Why Starting Over Feels So Hard, Even When You’re Ready

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Looking out over the Story Bridge in Brisbane ❤️

In less than a week (as I write), my husband & I are setting off on our next big nomadic adventure. Phuket, London, Italy, Spain, maybe Cape Verde, and South America early next year.

With backpacks at the ready (and the knees a little less flexible than they used to be), we’re off to soak up as much life as we can.

And the other morning, looking out over the Story Bridge here in Brisbane, I caught myself thinking… how lucky am I?

But then I stopped. Because my lifestyle hasn't been luck. It's been by design.

The Decision to Live an Extraordinary Life

Fifteen years ago, I read The 4-Hour Workweek by Tim Ferriss and made a huge decision to design my work around my life, not the other way round.

I left my “normal” behind, sold the house, walked away from my career, and took a leap into the unknown.

I didn't know much at the time, but I knew I wanted to live an extraordinary life.

I wasn’t going to lie on my deathbed full of regrets. I wasn’t going to live by someone else’s definition of success, and I wasn’t going to wait for permission to live the way I wanted to live.

That one decision — to stop following the rules and start writing my own — changed everything.

Since then, I’ve spent 15 years travelling the world, working from beaches and balconies, sometimes flying high, sometimes figuring it all out as I went.

And now, with my daughter off to chase her own dreams, my husband and I are off to squeeze the absolute juice out of our next chapter.

But here’s what I know to be true:

This kind of life isn’t reserved for the lucky, or the rich. It’s available to anyone willing to walk a different path, and trust in their own dreams.

Why Freedom Can Feel Like a Risk At First

If you’ve spent the last 35 years building a solid career, providing for your family, and doing all the things a responsible adult is supposed to do, the idea of starting something new later in life can feel incredibly uncomfortable.

Especially if circumstances mean you're staring down a future that looks a lot less stable than you expected.

It’s not that you don’t have skills. You do. Decades of them.

It’s not that you don’t want more freedom. You’ve probably been craving it for years.

But stepping away from the safety net of a job, even after the net’s been taken away, can feel like jumping without a parachute.

We Were Raised to Value Stability, Not Risk

Our generation was taught to find a good job, stick with it, and slowly work our way towards retirement. Responsibility was the goal. Security was the prize.

So now, even when the opportunity for freedom presents itself — or the push comes whether we like it or not — doing something outside the norm can feel risky, even reckless.

• Starting a business?

• Putting yourself out there?

• Becoming a consultant, or a coach, or a creator after decades of being part of a company or system?

It’s no wonder people hesitate.

There’s often a voice inside that says:

• “What if I fail?”

• “What if no one takes me seriously?”

• “What if I spend time and money on something that doesn’t work out?”

Doubt Grows In The Silence of Inaction

The longer we wait, the more those questions start to feel like facts.

What begins as hesitation turns into nagging self-doubt. And over time, we start to forget just how capable we really are.

It’s easy to overlook our own experience when we’re not using it every day.

You might forget that you’ve led teams, solved complex problems, navigated crises, coached others, and built systems from the ground up.

You might discount the value of your knowledge because it’s second nature to you — but that doesn’t make it any less valuable.

What it means is that you're sitting on a lifetime of expertise, and the only thing holding you back is the belief that it’s not enough.

You Don’t Need a Big Leap. You Need a Clear Path.

The good news is, you don’t need to quit everything, risk it all, or try to build a seven-figure business overnight.

You just need a structured way forward. Something that helps you take your experience, your interests, and your goals and turn them into a meaningful, portable income stream.

Something that fits the way you want to live now — with more time, more flexibility, and the freedom to travel, explore, or simply work on your own terms.

That’s exactly why I created:

👉 The FREEDOM Path™ — a simple 7-step framework to help you build portable income and reclaim your time, so you can live your best years with more choice, purpose, and joy.

🎥 Watch the FREEDOM Path™ Workshop

In this 45 minute workshop, I’ll walk you through the exact steps I’ve taken (and taught) to:

• ✅ Break free from self-doubt and imposter syndrome

• ✅ Define your own version of freedom — clearly and practically

• ✅ Turn your experience into a simple, portable income stream

• ✅ Choose a business model that fits your life, not fights it

• ✅ Create momentum (even if you’ve fizzled before)

It’s not a magic bullet. But it is a real, doable path.

And it might be exactly what you need to get unstuck and start moving again.

If this resonates, I’d love to walk the path with you.

$600+ Value for $150 - This Week Only

Inside The 50+ Nomad Club, I’ve bundled everything I know, from how to start your first side hustle, to launching digital products, building an audience, and growing income on your terms.

As a First Class Member, you get:

• Weekly side hustle guides you can start from anywhere

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Right now, during launch week, it’s just $150 (normally $297).

Once doors close Monday 4th August, that price is gone.

You’re Closer Than You Think

We spend so long being told to play it safe.

But deep down, you already know when it’s time for something different.

So if you’re feeling that pull — to live with more freedom, purpose, and adventure in this next chapter — consider this your sign.

You don’t need to be fearless.

You just need to start.

And I’ll be right here to walk it with you.

Jo 😊