From Desk Job to Dream Job

My New Office Has Windows to the World

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.

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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.

This hybrid career works for me, but this is certainly not a cake position. It has some tremendous perks, but also there are sacrifices.

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.

Get to travel and meet new people

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I consider the more people you meet and cultures you know the richer and smarter you become. Some of the most intelligent people I’ve met are not only multi-degree holders, but also they put a high priority on travel.

The número uno perk of a life change like mine is that you get the best education. I tell many that traveling is better than any Ivy League education.

The número uno perk of a life change like mine is that you get the best education. I tell many that traveling is better than any Ivy League education. You invest in travel, but continue to reap the benefits for a lifetime. So if there isn’t a traveler’s alma mater club already, I’ll start by saying: Hi! My name is Heidi. I’m a perpetual student and traveler. Carpe diem and that next trip and lesson!

Not the same every day

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There is no set routine when guiding a tour. This means you have to be flexible. Regardless of itinerary or how you travel, you have to let travel happen, which means there may be clinic visits, an impromptu photo opportunity, a brilliant sunset or flat tire that delays the trip, or pouring rain that make it impossible to see the only performance of a world-renowned company while in a bucket list destination. Of course, not all of the changes will be positive, but you also need to become the master of spin, which is not just for public relations professionals anymore. As a leader of the group, you never can let the group see you sweat. Your spin of a situation is crucial.

Opportunities present themselves for YOLO

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After returning from a trip to Cuba, I was presented with something I couldn’t refuse, a trip to Machu Picchu with another company. Although I wasn’t an expert in Peru, I would quickly become one of the most resourceful guides, including tapping my three great Peruvian girlfriends about their trips to Lima, Cusco, and Machu Picchu, Trip Advisor, guidebooks, videos, and hitting the streets with my morning jogs to get the lay of the land.

Because I seized the opportunity, I celebrated a major anniversary amongst the mystique of Machu Picchu. Nearly four years earlier, I suffered a major accident, breaking my neck. What would highlight my personal triumph more than climbing Huayna Picchu? I couldn’t think of anything better. I was surrounded by the magical essence of Machu Picchu and sharing it with new people. I missed my family and friends, but I knew they were with me in spirit.

Not 9-5, but there are still deadlines

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Tour guiding has a longer, more grueling schedule than 9-5. I typically think that the schedule is roughly 18 hours a day. You are the first awake and one of the last to go to bed. After everyone else goes to bed, you are preparing for the next day, whether tip envelopes or booking activities. With fewer hours for shuteye, you need to be a good sleeper under any conditions (hard bed vs. soft bed or noisy disco vs. traffic outside).

You might think that while tour guiding there is time for writing, but there is not really much down time. Although a leisurely lunch with the group is enjoyable, you are a participant, but not thoroughly relaxed. You are looking to see that everyone has their food first, seeking for a great photo of the group eating, or dealing with a bit of traveler’s diarrhea yourself. Yes, you are not immune to it either. In order to capture story ideas, you need to carry a small notebook or just add a note in your iPhone for thoughts that you can develop at another time.

Also, it is important to note that although the trip ends for your guests when they arrive home, your job is not done until the paperwork is completed. You will be working on your expenses, internal company reports, and in the case of legally bound trips like those to Cuba, a government report and hundreds of pictures to be submitted. It typically takes three days after arriving that I feel that I am done with the paperwork, phone calls, and well getting back into a normal “home” routine.

You miss birthdays, holidays, and anniversaries

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If you travel a lot, you will miss important holidays. You may even be missing your own birthday or special anniversary while on the road guiding or seeking the next article or book idea. Once again, you must remember that communication is much easier than it once was with the addition of Facebook, Skype, and Viber. You can, with relatively little money and time, send out a quick message or call that you are thinking of your special someone. Yes, it doesn’t completely make up for not being there, but you can bring back a lovely gift from an alpaca rug or shell lei to a musical CD that will kick off your in-person celebration with your friends and family upon your return.

You have great content

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When you are observing the world from another vantage point, you will constantly be creating great stories with amazing photos and videos. Plus, you will be collecting recipes of your favorite drinks and dishes while growing your global music repertoire. All are timeless souvenirs.

Like all change, this too was a gamble. I put everything that I knew on the line: predictable daily grind schedule, water cooler chats, regular paycheck, and an easy 15-minute commute.

For me, I needed something that allowed me to participate in what I loved from outside of the four walls of an office and/or cubicle rows.

For many what I just described is comfortable. However, for me, I needed something that allowed me to participate in what I loved from outside of the four walls of an office and/or cubicle rows. My new office is mobile. Sometimes it is a bus or a train. Other times my office is a favorite café or bar to snag an Internet connection and time to write before repacking for my next journey. Here’s to more good times and good stories from my remote office located in Kauai, New Zealand, Australia, and more this year.

Read more about people who gave up their 9 to 5’s for a life of travel:

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