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What I Should Be Doing: Travel Sabbatical

Ann Woodward > Briefcase to Backpack

In 2001, a boyfriend and I were traveling in Thailand (Koh Phi Phi. Go there – it’s awesome!) and we came across this ad: Crew wanted on private sailboat charter to South America. We looked at each, drunk with excitement, and well, drunk. “LET’S GO!”

We didn’t go though, and I returned to an agency that folded weeks later, married the boyfriend, bought a condo, had kids, etc. If it was 2001 in Thailand again, I’d be on the damn sailboat… because how many times in our lives do we have those opportunities?!

That was the choice Ann Woodward faced. After 12 years with Ogilvy, she was ready for a change. Having already visited 23 countries, Ann was an intrepid globetrotter. The sluggish economy presented an opportunity for her to slip away for some extended travel. So she sublet her Manhattan apartment and jetted off with a list of new places to see – Jordan, Thailand, Vietnam, Cambodia and India.

That was October and Ann is still traveling!  Maybe she’ll be back in… April? It depends. Facebook Timeline may have been invented just for her. Her profile page looks like National Geographic and she writes a fantastic travel blog:

As the pictures roll in from exotic places like Beirut, Siem Reap, Ho Chi Minh City, I think: “WTF, that’s what I should be doing!” but also…

JS:       Why are you glad you did this?

AW:      It used to bother me that Southeast Asia was a huge gap on my travel resume, so I’m very happy to finally be seeing this part of the world. I’m discovering how amazing slower travel can be. There’s no rushing around, trying to compress as much as possible into the typical American vacation timeframe of 1 or 2 weeks. I can stay longer in a place if I like it, and stop somewhere I hadn’t originally planned if I hear good things about it.

I’m also receiving positive feedback that my photos and my writing are helping others learn something new or think differently about a place. It’s rewarding to know that sharing my experiences helped shift someone’s perceptions. This is particularly important for regions that are very misunderstood, such as the Middle East.

JS:       What’s your best trip experience to date?

AW:      Loi Krathong celebrations in Chiang Mai, Thailand. During this festival, it’s customary to launch lanterns on the river and into the sky. As your lantern floats off, it supposedly carries away your negativity and misfortunes. Being surrounded by thousands of locals releasing lanterns was a moving experience. Some Westerners participated, but unlike some festivals which have become gigantic tourist attractions, Loi Krathong felt very authentic.

JS:       What’s part of a perfect day?

AW:      I really enjoy wandering through the morning markets, where locals buy ingredients for cooking the day’s meals. The arrangements of fruits, vegetables and spices are rather beautiful, and there are usually plenty of other interesting things for sale – frogs, rats, eels, you name it!

JS:       How connected do you feel with your home and friends in NYC? How has social media changed your travel experience?

AW:      It’s been fairly easy to stay connected on the road; most places have Wi-Fi. However, I made a conscious decision to make this trip about experiencing things. After being tethered to a Blackberry for several years, I don’t want to spend endless hours trapped in a hotel room with my laptop.

I use Skype to call my mother about once a week. I’ve been a heavy Facebook user for over 4 years; it’s the main way I communicate with friends back home, as well as fellow travelers I meet along the way. Social media has definitely impacted my trip in positive ways. Before I left New York, I began following lots of travel bloggers on Facebook and Twitter. This enabled me to easily ask them specific questions about places they’d gone and where I was also planning to go. A few times, I realized I was in the same city at the same time as a blogger and we were able to meet in-person.

JS:       What advice would you give to others wanting to travel?

AW:      For those seriously considering a career break or sabbatical, visit, an incredibly helpful site where you can read other people’s experiences for inspiration and find useful logistical information for trip planning.

For everyone else:

  1. Get a passport. Only 30% of American citizens have one! If a cool travel opportunity crops up, at least you’ll have the proper documentation.
  2. Use your vacation days. The average American worker earns 14 vacation days a year but only takes 12. A former boss told me, “No one ever remembers the vacation days you never took.” Sacrificing your vacation for work is unlikely to advance your career.
  3. Do things in your own town. Visit a neighborhood you’ve never gone to, try a type of cuisine you’ve never eaten before, or explore an unfamiliar park. There are endless cultural offerings in New York City (concerts, theatre, museums, etc.); many are free. is a good source of ideas.

JS:       How will you know it’s time to come home?

AW:      I have a budget for this trip. I’ll know it’s time to head back when the money runs out!

JS:       Has your travel experience changed what your next life chapter will look like?

AW:      Of course, I think it would be difficult to remain unchanged following a journey like mine. The dynamic nature of extended travel is teaching me to be more flexible and patient in dealing with other people and unexpected situations. And though I considered myself to be pretty minimalist and unmaterialistic in New York, living out of a backpack definitely demonstrates how little stuff a person actually needs.


 Drool over Ann’s travel

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