No direction home – a conversation with professional nomad Sherry Ott

Sherry Ott headshot
Travel blogger Sherry Ott is a leading voice in the emerging career break movement in North America. A self-described “corporate American runaway,” she’s been traveling full time for over seven years. (Photo courtesy of Sherry Ott)

When travel blogger Sherry Ott quit her corporate IT job in 2006 to travel the world, she thought she was taking a temporary break from her fast-paced life in New York City. But after a few months on the road, Sherry realized she didn’t want to return to that life. She’d fallen in love with traveling.

Sherry eventually found a way to keep going. In 2008, she moved to Vietnam and taught English for a year. All along she was building her blog, Ottsworld, which chronicles her intrepid existence. By 2009, she noticed she had “itchy travel feet” again, so she packed up her suitcases, left Ho Chi Minh City on a one-way ticket and became a radical nomad. In the ensuing years, she discovered how to parlay her wanderlust into a new career as a professional adventurer.

It’s worth noting that Sherry, now 43, didn’t get her first passport until she was 30. Throughout her early adulthood, Sherry’s major life decisions were driven by “the idea of security and setting myself up to have some sort of perceived ‘control’ over my future.” This attraction to safe choices motivated her to become an accounting major. But by the time she pulled the trigger on quitting her six-figure job, Sherry’s curiosity about traveling the world had trumped her fear of becoming a bag lady.

When Sherry was plotting her initial career break, she had to figure everything out herself – from where to buy travel health insurance to how to tell her boss that she was quitting. So to help make the process less lonely and confusing for others, she co-founded an organization called Meet, Plan, Go! that offers practical tools and social support to aspiring career breakers.

I recently had a chance to catch up with Sherry while she was in Minnesota visiting family for the holidays. Now that I was newly-returned from my three month career break to South America, I wanted to talk to her about the challenges of reentry and how she experiences travel differently now that she’s been on the road for so long. What follows is an edited version of our December 2013 conversation.

Sherry Ott, Ottsworld
Sherry Ott in her element in Chile, 2013. (Photo courtesy of Sherry Ott)

Q: You quit your job and took a 16-month around the world career break in 2006. While you were still on that trip, you realized that you didn’t want to go back to your old life in New York. What did you fall in love with that you wanted to keep doing?

Sherry (S): I liked the process of constantly seeing something new everyday. And maybe I was so bored in my old life of commuting, going to work and seeing friends. It was a very fun life but there was nothing that surprised me. And nothing excites me more than when someone or something surprises me. That’s very much a piece of my character that I actually wish I could shut off sometimes. But I can’t.

Q: You’ve been on the road for over seven years. Do you still experience that sense of newness as a traveler or has travel become routine for you?

S: You know I’ve never thought about this before but it’s kind of like a drug. I don’t think I’ve ever been addicted to hard drugs but I can imagine that once you start doing them, you want more and more. And it gets harder to get that same high. There are still absolutely those moments where things will utterly surprise me and mystify me and confuse me. But it happens less. So sometimes I feel like I have to go further and do crazier things to get that feeling.

Q: You were just saying that you wish you could turn this part of yourself off that needs to be surprised. Why?

S: Because I wish sometimes I could just be happy with the status quo. Because life would be so much easier, wouldn’t it? I would probably still be in New York working. But instead I’ve chosen this path that is fulfilling, super-exciting, what everyone probably wishes they could do. But it’s not an easy path at all. And so you have your ups and downs.

Q: It’s been over seven years since you had a home. Do you have a longing for a physical home? What does home mean to you now?

S: Honestly, I don’t know if I know what home is. Home is when I’m happy. And I don’t know that it’s a place. It’s definitely a feeling. It’s when I’m around my friends and family and can be myself — when I feel comfortable. But I can feel comfortable in a lot of different situations.

I would like a place where I can unpack and hang up stuff for a while and not have to always think about where I’m going to sleep next or how long I can stay in a certain place. That gets exhausting. I talk about hangers. I love hangers and being able to unpack my toiletries. That’s so nice I can’t even tell you. When I’m on the road, the majority of the time I’m staying with someone. So I’m constantly trying to make as little of an impact as I can in their lives. I feel badly because I do this everywhere and so I start feeling self-conscious. So it’s more of a mental thing for me. I’m trying to constantly be a good guest.

Q: And that’s tiring.

S: It can be. Because you know what? Sometimes I just want to leave my shit out and not clean up right away and not have to worry about being in the way.

Travel blogger Sherry Ott does not have a permanent address. In 2013, she slept in 107 different beds all around the world. (Photo collage courtesy of Sherry Ott)

Q: You co-founded an organization called Meet, Plan, Go! that provides community and practical support to people who want to take career breaks. The messaging around Meet, Plan, Go! is ‘Don’t stay stuck in your cubicle. There’s a whole bigger world out there. Go and experience it.’ You’ve been out of a cubicle for a long time now. Do you still relate to the ‘escape from your cubicle’ message?

S: Yeah, I absolutely relate to the idea that change is good and you do need to figure out how to make change and take risks in your life. And I think when we’re in the cube, or in our normal career we start to define ourselves by that career only. We can’t think out of the box to figure out that we have other talents. One of the things a career break can do is make you realize that your possibilities are way larger than you could ever imagine. But you’re not going to see that until you step out. So in that sense, it’s the same for me right now. I’m sitting here kind of stuck thinking, ‘Well I’m this blogger. How do I change that? Am I always just a blogger or can I do other things?’ And even I have trouble seeing that now. Which is why you need a tribe.

Q: What do you feel like you need to do now and what tribe are you seeking to help you get there?

S: God, I have no idea! What do I think need to do? I need to have more stable income. Being on the road for this long has certainly thinned out a lot of my relationships. I need to figure out how I can feel like I’m not sitting out on an island and build those relationships again a little bit more.

Sherry Ott quote

Q: How does your life work financially? I remember you telling me that you live on about $15,000 a year. My understanding is that you have a mix of sponsored travel and then Meet, Plan, Go! is a business. I assume you earn some money from your photography and blogging. Are there other pieces to your financial life?

S: Yeah, a few. But you’re right. The blogging makes some money from advertising. There are some projects that I actually get paid for that have to do with social media marketing campaigns. But none of this stuff alone is enough to sustain me. Yes I sell some photography. Occasionally I’ll do some consulting. But that’s a hundred bucks here and there. But that’s kind of my life. I also run a Facebook page for another company. It’s all little stuff. Honestly, there are two big pieces that make my life work. One is that my expenses are really low. That’s why I don’t have a home. It’s expensive to have a home and it’s much easier for me to continue to rely upon friends and family than to have to pay rent. But my expenses are low because about 50% of my travel is sponsored.

Q: Who sponsors you? Is it tourism boards, tour operators, chambers of commerce?

S: It’s all of the above.

Q: What does it mean to be sponsored?

S: It’s paid for. A dime doesn’t come out of my pocket. For example, this coming year I’ll be going to Australia. I’m not getting paid for that. But I’ll be flown out there by Tourism Queensland and put up for two weeks. All of my food and living expenses will be covered. What I’ll probably do is parlay that airfare into a longer stay and go to Tasmania. So now instead of $2000 to get out to Australia I’m really just spending a few hundred dollars to travel within the country or region.

Q: Why would someone want to sponsor you to come to Australia?

S: Because I’m going to write about it and I’m going to be on social media talking about it. It’s not that I’m just going there to sit around. It’s all work. So what I’m doing is trading. It’s bartering. That’s a big part of how I live. I told you there are two things that make my life work financially. Keeping expenses low is one thing. And then the other thing is I get gifted money from my parents every year. They’ve been doing that since I was 25. That amount isn’t huge but it helps to sustain me. Any one of those things alone could never sustain me, even in my very cheap, non-expensive life that I live. But if you put all those things together, it works. If one of the things went away, it would put me under a lot of stress.

Sherry Ott in Antarctica
Sherry Ott in Antarctica, 2012. For years, it was her dream to visit Antarctica. Ever since she realized that dream, she’s been asking herself, “Now what?” (Photo courtesy of Sherry Ott)

Q: You had this dream all these years ago, which was to travel around the world and you made that happen. What is your dream now?

S: Oh boy. I don’t know. Ever since I went to Antarctica I don’t have an answer for that. My dream was always, ‘I want to get to Antarctica.’ And then I got there a year ago and I came back and I’m like, ‘Now what? What is my dream now?’ I think it’s always to just continue to live a life that’s unique and different and inspiring and not be afraid. Because even though I go and I travel all over the world and I have this weird unconventional life, I’m still scared of things. I need to push myself in areas where I know I should be pushing myself. And whether that’s doing more print writing or consulting or presentations and public speaking — whatever that is — I need to do that. My dream is to be true to myself and continue on a really unique and different path, but have it be sustainable so that there’s a little bit more security. Yet I don’t need a lot of security. Security isn’t necessarily the end-all-be-all. I know that from going all around the world and seeing how people with less money (compared to how we live here in the U.S.) are the happiest. It would be nice to have a little more security but sometimes I think not having it is what keeps me going. Because you’re always reaching–

Q: You mean not having security keeps you going–

S: Yeah.

Q: You’re not complacent.

S: Definitely.

Q: Or too comfortable.

S: No I’m too comfortable (laughter). I always say when you freelance you become really scrappy, which is a good trait to have. But it’s hard to be scrappy all the time. My dream is for a few moments–like for a few weeks or a month–where I can just sit back and not have to be scrappy or worried. Just for a little while. And then I’m fine. It’s like a boxing match. You need the bell to ring and I need to go sit down for a little bit. I need someone to wipe my brow, give me some water, and then I’m back at it.

Q: So you need a break from living the life of a career breaker…

S: You asked before if I relate to being a career breaker. I’m not anymore.

Q: You have a new career.

S: Yeah, I don’t know what I am anymore. But yeah I can’t say I’m on a career break still. But I do always refer to that first 16 months as my career break because that’s really what it was.

Sherry Ott Mongol Rally
In 2011, Sherry Ott participated in the Mongol Rally, a 10,000 mile road race from London to Mongolia. Ott says she has to “do crazier things” to experience a sense of surprise as a traveler. (Photo courtesy of Sherry Ott)

Q: Is there anything we haven’t talked about that’s on your mind?

S: On the topic of a break–with our lives getting so plugged in and busy, our answer has been to work more and more and make ourselves more available so we can get more things done. But the problem is there’s always only going to be 24 hours in a day and that’s it. And at some point I think the whole tide is going to turn and we’re going to figure out that you can’t make time. So what have you got to do? You can renew energy. And so I think that’s why there’s a need for career breaks, sabbaticals, whatever you want to call them. We need to let the bell ring, step over to the side and sit down for a second. That’s important because that actually helps you rebuild energy. And that’s what you’re going to need to just live in this world. Otherwise I think we’re just going to self-destruct. The other thing I would say just on the topic of fear. Everyone’s always scared.

Q: Here in the United States?

S: Yeah–well we’re scared to take this leap right? We have a lot of fears. And fear can paralyze us. We think about everything that can go wrong. And I always love to challenge people to take an equal amount of time to allow yourself to think about everything that could go right. I wish that every time we sat here and thought, ‘Oh my gosh, is it dangerous? Am I hurting my career (if I take a sabbatical)?‘–all these things that we’re scared about–being alone–whatever it is, what if we think about all the things that can go right for a while? There are so many things that can go right. You unearth a talent that maybe you had as a child but never pursued. You figure out you believe in God. You meet your future husband or wife or whatever it is. There are all kinds of things that can go right and we never think about it. I wish we could all do that exercise.

You can follow Sherry Ott’s unfolding adventures at Ottsworld. One of her upcoming escapades in 2014 is the Rickshaw Run, a 2,000 mile race from Southern to Northern India. Sherry will be raising money for charity:water. She doesn’t know how to drive a rickshaw…yet. But she’s confident she’ll figure it out.

3 Replies to “No direction home – a conversation with professional nomad Sherry Ott”

  1. I’ve read several of your interviews – I think this one is my favorite! I, too, am wondering, “What’s next?” I’m nearly paralyzed by indecision, the inability to figure that out. Unmotivated to work (well, that’s getting better, thank god!), and I am also “homeless and jobless.” It’s scary; I’m trying to embrace that freedom vs. clinging to the idea of home and hearth as the only form of security. For years, I’ve wanted to temp for a living so I could have the time to travel. But I also want that security of a lease. What a conundrum! It’ll all work out somehow, I’m sure…I just hope it’s soon…and uncomplicated!

    1. Wynne – One of the things I learned from Sherry (and others) is to act first and reflect later. In other words, give yourself permission to try something so that you can move beyond paralyzing indecision into the realm of playful experimentation. After her career break, Sherry decided to get her CELTA (Certificate in Teaching English to Speakers of Other Languages). This was her initial plan for moving abroad and having a way to support herself. She doesn’t make a living teaching English now, but it’s how she first got started on her nomadic path. Roman Krznaric, author of “How to Find Fulfilling Work” also talks a lot about the “act first, reflect later” approach to life and career change in ways I think are extraordinarily helpful. You can learn more here:
      Good luck, Nancy

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