Seeing the World As A Digital Nomad In Your 50s

If you’re the type of woman who wants to live a life of freedom and adventure, maybe becoming a digital nomad in your 50s, working remotely from anywhere in the world, is what you should consider. Today, an estimated 40–50 million people worldwide identify as digital nomads, including more professionals over 50, and over 18 million Americans alone in 2024. Many hold full-time remote jobs, earning competitive salaries while contributing billions to local economies, and more than 40 countries now offer nomad visas to support this growing movement.

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. 

Becoming a Digital Nomad in Your 50s

Ever wondered what it’s like to take your career anywhere in the world? It happens in my life that I like to challenge myself,  to step beyond what feels comfortable and test what’s possible. So instead of staying in my office, I packed my laptop and chose a different view.

As a lawyer, I swapped my usual routine for the cobblestone streets of Antigua, living for a while among its colonial charm and vibrant culture. From there, I explored Belize, and my journey continues with plans to work remotely from Puerto Escondido, Medellín, and Buenos Aires.

Challenging myself in this way has shown me that work doesn’t have to be tied to one place ,  sometimes, the biggest growth happens when you allow the world to become your workspace.

Choosing the Right Program as a Digital Nomad in Your 50s

The idea of working anywhere in the world as a digital nomad, with just a laptop and an internet connection, untethered from a single office, has long captured my imagination. Untethered from a single office, free to choose my horizon, it felt like the ultimate midlife adventure: not an escape, but an expansion.

It’s more than “working with a view”, it’s a lifestyle that values freedom, adaptability, and experiences over the traditional 9‑to‑5.

However, I wanted more than a solitary experience, I wanted to be part of a community. Having a network of like-minded people was far more rewarding, 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. 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.

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 also 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 , Wifi Tribe and Hacker Paradise which all 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 other organisations, instead, costs less and is more likely to attract younger digital nomads.

Of course, each company has a slightly different approach. When choosing a remote work travel group, I focused on three things: community, logistics, and reputation. I wanted built-in connection without pressure, seamless transportation between destinations, and a company with strong reviews and experience. Age diversity also mattered to me — I was less interested in a party crowd and more interested in curious, open-minded professionals. The right group should support your work goals while expanding your world — not distract from it.

Take the Leap: Life as a Digital Nomad in Your 50s

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.

Ready to Start Your Nomadic Lifestyle At 50s?

If you want to experience remote life as a digital nomad in your 50s, I strongly recommend organizing well from the start. Check visa requirements, healthcare coverage, reliable Wi-Fi, time zones, and create a realistic work schedule before you go. Freedom feels even better when the practical details are handled.

Here are top 4 resources to help you start and thrive as a digital nomad,  from planning and visas to work, community, and tools you’ll use every day:

1. Nomad List – A hugely popular city database and community for digital nomads, with data on cost of living, Wi‑Fi speeds, safety and quality of life. It helps you choose where to go next and connect with nomads already there.

2. Remote Job Boards – These are essential for finding remote work opportunities that let you earn money from anywhere — whether it’s full‑time employment or freelance gigs.

3. Digital Nomad Visa Guides (e.g., country lists & visa info) – Comprehensive resources that explain which countries offer digital nomad or remote‑work visas, including length of stay and requirements for working legally abroad.

4. Digital Nomad Hub & Resource Sites – Sites that curate travel guides, coworking spaces, accommodation options, co‑living communities, health, insurance, and more — all specifically tailored to nomads.

In the end, being a digital nomad is about discovering what freedom truly feels like, building connections that last, and embracing the unexpected at every turn. If you’ve ever wondered what it would be like to make the world your office, there’s no better time to start than now. Adventure is out there, and your life is waiting; let the world be your office.