From Desk Job to Dream Job: A true story of leaving the cubicle for Cuba

January 30, 2017 | By | 4 Replies More

What I’m about to share may seem like fiction, but I’m disclosing it to convince you that by taking risks, being adventurous, and believing in serendipity dreams can come true.

Six years ago, I would daydream from my cubicle about travel. It didn’t matter where. I would escape my cluttered desk of press releases and marketing pamphlets to a tropical beach, canyon, enchanted forest, or other adventure.  At the time, I was a Vice President of marketing and public relations for a start-up company in Fort Lauderdale, Florida. My commute was fifteen minutes. I was well paid. I even liked my boss. However, I wanted more.

Over an impromptu holiday long weekend, I decided to embark on a solo adventure to an island that repeatedly appeared in those cubicle daydreams, Cuba. Everything that I pictured about Cuba was true: the explosion of colors, music in the streets, the aroma of cigars, and a rolling museum of classic 1950’s American cars. However, I didn’t expect to fall in love. Now don’t get the wrong idea, I didn’t fall head over heels for a Cuban lover, although muchos tried. It was the culture, its people, and this contagious vibe of happiness that got me. On New Years Eve, underneath a Banyan tree with a mojito, I made an audacious resolution to architect the job of my dreams, a hybrid career of traveling and writing.

The maiden voyage to Cuba was the start of a new life, a new career, and ultimately leaving my desk job behind. It didn’t happen right away, but all of my decisions led to receiving a call only two months later. At my desk covered in manila folders and dozens of Post-its, I received a call from a former colleague. After seeing my pictures from Cuba on Facebook, she approached me with an offer I couldn’t resist, leading educational tours in Cuba for Americans.

The lifestyle would be on the road with less pay, but with more free time to write. Although risky, I jumped in with two feet, quitting my desk job and heading to Cuba. Often times, I look back on that decision as the turning point to my Life 2.0. All the decisions, studies, travels, and jobs I had previously done or made paved the path for this hybrid position.

Since, I have led nearly thirty educational tours to Cuba, visiting Cienfuegos, Trinidad, Varadero, Viñales, Santa Clara, Bay of Pigs, and of course the capital of Havana. In a mobile classroom, I have guided hundreds of adventurous travelers through the often times complicated lessons on Cuban history, politics, education, religion, and more while enjoying its cuisine, libations, music, and dance.

Although life on the road is the hardest job I’ve ever done: 18-hour days, unpredictable outcomes, and many scary moments: hurricanes, hospital visits, and lost passports, it continues to challenge me. I have been able to witness Cuba in transition. Just like my transition to Life 2.0, Cuba is in flux and becoming her own Cuba 2.0. From that Banyan tree years ago, I couldn’t have imagined the role Cuba would have on my life, but also I didn’t understand that I as well as all the travelers that have come with me have helped Cuba transform into her next phase.

I share my adventures in Cuba and beyond in my latest book, Cubicle to Cuba. Through down-to-earth, short, and sassy vignettes, Cubicle to Cuba will teach you about Cuba, but also inspire you to think outside of the cubicle, travel more, and live a life full of adventure.

What’s your next adventure?

Perhaps it is writing your own book or traveling to a far-flung place. If you are interested in traveling to Cuba with me, come along for the ride in May or October 2017. I’d love to show you around the once forbidden island.

Here’s to looking up!

Heidi Siefkas

Author, Speaker, Adventurer


Category: How To and Tips

Comments (4)

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  1. Julia Gibbs says:

    I am so inspired by this – well done, you! When I am free from family obligations, I hope to go and live in Spain full time. I look forward to reading your book.

    • Awesome adventure! I love Spain. I feel like I became an adult in Spain. I studied in Madrid for two years when I was in college. It changed my life. The appreciation of life outside of the home (getting out in the community and eating/having coffee in your barrio) was eye-opening coming from small-town America. I came back to the States after my time in Spain, but I continue to return. In fact, my accent is so Castillian when I’m in Cuba, most think I’m Spanish.
      Here’s to looking up!

  2. Thank you Women Writers for the opportunity to share my story. I do so to inspire others to think outside of the cubicle, travel more, and live a life full of adventure. My path was not without hiccups and tremendous obstacles. Check out my other books: When All Balls Drop: The Upside of Losing Everything and With New Eyes: The Power of Perspective.

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