My Experience with Constantly Traveling for Leisure or Work (Pros & Cons)

As some of you know, I’ve been traveling around the USA for over a year for leisure thanks to remote work. It’s been some of the most enriching time of my life.

Now, some people are curious about how things are different or the same when I go from city to city. Or what my favorite place has been.

highest point on east coast

I like to say that there are a lot of things that are the same and a lot of things that are different. Certain human behaviors or trends and any chain brands are consistent wherever I go. One can actually argue that’s a good thing because it’s familiar and comforting. I can walk into a Chick Fil A and get the same experience. Home Depot, Costco, Walmart, McDonald’s, H&M, Zara, Uniqlo, Popeyes, Target, and so on are generally there for you. It eases the anxiety when you’re scared of being alone in a foreign place. Some of this also holds true when I would go on vacations to foreign countries.

Additionally, certain pop songs are universally popular. People currently seem to love Lizzo wherever I go, and I do too. And certain hobby groups I attend have the same type of behavior. CrossFit remains CrossFit wherever you go. Hip hop dance classes have the same structure. Board game or chess meetups generally have an excess of nerdy men whether I’m in the north or south. I find this to be a good lesson on how human nature doesn’t change and how to use that to predict what events to go to and what to expect. I take comfort in some of these things because there’s a lot of differences too so it helps to know that I can still connect through Lizzo or CrossFit or swing/hip hop/salsa when I’m in a new place with new people.

Mount Mitchell

Now, onto the differences…

There’s a lot I can say here. To explain it concisely, there are a few key factors that seem to influence differences in culture, architecture, activities to do, and general vibe of a place. Those things are the terrain, climate, resources, profitable industries, and size/real estate. Some places, like Texas, have a lot of space and a lot of people to fill it. Therefore, you get a lot of new buildings and restaurants that stretch for miles and look so clean. That couldn’t exist in Maryland or Virginia because they would go out of business. That’s why you see a lot more old buildings out there. You can also sense the influence of the medical industry in a place like Houston because you bump into many people who work in that industry. Then, some places have a lot more beach tourists, so the tropical climate affects how the buildings are painted, the relaxed vibe, and there’s palm trees everywhere, even by McDonalds or Targets. There’s also smaller town mountain areas like Asheville, NC, with not as much to do but beautiful views and hikes. Those places have really hilly roads where your car is struggling to climb up. The houses and buildings sit around lakes or little towns. Their design has a old timey look, no doubt influenced by the history of people who lived there, the culture, and the slower pace of life.

North Carolina mountains

With new beginnings in constant new lands, it can be a little scary and amazing at the same time. It’s energizing and invigorating to get off work and explore something new rather than the same old park trail I would walk for years. I’m grateful to be able to explore.

And that gets us to the theme of this post, which is constantly seeking new beginnings versus the benefits of one place to grow your roots, community, and long-term social circle/network. There’s probably a season of your life when you’re still single when it’s best to pursue a life of travel, adventure, and nomadic living that you have seen on social media. That said, I’ve noticed clear drawbacks to it compared to growing your roots in one place.

Many travel influencers I’ve followed who have lived the dream life of traveling the world have settled down in a way in one place as their homebase after years of adventure. The Blonde Abroad in Cape Town, Nomadic Matt in Austin, and Lost Leblanc in Bali. Nadine Sykora (Hey Nadine) has also entered that stage as she has gotten married. They still travel with family, so don’t let having children deter you, though one can sense the shift in mood as their priorities change a bit. While they’ve found a way of making it work for many years, I can see how having one place to live leads to more chances to settle down with people for long term friendships and relationships.

Mountain shot

When you’re moving, the friendships you meet can’t be as easily maintained. You can’t continue to hang out with the people you met because you’re gone. The best you can do it keep in touch digitally through messages or Facetimes. Building a social network and good friends is a skill, so some people will fail at that even if they’re living in the same place permanently. I’ve been there myself years ago and seen others there where you’re just going to work, gym, and back home to play video games/watch TV. That sort of behavior can lead to a life that’s not much different with not many friends a year or two later.

That said, I’ve recently seen the value of building a strong social network and the skill to do that first hand. In Austin, I met Nick Gray who wrote a book The 2-Hour Cocktail Party. I saw on social media how he’s constantly invited or part of these high value social gatherings across the country in NYC and other cities. These gatherings have a lot of high-quality people who are successful in life and they seem like a lot of fun. I asked him how I can do that myself, and he pointed to the book and the fact that if the events you’re going to suck, you need to start hosting your own events. I found that to be intriguing and it hit the nail on the head for me because I’ve been to over 500 (probably 1,000+) MeetUp events and undeniably, some of them sucked! (Some were cool too, though I’d love more consistency with the time I was investing).

mountain range east coast

The fact of the matter is if you’re a young person new to a city, and you’re not super attractive, you’re not going to be invited to cool things or get many opportunities to meet cool, high-value people. You have to make your own way. No one’s going to hand anything out to you. And that’s many people after they graduate college and get a job in a new city. It pays to develop a skill to make that happen. The benefits are clear: meeting awesome people who could help your career/income, help your love life, getting invited to valuable events through them, having a non-boring life, or just be an awesome friend that you can rely on and laugh and have a good time with.

I wish it was as easy as just going to your hobbies and meeting people that way. Sometimes, it is. However, in NYC, for example, I struggled at times. I could go to a fitness class like Sweat 440, and most people were there to work out, not talk. A lot of the public, free networking / entrepreneur / career events I could find sucked. There were few people there and they were often trying to get a job or take value. A couple public YouTuber/content creation events I went to were also very low attendance. It felt like I was in the “best city in the country” yet really wasn’t hitting a stride. I was sure the good events and people were in the city yet those events were likely invite-only.

So, I don’t have all the answers. Even if I could stay in one city, I don’t think I would have the skills to be thriving or turn acquaintances into recurring friends as much as Nick. What I can say is that Nick’s book is worth a read. (I’m not paid to promote it or anything). I’ll definitely be taking a look. Other influencers like Michael Sartain have also given some great advice on social media about building a strong social circle. I recommend checking him out as well on YouTube or TikTok.

And you don’t have to be a master at this. Take it one step a time. Funny enough, looking back, even at Sweat 440, I persevered until I found one positive classmate who was upbeat and willing to talk to me. In many new places I go, I join a running club, and depending on how social that club is (some cities are better than others), I bond really well with a couple of the people there and really feel welcomed. One time, I went to a rooftop lounge, met a bunch of young med students, and we connected. One of them bonded with me over our love of One Piece and he invited me to a sold out front-row seat at a comedy show a couple weeks later when his friend backed out. My point is that I’m no master yet I’m trying and sure, these aren’t epic events I’m coordinating, however, I’m not doing that bad. These are inklings of starts of potential friendships, and I do try my best to stay in touch with these folks through Instagram and digital even after I’ve left a city. Even if you don’t have the fortune of traveling like I do, where you are has a lot of hidden benefits. You just need to see the opportunity around you and develop the skills necessary to start to take advantage of them. If I remained in one of these places, my next. goal would be to cultivate turning these into relationships where I see them again and again if I find value there. And perhaps, eventually, host my own event or invite a group of them out. I will continue to ponder how I can do this as a I move.

Best of luck!

If you could choose, would you prefer to live in on place or travel constantly? Copy and paste a choice and reply and let me know. I’m curious!

  • “live in one place”
  • “travel constantly”
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By Will Chou

I am the the founder of this site and I am grateful you are here to be part of this awesome community. I help hard-working Asian American Millennials get rich doing work they love.

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