5 Profound Mistakes Every Aspiring 50+ Digital Nomad Should Avoid

Spoiler: I've made them all!

When I first left the UK in 2010 with my partner and four-year-old daughter, I had no clue what I was doing.

There was no roadmap. No Facebook groups for 50+ nomads. No Substack newsletters or digital product playbooks.

Just a gut feeling that there had to be more to life than mortgage payments and endless rainy commutes.

Fast-forward 14 years, over 45 countries, and multiple businesses later — and I can safely say I’ve learned a lot.

Mostly the hard way.

Here are 5 of the biggest mistakes I’ve made or seen others make — especially those of us who didn’t start this journey in our 20s.

Avoid these, and your nomadic path will be smoother, richer, and a lot more fulfilling.

❌ Mistake #1: Thinking You’re “Too Old” for This

One of the most heartbreaking things I hear in my community is:

“I wish I’d done this when I was younger.”

Here’s the truth: your age is not a disadvantage — it’s a superpower.

In the digital nomad world, you always feel like you’re going to be the oldest person in the room. But in reality that’s rarely the case.

Sure I’ve shared meals with backpackers in their 20s, and masterminded with entrepreneurs in their 30s, but I’ve also had dinners with retirees in their 70s who were just getting started.

Your experience gives you perspective, patience, resilience, and usually a bit more savings or freedom than the average 23-year-old on a gap year.

You’ve survived breakups, meltdowns, career changes, tech revolutions, and maybe raised kids or cared for aging parents. Trust me — you can handle a visa form or a dodgy Wi-Fi connection in the middle of Vietnam.

Reframe it: You’re not too old to travel. You’re too wise to wait.

❌ Mistake #2: Underestimating the Power of Community

During my first few years on the road, I felt like a lone wolf. I had online friends, but I didn’t really have a support system. Not one I could grab coffee with in whatever town I happened to land.

But the more I travelled, the more my network grew. Online friends became real friends. People I met at networking events, hotels, in visa queues (true story), became people I’d meet up with all over the world.

And even my online communities led to lifelong relationships with some people I have the pleasure of speaking to regularly, but still haven’t met in person!

As a nomad, community doesn’t just happen. You have to create it. Proactively and intentionally.

Join coworking spaces. Say yes to the weird Airbnb dinner invite. Comment on posts, join groups, book that meetup even if you feel shy.

Freedom doesn’t have to mean flying solo, in fact it expands the pool for you to choose who you share the ride with.

❌ Mistake #3: Letting Health Slide While You “Live the Dream”

I’ve gained weight, lost strength, and ignored more than one aching joint while chasing sunsets across the globe (and sitting too long behind a laptop).

And now, at the young old age of 52, it’s come back to bite me.

Arthritic knees too early in my life and an auto immune disease I didn’t see coming, have forced me to put my health front and centre of everything!

When you’re in your 50s and beyond, your health isn’t optional — it’s the foundation of your freedom.

That doesn’t mean you need to live on kale and kale alone. But you do need to build strength, move your body, and listen to the aches.

Carrying bags up five flights of stairs in a Lisbon Airbnb isn’t going to get easier.

These days, I prioritise clean eating, daily movement (hello pool workouts!), and getting stronger, not just lighter.

Because this lifestyle is active. And the more mobile, flexible, and energetic you are, the more of it you can enjoy.

❌ Mistake #4: Believing You Need a Massive Nest Egg

I used to think I needed a million bucks in the bank before I could “afford” to live this way.

I now know that’s nonsense.

Some of my happiest travel years were when I was making $2k–$3k/month from lightweight digital income streams and living in low-cost countries like Cyprus and Thailand.

If you understand geoarbitrage — living somewhere beautiful but affordable — and you’re willing to get creative with your income, you can thrive on far less than you'd spend at home.

You don’t need passive income. You don’t need a massive online business.

You need portable income. Just enough to keep you moving, growing, and living fully on your own terms.

My first six-figure launch came from a small but loyal email list. Not a fancy website. Not an Instagram following. Just a few thousand subscribers I showed up for consistently.

❌ Mistake #5: Letting Fear Drive the Bus

This one almost stopped me.

I nearly didn’t leave the UK. I had a toddler, no fixed income, and a thousand reasons to stay put.

But I also had one reason to go: I couldn’t not do it.

If fear is whispering in your ear right now, saying you’re too old, too broke, too tech-challenged, too set in your ways — here’s what I want you to know:

You don’t need to do it all at once.

• Start with a scouting trip.

• A 3-month adventure.

• A new online course.

• A client on Upwork.

• A blog post.

• A backpack.

Build the lifestyle gradually. Expand your comfort zone week by week. Courage is built, not in one giant leap, but through repeated small steps.

What to Focus on Instead

Avoiding mistakes is a good start — but choosing the right focus is what moves you forward.

Here’s what I recommend instead:

Start building portable income sooner than you think you need to

Even a few hundred dollars a month gives you momentum. Try freelancing, selling a digital guide, offering a skill. Tiny streams grow fast when you’re consistent.

Choose one place and stay a while

Slow travel is cheaper, more enriching, and far less exhausting. Pick a country with great infrastructure, a low cost of living, and a thriving nomad scene — then settle in for a few months. Montenegro, Thailand, Portugal, and Mexico are all favourites of mine.

Make your health part of your business plan

The fitter and stronger you are, the more freedom you’ll have on the road. Think: stairs in Europe, tuk-tuks in Asia (you won’t know what I’m talking about until you’ve tried to get in or out of one of them), hikes in South America. Your body is the vehicle, look after it.

Find or create your people

Loneliness is real, but so is connection. Join a Facebook group. Comment on someone’s post. Host a coffee meetup. One real conversation can change your entire experience of a place.

Keep your dream front and centre

Write it down. Print it out. Stick it on your laptop. You don’t need to escape your life, you need to build one you’re excited to wake up to. Let that guide you.

Final Thoughts: Make Fewer Excuses, Take More Steps

I’ve made all of these mistakes — some more than once — and I’m sure there are still plenty of lessons waiting for me up the road.

But every mistake teaches me something, and makes the next leg of the journey easier.

So if you’re standing at the edge, wondering if it’s too late, or too hard, or too crazy…

Just remember:

🧭 Your age is your advantage.
🤝 Community is your safety net.
🏃‍♀️ Health is your passport.
💸 Simplicity is your superpower.
💥 And fear is just your brain trying to protect you.

The world is wide. Your story isn’t over. And the best chapters might still be ahead, if you’re brave enough to write them.

What’s your first step?
Reply and tell me. Or better yet, take it today.

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