Plan The Perfect Worcation And Stay Productive While You Travel

If you want to build the ideal worcation, base yourself somewhere exciting with like-minded people, and use that base to propel yourself toward further adventures.

Photo: Brian David Crane, founder of CallerSmart; Source: Courtesy Photo
Photo: Brian David Crane, founder of CallerSmart; Source: Courtesy Photo

Traveling to exotic locales can be intoxicating. The more you do it, the more you want to continue. But what if travel wasn’t tied to a singular desire to escape the daily grind?

What if your income traveled with you? What if your ability to make money didn’t depend upon being chained to a desk?


Reinventing the Worcation

I sold my first company, a regional plastics recycler, when I was 24. To celebrate, I planned an elaborate round-the-world trip. It was meant to last a year, starting with my 25th birthday and covering 25 countries — my own “25 at 25.” I didn’t just want to travel and goof off; I wanted to be productive at the same time. So, armed with my laptop and a backpack, I set out on what I expected would be an amazing journey.

I made it to two countries before I decided to cancel the trip.

Why cancel what sounded like a dream trip? I had planned my travels all wrong. I started out on a vacation when I was really looking for a “worcation” — a trip designed not just for exotic destinations, but for productivity and personal growth (i.e., half work, half vacation).

Since then, I’ve pulled off multiple worcations, having traveled to almost 40 countries and lived on four different continents — all while becoming a successful entrepreneur.

Here’s what I’ve learned along the way:


  • Stay away from hostels.

    So what happened with my round-the-world trip? Why did I cancel it so soon? For one thing, I was staying in hostels, and I found that the people I met on the backpacker circuit were not entrepreneurs.

    They were traveling with a completely different mindset from mine. Second, the constant traveling, lack of sleep, and distractions left me drained. I found it hard to get much done while continuously on the move. Other digital nomads who have traveled this way report similar experiences.

    Photo: © Fxquadro
    Photo: © Fxquadro

    One friend, Andreas Kambanis, did a year-long overland trip from Canada to Antarctica. During this time, Andreas’ company launched two iPhone apps, each of which topped the bestseller list. Andreas did what many digital nomads default to: He stayed in hostels during his journey, meeting only a small handful of other entrepreneurs.

    Most of his fellow travelers weren’t working at all. Instead, they were living off their savings or their parents, or they’d gamed the unemployment system to fund their trips. Because the hostel environment wasn’t conducive to building his business, Andreas had to sequester himself in an Airbnb for weeks on end to get some actual work done.

    Environment is stronger than willpower; you need a healthy environment to thrive. Find a dedicated workspace outside the hostel circuit, whether that’s an Airbnb rental or — ideally — a local co-working space filled with other entrepreneurs.

  • Stay put for two or three months.

    Staying on the move takes up mental energy, no matter how well-planned your travels are. That’s why I prefer to set up a home base — somewhere exotic but still connected — and then use that for exploring neighboring countries via shorter trips.

    Let’s say you want to go on a worcation in Southeast Asia. If so, Hong Kong is a terrific base — it’s filled with entrepreneurs, and the infrastructure is world-class for travelers. There’s a direct train to the airport with quick flights to Thailand, Vietnam, Malaysia, the Philippines, and many other options throughout the region.

    Photo: © berc
    Photo: © berc

    Establishing a base and traveling outward from there gives you the best of both worlds. You get an exotic locale with even more adventures close by, as well as a reliable, productive place to get work done. There’s no need to constantly pack and unpack.

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

  • Find people who share your values.

    Being a digital nomad has become more popular, which means it’s possible to meet folks who share your values if you look in the right places. Personally, I’ve found that joining a co-working space with an active social calendar gets you tapped into the local entrepreneurial scene quickly.

    Another option is to join an established group of digital nomads. There are plenty of communities across the world where entrepreneurs and creators can gather in nurturing environments and make the most of their time abroad.

If you want to build the ideal worcation, base yourself somewhere exciting with like-minded people, and use that base to propel yourself toward further adventures. You’ll be more productive and still be able to get into all the adventure you can handle.


This article has been edited and condensed.

Brian David Crane is a serial entrepreneur and technology investor. When he’s not working on making iPhone caller ID better with his business CallerSmart, you can probably find him dancing Zouk or reading on his Kindle. Connect with @CallerSmart on Twitter.


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