Jesse Schoberg, co-founder and CEO of software start-up DropInBlog, has lived and worked abroad for 14 years, splitting his time in more than 40 countries.
“I think being an entrepreneur and being a nomad go hand in hand because both types of people are looking for adventure and freedom in their lives,” the Wisconsin native tells CNBC Make It. “I feel excited by both in my life.”
In between his travels, Schoberg, 41, now calls Bangkok home. He moved 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 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 to help you succeed:
Get the most out of your short term rental
As a digital nomad, you likely spend a lot of time living in an Airbnb or other short-term rental.
Schoberg recommends booking rental properties for “at least a month,” as platforms like Airbnb will offer discounts for longer stays.
Before booking your stay, contact the host to negotiate weekly cleaning if you’re staying at the property for an extended period of time, and ask for a further discount, he adds, if you plan to stay for several months.
Be sure to confirm the property’s internet speed and reliability, adds Schoberg, especially if you plan to work from your new temporary home. Or, bring your own supplies — Schoberg started traveling with his router a few years ago, which can cost anywhere from $60 to $200.
Schoberg also budgets several hundred dollars each month for items he might need that are missing from the apartments he stays in.
“Often, an Airbnb [apartment] it might not have a big frying pan, a bedside reading lamp, or a nice extension cord that allows you to work in the best place,” he says. “Don’t be afraid to buy a few of these things on day one. it will make your entire stay that much more enjoyable.”
Jesse Schoberg and his fiancee, Janine.
Photo: Jesse Schoberg
Learn the local language
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 few phrases like “hello” and “thank you.”
Understanding different languages can help you order food more easily, find directions, read menus, and negotiate at the market, among other benefits. “It also shows an appreciation and respect for the locals,” adds Schoberg.
He is taking two Thai classes a week and has found that “you can really engage in the culture and have a better life” in Bangkok if you can understand Thai.
Jesse Schoberg in Bangkok
CNBC Do it
Find new friends online
When Schoberg first left the US for Panama City, Panama, in 2008, it was a difficult adjustment – he didn’t speak Spanish, didn’t know much about the city and, most importantly, 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 friends yet,” he says. “But the more you travel, the more you tend to flex the muscle of meeting locals as well as other travelers … then you can build 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 bands will show up, which is a great place to start,” he notes.
Schoberg also suggests checking out Nomad List, a website that organizes online meetups and chats between people in different cities around the globe.
While making friends abroad is a “hard skill that takes time to develop,” he adds, it can help you discover more fun and local activities; open the door to new job opportunities; and, ultimately, make the new place you’re living in “feel more like home.”
Watch:
This 41-year-old left the US for Bangkok and lives a ‘luxurious lifestyle’ on $8,000 a month.
From Bali to Bermuda: 6 tropical destinations that make remote living and working easy
I left the US for Bali and was ‘desperate’ at first: Doing these 2 things every day made the experience ‘amazing’
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