I would have laughed ten years ago if someone had told me I’d be writing this blog post about how to become a digital nomad after 50, from a cafe overlooking the Chaophraya River in Bangkok. I didn’t think people in their 40s or 50s could experience this lifestyle. I thought digital nomads were twenty-somethings, not someone like me.
Here I am, though, and I want you to know it’s not too late. In fact, your 50s might be the perfect time to become a digital nomad.
If you’re anything like me, you’ve spent decades working, chasing career goals, and doing all the “right” things. Now you’re craving something different. Not retirement, necessarily — just more freedom.
The chance to see the world while still earning an income, the space to design life on your own terms. That’s exactly what I set out to do, and in this blog post, I want to share how I made the leap and how you can, too.
Why I Decided to Go Nomadic
I didn’t wake up one morning, quit my job, and jump on a plane. It was a slow process, a feeling that built over time. The 9-to-5 started to feel more like a cage than a comfort. I kept thinking, Is this it? Is this how I want to spend the next 10 or 20 years?
When I started questioning my life, I realized I was looking for purpose and space, more mornings without alarm clocks, more time outdoors, fewer commutes, and grey office walls.
Rather than counting down to Friday and living for the weekend, I dreamt of waking up in a new country every week and experiencing more of the world around me.
I was intrigued when I discovered that people my age lived as digital nomads. The idea of working from anywhere, exploring new places, and simplifying my life hit something deep. I wasn’t chasing beaches or bucket lists; I just wanted a lifestyle that gave me more freedom.
What Kind of Work Can You Do?
My biggest question was, how do I earn a living while traveling? This challenge kept me from initially quitting my job.
After researching, I realized I have a few options: I could be an employee for a remote company, freelance for clients, be a contractor on short to medium-term contracts, or even start my own online business.
There are so many remote jobs these days: customer service, sales, writing, video editing, quality assurance, consulting, coaching, you name it. I leaned into work that used my technology skills and customer support background.
The trick is to look at your skills and think, “How can I do this online?” You might be surprised how many people look for someone like you. If you’re thinking, “I’m not tech-savvy,” let me tell you—I learned what I needed to learn as I went. You don’t need to know everything.
Sites like FlexJobs, Remote OK, and We Work Remotely are great places to look for legitimate remote jobs. You could also reach out to your network on LinkedIn or Facebook — sometimes, the best opportunities come from the people who already know what you’re good at.
The Practical Stuff: Planning for the Leap
This lifestyle isn’t all sunshine and sunsets. It takes planning, but it’s doable, even if you’re not ready to go full-nomad.
My goal was to save enough money to last me six to eight months in case finding a remote job took me a while. It did!
I could only achieve this by freelancing in the evening and at the weekend and taking on as much overtime as possible in my full-time job. I had to make sacrifices, and you will have to, too.
We all live a materialistic life and buy items to impress our family and friends, but you learn that being a minimalist is a fantastic way to live. I’ll discuss this topic in an upcoming blog post.
Over time, I sold a lot of furniture, gadgets, and other items I knew I couldn’t travel with.
I didn’t want to start the digital nomad lifestyle with debt, so I cleared my credit cards and paid off a loan. Having savings and no debt was why I felt comfortable quitting my 9-to-5 job.
I gave serious thought to healthcare. I looked into travel insurance that covered longer-term stays and pre-existing conditions, as I am diabetic. I also researched destinations with a low cost of living, which led me to some fantastic places I might’ve otherwise overlooked.
It’s important to know that it took me two years to get to a position where I felt comfortable quitting my secure office job. I didn’t wake up one morning and decide to quit and jump on a plane. It will take time, as you do not want to go into living this lifestyle with debt and no savings.
Picking Places That Work for You
This isn’t about chasing the most Instagrammable locations. For me, it’s about finding places that feel good—places with decent Wi-Fi, safe neighborhoods, walkability, good healthcare, and friendly locals.
I travel slowly. I stay in one place for 30-90 days, giving me time to settle in and live, not just pass through. Places like Kuala Lumpur (Malaysia), Tallinn (Estonia), and Tirana (Albania) have been incredible, affordable, welcoming, and full of fascinating cultures and people.
I also consider time zones when I pick a location. If I work with a company in the UK or US, I find that living in Asian cities is the best for my work-life balance because I work in the evening and have the day to explore, relax, or socialize.
I prefer warmer weather, but you will need to factor in the type of climate and ensure you travel at the right time of the year to avoid typhoons, hurricanes, and other natural disasters.
What About the Fear?
I’ll be honest: I was scared. I was terrified I wouldn’t be able to make enough money, I was afraid I’d get lonely, and I did not want to regret quitting my secure, well-paid job to go around the world.
Here’s what I learned: fear shrinks the moment you take action. On the first flight, at a remote job, and at night in a new city, I leaned into the discomfort and grew as a person. No more living in my comfort zone; it felt liberating to live on my terms.
The loneliness? I’ve made more friends as a digital nomad than when I lived back home. I’ve joined coworking spaces, local groups, and online communities like Instagram and YouTube. So many of us are out there—you just have to look.
The biggest challenge? Stepping out of the comfort zone.
I had routines, a fixed address, and steady work for years. Trading that for something unknown felt exciting but also scary. There were moments when I doubted my decision, especially in the first couple of weeks.
I remember taking my first steps off the plane, the heat and humidity of Bangkok hitting me in the face, and thinking, “Have I made the right decision?”
There were other challenges, such as figuring out visas, dealing with new currencies, and finding reliable Wi-Fi when I needed it most. Each time, I reminded myself: You’re learning, and the more action I took, the more confident I became.
I also learned to ask for help. Whether asking a local for directions or joining online forums, I realized I didn’t have to do it alone. That helped me most — staying connected and flexible and allowing myself to feel uncertain while I figured it out.
Looking back, those early hurdles were part of the transformation. They pushed me to grow in ways I never expected.
Whenever something tricky happens, I remind myself: You’ve done this before. You’ll figure it out again.
You’re Not Too Late — You’re Right on Time
If you’re reading this and thinking, I’d love to do that, but I’m not sure I can, let me say you can.
You don’t need to have it all figured out; you don’t need to be an expert. You just need to be willing to take the first step. That might mean applying for a remote job, booking a one-month stay somewhere new, or joining a Facebook group and asking questions.
Start where you are. Use what you have. Take one small action.
This lifestyle isn’t about being on holiday all the time. It’s about wanting to live a life that gives you joy, flexibility, and freedom—and doing it in a way that suits you. Whether that means working from a beach town for six months or just having the freedom to visit your grandchildren across the country without asking for time off, it all counts.
If I can do it in my fifties, you absolutely can, too.
So… what’s stopping you?