How older digital nomads Live & Work – Interviews with Gen X and Baby Boomer Location Independent Entrepreneurs

I used to think that the idea of travelling the world while working from a laptop was something one would quit by the age of 40. In my case, I started my digital nomad lifestyle at around the age of 40 and haven’t stopped since then. But all this (short) time I felt like an imposter. However, the more I looked into it, the more I realised that the over-35 crowd makes up a significant portion of the digital nomad community. In fact, I believe that digital nomadism (if that’s what we want to call it) is fueled by generation X and the lifestyle feels even more fulfilling as I get older.

According to Forbes, most digital nomads are over 38.

The digital nomad lifestyle isn’t just for twenty-somethings with years in the bank to offset any “wasted” time, mistakes, or business experiments.

This article offers some of my thoughts on travelling and working online, taken from my experiences as a 40-something location independent business owner. I’ve also posted interviews with older entrepreneurs and digital nomads about their own experiences. I’ve highlighted the most important learnings from each one.

There’s no true path or “best way” but I have found that age is no barrier. In fact, age and the experience that comes with it can be a big factor in the success of remote workers.


When I was 24, I stayed for a month in a dark and dingy concrete-walled box near Kuta Beach in Bali, Indonesia. Even back then, I knew the accommodation sucked, but it didn’t matter. I was young, and all I cared about what surfing. I was also running out of money. This was long before I was a digital nomad and money was hard to get on the road.

These days, I’m less worried about my money running out. My accommodation must be comfortable and quiet, and it has to have fast wifi. These are extra expenses that I would have considered luxuries in my twenties. These days, they are non-negotiable. But I still look for great value digital nomad destinations like Tbilisi, Bangkok, Medellin, and Buenos Aires. Cities like these offer modern, affordable amenities close to plenty of adventure

Insurance / Medical tests / Health

Medical tourism is a thing. Thailand, The Philippines, Turkey, and the Czech Republic (to name a few) receive hundreds of thousands of people every year that visit solely for the purpose of getting their teeth fixed, face lifted, or health conditions treated at a much lower cost than in their own countries.

Health insurance was something I didn’t think about as a young man. It’s easy to feel invincible when you have just reached adulthood. But it would be irresponsible and downright reckless to travel without comprehensive medical and travel insurance right now. 


One thing I learned from my experience working as an ex-fitness instructor is that many people over the age of 40 have “bad backs”. A bad back can mean many things but one thing is for certain, backpacks will aggravate injuries and complaints. Young travelers can handle backpacks. 

I’ve always taken care of my health and I’ve always focused on back health (I use a standing desk, I do yoga, and other exercises). I use a backpack almost every day, but my back is strong. Many friends in my age range consider backpacks a form of torture. 

I see many young digital nomads using the Roost stand or Nexstand and I’m happy to see that. These “new” inventions should also be essential items for older laptop entrepreneurs. The years of hunching over desks will take a toll on your neck and upper back. Anything you can do to offset this problem is worth the price of a laptop stand.

Long Haul Travel

Economy tickets are great. But the older I get, the harder it is to recover from cheap airfares that involve two flights with an 8-hour stopover in the middle. Saving a few hundred dollars is great but I avoid the real bargain basement flights. They might save me money, but they cost me days of my life.

When I was younger, I was happy to sit on a bus for 2 days. I won’t do that anymore. And that makes me wonder if I am a worse traveller now? Am I now a tourist because I don’t put myself through extreme discomfort? 

Some travellers and digital nomads brag of the dangerous situations and extreme discomfort they endure. But if that’s how you get your kicks (it used to be mine) that’s great. But as an older traveller, you shouldn’t feel intimidated or pressured to do what everyone else is doing. The great thing about experience is that you are happier with your own viewpoints on life. 


I have anecdotal evidence of this, but you’re less likely to get stopped at immigration and interrogated as you get older. Countries like Thailand become even easier to access. Retirement visas are available to people over 55 years of age as long as they can prove a regular income.  


I used to love the noise and bustle of big cities. In a way, I still do. Bangkok is one of my favourite cities. I spent 5 years living in Argentina, which holds the world record for the noisiest street corner. But hostels with blaring night clubs downstairs are a red flag for me now. I generally avoid hostels unless I can get a private room. But if there’s a bar in the place I won’t go near it. 

Socialising, Friends & Family

I don’t want to make it sound like the old days were better (they weren’t), but there are benefits of having traveled long before social media and mobile phones. I learned to pose questions to complete strangers. It’s easy to avoid talking to real people these days.

That’s a shame. The interactions we have with people create the memories that last the longest. I can still see many of the sunsets. I can remember the warm air on my skin as I walk through Bangkok, Buenos Aires, or Barcelona. But what I remember best of all, are the people.

I’m not suggesting that merely asking questions on the street will enrich your travel experiences. But serendipity can change the course of your life, not to mention your travel experience. Sometimes it’s good to get lost.

And that brings me to my point. If everyone is on their mobile phone (again I’m not millennial bashing here – everyone does it), it’s harder to meet people by accident. 

Leaving your apartment with just a hotel card and a few dollars is a liberating experience. Not checking your social media feed for a week will make you feel more connected to the place your living in. I’ll dare to say that this kind of disconnection from tech is easier for older digital nomads.

Today’s world is full of distractions. My younger cousins and second cousins literally live on their phones and switch between apps like it’s a game. Social media isn’t making them happier. In some ways, I’m glad I missed the iGeneration.

The older you get, the more likely you are to be married and have kids. Children add a whole new dimension to your life and your digital nomad experience. Having kids (for better or worse, but mostly better) will probably reduce the time you spend travelling. Unless you bring them with you, as The World Travel Family did. 

Digital Nomad Interviews

I Interviewed many location independent workers in researching this blog post. The community was very generous with their time and asked for nothing in return. Thanks to everyone that answered my annoying questions 🙂

The World Travel Family

alyson long world travel family photo

The World Travel Family blog is a popular blog about full-time travel, travel blogging, trekking, food, and a host of other topics. The blog, started in 2012, by Alyson Long, is both a diary of Alyson’s family adventures around the world and a guide to travel planning. Travelling the world and managing a business while bringing up two teenage boys presents a fascinating case study in prioritization, responsibility juggling, and determination. Despite the word “family” in the website URL, this is a blog for everyone. Solo travellers and adventure seekers will find tons of great articles on the site.

Alyson is a proponent of homeschooling and has put together a huge post on homeschooling and travel. This is a must-read for passionate travellers who care deeply about their children’s education.

What are your primary motivations for taking the family on a journey? Wouldn’t the kids be safer/happier/healthier at home?

“No” is the very firm answer to the second part of your question and my younger son, who is sitting here helping me, was a little cross with you about that!  Our motivations were several, but primarily we left to travel because of the kids’ education. Living in Australia, in Tropical North Queensland was nice, but it was limited. I wanted them to experience more of what the world has to offer.

I wanted them to see London’s great museums, experience historical sites first hand, explore cultures, foods, cuisines and the many people that make up the world. So their education was number one but also we wanted more freedom, more family time, no ties and a more enjoyable lifestyle that the “ Australian Dream”. It wasn’t our dream.

Did you travel before you had children and if so, what is the single biggest difference between travel then and now?

Yes, absolutely, I met my husband while travelling and shortly after getting together we took a 12 month round the world trip together. In all honesty very little is different. We have a greater eye on safety and are more cautious, but the biggest difference is of course cost. Now that they are bigger, 12 and 14, it’s just like travelling with 2 extra adults and paying for them.

Do you feel that digital nomadism is achievable for anyone with children?

Yes, so long as they are smart, confident, and understand how education works. I have a friend with an autistic child who just can’t travel, it’s hell for him, but for families unaffected by these things, certainly. Too many people still believe that school is compulsory or in some way necessary.

How do you feel your children benefit from this lifestyle?

Freedom is the biggest benefit. They are free to be themselves and to enjoy their lives their way. No restrictions on how they look, what time they get up or go to bed, meal times, no need to put their hand up to go to the bathroom, no being confined all day, 5 days a week. They spend more time with us and with other adults, this presents far greater learning opportunities and real-life experiences than being kept with same age kids. They learn about social interaction and real-world issues mostly from adults, not kids.

Educationally our kids are free to pursue topics of their choosing to whatever depth they prefer.

This generally makes them more mature and worldly. Their knowledge of most things is deeper and they are superbly good at computer games. Don’t scoff at that, computers are vitally important and they both make some money and have small online jobs already. My elder son has also had a real-life job helping a friend with her hotel, they have far more options than kids in school. They are good friends with British kids and adults, Americans, Romanians and Australians, they mix with Muslims, Christians, Scientologists, Mormons and Atheists, they get diversity, they get that no group of people is to feared and that they are all human beings with the same basic wants and needs.

Educationally they are free to pursue topics of their choosing to whatever depth they prefer. They have far more time than school kids to read and they read because they choose to, not because they are forced. They enjoy life, and deserve to enjoy life, just as adults are free to do.

The media portray digital nomadism as an option for Millennials only. Do you have any advice for digital nomads in their late 30s or older about getting started?

Really? Do they? I think that’s a little odd as most of the nomads I know are in their late 30s, 40s, even 50s ( I am 52). I think being older is a huge advantage as we had our ducks in a row financially, we’re already married and our kids were old enough to travel. We didn’t set out until my younger one was 6. So as a very experienced parent, homeschooler and traveller I knew what to expect and what we were getting into.

The people who burn their bridges and fully embrace a new travelling lifestyle do better and work harder at achieving their goals, but that financial cushion is still great to have

We older folks also have a lifetime of experience and knowledge to draw on, that certainly makes me better able to run my business, support my family and keep them safe and well. I wouldn’t suggest anyone sells their house to do this. That’s a bad move. We kept our property and have it rented out so we always have that investment to fall back on. In many ways, the people who burn their bridges and fully embrace a new travelling lifestyle do better and work harder at achieving their goals, but that financial cushion is still great to have.

Palle Bo: The Radio Vagabond

palle bo the radio vagabond interview

Palle Bo is the host of The Radio Vagabond, a popular podcast that focuses on interviews with travellers, expats, and digital nomads. 

What are your primary motivations for working and living online around the world?

To be a life-long learner and make friends all over the world. To open my senses, learn about different cultures, and break down any prejudices I might have. 

When did you get started and was it a difficult process or something that came naturally to you? 

I decided in 2013 to start traveling in the summer of 2016 when my youngest daughter would graduate and move out. So for three years I did a lot of planning and sold my house and all my furniture. Two months before my journey I was getting out of my comfort zone – as my house was getting more and more empty. I thought ‘what the hell am I doing?’ and ‘Is this a mistake?’.

I feel I learn so much from the young nomads – even though I don’t feel the difference between us is so big. We’re all part of the same tribe.

But after I left Denmark, I haven’t looked back and only decided to extend my journey. In the beginning I thought it would be two years, and now I’m saying 10-15 years, basically until I become a grandfather at some point. My daughters are now 21 and 24 and have no plans to start a family any time soon. 

What are your main skill sets?

Radio producing. I’ve been doing radio since 1985 and have my own production company, called Radioguru. I support myself by producing radio advertising mainly for Danish clients. Also I do sound design and voiceovers for online videos, and then I do podcast production for clients. I just hosted and produced The LEGO® Technic Podcast. 

What advantages (if any) do you have over younger digital nomads?

I have total respect for the younger nomads. If I were to say anything, I would say basic life experience, and experience starting and running companies (in my early 20s I co-founded a radio station, and now I’m still a co-owner of a group of 17 radio stations in Denmark). But again I feel I learn so much from the young nomads – even though I don’t feel the difference between us is so big. We’re all part of the same tribe. 

Do you think the media portrays digital nomadism as an option for Millennials only. Do you have any advice for digital nomads in their late 30s or older about getting started?

It’s never too late. I was 51 when I left. I never had any regrets about the life I had until then, this is just a new chapter. And I feel I have lived more the last two years than I had the first 51 years of my life. I thought: If I don’t like it, I can always go back. But I do, and I will never get the big house again. Once I stop traveling at some point, I will get a small apartment or a tiny house so I can still use my money to travel a lot every year. 

So my advice is really quite simple: Take a chance and just do it. Start planning, set a date and say it out loud what you’re planning to do. 

And don’t worry so much about the money. Traveling the world is (in many cases) much cheaper than staying in a western country – with all the stuff that goes with having a house and all the stuff you buy because you have a place to put it. It might not make you financially rich but you’ll be rich in memories, new friends and laughter lines. Get out there and meet the world. Tell them I sent you. 🙂 

Matthew Karsten: Expert Vagabond

Matthew Karsten the expert vagabond

Matthew Karsten is an adventure travel blogger & photographer. He’s also one of the most recognised names in the travel blogging world. Matthew’s Expert Vagabond blog documents his travels during the last decade. Matthew is a true professional blogger and uses the income from his blog to fund his worldwide travels.

What were your primary motivations for working and living online around the world?

Freedom! The freedom to work for myself, set my own hours, and see the world while I’m young. I was sick of making money for other people and wanted to make money for myself, without being tied down to one place.

When did you get started and was it a difficult process or something that came naturally to you?

I started in 2010 after reading some blogs and books on the subject. Like “Vagabonding” by Rolf Potts and “The 4-Hour Workweek” by Tim Ferriss. I think I had an advantage in that I was already accustomed to building websites and shooting photography, two skills that are helpful in this work.

There are a lot of creative people out there who don’t know much about business. And you really need both to be a successful digital nomad

What would you say are your main marketable skills?

Creativity, a business degree, experience building websites, photography, social media savvy. There are a lot of creative people out there who don’t know much about business. And you really need both to be successful with this. An understanding that you must spend money to make money helps too.

What advantages do you have over younger digital nomads?

Experience. I’ve already tried everything and failed, to learn what works and what doesn’t. Being “early” in an emerging market helped too. There wasn’t as much competition when I was starting out. But at the same time, it was a lot riskier too. Everyone thought we were insane for trying to make a living online. Now there are far more examples of people having success with this lifestyle, which is helping to convince others to jump in.

Be open to change and learning new skills!

Do you have any advice for digital nomads in their late 30s or older about getting started?

I think younger people have an advantage because they understand the online world a bit better, and able to take big risks (living in cheap digital nomad hubs like Chiang Mai or Bali to reduce living expenses while they grow). But in my opinion, there’s nothing you can’t teach yourself if you put in the time and effort it takes. Being flexible and staying on top of trends is important. At one time, concentrating your efforts on a platform like Facebook was important. But that’s moved on to platforms like Instagram and YouTube.

So you need to be open to change and learning new skills. If you’re older, you generally have more responsibilities or family which makes drastic lifestyle changes a bit more difficult. It’s not impossible, but you need to be more efficient and productive with less free time to spend on side-projects.

Brenda: Solo Female Digital Nomad

Brenda kindly agreed to answer my questions but wanted to stay anonymous. Thanks for the insights into digital nomadism for the over 40s, Brenda!

What are your primary motivations for working and living online around the world?

My main motivation is to escape the Canadian winter. My partner and I split up a couple of years ago, and I’m on my own now, so I don’t have to stick around for anyone else. My son is 32 and lives in a nearby city, and we are close, but we just talk on FB Messenger video and audio while I’m travelling and “It almost seems like you weren’t away,” according to him.

My second motivation is that I’ve fallen in love with New Zealand, so this coming winter will be my 4th there (where it’s summer of course). I’ve travelled around to most parts of it, house-sitting anywhere from 1 to 6 weeks at any particular place. I also have family and old friends there who I visit but only for short periods, a few days. I have added other countries into the mix: Cook Islands on my way home a couple of years ago, Vietnam for a month this year.

When did you get started and was it a difficult process or something that came naturally to you? 

I travelled a lot when I was in my 20s and early 30s, often on my own. After that, I was a single parent with a kid and not much money for a long time. Now that I’m free to travel again, I’ve figured out ways to do it on a budget and since I have done freelance work for a long time, it was easy to just keep doing that while on the road.

I just need wifi and that’s one reason I chose the housesitting route.  I also have always loved travelling and seeing new things/meeting new people so it comes pretty naturally to me. Even when I was a kid, my mother used to talk about how I was always up for going off to other places with friends and relatives. I was never one to stick around with my family if I had another option. 

What skills do you have that have helped you become a successful digital nomad?

  • Regarding making money: editing and book design. I have publishers who are long-term clients.
  • Lots of skills useful for being on the road: adaptable, calm in a difficult situation, interested in people and ease of talking to strangers, and comfortable in my own company.
  • House sitting: years of home ownership so fairly handy in terms of minor problems, love animals and have experience looking after cats, dogs and chickens, and some with other farm animals.

What advantages (if any) do you have over younger digital nomads?

Not sure I do have advantages over younger DMs, although having a good client base means I’m not scrambling for work, so that is a definite advantage for travelling and work life in general. Also, in terms of house-sitting, I think many house owners would rather a mature person. As well, having travelled a lot brings a certain amount of experience and possibly not having unrealistic expectations. It’s not all roses! 

Do you have any advice for digital nomads in their late 30s or older about getting started?

First of all, you have to figure out a way to make money remotely if you don’t already have a job that allows this. Second, you need to figure out a way to travel on a budget. I love housesitting but it isn’t the answer for everyone. Read as much as you can in terms of travel blogs. Do a lot of research about possibilities. I would love to do some HelpX or Workaway stuff sometime when I have less of my other work. There are lots of Facebook groups. I’m on one called Digital Nomads over 40.

Travelling is not for everyone. You have to be pretty independent, ok to be on your own (if you are single), prepared to be lonely or face tough times now and then, and so on. You basically have to love of exploring new places to outweigh the uncomfortable times. You won’t have your usual support group so you need to be ok without it. On the other hand, you have to have faith in the basic goodness of everyone you meet.  If you are a paranoid person, you would hate it. 

Sara: 4 Years a Nomad

Sara also asked to remain anonymous but was kind enough to answer my questions. Thank you Sara and I wish you the best of luck with your projects!

What are your primary motivations for working and living online around the world?

There are a few, but mostly to explore and experience different places, cultures and lifestyles. And also to live a lifestyle that would be difficult in my current hometown (London) due to crowds, transport, climate and finances. For example, I spend a lot of time in rural/coastal Thailand where everything is a 3 minute scooter ride away, so I can fit into my day more things like exercise and socialising. Things are easier.

And to escape winter.

When did you get started and was it a difficult process or something that came naturally to you? 

I started nomading in January 2015, so almost four years now. I was already self employed and working remotely for the 7 years before that, so in those terms it was not a big leap at all.

What are your main skillsets?

Bringing people together is often noted as a good skill of mine. Attention to detail and an organisational focus (when required).

What advantages (if any) do you have over younger digital nomads?

As with everything in life, experience brings perspective so I do not fall prey to huge dramas or swings when things happen or go bad. Typically someone older can see things more in a context or perspective. I know what I like and peer pressure does not apply. On a different note, I have more of a solid base, both in terms of work experience and financially, having bought a property.

There is never a “right time” to do things, just what feels right to you

The media portray digital nomadism as an option for Millennials only. Do you have any advice for digital nomads in their late 30s or older about getting started?

I don’t think it’s just the media, I think it is society. In your 30s it is when you’re “supposed” to settle down, buy a house, start a family, etc, but this does not resonate so much with people anymore, in the sense that we don’t all need to follow a predestined path. We can make our own lives and experience things in the order that is most suited to each one of us.

My advice for late 30s people wanting to “nomad” is… just do it! It will be better than you think and less scary. You will meet many people of all types and ages, and age does matter less when you’re in this situation. I now hang out with both a lot of younger people (not always) and older people, and it is amazing what connections you can make. There is never a “right time” to do things, just what feels right to you.

6 Years Searching For A Deeper Connection

Nomadility (not his real name) has been a full-time nomad for 6 years but believes that removing himself from the digital nomad community helps him experience a deeper connection with local places. 

What are your primary motivations for working and living online around the world?

To see and experience the world before it changes too much from globalization and other human intervention. The uniqueness and quality of places both culturally and environmentally are disappearing. 

The most amazing initial feeling in my remote living/working experience was creating a sense of home in a new place.

I have tended to be relatively removed from the digital nomad community in most but not all places. If I am meeting and hanging out with digital nomads, then it decreases the opportunity to experience the uniqueness of different places.

paris rooftops and eifel tower vista

When did you get started and was it a difficult process or something that came naturally to you?

2004 to Paris for about 10 days was my first solo trip while trying to work. This was before decent internet was available. I bought temporary international dial-up access through ATT and tried doing Skype calls from my apartment which I found on Craigslist. The connection was not good enough, so I ended up going to internet cafes in the neighborhood and the local MacDonald’s frequently.

But I was hooked on being able to work remotely while seeing different parts of the world. I knew technology would catch up, eventually. I gradually increased my time away from my home in New York every year and was going away for 3 months during winter for a few years. I decided to do it full time about 6 years ago.

The most amazing initial feeling in my remote living/working experience was creating a sense of home in a new place. I had an apartment in Paris in 2006, traveled to Bruges and Amsterdam, and then came back to the apartment in Paris. That feeling of returning to Paris was a feeling of returning home even though my time there was limited. I didn’t have to figure anything out coming back to the city and the apartment. It conveyed a sense of no longer being a visitor or traveler, but now being a resident. That is what I still seek when I go to new places.

What are your main skills?

Openness to experiences, being comfortable as an outsider in almost any situation

What advantages do you have over younger digital nomads?

It’s just differences in lifestyles when you are in your 20s vs. 30s vs. 40s and beyond. Maybe there is more maturity as you get older, but that’s not a given. Maybe also if you become a digital nomad in your 40s, you could be more established in your career so you have more financial flexibility, but this is also not a given either.

Do you have any advice for digital nomads in their late 30s or older about getting started?

This is for any age. Test the waters before committing, especially if it is solo travel. This is important both for your work and your lifestyle. Make sure your personal experience is rewarding enough.

Melissa: Remote Ecommerce

Melissa Hutcheson runs an ecommerce store while travelling the world and learning about new cultures.

What are your primary motivations for working and living online around the world?

The travel bug bit me hard when I was a teenager when I traveled with my parents and brother to Europe. After undergrad, I took a few courses toward a travel certificate and accepted a job to be a Tour Leader/Manager/Director for a large US-owned company and lead weeklong escorted tours of 40-46 people primarily in Quebec and Ontario. I hated it and moved on to planning international “escorted and FIT” tours for a few more US-based companies. From that point on I traveled internationally as much as possible.

Working at a desk 8-12 hours/day didn’t cut it. Ultimately I moved overseas, returned to the US, and moved overseas again in 2010 and have no plans to return. At this stage, my desire and interest to learn more about different cultures (food, traditions, music, daily life) and live within those cultures has become a way of living for me (and my husband).

When did you get started? Did the digital nomad lifestyle come naturally to you?

We got started in 2006 by founding a business manufacturing and selling products for cats. We saw a need and initially trialled an idea that grew and grew, taking over more space in our home and more hours outside of our ‘regular’ jobs. Eventually, we transitioned to overseas manufacturing and fulfilment by Amazon. Looking back, part of the process was natural and organic. International regulations and all that goes with this type of business had a large learning curve. But we knew that the business could support a nomadic lifestyle which was a focus for us since meeting in 2004.

 What are your main skills?

 Relationship building, business management, digital marketing, SEO 

What gives you an advantage over younger digital nomads?

Having worked at start-ups, founding another company and extensive international business and personal travel experience I am not often overwhelmed or stressed about the process of building and maintaining (this type) online work or the process of learning new visa requirements.

 Do you have any advice for digital nomads in their late 30s or older about getting started?

If you have a good idea, with an identified, solid market base and can support yourself while you begin a digital nomad life, then book a ticket and go. You will regret not making the leap much more than taking the risk. You become a more confident, self-supporting and well-rounded person as a digital nomad. For many folks, after the first few months, you settle into a rhythm and really begin to appreciate the changes you’ve made. m

Ignacio: The Micropreneur Maestro

Micropreneur Ignacio with his guide for digital nomads

Ignacio is from Mazarrón, Murcia, a small town by the sea in the south of Spain He runs the Micropreneur Life website, a blog about entrepreneur life and travel, and lives in Thailand and Bali. He also runs Your Company In Estonia, a website that helps worldwide entrepreneurs launch and manage a business in Estonia under the e-residency program.

Ignacio is a firm believer in non-specialization in today’s business world. This is something that I also believe in. Develop multiple ideas and generalize for success. No engineer would create a single point of failure in their code, but they often do in their career.

Ignacio taught me a word I didn’t know, but which I will now use to describe myself: multipotentialite. Thanks mate!

What are your primary motivations for working and living online around the world?

Difficult question. I would say “a lot of different things” and “nothing in particular”. Both my partner and I lived in Madrid. We both had our companies there. We enjoy traveling and have been spending one month overseas for some time now, merging with the local community and living like locals.

That is actually quite a very quick summary of how we transitioned from employees at cubicles to freelancers first and then entrepreneurs. It took us a while to break the chains of our steady jobs and become freer and financially dependent on ourselves.

Apart from the appeal of traveling the world, we also wanted more freedom. Freedom from the city, traffic jams, from the politics in Spain, and we had this desire to escape the monotony of a steady location. By the time, we learned about the e-Residency program and how you could open a company in Estonia that you can manage completely online. That’s when we decided to take the leap and become digital nomads.

When did you get started and was it a difficult process or something that came naturally to you?

Well, when it was clear that we could carry our business with us while traveling, we sold all our properties in Spain, finished our businesses there, and moved to our first destination for some months. I won’t say it was difficult or especially traumatic. Luckily we are both not only very flexible, but early-adopters by heart. We like trying new things and we didn’t have many things tying us down in Spain.

My memories of that moment are not something I would call an “event”, it was more like a smooth process. Once we made our decision, we started working in that direction.

Of course, it takes some time to re-adjust, and get used to the fact that all your belongings are now in a suitcase (and the work-bag :), but at least for me, it was quite natural and smooth.

What are your main skills?

I would say that I am lucky to know a little bit of everything. I am a multipotentialite at heart. While I have a strong technical background, and my main skills are programming and computers, I am also a composer, writer, blogger, and entrepreneur. 

The more you know of different areas and disciplines, the better.

I know a bit of design and can come up with a beautiful user interface in Sketch for a new app that I can program afterwards. When you become an entrepreneur, you have to learn some things -if you want to survive- like marketing, selling, etc. I would say I’m not quite good at that, but enough to make a living 🙂

I was taught that specialization was the way to go. The way of becoming successful and earn a lot of money. Now, I firmly believe it’s the other way around. The more you know of different areas and disciplines, the better.

What advantages do you have over younger digital nomads?

Well, I won’t say being older makes me better than any other younger digital nomad, or even gives me any advantage. I have a lot more experience, of course, so I know what I want, and more importantly, I know what I don’t want.

I don’t buy the startup hype, or the affiliate bullshit. Maybe that’s my main advantage, I have failed and fallen so many times, that I have learned what works and what does not. I know that people look for solutions to help them solve their problems, not someone talking about tropical beaches or discussing how cool they felt when surfing in Thailand.

Do you have any advice for 30-somethings or 40-somethings about getting started?

In fact, that’s a wrong image of the digital nomad, promoted by social media platforms such as Instagram. Actually, the reality is that most digital nomads are between 35-50. Then, why do we associate digital nomad with a young surfer? That’s maybe because there’s a lot of bullshit about the digital nomad world, probably for commercial reasons.

There are 20-something rich kids traveling through Europe or Asia while taking a sabbatic year (paid by their parents of course) and calling themselves “digital nomads”. There are young people trying to become influencers at Instagram, or YouTubers, and their way of getting there is presenting themselves as something they are not.

Stories about normal people in their 40s traveling the world while doing web design, for example, don’t have the same allure.

That makes a lot of damage to the community. Digital nomads are people of very different ages, young and old. We just have opted for a different way of living. More free, perhaps, but not better or worse. Just different. We need to work, do our groceries and visit the doctor like everybody else. What makes us different is this desire for traveling, visiting different places and getting to know different cultures and people. We have this need for freedom. And we are willing to sacrifice some things in exchange for enjoying it. It’s an exciting journey, and there’s no age limit to buy your ticket. 

I would encourage anyone to do it. I’m 38, my partner is 45. We are traveling the world for quite some time now, and we have met amazing people from 20 to 60 years old.

You are never too old, or too young, to join us.

interviews with older digital nomads
How older digital nomads Live & Work – Interviews with Gen X and Baby Boomer Location Independent Entrepreneurs

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20 thoughts on “How older digital nomads Live & Work – Interviews with Gen X and Baby Boomer Location Independent Entrepreneurs”

  1. Thanks for taking the time to get all those older digital nomads to reply for this blog post as a lot of the answers are really inspiring.

    I am nearly 40 now but was a digital nomad back in 2006 before I had kids and got stuck in surburbia again for many years. However I just want to let others know it is possible to escape again and get back to travelling even with 3 kids as we have just done living, working and schooling in a motorhome (RV) for a year as we travelled around Europe.

    Keep travelling, living and loving life everyone.

    1. keith travel writer and blogger

      Thanks for the kind words. You also have a great story. I’ll be following the Nomadic Dad blog. Maybe we can discuss it here one day.
      Happy travels!

      1. Thanks for your kind words too Keith. My blog will be quieter whilst we are regrouping in the UK but hopefully your blog will keep inspiring me over the summer 👍

  2. I’ve been wanting to become a digital nomad and I finally have a job with a company where I could work from anywhere in the world. My biggest question is, when you work for a company remotely, do you need to get work visas for the different countries you are staying in? I’ve tried asking Google but I’m having trouble finding anything about how that would work.

    1. keith travel writer and blogger

      Hi Pattie,
      That’s a great question. It’s a bit of a grey area. It’s not legal to “work” in any country without a visa. But if you are, say, on a tourist visa and you don’t conduct any business in the country you’re visiting, it’s easier to fly under the radar. But legally, it’s a grey area. And most countries do not want people spending months working and earning from another country without paying local taxes. There are some countries, like Mexico, that allow you to work on a tourist visa (for foreign companies).
      If you’re passing through and visiting a place short term, that should be fine. But don’t expect the authorities to let you stay for years without paying taxes.
      Everyone’s situation is different.

      1. Thanks for the quick reply! That’s kind of what I was thinking. I bet I’d have to have a long conversation with HR to determine if this would actually be possible.
        Thanks again! This is a great post BTW.

        1. keith travel writer and blogger

          Thanks! I’m glad it was helpful. Best of luck with your plans and let me know how it goes. It would be interesting to hear the HR opinion.

  3. Excellent article. Almost 11 months ago we left Australia for what was to be a 12 month sabbatical. However, a sabbatical implied I was going back to how things were. Now Location independence is now the preferred option. Great to hear of older people (40+) choosing it as a lifestyle. It’s great to be able to afford this life while building income streams. Thanks.

    1. keith travel writer and blogger

      Glad you liked it, Mitch. I appreciate the kind words. 😌
      Well done on your location indie life. How’s business going?

  4. I’m trying to find out what really are the bare minimum belongings that people like Ignacio and other DN’s have. What fits in one suitcase and a backpack. Do you put other stuff in a long-term storage (if so, what exactly)?

    So far I’ve always returned to a “safe” base where all I live (maximum I spend as a DN was 3 months). But the minimalist lifestyle sounds exciting and scary at the same time, especially for us older ones (I’m 50+) that have amassed “things” over the many years.

  5. I backpacked on a shoestring in 1996 and the goal was to make my meagre money last as long as possible. I had many nights in a $1 room that I wouldn’t dare set foot in now. Back then there was no digital – so a nomadic or location independent lifestyle didn’t seem feasible. But the dream festered, and after quitting my lucrative corporate career, corner office and relinquishing my expense account I finally started my DN adventures three years ago – and not a day too soon. I was surprised how many other Baby Boomers are doing the same, and the biggest challenge is the negative response from others in traditional lifestyles who can’t understand why we’d want to give up on the “having it all” … you just have to turn a blind eye and a deaf ear to the detractors and take that leap of faith. No regrets!

  6. Cynthia Morgan

    Left to backpack around Asia in 1995 and never went home again. As you so beautifully described, there was no digital anything back then. When you needed money to continue traveling, you stopped and worked. When you wanted kids to have roots, you stopped and planted some. Now, at 53, I’m into the third phase of life on the road, gathering online skills. Love this article and love there’s so many of us. Baci from Italy

    1. keith travel writer and blogger

      Thanks. And congratulations on a life of travel. I started travelling around the same time (1994) and it was a lot more challenging to travel (no credit card, no internet, no mobile phone). But it was part of the experience.

    2. A different life then- non digital. Travel was on the fly – no google to help you out. I left to backpacker late 80’s until early 2000’s. Put down roots for child. Now at 54, I also am ready to fly the coop and hanging to get back on the road.

  7. Hi Keith,

    Just wanted to say thanks for this article. I’m 55 and about to transition to retirement, got some mobility issues now that make work too difficult. Looking forward to visiting other countries mainly in SE Asia area, at this stage. So, the info here was timely and handy! Have bookmarked your site for further studies. Keep up the great work mate,

    Cheers from Australia!



    1. keith travel writer and blogger

      Hi Shaun,
      That’s awesome you are going to do some long-term travelling. Glad to hear the post was helpful. It was fun to write.
      Let me know how you find the SE Asia experience!

  8. Great article and very interesting. I am a 58 year old woman and I am so keen to give this a try. I work remotely for a US based company earning dollars and live in South Africa, but am very keen to see the world while working remotely.
    I don’t necessarily think it will be easy but definitely keen to do it!

  9. Hi Keith,
    Great article!
    one segment I’m looking for and couldn’t really find there was the Over 40, full time employees, working fully remote and traveling the world.
    We (husband and me) are currently doing so, holding 2
    normative full time jobs for 2 companies from 2 different countries, while living in a campervan.
    Looking for like minded pips 😊

    1. keith travel writer and blogger

      Hi Taly,
      It’s quite possible these people are just so busy working and travelling that they don’t have social media presences and rarely comment or write online.
      They’re hard to find. Maybe they don’t want to be found. But there are plenty of them.

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