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Digital Nomad | CrunchyTales

Seeing the World As A Digital Nomad In Your 50s

4 min read

If you’re the type of woman who wants to live a life of freedom and adventure, maybe becoming a digital nomad, working remotely from anywhere in the world, is what you should consider. Life doesn’t stop in middle age: it’s never too late to explore and you are never too old to embark on a new quest.

Once ready, all you have to do is choose the right remote work community to travel with – as our expert, Diversity Promoter Maria Olsen, demonstrates to us with her latest personal experience. 


As quarantine restrictions eased, I took my job on the road. I’m a lawyer and this summer I lived for a month in the lovely former colonial city of Antigua (Guatemala). From there, I travelled to Belize and will soon be working from remote workspaces in Puerto Escondido (Mexico); Medellin (Columbia); and Buenos Aires (Argentina).

Plenty of people during Covid rented far-flung places to work remotely in a new location via Airbnb or VRBO, but having a community was more fun for me, so I chose Remote Year, a well-known company that helps digital nomads like me.

It provides week-long retreats, as well as trips that span one, four or twelve months. With the latter two, in particular, the organisation arranges all transportation between destinations. Some of the itineraries are regional; others hop continents. All are well-supported, with local city guides who know the location well and who are terrific resources for travellers. A plus was having an instant community as I travelled, someone I could socialize with as little or as much as I wanted.

Remote Year also organizes add-on excursions and field trips which, in my experience, are wonderfully enriching. For instance, I took two excursions that featured Mayan shamans and their families, who opened their homes for us to visit, and I felt like I received authentic insights about what it means to be Mayan in today’s Guatemala.

I visited locations off the beaten track. One time was a pilgrimage site at which sacrifices of chickens were performed; the other was a coffee farm where I had the pleasure of attending a cooking class at the owner’s home. This was an incredible place, where they used to grind their harvested beans on mechanisms powered by homemade stationary bicycles before they could afford a proper coffee bean grinder.

Some of my friends have tried other remote work travel groups. Unsettled and Hacker Paradise both received good marks. The first one is slightly more expensive, which may appeal to a different clientele, and has more short-term trips than the others I have researched. The latter organisation, instead, costs less and is more likely to attract younger digital nomads.

Of course, each company has a slightly different approach. I chose Remote Year because it had the most city hubs, and most positive reviews and seems to have been around the longest. Something worth noting is the organisation’s offerings may start to increase exponentially as they have been recently acquired by Selina which provides hostels, workspaces and activities in many places around the globe.

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The average age on my last trip was 35. I was the oldest of my group but that didn’t bother me at all: being around Millennials helped me gain a certain understanding of my adult children and their friends. We were all respectful and, I think, learned from each other.

Actually, I enjoyed the nickname some of my fellow travellers gave me: they called me “Tia Loca,” which in Spanish means “Crazy Aunt” (mostly because I tend to be on the bold and daring side).

One of the biggest challenges, I have to say, was having the discipline to get my work done. Travel is my favourite pastime and I was so stimulated by my new surroundings, walking along the streets and exploring for hours, that sometimes my job was often relegated to early mornings or late evenings because there was so much I wanted to see and do during the day.

I made long-term friendships during my month-long trip to Antigua. Some became friends on the road; others stayed around for the long haul. Both served my different needs along the journey. One of the women in my cohort will soon travel with me to South America for several months and I am planning to accompany a man of Cuban ancestry from my Antigua group on a tour of his father’s country.

If you’re thinking of doing the same, why not take the leap? Let the world be your office. Your life is happening right now!

About The Author

Maria Olsen | Diversity Promoter

Maria Olsen | Diversity Promoter

Maria Olsen is an attorney, author, public speaker and radio show host. Her radio show in Washington, D.C., “Inside Out,” focuses on LGBT and diversity issues. Her first nonfiction book, Not the Cleaver Family–The New Normal in Modern American Families, examined the changes in families in this decade. Her latest one, 50 After 50: Reframing the Next Chapter of Your Life, which chronicles the 50 new things she tried in her 50th year to determine how she wanted to live the next chapter of her life after getting sober and divorced, has been used as a vehicle to help many women reinvigorate their lives. Maria worked on diversity issues while in private practice and as a political appointee in the U.S. Department of Justice.

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