Desk Job to Dream Job – My New Office Has Windows to the World

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When I made my decision in 2013 to officially leave an executive level desk job conveniently located just 15 minutes away from my home to become a freelance writer and tour guide, I made some heads turn. Not only was I taking a gamble, but by colleagues I was viewed as taking a big risk financially and professionally.

Let’s face it. Change is not everyone’s friend. Most are deathly afraid of even slight change. And this was major. To top it all off, I was going to be spending more than half of the remainder of the year in Cuba, a place that is considered to be the forbidden fruit of the Caribbean for Americans.

At the time, I thought I knew what I was getting myself into: traveling a lot, meeting new people, being a 24/7 concierge, and viewing the world from something much better than a cubicle or a desk. My new perspective would be via foot on the cobblestone streets of Trinidad, the Sleeping Beauty of Cuba, in a bus near the Bay of Pigs on the Caribbean Sea, or in a classic, convertible cab along the Malecón in Havana. However, with all of that said, I didn’t know all that I was getting myself into.

I would like to share with you what I have found, the pluses and the minuses of my change. This hybrid career works for me, but this is certainly not a cake position. It has some tremendous perks, but also there are sacrifices.

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