Considering the art and science of a skill is a powerful tool for achieving mastery. Too often we categorise disciplines into binary boxes—an ‘either/or’ state that separates the arts from the sciences like they’re opposing teams. This phenomenon begins at universities where degrees are labelled Bachelor of Arts (BA) or Bachelor of Science (BSc). Taken too far this can prevent us from thinking about how much a field is made up of both and how we stand to gain from this crossover.

Would Leonardo da Vinci’s art be as revered if he hadn’t studied anatomy or engineering? How would Apple products be if Steve Jobs never took a calligraphy class at college? Why did Einstein claim that “…arts and sciences are branches of the same tree”?

Let’s examine the tree that is vagabonding.

The ultimate combination of freedom and exploration

The word ‘vagabonding’ evokes different ideas for different people. Some associate it with careless and wasteful wandering done by good-for-nothing layabouts who lack a purpose. Others equate it as the ultimate rite of passage—a hero’s journey of self-discovery and wonder.

Simply put, vagabonding is a conscious choice to travel freely for extended periods of time. It places freedom and exploration at the heart of life. Those who scoff at the activity are unlikely to place high importance on freedom and exploration as part of their value system.

Nonetheless, those values are important for everybody—they’re baked in to the human condition. Chances are if you’re reading this, you have a taste for them too.

Freedom is essential for human flourishing. No person can reach their full potential in a constrained state. With few exceptions, since the Enlightenment period most countries in the world formally respect individual liberty (through democratic governance). Even in countries which aren’t official democracies, individual autonomy is at its highest level compared to previous centuries.

At the level of the human brain, freedom of thought is universal. Anyone who has attempted to get a young child to follow instructions knows the impossibility of trying to control what someone is thinking. Regardless of the questionable beliefs some people may hold, they can never be forced into thinking them at the neuronal level. As Noam Chomsky and Steven Pinker have said: “a blank slate is a dictator’s dream”. Fortunately it doesn’t exist. Volition of thought is foundational, if not we’d be mindless zombies orchestrated by autocrats.

Exploration is also vital in a thriving life. It’s the default frame of mind for babies and toddlers for whom everything is a discovery and crucial to healthy development. What a lot of people don’t realise is this childlike spirit to explore is useful at any age and most adults stop exploring too soon.

The polar opposite of exploration (exploitation) can only be reaped if the benefits it provides have been found by exploration in the first place. Those who explore increase the likelihood that they’ll come across more opportunities and potential upside. Exploration forces us out of our comfort zones and into a phase of learning and growth. If you’re feeling too comfortable in an area of your life, it’s probably time to explore.

Vagabonding is the ultimate combination of freedom and exploration.

Nothing else gives you as much of a chance to ponder and discover the world on your terms. As the author of quintessential book ‘Vagabonding’ Rolf Potts says: “…as much as anything, vagabonding is about time — our only real commodity — and how we choose to use it.” Taking the time to travel can lead to personal discovery that you wouldn’t get via any other means.

Commitments vs Obligations

At this point, many of you may be thinking along the lines of “Personal discovery, freedom, exploration… all of this sounds terrific but it’s just not realistic for me, I can’t simply give up my obligations to travel…”.

To which I’d respond by suggesting you first distinguish between commitments and obligations.

Obligations are our mindless ‘have-tos’ and ‘shoulds’. They are the prescriptions of others. They are self-imposed burdens. They are people-pleasing propositions. They are not in accord with our values.

Commitments on the other hand are mindful ‘have-tos’ and ‘shoulds’. They are ‘auteured’ from the heart. They are intention into action. They stake a claim to what is important and meaningful in our lives. They are aligned with our values.

Obligations make us feel like we’re living in someone else’s screenplay. Commitments allow us to direct our lives with intent.

A meaningful life is one that prioritises commitments over obligations. A life that doesn’t treat past decisions as sacrifices because the conviction behind our choices is clear.

Vagabonding can never be an obligation, like oil and water the two don’t mix. More than an undertaking, it’s a state of mind and commitment operating from the values of freedom and exploration. When you choose to vagabond, it’s because you are mindful that you’ll leave the orderly world to travel that you then become ready for the experience, adventure, personal discovery and more. You prime yourself with the conscious commitment.

When you prime yourself with the commitment to vagabond, you’ll be surprised at how you’ll come up with inventive ways to adapt your obligations around it or even turn obligations into commitments.

Here are some example scenarios from people I’ve encountered or learned of who vagabonded despite obstacles:

– A friend who decided that travelling for several weeks was worthwhile despite having a mortgage. It’s a matter of saving extra money and acknowledging that travelling can provide a qualitative experience that a house never can without losing out on either.

– A couple with a young sons who work online, homeschool their children on the road and deepen their relationship in ways never foreseen due to the incomparable personal traits required as an itinerant couple and parents.

– A high-earning professional who took an extended sabbatical after negotiating with her employer. This gave her the unparalleled flexibility of a ‘safe’ position to return to or pivot to another job after returning due to her desirable experience.

– A student postponing entering university to travel the world during a gap year. This gave him a greater ‘personal education’ as well as upgraded his CV with the soft skills acquired during his travels to levels that a student solely in higher education could never attain.

If you’re still on the fence, realise that no person who travelled had the perfect setup to do so—perfect timing is a myth and the successful wayfarers of past and present did not wait for the stars to align before setting off. To quote Tim Ferriss: “…the traffic lights of life will never all be green at the same time.” If you desire to travel but push it back to an indefinite ‘someday’, you’re demoting freedom and exploration to insignificance and that day will likely never arrive.

A proverb states fortune favours the bold. Vagabonding favours those with an adventurous spirit. You generate the adventurous spirit before travelling, not the other way around.

The art of vagabonding

Since vagabonding is more a way of viewing the world rather than a particular set of behaviours, it’s best to see it primarily as a principled art form. Understanding these principles can mean the difference between a transformative journey of self-actualisation or an anticlimactic jaunt of drudgery. Let’s explore the principles.

Vagabonding is a quest for rediscovery

“Once in a while it really hits people that they don’t have to experience the world in the way they have been told to.” wrote the author Alan Keightley.

At its core, vagabonding is the art of rediscovery, external and internal.

Rediscovery of distant lands the voyagers of old traversed to uncover the wonders of the Earth. They encountered exotic cultures, peculiar architecture and mesmerising nature and passed on their tales. Centuries later, so can we. All the landmass of the world may have been already mapped, registered and photographed but that doesn’t mean there’s nothing left for us to explore for ourselves. No Instagram carousel can replicate the power of direct experience. In person, we create our own narratives about a place that text or visual recordings alone can’t.

Yet more important than the exploration of the external world is the rediscovery of the self. Vagabonding is a journey that uses the discovery of new lands in order to satiate one’s psyche. It’s answering the call from within that requires positive change from the stagnation of daily life.

It’s about humans stripped bare facing the elements (metaphorical and literal) to see what they’re made of. Travelling is the ultimate selection test—when almost everything you own is back home and it’s just you and a few belongings, how will you fare? Only when we remove the trappings of modernity do we find the essence of the human condition, that is where real beauty lies.

The real reason we travel is for the stories, experiences and memories—how the world made us step out of our comfort zone and the enthralling results from doing so. Vagabonding gives us stories galore to fill the book of our life with.

Vagabonding and Travel Rediscovery

Adventure cannot be gleaned from following a beaten path

Rolf Potts writes: “The secret of adventure, then, is not to carefully seek it out but to travel in such a way that it finds you. To do this, you first need to overcome the protective habits of home and open yourself up to unpredictability. As you begin to practice this openness, you’ll quickly discover adventure in the simple reality of a world that defies your expectations. More often than not, you’ll discover that “adventure” is a decision after the fact — a way of deciphering an event or an experience that you can’t quite explain.”

If you could explain how a trip or situation will unfold in advance, then it wouldn’t be an adventure. 

It’s the serendipity of circumstances, the novelty of the unanticipated that create our epics. Good or bad, we return home with a twinkle in our eye knowing our biography got a whole lot more interesting as a result.

Key then is an openness to experience, free of loaded priors. “Travelers are those who leave their assumptions at home, and [tourists are] those who don’t,” wrote Pico Iyer. Your perception will colour your experiences. Vagabonders have more adventures because they allow themselves to see what they see. Their glasses are neither rose-coloured nor dark but clear.

Seeing your travels through other types of lenses than clear can lead to the ‘Expectancy Effect’, a phenomenon where your perception is distorted because you have strong beliefs that influence your behaviour beforehand, even if those beliefs don’t represent reality. On one hand you might be overly cautious and pessimistic which prevents you from improvising and dynamically responding to your environment. On the other, your opinions about somewhere may be overblown and when the place doesn’t live up to your hype, you leave disappointed.

“Whatever the original motivation for going someplace, remember that you’ll rarely get what you expect when you go there—and this is almost always a good thing.” states Potts. Experienced travellers know that places never quite match prior assumptions but if you allow yourself to truly see what is there instead of relying on expectations, the experience may just exceed them.

Occam’s Roaming Razor

Simplicity is pivotal to vagabonding well.

At first glance, this seems paradoxical. How can extensive travel, often across multiple countries and even continents be simple?

Hitting the road for a while streamlines what you own when travelling. You’re forced to reduce the belongings you take to a minimum out of necessity. This needn’t be a problem. The parsimony of a backpack or suitcase is a welcome simplifier in a world full of excess.

Travel and vagabonding force prioritisation over possessions, minimalism over multitude, and resourcefulness over riches. By leaving behind the holdings of daily life, you free your mind to focus on loving experiences, not things.

The pragmatism of simplicity when travelling also helps to deal with the paradox of choice. Whether you set out with an adventurous mindset or a (less desirable) rigid itinerary, at some point you’ll become stuck deciding what the ‘optimal’ path is. You’ll question whether to take that day trip today or tomorrow, book those flights now or later, or return to a place you loved instead of heading to pastures new.

Instead of looking back on a travel decision and fretting about whether it was maximal, by accepting the parameters of the choice you’ve made, you overcome the cognitive dissonance of the paradox and commit to the present scenario.

The razor also applies to the speed and course of your trip. If you try and bounce around destinations too fast or complexify how much you want to do and see, you’re probably going to burn out sooner or later and at worst, you’ll end your whole trip prematurely. One way or another, vagabonding compels you to slow down which allows you to better savour your immediate surroundings. Taking your time is essential to a quality trip which leads to the next point.

Focus on quality over quantity

Be wary of the phrase ‘don’t miss out’ and related notions that are often found in guidebooks and travel posts. A common mistake for first-timers is to plan huge itineraries for ‘fear of missing out’. Nothing is an absolute must no matter what some other person says and you don’t need to accommodate everyone else’s recommendations. 

Do what’s important and see sights that you want, but don’t undertake a FOMO-planned trip. Travel is not a race. Concentrate on immersing yourself in a few places well rather than rushing around indiscriminately seeking to cross-off another location on a photo op checklist.

If you have a schedule, don’t over plan it so that you have no extra time for something spontaneous. Those who jam pack their schedules with nothing but tourist-style plans often travel around frenetic trying to get everything in instead of soaking up atmospheres or finding something curious about where they’ve travelled to.

The principles covered will serve any traveller well but they aren’t the only considerations. The title mentions ‘The Art and Science of Vagabonding…’, so what is the science?

The science of vagabonding

Once we understand the principles behind the art of vagabonding, we can affix it with techniques that help us enhance our trips. While we don’t have to apply strict scientific methodology, we can still examine which aspects of our journeys benefit from a more methodical approach.

Walk until something happens

You might not arrive in a country on foot but few things will benefit your journeying more than good old fashioned walking. Human ingenuity has created all kinds of transportation devices from the bicycle to the Segway but nothing beats discovering a place on foot.

As writer, photographer and avid travel walker Chris Arnade asserts “…walking forces you to see a city at its most granular. You can’t zoom past anything. You can’t fast forward to the “interesting parts.” It is being forced to watch the whole movie, and more often then not, realizing the best parts are largely unseen by tourists.”

Walking allows you to delve into the intricacies of a place unrestricted by the dividing lines of roads. It allows you to slow down as recommended unburdened by transportation equipment.

You don’t need to trek for tens of miles everyday but if you make an effort to keep walking long enough, often you’ll encounter someone or something interesting—a chapter in your travel narrative.

By walking, you become one of the ‘pedestrians’ granting you a better chance to relate to the locals since you’re not speeding past on transport. This increases the likelihood of meaningful interactions and a deeper understanding of where you are.

Chris adds “By walking through a city, you meet the people who live there, and engage with them and their culture, on their terms in their environment. It allows you a small window into how they live. How they think about and experience the world. Consequently, it can change how you see the world.”

This doesn’t mean that domestic transport isn’t useful. The right use of transport has its own riches for the aspiring traveller.

Choose the mode of locomotion that will create the best stories

The average traveller will not get to every destination by walking or hiking and so the transport you use for longer distances can influence how well your trip goes.

This era of budget airlines makes flying from A to B a lot easier. However, this can actually reduce the number of experiences that someone has that they get from making journeys. In a not too distant past, it was often the norm to travel from country to country via trains or ferries if the continent(s) allowed for easy connection (for example in Europe).

Trains can offer a more social experience. Multiple times when travelling, I found myself in the same carriage as other travellers or friendly locals who where curious about what I was doing in their part of the world. If you sense that the people next to you are heading to the same destination as you are, it’s not hard to strike up a conversation about the place. 

This simple curiosity has led to me to receive insider knowledge, invitations from locals and ongoing friendships. Yes, long-distance train journeys may take longer in some instances but along with seeing more of the landscape on the way, you put yourself in the path of potential connections and stories.

Buses can also offer these opportunities although this tends to happen on national buses going from city to city rather than local transit buses. Compared to trains, buses can be restrictive with seating whereas trains usually have more seats available and chances to move between carriages if you wish.

Local transportation can be more enthralling so consider it on your journeys.

Geonavigate like a boss

In our ancestral past, many people had the ability to discern their location and time of day based on nothing more than their knowledge of the surrounding environment from sea to sky.

Smartphones, watches and other technology have made these skills all but obsolete but there are certain occasions where such knowledge can prove helpful. Travellers who trek in rural environments may find themselves without a signal or battery on their phone. Or you may find that knowing which cardinal direction you’re in without looking at a compass or phone is useful (and impressive) to the group you’re with. These tips won’t make you navigate the world unaided like a master scout overnight but they will provide you with immediate, practical knowledge that more than 99% of the world doesn’t have.

Many of our ancestors had naturalist wisdom that allowed them to use the sun and shadows to find the cardinal directions. Once you locate one direction such as north or south, you’ll know the others from that reference point. There are a few ways of doing this:

– Since the sun rises in the east and sets in the west, by facing the sun when it’s close to sunrise you’ll be pointing east and when it’s close to sunset you’ll be pointing west. If you’re in the northern hemisphere, when the sun is at its highest point in the day (around noon), it’ll be directly south so the shadows it casts on objects will point north. If you’re in the southern hemisphere it’s reversed—the sun will be directly north at midday and the shadows will point south.

– If it’s not around midday and you want to be more accurate, use the shadow stick method:

1. Place a stick upright into the ground in a place that has access to sunlight.
2. Mark the tip of the end of the shadow—this is west. You can use a rock or stone as a marker.
3. Wait a short while (10-20 mins) while the position of the sun’s movement changes the direction of the stick’s shadow. Mark this second position after the time has passed—this is east.
4. Draw a straight line through both markers to create a West/East line.
5. Place your left foot at west and your right foot at east. The direction you’re facing in is now due north and directly behind you is of course south.

– A technique that doesn’t require the sun is the satellite dish method. The satellites in space that deliver telecommunications orbit around the Earth’s equator. This means that satellite dishes receiving signals from them should be pointing towards the equator. If you’re in the northern hemisphere, satellite dishes will point south and if you’re in the southern hemisphere they’ll point north. If you’re close to the equator they’ll tilt upwards more in a vertical position. Use this to roughly discern north and south.

Vagabonding and Travel Geonavigate

Stay safe

By its nature, travelling takes you out of your comfort zone and while that can bring so many positives as discussed, it can create an element of risk depending on where you are and what you’re doing.

The optimal goal when it comes to safety concerns is calibration. Most people overweight concerns (paranoia) or underweight them (naivety). 

The first understanding to have is that everywhere in the world has locals who’ve lived there for generations and thus must be safe enough to have a lifestyle. For this reason, safety risks tend to be low in most parts of the world. The days of indigenous folk attacking explorers arriving by boat and vice versa are long gone. It’s a globalised world and the majority of people even in very remote parts understand the flow of foreigners in and out of their land.

Nonetheless, since your surroundings are probably new when you travel, the risks of something going wrong are higher than on your couch at home. Here are some tips for reducing those risks:

  • Things that have a possibility of being awkward shouldn’t be mistaken for things that have a possibility of being unsafe

    This one is related to calibration. Understand how to assess the likelihood of either awkwardness or danger so that you don’t over assume large risks and you can determine that your odds of being safe are good.

    If something doesn’t feel right, always trust your instincts. It’s better to be safe than to be polite.
  • Get multiple opinions

    Before or during your travels you’ll get opinions on places from others. These can be helpful but it’s better to consider more than one opinion about somewhere than to overweight one person’s viewpoint even if that person is your friend.

    A single opinion can be full of biases or based on a different context. When someone tells you that somewhere is unsafe because of the people there, get a second opinion or more so that you can assess whether it’s the whole truth or not.
  • Read other people

    Watch out for certain behaviours from others who interact with you which can indicate a suspicious person. If someone seems nervous or anxious or if they’re looking around to see if anyone is watching them—be cautious. If someone is rushing you to do something such as make a decision or go somewhere, that’s another red flag.
  • Stay visible

    If you’re ever unsure of your safety, be in public places where others can see you. In some situations, it’s effective to ask another person to help you deflect someone you want to avoid. If you’re being harassed, don’t be shy about drawing attention to the situation such as by yelling.

    If you agree to go somewhere and then you begin to question your safety, it’s always fine to change your mind. You can even request to the person that you’re worried about getting lost as a foreigner and that you want to stay in a more public area.

Remember just because travel has some risk involved doesn’t mean you should never do it. The only foolproof way to avoid these risks is to never travel. It’s because travel doesn’t neatly fall in our comfort zone that we decide to do it in the first place. As mentioned before, opening yourself up to unpredictability is what cultivates adventure. 

By taking the steps discussed you allow for positive experiences without letting the overall lower chance of adverse risks hinder you. I included this section because even though most people won’t need to resort to it when they travel, if it helps prevent even one person from a bad situation, it’s worth it.

Advice on vagabonding with others

Vagabonding doesn’t have to be a solo journey. Many people travel with partners or friends for a variety of reasons. While a large part of journeying is self-discovery and testing your own resourcefulness away from home, these can be achieved with others if done in the right way.

If you travel with others, the people you choose will make or break your journey no matter what the places you visit are like. My mother was once asked to be the travel companion of a lady she had only a slight acquaintance with because the lady considered her personality ideal for travelling. She couldn’t consider anybody from the entire network of friends she had in the same light.

It’s important to select the right accomplices before starting your trip than to find yourself stuck with someone less than ideal halfway through it. At worst, the wrong companions can feel like a gremlin on your back bogging you down with a miserly attitude. 

If you travel with a partner or partners, screen for non-ideal traits beforehand. Some red flags include excessive complaining, undue cynicism, giddy naivety and needy over-reliance on others.

Also watch out for what Rolf Potts calls “self-conscious hipsters”. My interpretation of these types of travellers is that they fetishise places to fit a world that they want to see rather than observing reality itself. These types of people tend to be absorbed in using where they visit to collect reference points that can prove how ‘cool’ they are to others instead of appreciating an experience for what it is. With the advent of social media, certain destinations have arguably become appropriated for the purposes of saying ‘I was there’ while the actual essence of those places is ignored.

Contrary to expectations, there’s rarely an obligation to spend the entirety of a trip with the companions you set out with. Temporary separation for days or sometimes weeks can benefit you and them in creating space for independence. All sides get to do what they want and for however long they wish during this ‘interval’ without compromising to balance the rest of the party. 

If you’re experiencing a lull or disagreement with companions while travelling, thinking outside the box this way can reset the dynamic between you all once you rejoin each other. Of course such decisions suit certain personalities more than others but it’s worth considering if the individuals are able.

As a final point, remember that no matter the compatibility you have with the people you set out with, you can never be certain if they’ll make it to the end of a long-term vagabonding trip. You should always be ready to go it alone even if you don’t think you will before starting.


Vagabonding epitomises freedom and exploration. It reconceptualises time and allows us to discover the realities of the world for ourselves and not just through the lens of others. More important than the destinations is the rediscovery of who we are through the journey.

Vagabonding is more of an art than a science but those who understand both stand to gain the most. The art of vagabonding involves mastering your mindset—embodying the spirit of an adventurer by journeying with an open mind, travelling with simplicity and being mindful to ponder the places you visit rather than rush through.

The science of vagabonding involves understanding the power of walking for immersion into experiences, using transport wisely, geonavigating when appropriate and knowing how to stay safe in a calibrated way.

For those who travel with others, ensure you select the right companion(s) before setting off by watching out for traits which are not ideal for long-term travel. This may mean certain partners or friends are not the people you want to go with. Understand the power of going alone—so many people get the travel bug but suppress it unless they can plan it with others. Ironically, the resourcefulness of not relying on others is what’s cultivated when journeying along with other positives.

Despite nobody ever regretting the act of vagabonding, most people will never experience long-term travel but it doesn’t have to be this way for you reading this. Vagabonding gives us the chance for incomparable chapters in our life story. As the saying goes: “A journey of a thousand miles begins with a single step”. Take that first step and see how the pages of your own book unfold, it may just change your life.