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

From Desk Job to Dream Job 

My New Office Has Windows to the World

Desk Job to Dream Job by Heidi SiefkasWhen 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.

Get to travel and meet new people

Dream Job by Heidi Siefkas Havana CubaI 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. 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

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

Desk Job to Dream Job Heidi Siefkas in PeruAfter 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

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.


In order to comment on, you'll need to be logged in. You'll be given the option to log in or create an account when you publish your comment. If you do not log in or create an account, your comment will not be displayed.