When Kari DePhillips and Kelly Chase jetted off to  the coastal town of Aguada, Puerto Rico in January, they weren’t headed there just for poolside piña coladas and beachcombing. But they weren’t exactly on a business trip, either.

The women spent a month in the seaside village “workationing,” a combination of work and play defined on their Workationing blog as “methodically bouncing around to different locations around the world, working along the way.”

DePhillips got inspired to take a yearlong workation after a two-month stint last spring working from six European countries. “I didn’t want to come back,” she said.

DePhillips and Chase are part of a growing group of knowledge workers who have embraced the digital nomad lifestyle. These workers live a nomadic lifestyle, giving up a regular apartment or home in favor of always traveling to an exotic locale.

Many digital nomads travel through foreign countries in Asia, Australia, Europe, and South America, staying at Airbnbs and other unique accommodations

How do they do it? Keep reading to find out if the digital nomad lifestyle is for you.

Change of Course

A post shared by Kari D. (@karidephillips) on

DePhillips also decided last year to start living life “more intentionally” after reading The Power of Habit: Why We Do What We Do in Life and Business, which examines habit formation and change, especially when it comes to stumbling through life on automatic pilot.

“My mother died when she was 42, and I’m fully aware that time is of the essence, and I should maximize it to the best of my ability,” says DePhillips. “None of us knows how much time we actually have.”

So last December DePhillips loaded a rented truck with everything she had and bumped along a remote New Hampshire road to the 10 x 10 storage unit where she left her possessions behind.

“My belongings are secure, and they’ll be right where I left them when I return,” says DePhillips. “In the meantime, I’m completely untethered.”

Becoming a Digital Nomad


At first glance, being a digital nomad may seem like a vacation but it’s not completely idyllic. Instead, this lifestyle is about fully immersing yourself in your work while enjoying new and stimulating surroundings to unwind and be more productive.

That means DePhillips and Chase, who works for DePhillips’ marketing agency The Content Factory,  might spend an entire balmy day holed up in their Airbnb apartment slogging away on a work project—but by night they are strolling barefoot on the beach or clinking wine glasses over exotic cuisine.

“It can be easy to get caught up in what’s around your city and lose sight of what you’re doing,” says DePhillips, who intends to stay in each city until that destination’s work goal is accomplished.

In January, DePhillips and Chase created podcasts and implemented marketing strategies in Aguada. Then they spent February fine-tuning the marketing plan in Medellin, Colombia, the city formerly terrorized by cartel drug lord Pablo Escobar, depicted in the Netflix series Narcos.

Next, they’ll fly to Sofia, Bulgaria, one of the cheapest destinations in the world for lodging. “We also plan to hit Spain but the rest of our travel plans are up in the air,” says DePhillips.

Proceed With Caution

Workationing abroad isn’t without challenges. DePhillips and Chase didn’t realize until they left Puerto Rico that they hadn’t paid enough attention to safety concerns, especially since the men working in the store beneath their Airbnb rental knew they were two women traveling alone.

It can also be quite a rat race. Unless you have several clients locked down, you might find yourself frantically searching for freelancing gigs and other remote work. You have to keep a careful eye on costs, to make sure that you aren’t spending more than you are earning. If you end up wracking up a monumental credit card debt, your digital nomad lifestyle might not be sustainable.

Think You’re Ready?

Cueva Ventana

Here are some essential tips for living the nomadic lifestyle:

1. Have a Skill You Can Do Remotely. 

Jobs where you can earn money in the gig economy or as a remote worker including:

  • Writing online content
  • Graphic or website design
  • Social media marketing
  • SEO
  • Translating
  • Owning your own online business
  • Computer coding
  • Business consulting
  • Teaching English
  • Become a virtual assistant

2. Make More Money Than You Spend.

You’ll need to make enough money on the road to survive without tapping into or depleting your savings. Consider visiting countries with a low cost of living where the US dollar will go the furthest.

3. Travel Light.

You don’t want to lug a 50-pound suitcase while sprinting through airports or climbing six flights of stairs to your Airbnb rental. Plus, you’ll save money on airline baggage fees  if all you have is a carry-on bag and a personal item.

Buy cheap clothing wherever you stay that you can donate to locals when you leave.

4. Keep Focused.

Stay in one place long enough to accomplish a focused work goal.

5. Practice Good Road Karma.

In other words, be kind to others and that kindness will be returned to you.

6. Save Enough Money to Come Home.

Make sure you set aside enough money to buy a return ticket home, get your stuff out of storage, put a deposit down on a place to live and buy a car if you’ll need one, just in case you ever come back.

7. Maintain a Home Base.

Whether it is a room in your parent’s basement, or you buy a condo that you can rent out when you aren’t around, it is important you have a lair you can retreat to when things get hectic or you need to reconnect with your family and old friends.

8. Earn a Passive Income. 

Speaking of a condo, you will have a better safety net if you do have some sort of a passive income. Invest in a rental property or a family business so you don’t go broke when the freelance work dries up. This might be financially possible for everyone, but it is worth considering.

9. Find Extra Work.

It is important that you always be planning ahead, keeping an eye out for your next gig. Joining freelance platforms like Upwork or Fiverr is a great way to quickly find work, should you need to.

10. Plug into the Digital Nomad Community

Don’t try to do it alone. Reach out to other digital nomads wherever you go. Join an online community to make connections. Visit popular nomad destinations like Chiang Mai in Thailand or Bali in Indonesia. Not only can they give you local tips, but they can also help you find remote jobs.

11. Stay Online

A good internet connection is the life blood of being a digital nomad. Make sure wherever you are staying has a fast connection available. Unlike the United States, you can’t expect every coffee shop to have blazing fast Wi-Fi.  Developed countries likely will have coworking spaces that you might be able to work from, or you can invest in a portable hot spot with your mobile carrier that will allow to connect from anywhere.

Just make sure you remember to charge it!