When I was 27, I packed a bag that was far too big, hugged my parents goodbye, and boarded a one-way flight with my then-girlfriend (now wife). No itinerary. No real clue. Just two backpacks, two open-ended tickets, and a loose plan to “see what happens”.
We kicked things off in Thailand. Sweaty, wide-eyed, and clinging to our Lonely Planet like it was a sacred text. From there, we made our way through Australia, New Zealand, Fiji, Hawaii, and spent three glorious months zigzagging across the US mainland. We slept in hostels, huts, a dozen questionable motels, and one terrifyingly night in a secluded camp site deep in the Daintree Rainforest which looked straight out of a horror movie film set. We rarely knew where we’d be next week – sometimes not even the next night. But we were happy. Raw, scrappy, wonderfully clueless… and happy.
These days, at 44, things look a little different. I’m the guy who pre-books everything. Flights, hotels, restaurants, museum time slots, guided tours — and once, embarrassingly, a coffee shop that got a good write-up. I’ve got spreadsheets. Pins on Google Maps. Instagram saves. I’ve got a packing list broken down by weather, region and charger type. I once spent 15 minutes choosing between two rainfall shower settings.
And sometimes, as I sip a welcome drink in a perfectly scented hotel lobby with jazz floating from hidden ceiling speakers, I get this strange, quiet thought: I’ve completely forgotten how to travel.
Backpacking taught me to be flexible. To roll with it. To show up in a town, walk the streets, and find a room with a fan that mostly worked and a shower that sometimes didn’t. It taught me to get comfortable with not knowing. Not planning. Not needing to curate the experience in advance. The magic wasn’t in the itinerary, it was in the unexpected.
“I once spent 15 minutes choosing between two rainfall shower settings.”
I once arrived in a town near Croajingolong National Park in Australia with no bookings and only a hunch it might be ‘nice’. We ended up in a sprawling house for $20 AUD a night with a shower that nearly power-washed your skin off. I still rank it among the top five showers of my life.
Now? I book months in advance and spiral if the hotel has less than 4.6 stars. I Google “best time to visit” and “common scams” before I’ve even clicked “Confirm”. I plan so hard, there’s barely any room for anything spontaneous to sneak in.
That trip at 27 showed me how to travel without needing control. It taught me how to deal with uncertainty; how to laugh when everything goes sideways. Like the time I found myself clinging to the back of a pickup truck in Thailand, legs dangling off the edge as we sped towards a ferry I wasn’t entirely sure existed. That version of me would’ve found my current self insufferable.
Luxury travel has its perks – don’t get me wrong. I’m not giving up proper mattresses or functioning air-con. But it’s also a bit… safe. A bit too curated. The uncertainty is part of the charm, and when you remove it all, you lose the stories. You lose the strangers who help when you’re lost. You lose the little surprises – the noodle shop with no English menu that turned out to be one of the best meals of your life.
“I plan so hard, there’s barely any room for anything spontaneous to sneak in.”
I miss the me who didn’t care about Wi-Fi, or pillows, or whether the breakfast was ‘artisan’. The version who didn’t need a plan to find adventure. Who didn’t even check the weather, let alone pack according to it.
Backpacking, especially with someone you love, teaches you more than any guidebook ever could. It teaches resilience. Patience. A kind of openness you can’t fake. It makes you realise that the best bits often start with discomfort or confusion and end with a story you’ll be telling for the next 20 years.
I’m not pretending I’ll go ‘full backpacker’ again. I like my creature comforts and have developed a strong liking for suitcase wheels, but I’m trying to loosen my grip. To leave gaps in the schedule. To say yes to something unplanned. To remember that the best parts of travel aren’t always the ones you booked in advance.
Because backpacking at 27 didn’t just teach me how to travel. It taught me how to let go. And honestly, that lesson might be more valuable now than ever.
