What If Dreaming Big Is How Freedom Begins?

The wildest changes – the ones that shift the entire course of your life – don’t always start with grand gestures.

They’ve started with a question.

What if I could earn money without clocking in and out?

What if I could be free to hike whenever I wanted?

What if I could wake up slow in a cabin near a trail and open my laptop not because I had to,
but because I’d built something worth showing up for?

What if financial freedom isn’t just for someone else?

These thoughts usually arrive quietly – while scrolling past someone else’s story, or watching the sun rise from the crew deck, or walking through a quiet mountain town on a port day and wishing I didn’t have to leave by 5 pm.

For a moment, the idea stretches out in front of me like a trail I haven’t walked yet.

And then I pull myself back.

Who am I to want more when I already get to travel for work?

Where would I even start?

What if I fail and waste all this effort?

What if I’m just tired and romanticising everything?

And just like that, I bury it. File it away in a folder called someday, or not yet, or maybe someone else.

But sometimes, I don't.

Sometimes the dream lingers long enough to become something I start building around.

Like the idea of hiking

I didn’t grow up hiking. I wasn’t athletic. I didn’t know the names of mountains or the difference between elevation and altitude. When friends invited me along, I always said yes – mostly out of curiosity, and partly because I didn’t want to miss out.

They were fast. I wasn’t.

They waited. I caught up.

And still, something in me liked it.

Not the sore calves or muddy shoes, but the small freedom of it. Moving your body for no reason other than to see what’s around the next bend. Watching the landscape shift as you slowly rise above it.

Later, I started doing easy hikes on my own. Paved trails. Short loops. The kind of walks hardcore hikers would scoff at. But to me, they still felt like something.

I wasn’t fast, or impressive, or technically skilled. But I was out there. And that already put me in a different category from the people who say hiking is absurd, or pointless, or a waste of energy.

Even walking has become a quiet rebellion.

I didn’t need to go far. I just needed to go.

That one hike was never just about hiking

It was about agency. About realising I could put one foot in front of the other – even if I didn’t have all the answers yet.

That’s the same feeling I chase when I sit down to work online. When I learn how affiliate links work. When I try to design a life where I don’t have to beg for time off just to feel free again.

Financial freedom doesn’t arrive all at once. It doesn’t come with fireworks or fanfare. Sometimes it comes in whispers – like:

What if I just kept going?

What if this slow start still leads somewhere?

What if I could live simply, quietly, and still thrive?

The dream isn’t about yachts or viral content

It’s about choice.

It’s about walking longer trails without rushing back to a deadline.

It’s about slow mornings, one-way tickets, knowing you can take time off and still pay rent.

Dreaming big, for me, isn’t loud or dramatic.

It’s subtle. Gentle. Like noticing you don’t want to go back to your old life – and realising you might not have to.

It’s not about wanting more. It’s about wanting something different.

A soft, spacious kind of life. A rhythm that doesn’t burn you out.

A version of freedom that still lets you rest.

What if this is your trailhead?

You don’t need to be certain.

You don’t need a perfect plan.

You just need to let the question stay a little longer than the fear.

What if freedom begins right here – with one small step, one hike you finally say yes to?

What if you let yourself imagine something bigger – freer – than your current reality?

What if your version of success isn’t flashy, but quiet and sustainable?

You don’t need to prove anything. You just need to keep going.

Even slow paths lead to somewhere beautiful.

Joanne Tai

An adventurer, and former seafarer.

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