Meet Sherry Ott, a corporate cube dweller turned nomadic traveler

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Meet Sherry, a corporate cube dweller turned nomadic traveler. Sherry travels to off-the-beaten-path destinations to bring you unique travel experiences, adventures, and photography from around the globe. But it’s not just about travel, it’s also about life experiences of a solo female wanderer. Sherry Ott, in 2006, at the age of 36 quit her office job in NYC to travel the world.

On your website you describe yourself as a digital nomad and ‘homeless’ since 2006. What made you take the plunge to give up a conventional ‘home’ and hit the road in 2006?

In 2006 I simply needed a break and I thought that taking a year off and taking a career break would be a good chance for me to get out of my routine, see the world, and think about what it was that I wanted to be doing in the future.  I wasn’t sure if I wanted to stay in IT or do something different – but I knew that I could never make that decision until I stepped away for a while.

Having had an office job - did you manage to plan in many trips around your 9-5 before you left your job?

I got my first passport when I was 30 years old, so I was a ‘late bloomer’ in the world of travel. Most of my corporate positions only provided 2 weeks of vacation for the year and I always used every bit of it – however it was very difficult that we didn’t have more than that.  I would take week long trips to Costa Rica, Europe, or Peru, but they were always rushed. That’s one of the reasons why I took the break – I wanted to have more than just 1 week in a destination.

How did you plan your travels? Was this a long-time ambition?

I decided I wanted to take a career break and then planned for 1.5 years saving money and getting prepared to go.  I had never planned anything like this before since I was really new to this type of travel.  Vacations and travel are two different animals after all! My original plan was to sublet my apartment and travel for 1 year. However once I got on the road it took about 3 months to decide that I didn’t want this career break to end!  

Now fast forward 10 years later and I'm still traveling and have made a career out of it. I ended up giving up my apartment in NYC and have been nomadic for a decade. Currently my travel is planned around projects that I’m working on with specific destinations typically.  However there are still plenty of times when I hear of something I want to experience and then will go to that area on my own, or contact the company to see if I can work with them in some way.  No this wasn’t a long time ambition – in fact I had no idea that I would end up being a travel writer/blogger and travel all around the world for 10 years…never in my wildest dreams could I have imagined this. A lot of it was timing and a lot of it was my own passion for travel that kept me on the road and traveling.

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Was every trip intentional or did you plan along the way?

I used to be a project manager – so planning is in my blood! However my life and travel  plan is normally only planned about 2 months out. My life is very short term in a way.  I often don’t know where I'm going to sleep or where I’ll be in the next month. I always say that the only thing certain in my life is uncertainty.

What was a particular highlight from your latest trip? Where did you go? Was there anything you found peculiarly interesting?

This winter I had the privilege of traveling to Antarctica via the Ross Sea.  It was a highlight because I left from New Zealand on a very small ship (40 passengers) and we traveled to the Subantarctic Islands (read me) , through the Southern Ocean for 6 days and to the Ross Sea in Antarctica (read me) .  We followed the path of the historic explorers and it really felt like I was on an expedition. My highlight was sitting among thousands of King penguins just observing them for hours. The whole journey took a month.  This is a route that very few people get to do and that is exactly why I found it interesting. The wildlife, landscape, and remoteness of it all was epic. I loved being on the ship for a month and being able to see this pristine and seldom visited side of Antarctica was such a gift.

What advice would you give to women who may read your stories and be filled with inspiration but don’t know where to start?

The first place to start if you want to travel is to set a date…then everything falls into place from there. I’m also the type of person who gets motivated by saying things aloud to other people – so I would suggest that you start telling the world of your plans – it will likely hold you to keeping your plan! I also suggest you get involved with your local travel meetups so that you can start to surround yourself by people who love to travel, can provide advice, and be your cheerleaders.  

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What’s the best thing about yourself you’ve discovered whilst adventuring?

I am so much more capable than I ever imagined. You really never know how capable you are until you test yourself.  We often take the safe, predictable routes, never testing ourselves.  But I love to do adventures that scare me or I’m intimidated by – such as the Mongol Rally (driving a rally car from London to Mongolia).  I love adventures that push me and put me right on that edge of not knowing if I can do it. Then when you do accomplish it, you feel invincible!  After all, if you know you are going to make it – then it’s not really an adventure is it?

Have you ever been placed or chose to be placed out of your comfort zone, and astounded yourself to what you were capable of?

All the time!  I lived abroad by myself in Vietnam, I walked 500 miles across Spain on the  Camino de Santiago (read here), and I did the Rickshaw Run driving a little auto rickshaw across India for 2000 miles.  I’m sort of addicted to epic adventures to intriguing places! However, I think the biggest way I have astounded myself and got out of my comfort zone is simply by living without any home for 10 years. It is harder than you can ever imagine. And I'm not 23…I’m 47 and a life constantly in motion is exciting, but it’s not easy – and it’s not for everyone.

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Does anywhere ‘feel like home’?

Yes – I feel like I have a lot of ‘homes’ around the world; NYC, South Dakota, Girona Spain, Berlin, Brussels, Ho Chi Minh City, and Denver to name a few. These are generally the places where I stay the most often in between travels or have the most friends/relatives there; something that makes me keep going back!

Since 2006, where have you resided for the longest period and why?

I guess that would have to be Ho Chi Minh City.  I lived there for an entire year in 2008/2009.  I went there to experience expat life and I wanted to learn how to ride a motorbike (read here)  in what I thought was the craziest motorbike culture in the world!   However since 2009 – the longest time I’ve ever been in one place has been maybe 1 month and that doesn’t happen very often.  On average I move every 3 to 4 days in a typical year.

Have you ever felt scared or intimidated whilst venturing out into the world and the great unknown as a woman traveller?

Honestly no.  In all of these years of travel I have not had anything bad happen, or have I ever felt really unsafe. I think so much of it is being smart and not putting yourself in questionable situations.  I do have my moments where I feel isolated though. That’s why I often travel with companies who do small group travel such s Intrepid.  They are great for female solo travelers who want to go solo but not alone.

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Tell us a little more about Ottsworld - a blog which has turned into a ‘business’ for you. How do you use your blog to generate ‘work’ whilst on the road?

I make very little money actually blogging (a little affiliate revenue and that’s it), but it is my blog that gets me other work that helps me make a living. That’s an important distinction. If you are ready to start a blog and think you are going to have money rolling in with advertisers and affiliates, then you’ll probably be disappointed. Sure, there are some people who make money blogging – pure blogging – but they are in the minority. Instead I use my blog to show that I’m an authority in travel and to get me other work.  I do a lot of influencer projects and social media projects – meaning people pay me to go to destinations to cover them on my blog and social media accounts. It has taken years to get to that point though – in the beginning no one would pay me!

I also do freelance writing, teach others how to blog, run social media for small businesses, I create travel content for other companies and sites, and I sell photography.

You also launched ‘Meet, Plan, Go’ - which inspires individuals and advises them through career break planning. Can you tell us a little more about that?

It’s a website that inspires and teaches mid career professionals how to take a career break and travel.  It basically helps you make sense of how to put your adult life on hold  (home, pets, career, stuff, etc) for a bit and how it can be life defining and not life defeating. We also talk about how you can then take those travel and career break experiences and market them back into your job search when you are finished with your break!  It’s a super community! It’s where you’ll find your ‘cheerleaders’ to help you take the leap!  

We occasionally hold in-person events (meetups and workshops), however I’ve been so busy with Ottsworld lately we didn’t do one in 2016!

Any words of wisdom or inspiring rally cries you’d like to share with our ‘She Went Wild’ women’s network?

I live by the mantra – “Conform and be dull” – and I think that’s what drives me to do many of the unusual things I do.  If you don’t want to follow the path of everyone else – then make your own way.  It’s ok to veer off the social norms (marriage, kids, owning a home, working until you retire in a job you hate), because once you step outside those norms you’ll find there are many other people also making their own way.

Interview by Sabine Zonderland

You can follow Sherry below:

Website: www.ottsworld.com

Facebook: /OttsworldTravel

Instagram: @ottsworld