From Vacation to Workation: An Insider’s Guide for Digital Nomads

Traveling to exotic places can be addictive. The more places you go, the more you want to see and explore. You realize how big and infinite the possibilities for adventure are. The one drawback is that traveling typically means giving up your income. You either have to quit or use your vacation days to escape the daily grind.

What if this weren’t true? What if you didn’t have to give up your cash flow to follow your wanderlust? To live your life as a digital nomad?

At 24, I sold my first company and to celebrate my achievement I planned a year-long trip. I would go around the world to 25 countries and it would start on my 25th birthday – a “25 at 25.” I didn’t want to end the trip broke, so I planned to work along the way. I packed my backpack, along with my laptop, and started off on what I thought would be an amazing journey.

After two countries I called it quits; the stress of seeing and doing everything and also working was too much.

I realized I had planned everything wrong. I had planned a vacation. What I really needed and wanted was a “workation” –  a trip designed not just for exploring international destinations, but also for productivity and personal and professional growth.

Since that misguided world trip at 24, I’ve pulled off multiple workations, living in four different continents (and traveling to more than 40 countries)  – all while still becoming a successful entrepreneur.

The most recent company that I’ve founded is a completely remote team, with employees spread across the world. Thanks to my experience as a dedicated digital nomad I’ve learned a few things, and I make sure my team members follows these tips:

1. Avoid Hostels and Find a Coworking Space.

Hanging out with Australians on their gap year is fun, but it’s not productive. (No offense to Australians on gap year.)

On my “25 at 25” trip, I was staying in hostels and found that the people I met weren’t entrepreneurs. They were traveling with a completely different goal than me. In addition to this, the constant traveling, poor sleep, and distractions left me feeling completely drained. It was difficult to get anything done while being on the move and surrounded by people who were either looking to party, or just looking to see and do as much as they could in one place before moving to the next.

I’ve discussed the hostel situation with several other digital nomads and they report similar experiences. One friend, Andreas Kambanis, did a year-long trip from Canada to Antarctica. During the trip, his company launched two best-selling iPhone apps.

Andreas did what I and many digital nomads default into at first: he stayed in hostels during his journey, and met only a small handful of entrepreneurs along his way. Most of the travelers he met weren’t working at all. They were living off their savings, their parents, a combination of the two, or they had unethically gamed the unemployment system to fund their trip.

The hostel environment was so distracting that Andreas ended up having to hole himself away in an AirBnB in order to accomplish his tasks.

When trying to get work done on the road, environment is more of an influencing factor than willpower. You need to put yourself in an environment that allows you to be productive. It’s best to find yourself a dedicated workspace outside the hostel circuit, whether that’s in an AirBnB, or  – ideally  –  a local co-working space, filled with other entrepreneurs who will foster the productivity in you.

2. Stay for 2-3 months in One Place

No matter how well you planned your trip, or how little sleep you can function on, being constantly on the move will burn you out. I prefer to setup a home base  – somewhere unknown but still connected  – and then use that for exploring neighboring countries via shorter trips.

If you were planning a workation to Southeast Asia, for example, Hong Kong is a terrific home base. It’s filled with entrepreneurs, and the infrastructure is fantastic for travelers. There’s a fast, direct train to the airport and quick flights to Thailand, Vietnam, Malaysia, the Philippines, and many other options in the region.

Establishing a base and traveling outward from there gives you the best of both worlds. You have an exotic locale with even more adventures close-by, a reliable, productive place to get work done, and no need to drag around your luggage constantly.

Staying put also lets you get into healthy routines, develop friendships with locals, and experience more of the culture. Weekly sports leagues, regular yoga, dance or language classes, and other activities are possible because you’re building a home away from home and not just passing through.

3. Find People Like You

“Digital nomad” has become a buzzword in the past few years, which means there’s a lot of other entrepreneurs just like you heading off to new destinations. It’s possible to find people wherever you are who are looking to develop their career and travel the world. Personally, I’ve found that joining a local coworking space allows you to network quickly with other entrepreneurs in your chosen locale.

Another option is to join an online digital nomad group, this allows you to start networking even before you get to your new destination. There are communities of digital nomads around the world and you can reach out to make coffee dates for when you arrive or ask questions if you have any doubts about moving to a location.

The best way to have the ideal workation is to pick a home base that excites you, find a co-working space or some other digital nomads online, start networking and having adventures.

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Written by:
Brian is a serial entrepreneur and lifelong learner. He is the founder of CallerSmart, a popular iPhone caller ID app that helps users deal with unknown or unwanted phone calls and texts, and which BuzzFeed nicknamed "turnt up caller ID." He's been featured on the likes of Entrepreneur, Inc., TheNextWeb, and Mashable. Here at, he writes about building digital businesses and distributed teams, as well as what it takes to be a successful founder as a digital nomad.
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