How to be a digital nomad (at 40) - Part 1

A practical guide on digital nomading for older people.

The 40-year-old you sat on your couch, exhausted as usual, eating Doritos chips, drinking the third glass of wine, watching Eat Pray Love the 5th time, flipping through pictures of an unbearably joyful niece Liza sipping cocktails on the beach of Portugal. 

A friend texted and asked you what you were doing this weekend. 

Nothing. 

You were too tired even to respond. 

You lifted your head, looked around your apartment - the grand prize you worked so hard and saved for after all these years - and all of a sudden, it dawned on you: 

You were no longer excited about all this. 

You asked yourself: 

Is this what life is all about?  Am I going to repeat the same daily routine for another 20 years? When can I realize my dream of traveling the world? When I retire at 60? 

I was you five years ago. 

I just took my employer to IPO after years of intense work. I loved my job, but my life was going stale. I was not living healthy, had little energy, and had no time for friends or dating. 

Today, on a sunny October afternoon in Barcelona, I’m writing this post while sitting on the terrace of my co-working space, with a view of the majestic Sagrada Familia, drinking hot ginger tea, as proof that digital nomading can also work for middle-aged and mid-career people like us. 

Yes, digital nomading can work for older people too.

Digital nomads boomed after the pandemic made remote work more common. Many people moved to Lisbon, Bali, Chiang Mai, and many other places to work remotely. You all saw pictures of that annoying friend on Facebook who loved to show off their amazing travels. 

The reality is that most digital nomads are young 20-somethings who don’t have family obligations, want to save money living in places outside of the expensive San Francisco Bay Area or New York, and don’t mind not climbing the traditional career ladders. They seem to all work in digital marketing, crypto, or coaching. 

For older people, however, the barrier is higher. Family, career, finances, and energy are all factors that stop most middle-aged mid-career people from trying to be digital nomads. What happens to my house? My mortgage? My money? My job? My spouse's job? My kids' school? My social circle? My routine? Oh my!  

After becoming a solopreneur and marketing advisor five years ago, I have traveled and lived in 10 countries and 30+ cities while working remotely: Portugal, Italy, France, Switzerland, Netherlands, Belgium, UK, Ireland, Croatia, and Spain. I worked remotely for two months while taking my parents down Highway 1 from San Francisco to San Diego, staying a few weeks in several cities along the route. I’ve also worked ‘remotely’ in my neck of the woods - San Francisco Bay Area, moving around Berkeley, Oakland, San Mateo, Santa Clara, and Cupertino, outside my San Francisco home.

I’ve made my fair share of mistakes. Only recently have I started feeling that I’ve distilled the best formula for myself. I wish someone had told me more about the ups and downs and the practicalities of digital nomading as an older adult. 

I’m sharing how I’ve been doing this and my hard-learned lessons here, hoping to help you consider your digital nomad future, or at least think about changing up your remote work routine, especially as an older adult. 

This guide will be a three-part series: 

Part 1: Money and Logistics

Part 2: Career and Work 

Part 3: Social and Family

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Part 1: Money and Logistics

An objection I often hear is: “I have a house and a mortgage, and traveling for an extended period is just too expensive.” 

If you’ve only been renting, it’s easier to rent at a cheaper or similar place at your destination. However, many older adults have already bought a place. Mortgage payments are a significant portion of paychecks. Spending on hotels on top of that mortgage sounds fiscally irresponsible. Two weeks might be OK. Two months? Six months? It simply doesn’t seem feasible. 

Many early-career digital nomads go to much cheaper locations like a beach in Thailand or a remote island in Portugal, and yes, Spain will pay digital nomads and remote workers in tech up to $17,000 to move to a rural village. Personally, I enjoy the conveniences of modern life. I need city life, vibrancy, energy, variety, culture, libraries, good restaurants, and public transportation. Honestly, I may enjoy living in a remote village for a month, but I’d get bored after that, so I’m not always staying at super cheap places and living in a way where money won’t be a consideration factor. 

Here are my top 3 tips on how to make digital nomading financially feasible while living a quality lifestyle: 

Tip 1: Rent out your house while you travel, ideally on Airbnb, with a property manager.

You can always find a trusted friend or family member to keep an eye out for your empty house. In my opinion, the easiest solution is to get your apartment ready for Airbnb, get a property manager to manage it for you, and forget about it. 

To do this, first, you’ll need to apply for a short-term rental license to be eligible to host. Check out your city's short-term rental office website, and get the proper paperwork done to apply and stay compliant. You’ll likely need to register the business with your city as well. While it sounds complicated, I found the actual application and approval process relatively painless in San Francisco. 

There are many choices when listing your property: Airbnb, VRBO, Booking, Idealista, and many more local options. I only list mine on Airbnb, as it provides the largest demand, and in San Francisco, you save on fees if you’re only listing on Airbnb. 

Each city has its own regulations, so, do your research or ask ChatGPT where to start. 

If you have time, you can manage the Airbnb yourself, and your return would be higher. I don’t enjoy that work, so I use a property manager, who charges a pretty sizable percentage of the rental income, but I still break even between my mortgage payment and rental income. 

You can also deduct expenses running the Airbnb on your taxes, which always helps. 

Tip 2: Stay in long-term rental apartments in a non-touristy neighborhood. 

Yes, especially now that you’re older, you have standards! You’ll no longer stay at hostels with six mixed-gender bunker beds for 10 euros a night. You want to stay at a minimum 3-star hotel and ideally with a pool. You don’t want to eat crap at McDonald’s, you want to try good quality local cuisine and occasionally splurge on a Michelin-star restaurant for the experience. You want to get around easily, so you probably need a car. Those add up. 

Unlike vacations, where the daily rate is high, the long-term rental option on Airbnb has significant discounts if you stay more than 31 days at a time, sometimes up to 40% cheaper than the daily rate.

Each country often has its own version of long-term rental marketplaces. Search for ‘furbished apartment in [location]’ or ‘monthly rental in [location]’ to find them.

Find nice furnished apartments in a residential and non-touristy neighborhood, yet still safe and easy to get around. 

You’d have a more authentic experience and pay local prices for groceries, haircuts, and restaurants when staying in a residential neighborhood. 

For example, in Barcelona, friends recommended that I stay in the Eixample neighborhood, where people from Barcelona still live in, but with fewer short-term tourists like the Old Town (Ciutat Vella). I’m staying in a building where people have lived for many years. It gives me the sense of normalcy that I crave.   

In places where I can’t stay for more than 31 days at a time, I try to at least book for more than seven days in advance. Many hotels and Airbnbs offer weekly and early bird discounts. 

Less touristy cities have much lower prices, so occasionally splurge for a 4- or 5-star hotel in those locations to pamper yourself without breaking the bank. 

In Portugal, I had an amazing stay at a nice spa hotel with natural hot springs and a terrace facing the mountain forecast. As someone whose default mode is very frugal, it was once unthinkable for me to book a room other than ‘single’ or ‘economy’. However, self-care is vital to recharge and rejuvenate when moving around, so I’m slowly shaking off the guilt about the occasional splurge.  

Tip 3: Live just as you do in your own city

Unlike a vacation when you probably eat out most of the time, try to cook most of your meals, which is healthier and saves on restaurant expenses. 

Go to grocery stores where you may discover local fruits, vegetables, and snacks that may be more expensive in touristy stores. I gasp at the grocery prices in Barcelona, where stores sell high-quality fish, fresh juice, yogurt, etc., for 20% to 50% of the prices of those at a typical Whole Foods, and a fraction of the price at restaurants. 

A bucket of 1 kg Greek yogurt for 1.60 euros? Sign me up! 

Use public transportation as much as possible, rather than Uber or Taxi. 

I like using public transportation as I can see what local residents are like, rather than other tourists like me. I observed London fashion on the Tube, listened to how Spaniards joke among themselves loudly on the metro, and also learned not to trust the Google Maps bus schedule in Croatia. Public transportation is a mirror of the spirit of the place. Among the sweats, the laughs, and the complaints, I felt that I got a glimpse of the core characters of its citizens. 

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Hopefully, this post starts to answer some of your questions about how to work as a digital nomad as an older adult. 

In the following posts, I’ll write about balancing work, career, and life. 

Let me know your questions or comments to make this more helpful to you!