"I think being an entrepreneur and being a nomad go hand in hand because both kinds of people are seeking adventure and freedom in their lives," the Wisconsin native tells CNBC Make It. "I get excitement from being both in my life."
In between his travels, Schoberg, 41, now calls Bangkok home. He relocated to Thailand in December 2021 and shares a one-bedroom apartment with his fiancee, Janine.
Exploring the world while working remotely is an experience "like no other," Schoberg stresses, but it's not without its challenges.
Whether you're thinking of becoming a digital nomad or planning a life of travel, consider these three tips from Schoberg that will help you succeed:
As a digital nomad, you'll likely be spending a lot of time living in an Airbnb or other short-term rental.
Schoberg recommends booking rental properties for "at least one month," as platforms like Airbnb will offer discounts for longer stays.
Before booking your stay, reach out to the host to negotiate weekly cleanings if you're staying on the property for an extended period of time and ask about a further discount, he adds, if you plan to stay for a few months.
Be sure to confirm the property's internet speed and reliability, Schoberg adds, especially if you plan on working from your new temporary home. Or, bring your own supplies — Schoberg started traveling with his own router a few years ago, which can cost anywhere from $60-$200.
Schoberg also budgets a couple hundred dollars each month for items he might need that are missing in the apartments he stays in.
"Often, an Airbnb [apartment] might not have a great skillet, a reading lamp by the bed or a nice extension cord allowing you to work in the best spot," he says. "Don't be afraid to buy a few of these things on the first day as it will make your entire stay much more pleasurable."
Jesse Schoberg and his fiancée, Janine.Photo: Jesse Schoberg
One of the most important qualities a successful digital nomad possesses is an open mind — which includes a willingness to learn the local language no matter where you travel, even if it's just a couple of phrases, like "hello" and "thank you."
Understanding different languages can help you order food more easily, find directions, read menus and negotiate at markets, among other benefits. "It also shows an appreciation and respect for the locals," Schoberg adds.
He's taking two Thai classes per week, and has discovered that "you can really engage in the culture and have a better life" in Bangkok if you're able to understand Thai.
Jesse Schoberg in BangkokCNBC Make It
When Schoberg first left the U.S. for Panama City, Panama, in 2008, it was a difficult adjustment — he didn't speak Spanish, he didn't know much about the city and, most importantly, he didn't know anyone there.
"It's easy to get lonely while traveling, especially when you're in a new place for the first time and you don't have any friends yet," he says. "But the more you travel, the more you tend to flex that muscle of meeting locals as well as other travelers … then you can build yourself a community that makes you happy."
The best way to make friends as a digital nomad, Schoberg says, is browsing different groups and pages on Instagram, Twitter and other social media platforms. "I usually start on Facebook and search for 'Expats in [insert city name here]' … at least one or two groups will pop up, which is a great starting place," he notes.
Schoberg also suggests checking out Nomad List, a website that organizes meetups and online chats between people in different cities across the globe.
While making friends abroad is a "hard skill that takes time to develop," he adds, it can help you discover more fun, local activities; open the door to new work opportunities; and, ultimately, make the new place you're living in "feel more like home."