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

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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. 

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.