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.

Change of Course

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.

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That book prompted DePhillips to question her own personal habits, starting with whether her dietary and thought habits were beneficial. If they weren’t, why did she create them in the first place, and how could she change them now?

“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, workationing may seem like a vacation but it’s not completely idyllic. Instead, this “digital nomad” 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 projectbut 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.

Despite the occasional travel snafu, the rewards of workationing are many. DePhillips and Chase lost weight from walking five miles a day in Aguada, developed healthier eating habits, got plenty of beach time and swam in a bioluminescent bay in Puerto Rico, all while accomplishing work objectives.

“This goal-your-way-around-the-world thing is working out well for us,” says DePhillips.

Cueva Ventana

Think You’re Ready?

Check out DePhillips’ tips below on how to do it right:

1. Have a skill you can do remotely before you travel.  Jobs where you can earn money remotely include writing online content,  graphic or website design, social media marketing, SEO and translating.

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.

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.

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.