Turning travel into a quest: How to find 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.

Reading changes lives.

“Work hard at your job and you can make a living. Work hard on yourself and you can make a fortune.”

— Jim Rohn


Formal education wears most people into the ground. When they think education, reading, learning, they remember the monotonous grind of sitting in a classroom with 30 other kids forced to learn the historical implications of the Treaty of Versailles.

Their memories of education tend not to be good ones.

Even in university, choice of subject was really just an after-thought to choice of city, which depended on how good the nightlife was and/or which of their friends were also going there.

This means that, inevitably, this sense of apathy continues throughout higher education. Even those who find a genuine interest in their subject tend to get ground down by archaic teaching methods & the apathy of other students around them.

So when we get into the real world, we wash our hands of it.

Reading becomes synonymous with the back page of the paper you find on the Metro or a trashy ’50 Shades of Whatever’ that was on sale at the airport.

Anything more than this is considered above the call of duty. A burden only borne in a state of dire boredom or necessity, such as when the internet is out for a few days.

Yet one book can change your life.

“It completely changed my perspective on …”

“Oh my god, I never thought of it like that!”

“You’ve got to read this book. I’m super motivated to do … now”


Whether you can identify an example from your own life or you’ve heard a friend raving about a book, you know the power a book can have on you. Particularly one that comes at the right time.

Yet do we find ourselves avoiding reading precisely because of this? Is our apathy not so much a dislike of education, but rather a fear of the world that books may open up?


Dreaming is easy

Let’s say you’ve always had this dream to start your own business & travel the world. It’s easy when it’s just a dream. It’s a comforting thought that sits there somewhere in your mind. You call upon it now and again, when you’re having a particularly shit day. It’s a comforting thought, the idea of a hypothetical, idealised future sitting on a beach with control over your time & resources.

But you prefer to keep it as a dream, rather than a goal.

Yet what happens when you read something like The Four-Hour Work Week, which provides you with concrete steps towards a life like that?

Suddenly those dreams start to become goals. You start to see a path forming towards them. The first few steps become clear. After that they become hazy. Yet you hesitate. You don’t take that first step because you are afraid of the unknown, of where the path might take you.

You find any excuse to not plant your foot on that first step.

“The book is bullshit. It’s a marketing scam. It’s only for young, single high-achievers. It’s only for people working in tech. I don’t even like the author, so why would I listen to him?”


If only your creativity with making excuses could be transposed elsewhere in your life.

You will find a million excuses to not take that first step. Some of them will be valid, to some extent, but most of them won’t.

So you never pick the book up in the first place. You can see where it might lead, so you retreat into your shell.


Are you ready to take action?

Yet for those that pick up that book & turn over the first page, a world of infinite possibility opens up to them.

Those ideas you’ve always had floating around in your mind, still without form? There’s a book for that. Someone has thought about it a lot more than you have, researched it & written it out in an easily-digestible format.

Your thoughts become more developed, you discover new subjects you never even knew about, you turn dreams into concrete reality. All through reading.

Some books come at the perfect time.

When I closed my first business, I didn’t know what to do next, so I read Essentialism, which helped me focus on one clear goal & wade through the infinite possibilities available to me.

When I got fired this week, I started reading The Four Hour-Work Week, a blueprint for starting a business on your own terms.

When I started taking life – & myself – too seriously, I read The Ego is The Enemy.

A lot of the time these books just appear at the right time, or you are drawn to them without realising the nature of their content. It is, in a sense, as if some books know what the next step in your education on life should be.


Yet I know that there will still be voices of scepticism & excuses at the forefront of your mind as you read this. If you think that you are already smart or educated enough, then you are entirely wrong. If you think that it is only an intellectual hobby to read, then you are wrong. If you think that people who do not continuously educate themselves will be successful in the long-term, you are wrong.

Warren Buffett, the most successful investor of all time, spends most of his time voraciously reading.

Bill Gates takes a week every year for a private “Think Week”, designated for reading without distractions of his day-to-day role at Microsoft. He has done this for a number of years.

Many top leaders, such as Elon Musk, Oprah Winfrey, Mark Zuckerberg, etc., also spend at least 5 hours a week designated for reading.


“In my whole life, I have known no wise people (over a broad subject matter area) who didn’t read all the time — none. Zero.”

— Charlie Munger, Self-made billionaire & Warren Buffett’s longtime business partner


Where to start

If you are feeling motivated to take action, then start now. Whatever problems you want to overcome in your life, there is a book for it.

Here is a brief list to start you off. Start with whichever draws your attention & read each book with a purpose, a clear desired outcome:


Side Hustle: From Idea to Income in 27 Days by Chris Guillebeau

How to start a side business whilst in full-time work. I’m using some of the practices from here to launch a freelance business in the next two months.


Principles: Life and Work by Ray Dalio

How to create a framework to govern your life & your business by one of the most successful investors & leaders ever.


The Dip” A Little Book That Teaches You When to Quit (and When to Stick) by Seth Godin

How to persevere through the inevitable dip, when you feel like progress is stalling. This has helped me persevere through language learning, programming & starting a business.


If This Is a Man and The Truce by Primo Levi

A look at the horrific reality of life in Nazi concentration camps & a look at the brutal nature of man by Primo Levi, an Italian Jew who survived the ordeal.


The Power of Habit by Charles Duhigg

A look at how habits form, persist & control over half of your actions. I’ve bitten my nails all my life. I finally stopped after reading this book & understanding the psychology surrounding habits.


The Subtle Art of Not Giving a F*ck by Mark Manson

A refreshing response to a lot of self-help books out there. By not giving a fuck about what people think, you tend to do more of what you want to do & only worry about the important things in life, like being happy & helping others.


Deep Work: Rules for Focused Success in a Distracted World by Cal Newport

A great framework for dramatically increasing your productivity by looking at the psychology surrounding how we can optimise productivity. Be warned though, you’ll find it hard to accept your company’s work culture after the learnings from this.


Ego is The Enemy by Ryan Holiday

How to tame your ego & live a more care-free, happy life. Also, by seeing how your ego will inevitably lead you to disaster through real-life examples, you will avoid a lot of pain in future.


Sapiens by Yuval Noal Yahari

This book radically changed my entire framework of belief, just by re-examining human history with the most plausible approach I have read to date.


The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss

How to finally do the things you’ve always wanted to do, whether it’s having the freedom to work remotely, start a new business, or earn enough to live a more free life. It opens up a whole world of opportunity & has radically changed the lives of many readers, whose stories are shared in the book.


Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferriss

Does what it says in the tin. The best book for quickly finding lessons from the world’s best. A book I constantly refer back to for quotes, learnings & guidance in all aspects of life.