3 tips for mastering the digital nomad life of a 14-year-old expat

Jesse Schoberg, co-founder and CEO of a software start-up DropInBloghas lived and worked abroad for 14 years, dividing his time between more than 40 countries.

“I think being an entrepreneur and being a nomad go hand in hand because both types of people seek adventure and freedom in their lives,” the Wisconsin native told CNBC Make It. “I’m excited to be both in my life.”

Between his travels, Schoberg, 41, now lives in Bangkok. He moved to Thailand in December 2021 and shares a one-bedroom apartment with his fiancée, Janine.

Exploring the world while working remotely is an experience “like no other,” Schoberg points out, but it’s not without its challenges.

Whether you’re considering becoming a digital nomad or planning a life of travel, consider these three tips from Schoberg that will help you succeed:

Get the most out of your short term rental

As a digital nomad, you’ll likely spend a lot of time living in an Airbnb or other short-term rental.

Schoberg recommends booking rentals for “at least a month” because platforms like Airbnb will offer discounts for longer stays.

Before booking your stay, contact the host to negotiate weekly cleanings if you’re staying at the property for an extended period and ask for an additional discount, he adds, if you plan to stay a few months.

Be sure to confirm the property’s internet speed and reliability, Schoberg adds, especially if you plan to work from your new temporary home. Or bring your own supplies – Schoberg started traveling with its own router a few years ago, which can cost between $60 and $200.

Schoberg also plans to budget a few hundred dollars a month for items he might need that are missing from the apartments he stays in.

“Often, an Airbnb [apartment] might not have a big stove, a reading lamp by the bed, or a nice extension cord so you can work in the best spot,” he says. “Don’t be afraid to buy a few of these things on your first day, as it will make your whole stay much more enjoyable.”

Jesse Schoberg and his fiancée, Janine.

Photo: Jesse Schoberg

Learn the local language

One of the most important qualities a successful digital nomad possesses is open-mindedness, which includes a willingness to learn the local language no matter where you travel, even if it’s just a few phrases, such as “hello” and “thank you”.

Understanding different languages ​​can help you more easily order food, find directions, read menus, and negotiate in markets, among other benefits. “It also shows an appreciation and respect for the locals,” adds Schoberg.

He takes two Thai lessons a week and has discovered that “you can really engage with the culture and have a better life” in Bangkok if you are able to understand Thai.

Jesse Schoberg in Bangkok

CNBC do it

Find new friends online

When Schoberg first left the United States for Panama City, Panama, in 2008, the adjustment was difficult – he spoke no Spanish, he didn’t know much about the city and, more importantly, he didn’t know anyone there.

“It’s easy to feel 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 build that muscle of meeting locals as well as other travelers…so you can build yourself a community that makes you happy.”

The best way to make friends as a digital nomad, says Schoberg, is to browse 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 appear, which is a great starting point,” he notes.

Schoberg also suggests checking nomadic lista website that arranges online dating and chatting between people from different cities around the world.

Although making friends abroad is a “difficult 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, making the new place you live in “feel more like home.”


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