My 5 Favourite Road-Worthy Business Models for the 50+ Nomadic Solopreneur

Ranked by ease, speed, income potential, and travel-friendliness

It was a warm afternoon in Cyprus, 2010. I remember balancing my ancient laptop on a dodgy garden table while trying to upload a video using Wi-Fi from the hotel across the street. I’d just learned what a domain name was, and had absolutely no idea how I was going to make money online.

But I knew two things: I wanted freedom, and I wanted it badly.

Since then, I’ve run a seven-figure Amazon business, launched digital courses from Airbnbs, coached clients from beach huts, and published newsletters from every time zone you can imagine. I’ve tested just about every online income stream there is.

And while some were better left in the archives (shout out to those JV giveaways and dodgy solo ads), others became the steady heartbeat of my location-independent life.

If you’re over 50 and dreaming of the freedom to travel while earning on your terms, these are the five business models I’d recommend most.

They’re not theoretical. I’ve used them all. And I’ve ranked them using the metrics that matter most to us nomads:

1. Ease of start,

2. Time to revenue,

3. Long-term return/scaleability,

4. And how well they work from the road.

Let’s dive in.

1. Freelancing: The Fastest Way to Get Paid

1. Ease of start - 5

2. Time to revenue - 4

3. Long-term return/scaleability - 3

4. And how well it works from the road - 5

Total Score - 17/20

If I had to start again tomorrow and needed money quickly, I’d freelance.

It’s simple. You take the skills you already have and package them as a service. Writing, admin, marketing, design, teaching, project management, editing, coding, customer support.

If you’ve worked in an office (or anywhere) for more than five minutes, you’ve probably got something someone will pay for.

There are marketplaces like Upwork, Fiverr, and PeoplePerHour, but your network is often the best place to start. Let people know what you’re offering. Be specific.

A good friend of mine used to build websites using only the Divi page builder. He had no brand, a simple one page website, a helpful offer and a PayPal account.

What I love about freelancing is the speed. You can go from idea to income in a week. The downside is that it’s active income. In other words you’re exchanging time-for-money. But when you’re starting out or in transition, it’s brilliant.

Best for: quick wins, confidence building, making money on the move.

2. Substack Newsletter: Slow Burn, Big Reward

1. Ease of start - 4

2. Time to revenue - 2

3. Long-term return/scaleability - 5

4. And how well it works from the road - 5

Total Score - 16/20

This is my current favourite. It’s not fast, and it won’t make you rich overnight, but the compounding effect of publishing a regular newsletter is powerful.

It builds trust. It creates a community. And best of all, it’s yours. No fighting algorithms, no dance videos, no constant reinvention. Just consistent, helpful writing for people who care.

Substack makes it ridiculously easy to start. If you can write an email, you can publish a newsletter. You can layer on paid subscriptions, digital products, affiliate links, or even run workshops and memberships later down the track.

It’s ideal if you like writing, sharing ideas, and building something steady. But you do need patience. Most newsletters don’t gain traction until you’ve published regularly for a few months at least. But once they do, they become a real asset.

Best for: creators who want a sustainable, owned platform and aren’t in a rush.

3. Coaching or Consulting: High-Value, Low-Tech

1. Ease of start - 3

2. Time to revenue - 3

3. Long-term return/scaleability - 4

4. And how well it works from the road - 5

Total Score - 15/20

If you’ve spent decades building experience in a profession, you’re sitting on a goldmine.

Coaching and consulting are brilliant because they require almost no tech, no inventory, and no upfront investment. You can run your entire business with Zoom and a calendar app.

Whether you’re helping people write a CV, transition careers, navigate menopause, improve their leadership skills, or plan a sabbatical. If you’ve been through it and can guide others, you can coach.

Consulting leans more towards done-for-you services or strategic input, often at a higher price point. The challenge here is positioning. You need to communicate your value clearly and find the right clients. But once you do, it’s a flexible, rewarding way to earn.

Best for: midlife professionals ready to share their wisdom in a meaningful way.

4. Digital Products: Scalable and Evergreen

1. Ease of start - 2

2. Time to revenue - 2

3. Long-term return/scaleability - 5

4. And how well it works from the road - 5

Total Score - 14/20

This was my holy grail for years, and it still is, when done right.

I’m talking about ebooks, templates, guides, courses, swipe files, printables. Anything that solves a specific problem and can be downloaded or accessed online. You create it once, sell it over and over again.

Sounds dreamy, right? And it is. But it takes effort upfront. Not just to create the product, but to build the audience who’ll buy it.

The mistake many people make is building something in isolation, then wondering why no one buys. My best-performing products have always come from questions I was already getting asked.

When combined with a newsletter or audience platform, digital products are magic. But they’re not ideal as a first income stream unless you already have an audience or a burning idea people are waiting for.

Best for: long-term thinkers ready to put in the groundwork.

5. Print-on-Demand eCommerce: Creative but Complex

1. Ease of start - 3

2. Time to revenue - 2

3. Long-term return/scaleability - 5

4. And how well it works from the road - 4

Total Score - 14/20

I love this model, but it’s not the easiest. Think of it as a creative outlet that can become a business.

Print-on-demand means you design something (like t-shirts, mugs, journals, posters), list it online, and when someone buys, it gets printed and shipped automatically. You don’t handle inventory or postage.

I prefer Shopify over Etsy because it gives you more control. You can build a real brand, optimise your store, and not be at the mercy of another platform’s whims. But it’s also more work. You need traffic, marketing, and good product-market fit.

It’s not a fast model. You’ll spend time testing, tweaking, promoting and building. But if you enjoy design, branding, and creativity, it can be really fulfilling.

Best for: creatives and tinkerers who want a hands-off product store.

Final Thoughts: Pick One and Start

Each of these models has paid my bills and funded my adventures at different times. I’ve freelanced to get quick cash, launched courses to build income over time, coached clients between flights, and built products while watching the sunset in Thailand.

You don’t need all five. You just need one that fits you right now.

Pick the one that matches your energy, your timeline, and your strengths. Give it 90 days. Focus, test, adjust. Keep going.

And remember, you don’t have to build an empire. You just need enough to live freely and fully on your terms.

Portable income is the key.

Start where you are. And build something that travels with you.