Everyone was like, you're crazy

Plus an interview with Ashlea, who speed dated America

Mar 16, 2021

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Dear friend —

If you could live anywhere, how many places would you try out before settling down?

For Ashlea Halpern, that number was 229. Yes, Ashlea traveled to 229 different places in America — with her partner Andrew and two dogs in tow, no less — before deciding, 16 months later, to call Minneapolis home. Granted, Ashlea is a travel writer who contributes to Condé Nast Traveler, NYMag, Bon Appétit, and other places, so she was more game to nomad than most. But she’s also enthusiastic about her newfound home — so much so that she cofounded Minnevangelist, a website about all things awesome in Minneapolis.

I found Ashley’s story about all this during a mad night of googling while trying to answer some nomading questions for myself, then immediately emailed asking if she might chat with me to share her experience and give me some personal advice. Lucky for me, she said yes!

We talked last week. Below’s the resulting conversation, in which Ashlea dishes on making free flowing travel plans, getting through the honeymoon period with new cities, and embracing wanderlust. The interview has been edited for length and clarity.

Okay, so you’re a once-nomad who speed dated more than 200 cities across America before settling in Minnesota. Before we get into the how and why, can you tell me a little bit about what the last year has been like for you, as a travel writer? Basically, how are you?

It’s been wild. I have to preface anything else I say with: Obviously, COVID has been devastating to so many people in so many industries, and my partner and I are incredibly lucky. The New York Times just did a one-year anniversary package of the people left behind — you see that stuff and it just rips your heart out.

So understanding that — it's weird to go from traveling six months a year for work to not traveling at all. A number of my titles froze their freelance budgets and some folded all together. I had to pivot from experiential travel, where you're actually in a place scouting things, meeting people, and writing about that experience — to reporting from afar.

I did a long series over almost 12 months for Condé Nast Traveler, interviewing different people in the travel industry, everything from hotel GMs to air traffic controllers to B-and-B guys, flight attendants, and tour guides. How were all of them pivoting? What were they doing to survive? And that was a real honor, to be able to talk to those kinds of people through every stage of this. Now of course, we see what seems like a pinprick of hope.

Glad you stayed healthy through all this. So — let’s start with your list of places you decided to try out. Why 229? That’s a long list! Did you have any criteria going in, or were you starting this exploration completely from scratch?

We’d been in New York City for close to 10 years. I loved that chapter, but I was working in the magazine industry as an editor and just starting to feel really burned out. You get 10 — if you're lucky, 15 — vacation days. It was really hard to go anywhere with that, particularly if you're flying to the other side of the world. I wanted to figure out a way to work remotely, to be able to work from the road.

So after I left my job, we actually traveled our first year. We went to 16 or 17 countries in Asia. We spent about six weeks in Australia. At one point for about nine or ten months, we had an apartment in Bangkok that we used as a home base.

Basically what drove us back to the U.S. is — my parents were very graciously watching our dogs and they were like, we're done being babysitters. So we had to go somewhere with our dogs. I had like a tiny little Nissan Versa, which is a worthless car for a road trip because it fits nothing. And it would go backwards in snow and ice, just roll down the hill. People, especially in places like Minnesota, would pull over and be like, are you okay? Do you need us to push your car?

We were super open-minded to — to anything. We wanted to give places that we had written off previously a shot. Like every place — Indianapolis, Birmingham. People have a lot of ideas about what a place is like. And a lot of those ideas are correct, but some of them aren't, and there were places like that all over the country.

Minneapolis just got planted in our minds. I knew one person from New York who’d worked in the coffee industry and had come here. She was always posting on Instagram about how much she loved it. And I was like, let's go check it out. We'll go spend a month there. A month turned into six weeks. It was the most beautiful time of year — fall. Everyone was like, you're crazy. Come back and winter, and then decide if you really want to live here. And we did, and we loved it.

Did you give yourself a deadline for making a decision about where to live permanently, or was it a free flowing sort of thing?

Definitely free flowing. I think I could have done what we were doing, surfing around, checking out different places, for probably two or three more years. But my partner is a little more rigid and a little more of a homebody. And he'd already been reluctant the very first year that I quit my traditional full-time job to travel. I was like, just give me two months! And then two months turned into four months, turned into six months, turned into four years. So at that point, I'd kind of like pressed my luck. I think he just really wanted a home. And I understand that.

Tell me about how you moved from place to place. Since I read your article in Airbnb magazine, I’m guessing you stayed at a lot of Airbnbs. But in some places, you stayed only an hour — others, 6 weeks! How long did you typically initially book a place for? Did you just extend the booking if you wanted to stay longer?

That's exactly what we did. Because we had our dogs with us, we were really limited by where we could find pet-friendly places. On Airbnb, sometimes you put on that pet-friendly filter and you go from like 300 listings to one — and the guy looks like he could be a serial killer or something. So in that case, then we’d stay at like La Quinta.

Usually we’d start by booking a week, because often on Airbnb, you get a discount if you book a week or more. We found that to be a way to save money and just to get more into the rhythm of a place. You could send me anywhere in the world and I would be like — “I want to move there!” — after three days. There's this honeymoon period where you're just so in love with everything around you. But around like days four, five, six, you start to notice more things. The longer you stay, the more you notice both the pluses and minuses.

Sometimes we would extend a stay, but sometimes we couldn't because we already had the next place booked. But we definitely came back to places too.

I have to say I’m really impressed you and Andrew were able to travel together for so long without, you know, killing each other or something.

[laughs] Oh, there were days. There were more than a few fights where I was just like, if you can't handle this, just go home. And he was like, we don't have a home. [laughs]

Were there places either you or Andrew liked and wanted to stay longer — but the other did not?

Not really. We've been together almost 20 years. We're pretty well synched at this point. There were definitely places where I think the exhaustion of being on the road got to us and we just needed to stay longer and not do anything. Just be in our Airbnb, just work, just catch up with emails, talk to family on FaceTime. You need some of those anchoring moments where you do nothing to kind of rejuvenate.

Did your criteria change as you visited more places? I tried out a few quaint, sleepy towns at the beginning, but quickly realized that some places are just too quaint and sleepy for me. What I’m saying is, after just a few months of travel I ended up crossing a lot of places off my list without even visiting them because I knew they wouldn’t meet my needs.

What we wanted definitely started to evolve. I don't remember specifically knocking something off the list that we were curious about. We might not do a week there but we would definitely do two, three days. There were definitely places too that were like, Oh, I'd love to live here when I'm like 65 or 70, like when you're at retirement age and don't care as much about going out and doing tons of stuff in a place.

So — the main reason I wanted to talk to you is because, you know, I need personal advice for my own nomad life and living decisions. Here are my criteria for the perfect city: I need a place big enough that I can expect a comfortable level of urban anonymity. I also need temperate weather, ethnic diversity (specifically, enough Asian people that I don’t “stick out” and feel uncomfortable), liberal-leaning neighbors, a walkable neighborhood, and, ideally, a large waterbody. The water thing is a nice to have, not a must have. What places should I seriously consider?

What do you think of New Orleans?

I've been there. It was cool. I wasn't there very long though. I was there as a tourist during Mardi Gras.

Oh god, you have to go back when it's normal, not Mardi Gras season. It checks a lot of the boxes you just said. And there are so many cool neighborhoods. There is so much that people who base themselves close to Bourbon Street or the French Quarter during festival season might miss out on. There's like incredible neighborhoody vibes, but man, if you can't deal with the humidity, I think it would be miserable.

One of our favorite places — have you been to San Antonio, Texas?

I'm going there tomorrow!

San Antonio I would say was our number two choice in the whole country, actually. Compared to Austin, San Antonio didn't feel as congested. It didn't feel as hip, I guess, for better or worse. The food was incredible. There's fantastic museums there. It's diverse. We really, really liked San Antonio. But then we also visited San Antonio again shortly before the pandemic, and we still really loved it, but we were also like melting. Like our faces were just melting off the second we stepped outside. And I was like, get me back to like Minnesota blizzards, please.

That's so funny. We're like the opposite, weather-wise

Yeah, yeah. I think Tucson's really cool, but I don't think there's a body of water really there. And I like things about Santa Fe, but like Santa Fe is so driven by tourism. Have you looked a lot around California?

I am going to probably in the second half of the year. I mean, I'm from LA….

What about — this is gonna sound crazy, but have you spent time in Las Vegas, like off the strip? I think Las Vegas is actually a really incredibly underrated city. The first time that we went there, we booked 10 or 14 days. And we were like, we're not doing anything on the strip. We're not going to be tourists. And we had an amazing time. But then I went back. This time I took my pseudo in-laws on a surprise vacation, and we did only strip and tourist stuff and it was also super fun. I think if you can strike a balance with a place like that, it's a curious and weird place.

Okay — Las Vegas is definitely on my list! Why do you think so few people go through this searching process? Are they just all content enough where they live? Or I don’t know — are there actually a lot of people who do this, unbeknownst to me? A huge network of people wandering about trying to figure out their perfect city?

I don't think so. I used to be really into astrology and I was like, clearly this is a Sagittarius thing — you're kind of just always footloose and restless. I grew up in a family that moved a bajillion times when I was a kid. My mom always thought, grass is always greener. The next place was going to be better, more interesting. So I don't know.

I think family ties a lot of people down. Jobs tie a lot of people down, but maybe less so now after the pandemic and more businesses realize they can actually be productive with remote workers. That's my hope.

Once you decided you liked Minneapolis, did you immediately settle there — or were you compelled to try out the rest of the places on your list?

We finished our list. But Minneapolis was, I would say, three quarters of the way through our list, so we decided to come back and cycle through in winter.

When I was younger, I dressed like such a fool. I just never wore appropriate clothing in cold weather. I went to school in Syracuse and I would walk to class wearing tights and Converse and then I'd be freezing and miserable. It's like, well, what do you expect? Then a number of years ago I had to report some stories in the Arctic and had to buy a bunch of special gear, including a lot of layering clothes that I still have to this day. That was a game changer for me. They have a saying here: There's no bad weather, only bad clothing. And it's really true.

You’ve visited so many places at this point and crossed a lot off your bucket list. Is the U.S. more boring to you now? Like there’s nowhere left you’re dying to visit?

No, not at all. I think I just have an insatiable curiosity about the world. It doesn't matter to me if I’m going to Iran for the first time or some small town in Minnesota. They're all equally exciting to me. I think it's all about attitude and having an open mind and just trying to see the beauty in every place you go.

What are your plans for 2021? Where do you see yourself going, and how?

Well, I hope to get a vaccine. President Biden says by May 1, so I'm keeping my fingers crossed. Once travel starts to reopen, I think the floodgates are kind of going to hopefully crash open for the travel industry. I expect to travel a lot for work, certainly Japan, probably one of my favorite countries in the world. And I really want to go to Iran.

Maybe this summer, before borders start reopening and Americans can actually travel again, we might do another couple of little road trips just around the U.S. — maybe go back retrace some ground in Montana and the Dakotas.

If you had been a single woman when you started traveling all over America, is there anything you would have done differently?

Oh gosh. It's so hard to think about. I probably would have sought out female hosts or families more on Airbnb, or paid very close attention to reviews of male hosts.

I would have probably wanted to look up each city to assess the dating pool. Or — I would just be like, you know what, screw all that. I'm picking a place that I'm most interested in and I'm going to get involved with cool things there. And if someone comes along, that's awesome. And if they don't, who cares?

I just think it's awesome when people do this. If you have a way to do this, I really think it's something you'll never, ever regret. I never want to be one of those people who's laying on my deathbed asking, what if?

Many thanks to Ashlea for sharing her nomadic wisdom! After this chat, I got more clarity — and finally made some travel decisions beyond Austin, where I am currently. By May, I’ll be in Brooklyn — by way of Dallas, Fayetteville, Memphis, Nashville, and Charlottesville. If you live in any of those places, send me travel tips.

Love notes from Siel

Everyone was like, you're crazy

Plus an interview with Ashlea, who speed dated America

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