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Introducing Your Career Break Role Model

Travel blogger and photographer Sherry Ott was 30 years old before she got a passport and went abroad for the first time. Now, a few years and more than a few countries later, the former IT manager has firmly traded corporate conformity for the freedoms of the road.

In addition to writing her blog Ottsworld, Sherry is a co-founder of the online community Meet, Plan, Go!, which provides inspiration and resources for those who might be thinking about a detour from corporate life. We caught up with Sherry—who is also an AFAR Ambassador—in between trips to talk about roadblocks, role models, and how Meet, Plan, Go!’s upcoming nationwide event on October 16th will help turn dreamers into travelers.

Meet, Plan, Go! is a resource for people who want to put their career on hold to travel. What sparked your own career break?
When I got out of college, I was a very focused person. I went immediately into corporate jobs, accumulating savings and trying to be the adult I thought I should be. I worked for large retail corporations in IT management, and it paid the bills. It was interesting, but I finally had to be honest with myself that it wasn’t for me anymore.

What roadblocks did you run into when you decided to take a trip around the world?
Well, I never had friends or family who traveled internationally. I wanted to do it, but I had no one to turn to. And when I started planning my initial career break back in 2005, there was no big travel blog presence or anything like that.

So I started researching and couldn’t find anything that related to all of my fears about putting my career on hold and how to address that choice with family and peers. As Americans, we think about our careers and about extended travel very, very differently from others. There were no role models who could answer my questions.

How does Meet, Plan, Go! provide those role models?
It’s important to have a place to go where you can get your questions answered, talk to people who did this, and find out that it didn’t kill their career at all—in most cases, you’ll find that it probably improved their career. I also feel really strongly that whenever you have a big, challenging goal in your life, you need cheerleaders.

As important as the digital community is at Meet, Plan, Go!, we wanted to build these in-person communities in big cities. This year is now our third year of hosting a nationwide meetup event, which will be held in 10 cities on October 16th.

What can would-be travelers take away from attending one of Meet, Plan, Go!’s nationwide events?
The events are part inspiration, part resource-oriented, and part networking. Each one will have a discussion panel, with career break veterans talking about how they got over their fears, how they saved money, and how they replugged back into their career.

We’re also going to have breakout groups in each location that will deal with specific topics. It could be volunteering, or health insurance, or packing, or it could answer questions like “What do I do with my pets?” “What do I do with my home?” Hopefully, people walk away with a huge dose of inspiration on why they should continue pursuing this “crazy” idea that they have!

In the past, ticket proceeds for your San Francisco event have benefited the AFAR Foundation.
Yes, and we’re doing that this year again. I’m a big believer in introducing travel into kids’ lives; we want to make sure that kids have mentors and can be exposed to travel early. It goes back to being role models, infusing the idea that you can go to these places.

What kind of feedback have you received from people who were inspired to take their own career breaks?
I can’t even tell you how many people come up to me after these events and say “Oh my God, I’m not crazy! I thought I was the only one who wanted to do this!” And I get emails on a weekly basis from people who are on the road, telling me how happy they are. I’ve never, ever met anyone who regretted taking that leap. Almost everyone comes back, plugs back in, and immediately starts planning their next trip. It’s not just a one-time thing—travel becomes part of your life.

It’s certainly a big part of your life! Where are you based now, and how do you choose where to go next?
I don’t have a home base now. For the last six years I’ve been traveling, and I stay on the move. On my first career break, I found that I loved traveling through developing countries, and I wanted to give something back. I looked into volunteering and it took me to India, where I taught English and computer skills.

When I came back to New York, I didn’t go back into the corporate world; I wanted to keep traveling. So I sold everything, got my ESL certification, and went to Saigon to teach English. Since then, I’ve done other volunteer work where I’m teaching ESL.

My life is very, very different than I ever thought it was going to be, but I like the freedom. Lots of times, where I go is based on a photograph. The whole reason I booked a trip to Morocco was because in Australia three months earlier, I’d seen a picture of the leather dying vats in Fes. I thought it was the most fascinating thing and decided to see it.

And then you posted a Highlight about it on AFAR.com!
Yes, and probably my favorite Highlight is also from that trip. One night when I was there, someone mentioned something about the tree-climbing goats in the south of Morocco. I didn’t believe them until they showed me a picture of it, and then it became like a pilgrimage for me—I had to find them and photograph them. People thought I was crazy, but when I finally found a taxi driver who said “Oh yes, I can take you to the goats who climb trees,” I ended up with four other people in the taxi with me! I loved the whole experience. It was just one of those quintessential travel moments for me.

Meet, Plan, Go!’s October 16 meetup takes place in 10 cities.