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Get Traveling, People! Tips to Make It a Reality

Our Nadexa Group happy hour drew over a dozen people last week: Ann Woodward fans, world travelers and aspiring world travelers — all with an interest in how to make extended travel a reality.

Ann also brought along a friend and fellow traveller, Erik Trinidad, who has made a career out of being a travel writer. Check out the trips he’s covered for National Geographic, Saveur and others:

For those who weren’t able to attend, Ann has prepared a list of common questions, below. She’s also available for private consultation, which could be handy if you’re interested in specific destinations or have a unique agenda. Here’s the link to Ann’s travel consulting page.


When you first started travelling, how long did you intend to be gone? What were your travel plans?

I thought I’d take a break for 6 months. I wanted to go to Southeast Asia and India – places that were far from the US and difficult to properly explore and experience within a typical US vacation timeframe. However, I fully expected to return to NYC, move back into my apartment and get another job in advertising or marketing.

At what point did it stop being a trip and start being a way of life?

In Week 3 of my trip, I encountered a sizeable group of people (mainly US citizens) in Chiang Mai, Thailand who weren’t vacationing or even backpacking. They’d rented apartments and were, for all intents and purposes, living in that city. They were doing a variety of things to sustain their lifestyle — teaching English, doing freelance writing and web work or monetizing a travel blog. This was an eye-opener, and I began to think about other things I could do outside the US aside from purely travelling. There was the possibility of experiencing a different culture, and perhaps even enjoy a higher standard of living for much less money.

I travelled through Southeast Asia & India as planned, but in May 2012 I went to Madrid, Spain to live with a family for two months and tutor their five(!) kids in English after school. That was my first ‘work’ overseas. I’ve now completed six assignments, ranging from helping a women’s empowerment NGO in India to serving as hostess at a vineyard restaurant in Chile. Most recently I had a six-month marketing gig at a surf school in Morocco.

How do you find your jobs?

I sign up for alerts from professional, skill-based job listing sites such as Escape the City, Jobattical and Moving Worlds.

WorkAway is another extremely popular site I’ve had success with. It offers some marketing and social media placements, as well as a variety of other opportunities such as working with kids, being a receptionist in a hostel, painting a house or planting a garden.

To be clear, many times the ‘jobs’ are exchanges where you do work in exchange for room and board. So, you’re not earning money, but you essentially have little to no expenses if your lodging and food costs are covered. Obtaining work visas for a permanent paying job in another country is much more difficult and complicated process.

How do you afford to travel?

I had some savings when I left to travel, and I still do small-scale consulting for NYC-area businesses for income. I personally prefer to travel in less touristed countries, which also tend to be less developed and have a lower cost of living. ‘New York money’ goes quite far in these places.

Long-term travel is about choices and trade-offs. In addition to choosing to do work exchanges, I make decisions with an eye to stretching my money so I can continue to travel. Here are a few examples of these choices: I’m totally fine with budget accommodation, as long as it’s clean (and preferably has hot showers and wifi). I also find that if I have an Airbnb rental, then I typically go grocery shopping and eat a couple of meals a day in the apartment (which is healthier and less expensive than restaurant dining). Finally, I travel slowly, preferably spending at least three or four nights in a place. Slower, overland, local travel generally costs much less than trying to cover lots of places in a short amount of time by flying and/or taking a guided tour, as you might do when in a vacation mindset.

What are travel resources for someone looking to make a career break?

Legal Nomads has an incredibly comprehensive world travel section on her site.

Nomadic Matt is also a well-known site for round-the-world budget travel.

I like This American Girl who covers life transitions, solo female travel, romance, how to make money on the road with unflinching emotional honesty.

If you’re interested in volunteering, Grass Roots Volunteering has a database of ethical and sustainable service projects around the globe.

Career breaks are still a relatively radical idea in the US. If you’re considering one, it’s important to have a support network of like-minded folks and to hear examples of people who’ve successfully completed such a journey. Meet Plan Go organizes meet-ups in New York City (in addition to having many career break resources on their website). I attended two of these events in 2011 before I left the US, and the conversations I had there were pivotal in getting me ready to take the plunge.

What’s the one thing you’d say to someone considering a career break to travel?  

You won’t regret travelling. The worst thing that could happen is you run out of money and need to come home.

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