Why You'll Never Feel 'Ready' to Travel (And Why That's a Good Thing)

The truth about travel, fear, and why the best adventures start before you feel prepared

Being practically dragged around the ski slopes by my husband and instructor!

Note this - You probably won’t ever feel ready. I never did.

We sold everything we owned and jumped on a flight to Cyprus within a week of getting the opportunity to house sit for a friend.

One minute we were living in the UK with a four-year-old and a business to run. The next, we were stepping off a plane with three suitcases, a small child, and a vague plan to “never come back.”

We weren’t ready. Not really. We hadn’t mapped out a route, we didn’t have endless savings, and I certainly had no clue how I was going to build a proper business on the road.

But we went anyway.

And that single, slightly reckless decision turned into 15 years of full-time travel and a lifestyle I wouldn’t trade for anything.

So if you're waiting to feel ready, to sell up, take the trip, launch the side hustle, or even just hit 'book now' on that flight, let me offer you a truth that might just set you free:

You probably never will.

And that’s the good news.

'Readiness' Is a Myth (And It’s Costing You Experiences)

There’s an idea floating around that you’ll suddenly wake up one day and feel completely prepared to uproot your life, board a plane, or start something new.

You won’t.

Readiness is a moving target we tell ourselves we’ll hit when the money’s right, the timing’s perfect, the kids are sorted, and we’ve read every article on travel insurance and backpacks.

But in my experience that moment never arrives. Not fully.

I ran my first webinar without knowing how to turn it off. I literally had to ask one of the attendees to help me shut it down. I was sweating bullets, half-laughing, half-panicking - but I did it.

And people loved it. And some even bought.

Same goes for scuba diving. I’d done one ‘joined by a rope’ discovery dive some 8 years previous when we boarded a boat in Thailand for a liveaboard in the Similan Islands.

A few days later I was underwater with giant manta rays and a newfound obsession. I now have over 100 dives under my belt, but I started with zero. Not a clue what I was doing. Not “ready” in the slightest.

The thing is, most of the best parts of life start before you feel prepared.

You jump. You learn. You grow.

And if you wait to be fully ready, there’s a real chance you’ll never go at all.

What Happens When You Leap

When you go before you're ready, two things happen:

1. You discover you’re far more capable than you thought.

2. You collect the best stories of your life.

My sister and I once backpacked across Europe with zero fixed plans. We booked trains and buses as we went, found quirky little hotels on the fly, and adjusted our route whenever something interesting came up.

No itinerary. No detailed research. Just the freedom to follow our noses.

It was one of the best trips I’ve ever taken.

Then there was the time we landed in China at gone 10pm, jet-lagged and foggy-brained, and I suddenly remembered… they don’t allow Google. My VPN wasn’t working, the taxi queue was two hours long, and we had no clue how to get to our hotel.

But with some help from a lovely lady at a desk, a bit of calm thinking, and a willingness to embrace the unknown, we navigated the metro system and found our hotel within the hour.

And then there was the time I decided to try my hand at skiing.

Ah, skiing. 😳

I decided to give it a go in my 40s. Turns out I’m awful at it. After one green run that felt more like a black diamond death drop, I now stick to the nursery slopes with the six-year-olds.

And honestly, I’m fine with that. Because I tried. I gave it a shot, and now know (with certainty) that my talents lie elsewhere. (Like sipping hot chocolate and cheering from the sidelines.)

The point is, none of those moments would’ve happened if I’d waited until I felt “ready.”

They happened because I said yes, even when I didn’t have a clue what I was doing.

You don’t build confidence and clarity by standing still and overthinking. You build it in motion. By getting on the flight. Booking the dive. Running the webinar. Taking the risk.

You leap - and figure it out on the way down.

Why ‘Not Ready’ Is the Sweet Spot

There’s a strange kind of magic that lives in the space between “what am I doing?” and “I can’t believe I just did that.”

That’s the sweet spot.

It’s where your edges stretch a little. Where you surprise yourself. Where the fear doesn’t disappear, but it gets drowned out by curiosity, excitement, and adrenaline.

Over the years, I’ve noticed that the more I know, the more hesitant I’ve become.

I ran my first businesses with barely a clue, just raw energy, late-night Googling, and the blind optimism of someone who didn’t know what she didn’t know.

And they worked.

These days, with more experience under my belt, I sometimes find myself overthinking things I would’ve just said yes to ten years ago.

The irony is, I was probably more fearless before I had a clue what I was doing. Sometimes ignorance is bliss!

Not feeling ready doesn’t mean you’re doing something wrong.

It means you’re standing at the edge of something new.

And that’s where life gets interesting.

To the Overthinkers (A Loving Nudge)

If you're still reading packing lists, comparing backpacks, and Googling “how to become a digital nomad at 50” for the third time this week… can I gently suggest that you’re already ready enough?

Seriously. If you’re even entertaining the idea, you’ve crossed the biggest hurdle.

The rest is admin.

You don’t need to sell everything or fly to Bali next week (unless you want to).

But you can take one step.

• Book the flight.

• Say yes to the housesit.

• Try a solo weekend in your own country.

• Join the group. Download the guide. Tell someone your plan.

You don’t have to know the whole route. You just need to take the first turn.

Or as Martin Luther King said;

Most people aren’t held back by a lack of money, time, or opportunity. They’re held back by the idea that someone will finally tap them on the shoulder and say, “Now you’re ready.”

No one’s coming to give you that permission. And you don’t need it anyway.

The Joy of Figuring It Out On The Way

Here’s what no one ever talks about: figuring it out as you go is half the fun.

You don’t need all the answers before you leave. What you need is the willingness to find them on the fly—in the moment, on the road, probably while battling dodgy Wi-Fi in a crumbling guesthouse with a view that makes it all worth it.

• You’ll learn how to get around.

• You’ll get better at booking the right places.

• You’ll laugh (eventually) at the time you packed three pairs of shoes and wore the same sandals for six months.

• You’ll adapt.

• You’ll get resourceful.

• You’ll surprise yourself.

And even when it all goes sideways, when you get sent to the wrong airport gate, or land in a city you didn’t mean to visit (hello, Seoul), you’ll realise: you’re okay. You can handle it.

That’s the bit that changes you.

Not the research. Not the planning. Not the gear.

But the lived, messy, brilliant doing.

You Don’t Need to Be Ready, Just Willing

I’ve built an entire lifestyle on the back of going before I was ready.

And looking back, the only thing that would’ve truly held me back was waiting.

• Waiting to feel prepared.

• Waiting for perfect timing.

• Waiting for some invisible green light to say, “Now you can go.”

If I’d waited, I’d still be waiting.

So if your heart’s pulling you towards a new chapter, whether it’s travel, reinvention, or something else, listen to that.

Don’t wait until you’ve got it all figured out. Because the figuring out is the whole point.

You don’t need to be ready.

You just need to be brave enough to begin.

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