthor Dan Denning in Colorado. Dan’s no stranger to life on the road. Three years ago, he spent several months on his own road trip across the U.S., trying to find the ideal “bolthole.”

During the recent visit, Dan and Tom got to talking about the merits of leaving the rat race behind and taking to the open road…

Dan Denning: Tom, for the past few months you’ve been traveling all over the country, after spending the previous two years traveling the world.

It’s similar to a trip I took in 2017 when I came back from London. I called it the American “Bolthole” Project. I was looking for nice, out-of-the-way places in America, where you could increase your quality of life and lower your cost of living.

When I started it, part of the thesis behind my Bolthole Project was that there would be a gradual migration out of the cities, for demographic reasons.

In other words, as people got wealthier, closer to retirement age, they’d want to simplify their life and lower their cost of living. And they could increasingly work from home because of technology.

Of course, COVID accelerated all that.

A poll I saw back in April said that a third of the people surveyed wanted to move to a less densely populated area of the country. And 39% of urban dwellers aged 18 to 34 said COVID had prompted them to think of leaving the city they lived in.

So it was younger people, not just retirees or baby boomers, looking to slow down.

In July, I saw another poll that said 20% of the people surveyed have already moved because of COVID. They’ve either moved back in with their parents, with a roommate, or with family. Or they’ve moved back to their hometown or to a smaller, less densely populated place.

Do you think this major migration out of the cities might be here to stay? Or is it very much COVID-related right now?

Tom Dyson: Both. I don’t think COVID is a temporary phenomenon. I think it might be here to stay.

But also, it’s expensive to live in cities, and it’s not quite as nice. Unless you really value the urban lifestyle of being able to walk and take public transport… and there are bars and restaurants right outside your building… why would you live in a city, if your employment didn’t make you, when you can live with more space elsewhere, for cheaper, and with more community?

Dan: You’ve certainly taken that to a whole other level with your road trip with Kate and the kids. You’ve visited 19 states since you left Kate’s parents’ house in Florida in mid-May. And right now, you’re looking for somewhere to settle down for the winter.

What were the main barriers to hitting the road, in terms of work, family, and things like that?

Tom: First, I’d just say this trip is the best thing we, as a family, have ever done. We didn’t know it would be when we started out. We got lucky, in that the circumstances of our life had all sort of fallen apart in different ways, so we didn’t have a lot to lose by traveling.

Then once we did – once we plunged through this portal – we discovered this life that was superior to what I would call the “normal” way of life. It’s cheaper, our kids are getting a great education, and, of course, we’re seeing so many things.

And the best benefit of all is that we don’t fracture our family every morning after breakfast while the parents go to work and the kids go to school, and then reconvene again at dinner time when everyone’s tired and snappy, and then it’s bedtime. We never do that. We’re together all the time. And that is the single greatest benefit.

But why wouldn’t everyone do that, and why wouldn’t I go around telling everyone to do it?

Because I realize it’s difficult to abandon your home, your community, and your job. And I know we wouldn’t have been able to do that, either, had we not gotten “lucky” through the sort of catastrophe I turned our lives into a few years back, when I was dealing with depression. So I say this with humility, but it really is a better lifestyle.

Homeschooling the kids I didn’t mind. I was pretty sure that was going to be a better education for the kids than going to school.

As for the home… my family is all fractured anyway, so that wasn’t an issue.

The thing that scared me the most was my age. I thought, “Well, if I leave my career now, I’m in my peak earning years, and I will never have a chance again to earn decent money.”

Financially, I was afraid this was going to be a really costly decision. Because when you’re in your 40s and 50s, that’s when you reap the benefits of all the hard work you’ve done earlier on in your career. And to throw all that away seemed like a big risk.

But it didn’t work out like I feared. We found a new way, and it ended up being better.

And not just financially, but in terms of seeing wealth as a bigger thing than just money. And in that sense, we’re far richer now than we were before we started this trip.

Dan: That’s a point Bill Bonner writes about all the time in his Diary e-letter… That when you’re connecting time to money, a lot of people think, “I’ll have time to do that later in my life.” But you might not have your health to enjoy it.

And the time you spend now doing it – reconnecting with your family, seeing the places you wanted to see, seeing things you never expected to see, being surprised by the generosity of total strangers – that’s the kind of wealth where there’s no withholdings from the IRS.

Tom: Yeah, and it’s a bit macabre, but if I had to die tomorrow, I would have a smile on my face because I’ve done something truly fulfilling that I can be proud of. And it’s far beyond money.

Dan: Agreed. Good to see you, Tom, and safe travels.

Tom: Good to see you, too, Dan.

Emma’s Note: Emma Walsh here again. Did you know that Tom writes all about his family’s road trip in his free daily e-letter, Postcards From the Fringe? Sign up here to read all about it.

And if you’re thinking about escaping the city lifestyle and want to learn more about the best small towns in America to retire or retreat to, why not check out Dan’s American “Bolthole” Project? If you’re a paid-up Bonner-Denning Letter subscriber, you can read it in full here. If you haven’t subscribed yet, click here to find out more.

Like what you’re reading? Send your thoughts to [email protected].