Turning travel into a quest & on finding joy & wisdom on the road

“People don’t take trips, trips take people.”

— John Steinbeck

We see the same quotes dotted around a hostel, a Facebook group or generic travel websites.

They leave us in wonder at the depths, the complexities, the meaning behind the words.

They invoke an image of ourselves as the intrepid explorer, trespassing into the unknown, digressing from social norms at every turn. We aren’t “tourists”, we are “travellers”, conjuring images of wise, experienced beings who have seen it all.

Yet this is far from the reality.

The reality is that we travel for its own sake. We travel to a small island in Thailand to get drunk with other white, middle-class people from Northern Europe, Australia & North America.

Yes, you may learn a lot about yourself & other cultures. What drinking games they play in France, how to say ‘Cheers!’ in Thai or the political landscape of the US, for example.

I don’t mean to trivialise this, either. Some of the best conversations & experiences I have ever had have come from having a beer with someone new in a hostel or chatting with a group of backpackers out on an excursion.

But what such experiences lack is purpose.

Are you traveling just to escape “real life” for a few months? To lose yourself in the hedonism of backpacker, beach life for as long as your money lasts? Or are you using this as an opportunity to face hard truths, make real change in your life & really learn something about yourself?

You could travel to every corner of the world & still come back as clueless about — & scared of — life as before you left without departing with some specific goal in mind.

So whenever I look at quotes like the one above, I find it depressing to think that many of us will never really experience their true meaning.

We trick ourselves into believing we’ve ticked the box & really learnt something about ourselves just by getting on a plane, rather than truly changing ourselves in any significant way.

4 monkeys & myself in the Amazon

I’ve been fortunate enough to travel a lot. I’ve spend around 8–9 months backpacking in total since finishing school & I have loved every minute of it (apart from the odd bout of food poisoning).

There was, however, always a niggling frustration somewhere in my mind during my first two trips abroad.

I felt like, yes, this is great fun: I’m seeing wonderful new things, having unique experiences & meeting some fascinating, diverse people. But where’s that sense of conquest & completion that we associate with long-term travel?

Where’s my Motorcycle Diaries moment? My big summit to climb?

There just wasn’t one. I went from hostel to hostel, country to country, person to person. Each was unique, but each was also the same.

Just a series of random events blurred into one.

So, 3 years ago I decided my next trip would be different. I decided it was time to go out there & find my summit to climb.

I had been living in Spain & had saved up enough money from teaching to go on a big trip before my final year of university started.

I had starting self-teaching a bit of Portuguese whilst living in Madrid, seeing a girl from Brazil & did a weekly language exchange. I wanted to set myself an ambitious target.

So I booked flights to Brazil to spend 3 months traveling by myself & learning Portuguese properly whilst on the road.

From angry ex-guerrillas playing cards with indigenous men in the Amazon, to football in the Maracanã, to being taught how to dance in Salvador. Each experience I will savour as an experience in itself, but also because I was constantly learning, constantly pushing towards my linguistic summit.

I even spent a week hanging out at a lodge 2 days from the nearest town, with 4 orphaned squirrel monkeys & an angry parrot as my only company. One of the monkey babies would sit on my head as I took walks in the jungle. It was awesome.

By the time I got to Southern Brazil, I had gone from barely understanding a word to having fluent conversations in Portuguese, even in a large group.

All because I had set myself a goal of getting to near fluency & had gone after that goal incessantly. I had sat on sweltering boats down the Amazon with my grammar books out, chatted to locals everywhere I went & avoided the tourist traps at all costs.

Hedonism is not the aim. Fulfilment is.

And the beauty of it? It was by far the most fulfilling trip I’ve ever gone on.

People view trying something new as a struggle. As an uphill battle with no guarantee of success. The summit is so far off that they tend to give up on the way.

Yet they don’t see the enjoyment found on that journey, during the process.

They never even start because they have no idea what they would start with or are too scared as they look up the mountain towards the distant summit.

But hedonism only gets you so far. We end up spending all our time sitting by the beach, drinking out of boredom & having the same conversations about where we’ve been & where we are off to next because of hedonism.

Fulfilment means you can still do that. I spent many a night enjoying drinking & chatting at a hostel, but it’s not the aim. You lose interest after a night or two & move on when you realise you get more satisfaction from the difficult pursuit of your goal.

Create your own quest

Whether you know what you want to achieve or not on your next trip, turn it into a quest. Create a game with different levels in your head.

The joy of games comes from confronting a challenge & overcoming it, yet when we confront challenges in real life we crumble in the face of the difficulty & adversity they represent.

Everything is framed differently. Everything is a new opportunity. Everything becomes an exciting challenge for you to overcome.

You change your mindset, from “I can’t be bothered” to “Where can I find the most outlandish challenge for my quest”.

This technique has even been used to help those struggling with mental health to radically improve the symptoms.

The main thing I want to get from my next trip, for example, is to spend as much time alone in nature as possible to think about starting ::my new business:: & what I want from it on a personal level.

This has led me to book 4 days in the desert in Jordan by myself. I’m currently working out whether I can rent a horse & go fully Lawrence of Arabia for a few days*.

Without my quest, I would never have thought of the idea. It even seems absurd — & a terrifying prospect — to most. But I know it will be a hugely enriching experience for me.

If you, like most, have no idea where you would even start, then just stop & ask yourself a big question you would like to solve whilst away.

Maybe you’re unhappy with your job? If so, set yourself the quest of knowing exactly what career you want to pursue when home.

Start reading about new industries, asking friends about their industry, maybe try an online course, most of which are free. Just do 2–3 hours of work on this every morning & spend the rest of your time enjoying meeting new people & discovering new places.

Be prepared to try ten things & end up only following one. Each failure becomes a learning. Each challenge you overcome gets you closer to that goal.

Say you go away & learn to programme for 3 months. There’s no reason you can’t come back with a good enough level for an internship or full-time employment, a few mentors in that industry & a good idea of who to contact for a job when you get home.


It’s always easy to think we are learning a lot about ourselves or becoming wise whilst traveling.

Usually we are lying to ourselves. We are learning variations of the same things as we jump from hostel to hostel.

So next time you feel that slight sense of feeling lost, of angst, of wanting something more, set yourself a quest. A simple goal you can achieve whilst on the road. Break it down into smaller goals you can start ticking off your checklist every day.

You’ll find you come back a wiser, more fulfilled person.

*“He who travels to be amused, or to get somewhat which he does not carry, travels away from himself, and grows old even in youth among old things. In Thebes, in Palmyra, his will and mind have become old and dilapidated as they. He carries ruins to ruins.

Travelling is a fool’s paradise. Our first journeys discover to us the indifference of places. At home I dream that at Naples, at Rome, I can be intoxicated with beauty, and lose my sadness. I pack my trunk, embrace my friends, embark on the sea, and at last wake up in Naples, and there beside me is the stern fact, the sad self, unrelenting, identical, that I fled from. I seek the Vatican, and the palaces. I affect to be intoxicated with sights and suggestions, but I am not intoxicated. My giant goes with me wherever I go.”*

— Emerson, Self-Reliance

(One excuse that is so common is lack of money to travel. Don’t travel to popular places (e.g. Barcelona, Paris) & piss money away on €8 beers & over-priced meals. For my desert trip, return flights from Berlin to Eilat, Israel were €39 in January. It’s €50 to pay the visa to get into Jordan, which is a 10-minute bus from Eilat. I am then spending €8 per night at a tented camp in Wadi Rum, Jordan. Renting a horse is still being negotiated.)

Fast-Track Your Product Career

Get our free 7-day Mini MBA straight to your inbox:

Henry Latham

Henry Latham

Founder, Prod MBA

Read More