How to Make Money Travelling When You're Trying and Still Stuck

You already made the decision. You wanted a business that funded a life on your terms, and you built something. But here you are, still trying, and the money isn't what you pictured and neither is the freedom. You're not asking whether you can make money travelling. You're asking why you haven't yet, or why the version you built quietly turned into another job.

To make money travelling means building income that follows you instead of tying you to one place - client work, digital products, services or a portable business you can run from a laptop in Fethiye or a house sit in Bulgaria. The mechanics are not the hard part anymore. Getting unstuck is.

I've been location-independent since January 2016, when Cam and I sold a lifetime of possessions for $10k and left Australia deliberately homeless. Sixty-plus countries later, I can tell you the thing nobody stuck in the messy middle wants to hear: the problem is rarely the travel. It's the shape of what you're carrying with you.

What does it actually mean to make money travelling?

It means your income is not attached to your postcode. You can be in Panama, Turkey or Mexico and the money still arrives, because what you sell doesn't need you standing in a specific building.

That's the clean definition. But you already know it, because you've done a version of it. So let me be more useful and tell you where this usually goes wrong for women who've been at this a while.

You built the freedom part and skipped the profit part. Or you built a profitable thing that eats every waking hour, which is not freedom, it's a well-paid cage. I know that cage. I lived in it.

My cake business, Cakes by Karen, did multiple six figures. It started as an accidental Facebook page when my daughter was eight weeks old - 100 followers and nine orders in 48 hours. I loved it, right up until it became a prison of 70 to 80 hour weeks while copycats undercut me until I was almost working for free.

The turning point was a Mother's Day painting from my three-year-old: "My mum's favourite thing to do on the weekend is sleep." A smack in the face. I had built something that made money and stole my life at the same time.

Why making money travelling feels harder now than when you started

When you started, everything was new and that novelty carried you. Now you know too much. You've tried a dozen things, half of them are unfinished, and the ideas that used to excite you feel like more work you don't want.

I understand this more than most. I was diagnosed with ADHD in 2023, and my honest throughline is that I struggled financially for years because I never stuck to one thing. I did the right things in the wrong order. The freedom only showed up once I finally focused.

If you're carrying a graveyard of half-built launches and abandoned pivots, that isn't a character flaw, but it is a cost. I wrote about how your unfinished projects quietly drain more than you think, and it's worth an honest look before you add anything new.

The second reason it feels harder: your confidence took a hit. Not beginner nerves, the specific dip that comes from being good at this for a while and still not getting the result. If that's you, the way your confidence drops after time in the business is a real pattern, and it's fixable.

How do you make money travelling when you're already stuck?

You stop starting. Counterintuitive, I know. When you're stuck, the instinct is to find the next model, the next platform, the next thing. That instinct is usually the problem.

Here's the sequence that actually moves a stuck business, in order:

• Name what's working. You already have assets - an audience, a skill, past clients, a product that sells even a little. Find the thing that quietly works and stop ignoring it.
• Cut what's leaking. The offers that don't sell, the projects you keep half-finishing, the clients who pay too little for too much. Freedom is subtraction before it's addition.
• Pick one. One offer, one audience, one channel, for long enough to see if it works. This is the hardest step for people like me, and the one that changed everything.
• Own your platform. Facebook deleted my 13,000-family community overnight. I never build only on rented land again, and neither should you.

Choosing one thing when you're used to running everything at once feels like loss. It isn't. I wrote about how to pick one thing when you're stuck doing everything, because focus was the exact thing standing between me and the freedom I said I wanted.

What are the realistic ways to make money travelling long-term?

You know the categories, so I'll be blunt about which ones hold up when you're doing this for real, not as a highlight reel.

Selling a skill you already have

Writing, design, coaching, consulting, done-for-you services. Fast to start, portable, and it pays now. The trap is trading time for money forever, which is just a job that follows you to nicer places. Good as a bridge, dangerous as a destination.

Digital products and your own audience

This is where the actual freedom lives, because it detaches your income from your hours. It's slower to build and less forgiving of the scatter, which is exactly why focus matters. This is the model I'd point most stuck-but-established women toward.

A portable version of a service business

Sometimes the fix isn't a new business, it's your existing one redesigned so it doesn't need your physical presence or 70-hour weeks. I've watched people do this well - for example a mum turning a scattered side hustle into a business that finally pays what she's worth rather than another underpriced hobby.

The money is real, by the way. Estimates put the global digital nomad population at around 40 million people, according to reporting compiled on digital nomad statistics. You are not chasing something unproven. You're refining something a lot of people have already made work.

Is making money travelling still worth it after all this time?

Yes. But I won't pretend the trying doesn't change the question. When you start, you're chasing the dream. When you've been at it a while and you're stuck, you're grieving the version you thought you'd have by now. Those need different answers.

Here's what living this since 2016 has bought me, so you know what's on the table. Over 80 house sits saving more than $250,000. World-schooling my kids - my daughter Sienna ran a boutique hotel's front of house at 10. A $250-a-month apartment in Fethiye. Skiing in Bansko. Ella, our Panamanian street dog, about to land in her fifth country.

None of that came from finding a clever new income stream. It came from finally stopping the churn and building one thing properly. I accidentally built the antidote to my own brain, and the freedom followed the focus, not the other way around.

So worth it, yes. But worth doing the same way you've been doing it, no. The travel isn't broken. The engine underneath it is.

Frequently Asked Questions

What is the fastest way to make money travelling?

Selling a skill you already have - writing, coaching, consulting, design - because it pays now and needs no build time. Treat it as a bridge to something more scalable, not a permanent setup, or you'll just recreate a job in nicer locations.

Do I need to start a new business to make money travelling?

Usually not. If you've been trying for a while, the fix is more often redesigning your existing business so it doesn't need your physical presence, and cutting what leaks time and money, than starting from scratch.

How much money do I need to travel and run a business?

Less than most people think. House sitting, longer stays in lower-cost countries and carry-on living can slash your costs dramatically - I've saved over $250,000 through house sits alone since 2016.

Why am I making money travelling but still feel stuck?

Because income and freedom are not the same thing. A profitable business that eats 70-hour weeks is a well-paid cage. Being stuck is usually a focus and design problem, not an income problem.

If you've been trying, still working too hard for too little, and can't see what to change next, don't start another thing. Get honest about where the current one is actually stuck first. That's exactly what The Reality Check is built to do - diagnose what's not working so you can course-correct instead of churn. You already chose this life. Now it's about making it pay you the freedom you were promised, and that's the whole point of No More Somedays.