Three encounters that changed my perspectives on life & money

The three most consequential people I met while travelling.

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When I was 25, I harboured a dream of travelling the US for a year in a campervan. In my mind, that would be quite the epic adventure. The idea was to do so in my 30s, have the most fun year of life, then continue life after that.

But life had other plans.

My mom had a stroke, and I was unceremoniously thrown into the deep end of adulthood. Needless to say, I gave up on that dream.

Instead I chose to chase financial freedom. And so instead of that van trip, I spent my 20s on side hustles and learning how to manage my money.

I used to feel a bit of regret for not being able to do that trip. Whenever I saw influencers and whatnot living it up on Instagram, I felt that I had opted for a boring, mediocre life.

These days, social media is replete with people sharing stories about how they regretted not travelling the world earlier, because they were working hard on their finances and whatnot.

While this is a popular narrative (for good reason), I also think it’s worth seeing the other sides of the story.

To the best of my memory, here are three encounters that forever changed my perspectives on the intersection of money, travel, and time.

The rider in Mongolia: Escapism isn’t free

Just before COVID-19, in Tsetserleg — the provincial capital of Arkhangai — I met another long-distance cyclist. He was in his late 30s then, and at the tail end of his trip. The guy had been to all the places on my bucket list: riding from Europe, across China, and then to Mongolia.

29-year-old me was in awe of this man. In fact, the 37-year-old version of me still is.

He had battle scars and stories to tell. He had stayed with the Taliban, seen snow leopards, and dodged trucks coming down the Pamir Highway. Objectively, it was a hell of a life.

But before we parted, over a campfire, he confided to me his fear of going back to Switzerland. His trip had first started as escapism from adulting, and somehow, he had just kept going.

For years, he lived cheaply, camping and staying in guest-houses. But he was running out of money. And the flight home would effectively empty his bank account.

And like in many big cities, his life back home was not cheap.

He worried about getting a job and renting a place, and he had lost touch with many friends back home. He had experienced extreme freedom when travelling. But now he would also experience — not by choice — extreme deprivation back home. He also didn’t know if he could ever travel again.

I’ve since learnt that while travelling the world may sound romantic, enriching, and exciting, unless you made plans beforehand, adjusting to life back home won’t be smooth. Especially if you want to return home to life in a big city.

There’s also an element of path dependence at play here. Early decisions affect the number of decisions you can make later on in life.

In your 20s, momentum is on your side. Employers will be more likely to take a chance on you. The money you save has a longer runway to compound. If you hunker down for a bit, and live below your means, you could build the optionality to walk away from that soul-sucking job sooner than you think.

Make no mistake, rebuilding your life from zero in your 30s is not impossible. But it can be difficult. Age discrimination starts to kick in. People sorta expect you to have professional accomplishments. Job security becomes an issue even for people who have experience, much less those without.

So take that year off in your 20s if you want. But just be prepared to put in the work after that.

The trucker in Australia: A simple life can cost you

In 2013, a trucker in his mid-50s offers me a ride after he sees me alone in Coober Pedy, Australia. The passenger seat is filled with burger wrappers and plastic bottles, but he empties it and I gingerly clamber into his vehicle, a dust-covered four-trailer road train.

On the 10-hour drive that ensues, we talk about everything from capitalism to immigration. He’s in the process of opting out of society. He hasn’t been to a major city in years, doesn’t read the news, and lives in the outskirts of Port Augusta, a mining city three hours away from Adelaide.

In his own words, he leads a simple life.

He has never travelled outside Australia, eats fast food at petrol kiosks. His hobbies include hog hunting (of questionable legality), boating, and fishing. The money he makes from trucking more than just barely covers his expenses.

In a very real way, he has escaped the performance of modern society. Free from the 9-5, judgement from peers. But as our conversation continued, I learnt that this man was almost certainly profoundly lonely.

He admitted that long hours on the road in isolation had dampened his social skills. He had no family, hardly any friends, and no sense of belonging anywhere. To fill the void in his life, he drank quite a bit, leading to some potential health issues.

The place he lived in had limited public services, and in his old age, he was beginning to worry about healthcare.

At the end, he expressed some self-doubt on his “simple life”: he had gained freedom, but at what cost, and for how long?

The hiker in Japan: Ageing might not be what you think

While hiking with my dad in 2015 at Mount Kumotori, we meet a hiker that passes us with blistering pace. Just as the sun sets, we catch up to him at the summit hut where hikers can stay the night.

We find out that he is almost 70, and he throws everything I knew about ageing out the window. Hiking might have given him UV damage and wrinkles, but he had far greater stamina than we did.

In my 20s I subscribed to the idea that somehow when I turned 30, I would become decrepit and have random backaches for no reason. I’d also be married, have lots of responsibilities and therefore, I should pack as much travel as possible into my 20s.

But here’s the thing. Now at 37, I’m somehow the fittest I have ever been in my life. I could still easily ride mountains in Oman, or climb hundreds of stairs to see some ‘hidden gem’.

Part of it is because very few millennials (including myself) strictly adhered to the timeline drilled into us by our parents.

But I believe a large part of it is because of the financial foundations built in my 20s. I have the optionality to walk away from jobs that I don’t want to do, and get more free time, which I in turn spend on keeping fit and healthy.

(And of course, not having children, as the parents who are sure to point out in the comments section. Come on guys, you don’t always need to make it about you.)

For a long time, I beat myself up about that missed campervan trip.

But with time I’ve come to realise that by hunkering down in my 20s, I’ve built something better: a life where adventure doesn’t have to be a one-time event.

The rider in Mongolia taught me that escapism is not an exit strategy. Travel can feel like freedom, but if you come home broke, disconnected, and starting from zero, that (temporary) freedom comes with a price.

The trucker in Australia taught me that the “simple life” also has its own costs. Walking away from the rat race sounds romantic, until freedom turns into loneliness and independence turns into having no one to call when life gets hard.

Last but not least, the hiker in Japan taught me that life doesn’t end at 30. Even if everyone in your 20s insists it does.

Like I said, at 37, I’m somehow fitter than I was at 27. Because when you spend your 20s building foundations, your 30s can become your best years — with more money, more perspective, and still enough strength to climb a mountain.

So no, I never spent a year driving across America in a campervan. But I also didn’t waste my 20s.

I almost died in Mongolia. I cycled from Tokyo to Hiroshima. I saw Myanmar before the coup. I climbed mountains with my dad.

TL;DR; I believe the goal was never to have the most epic year of my life. It was to build a life where adventure didn’t have to be something you only look back on fondly.

So yes, maybe I gave up one dream in my 20s. But in exchange, I built the option to keep dreaming in my 30s, 40s, and hopefully far beyond.

For what it’s worth, I think that is a trade worth making.

You can have adventures. You can have stability. You can have freedom.

Just probably not all at once.

Stay woke, salaryman.

Stuff we foresee in the comments section

Q: What if I spend my 20s building stability, and life still goes wrong before I ever get to enjoy it?

You could spend your 20s building stability and still get unlucky — illness, loss, even an early death. That risk is real. But there is also a much higher chance you live into your 50s, 60s, and beyond, carrying the consequences of your earlier choices. Old age is long. Being broke at 65 and forced to work when your body is tired is far less romantic than going on one trip in your 20s. People obsess over the dramatic risk of dying young, but ignore the far more likely risk of living a long life without money, health, or options.

Q: Isn’t this just postponing life and calling it wisdom?

If the choice is between working hard for 10 years and having freedom for the rest of life, or enjoying 10 carefree years and struggling for the next 40, I would choose the former every time. Suffering is rarely optional — it’s usually a question of when you pay it. I would rather front-load the difficult years when I’m young and healthy, and when momentum is on my side, than back-load them into old age when my body is tired and my options are fewer.

Q: What if I need adventure early, not after financial freedom?

Then take it! But do it with your eyes open. Some people genuinely need exploration before they know what they want. The problem is never adventure. It’s mistaking escapism for a long-term plan.

Q: I still disagree.

Someone who values spontaneity more than security may find this perspective too cautious. Someone from family wealth may not feel the same urgency around financial foundations because failure comes with a softer landing.

You might also come from a country where generous welfare, subsidised healthcare, unemployment support, and stronger social safety nets make failure less punishing. In many cases, that stability was built over generations of accumulated wealth and historical advantage (but that is another story for another time hehehehe).

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