I Told My Boss I Bought a One-Way Ticket to Kenya and Wasn't Coming Back


Sometimes quitting your job is the best career move you will ever make. (Photo: Sherry Ott)

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Who: At 36 I decided to fight the career burnout battle with a one-way ticket out of the country. I was in a job that wouldn’t let me take more than one week of vacation at a time, which kept me on a tight geographical leash. I was exhausted with living the addictive NYC lifestyle, working in the IT industry, and constantly being on call for a job I didn’t love. I hatched a plan to quit my job, take a career break, travel solo around the world, and figure out the next steps in my life and career.

How: I sat in my boss’s office for my performance review and finally said the words I was dying to say, “I’m going on a vacation to Kenya on a one-way ticket and not coming back.” My boss was perplexed. After all, he was about to deliver a glowing performance review complete with stock options and a raise, but I hijacked our conversation with this shocking news of my departure.


The author on a trip to Mongolia (Photo: Sherry Ott)

I still remember the moment when I sat in my Upper West Side apartment looking around and deciding that all of the stuff that I spent my 20s trying to accumulate was all holding me hostage in a career that I didn’t really care for. I was terrified of leaving the lifestyle I had become accustomed to, but I was also terrified of the trajectory of my life and my lack of work-life balance. Eventually the pain of staying in my career path, no matter how financially lucrative it was and how good I was at it, became more painful than making the change and taking on the risk of unemployment and the dreaded gap on my résumé.

Related: 8 Tips on How to Quit Your Job and Travel the World

My biggest challenges: My road from contemplating a career break to actually getting on a plane and making it happen was fraught with doubt and worry. I think I am the only person who has left on an around-the-world trip for a year who was crying when I got on the plane. They weren’t tears of joy — they were tears of fear. I wasn’t a traveler; in fact I didn’t even have a passport until I was 30. I had no idea how to plan such a trip, and in 2006 there weren’t the plethora of resources that we now have online to ease those concerns. Each planning decision seemed insurmountable, figuring out insurance, giving up my cat, subletting my apartment, and especially determining where to go and what to do. Don’t even get me started about the worry over what I was going to do when I came back a year later! Even though I was about to embark on an adventure most people daydreamed about, I was still uncertain of my path ahead.

Where I went: My career break journey took me to 23 countries over 16 months. I went completely off my original plan and ended up spending the majority of my time in Asia. I visited countries that had never been on my radar before such as India, China, Borneo, and Laos. As I traveled more, I slowly learned what I liked and didn’t like. I gravitated to more undeveloped countries, and I couldn’t get enough of Asia or the food. I originally thought I would end my travels by going through Europe; however, as soon as I got to Europe, I knew it was no longer interesting to me, so I went back to Asia.

What I learned: There was nothing routine about my life in those 16 months. Each day I learned something new — even if it was just realizing what an amazing feeling it was to get eight hours of sleep a night regularly. It opened my eyes to new ways of doing things, and it showed me I was capable of much more than being an IT manager. Most importantly, I had time to contemplate my wants and desires without the constant buzz of my BlackBerry and overscheduled day. Of course, it was a bonus that I could contemplate these things while gazing at the Taj Mahal. The most important thing I learned was that I knew I didn’t want to go back to what I was doing. The career break needed to be a career change.

Related: I Quit My Job to Visit All 50 States in 365 Days


Sailing lessons in Italy (Photo: Sherry Ott)

How I changed: I loved being on the road, writing, and doing photography. I knew I didn’t want my travels to stop, and I would need to consider how I could make a living and keep it going. As I moved around the globe, slowly I tapped into something that I thought I had lost — creativity. I found something that I didn’t know I had — an entrepreneurial side. But most of all, I learned how to be confident in my abilities and cherish them instead of dismissing them. I emerged with the desire to help others escape their own burnout and reap the benefits of travel. I decided to start a career break company geared toward helping others make and plan the leap — Meet Plan Go.

My advice to others who want to escape burnout by traveling: There’s never going to be a perfect time to go, there will always be excuses, and people will always think you are crazy. Pick a date and work toward it. Surround yourself with others who have done it or have a similar interest. There are tons of websites and meetups focused on around-the-world and career break travel — go find those people and let them fuel you during your times of doubt.

Related: Losing a Friend on 9/11 Inspired This Guy to Bike Around the World


The author in Laos (Photo: Sherry Ott)

My career break tips: Don’t go crazy and plan your whole trip. Just plan out the first third of your trip and leave the rest open. You will learn so much about yourself and what you like and don’t like. Also — go slow. Don’t rush your way around the globe. Pick fewer places and stay a while. Get an apartment so that you can be more immersed into the local culture. If you try to fit too much in, you’ll get travel burnout just as bad as your career burnout. You don’t want to come home exhausted; you want to come home refreshed.

Most memorable moment on my journey: One of my favorite things I did on my trip was never on my radar when I did my initial planning — volunteering and teaching in India. I discovered that I loved teaching and working with young adults.


Teaching in India was a surprisingly rewarding adventure. (Photo: Sherry Ott)

Related: Real Travel — I Fell in Love in an Ecuadorian Jungle

Next location:

After that initial trip, I came back to the U.S., sold everything I owned, and kept going — to 40 more countries, touching all seven continents over the course of seven more years. I still run Meet Plan Go and hold events to teach others how they can take a career break. I do travel writing and photography. This fall I’m off to Ireland to do a solo road trip along the Wild Atlantic Way.

Sherry Ott is a refugee from corporate IT who is now a long-term traveler, blogger, and photographer. She’s a co-founder of Meet Plan Go, a website offering career break or sabbatical travel inspiration and advice. The next upcoming event is on Sept. 20 in NYC.

She also runs an around-the-world travel blog about her travel experiences at Ottsworld.com.

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