How I've traveled the world while working for more than 3 years

Elaina Giolando

I've been overseas for three and a half years now — two and a half working, one as a gap year to explore freelance writing and coaching — and people always want to know "how I do it." 

And almost everyone back home says something like, "I wish I could do that, too!" 

Well, you can, you just have to be ready to put up with all the crap I put up with to make it a reality.

People shoot me emails all the time about where I live, how I decide where to go, how I fund my travels, what job I had to let me travel, and how I plan my wardrobe.

This post is an attempt to concisely answer as many of these questions as I can.

In a nutshell, my life is a bit of a logistical nightmare. But I wouldn't have it any other way right now.

Where do I live?

I haven't had a home base since May 2013 when I left my apartment in New York City. I do keep my extra clothes and childhood memories in my parent's house in upstate New York where I grew up.

I don't own any furniture and travel with maximum two suitcases of 50 pounds each when I'm abroad for work and one suitcase of 50 pounds when I travel for pleasure. When I backpacked for 8 months straight, my backpack weighed 15 kg at its peak. 

When I travel for work, my company provides my housing. When I travel for pleasure, I rent apartments via AirBnb or stay in hostels or family-run guesthouses depending on the country and my budget. I try not to spend over $600/month on housing when I travel for pleasure.

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How do I decide where to go next?

When I travel for work, my company decides. They send me to Nigeria or South Africa or Guyana at the drop of a hat and I have to go, or I'm fired.

When I backpack, I pick countries that are cheap, safe, culturally dynamic, have excellent local cuisine, and are actively challenging, like India. I might travel for nature, like when I went trekking in Nepal, or for a cultural icon, like Bagan in Burma. I like places that lend well to interesting street photography and are safe for solo women. That said, I'd go almost anywhere alone and anytime, so my barriers aren't very high. I also like to go a little off the beaten path, so Laos vs. Thailand, Taiwan vs. China, Bolivia vs. Peru, Ethiopia vs. Tanzania, and then seek out non-major cities and villages. I stay a minimum of one week everywhere I go (and I usually try to stay at least a month per country).

When I pick somewhere to live and write and work on my blog, I select somewhere attractive to young people, artists, and start-ups, walk- or bike-able, relatively inexpensive, and easy to integrate quickly (ie. young, liberal, diverse, open-minded). I'm currently in Berlin, but other cities that fit the bill and interest me in longer stays are Bologna (Italy), Melbourne, Lisbon, Seoul, Santiago (Chile), Cape Town, Portland (Oregon), and Tel Aviv. 

How do I fund my travels?

I save money like a pro and make money as a freelance writer and career consultant while I'm on the road. About 50% of my funds come from independent work and 50% from my savings. 

I recently wrote a detailed piece about how to travel the world for $20,000 or less, so read that for all the juicy details.