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  • Tim Mathis

Pilgrimage means finding a place with a good story and moving your ass towards it.

Updated: May 28, 2023

We've introduced the concept of a GAP Month as a reliable framework for transformational travel. In short, it's a month of goal-directed adventure or pilgrimage with the following characteristics:

In this post we’re focusing on movement towards a specific destination - not the personal one yet but the physical goal.

In summary, if you're looking for a transformative trip, it’s both the journey and the destination.

Cathedral in Santiago de Compostella: the Camino finish line

When it comes to organizing a transformational travel experience, is it the journey or the destination that matters?

The answer is yes.

Where you go will determine the impact of your experience.

How you get there will matter just as much.

Let’s talk about it.

Pilgrimage is about the destination, not the journey

The question “Why does it matter where you go when you travel?” seems a little bit silly. The answer is obvious, right?

You go to a place because it has what you’re looking for.

If you’re looking to relax for a week, you go to the beach and sit on lounge chairs sipping Mai Tais. If you want to go hiking, you head to the mountains and set out on trail. If you want to experience culture, food and entertainment, you catch a bus to the big city.

All that’s true, and it is a silly question. It’s just that in relation to life-changing travel, the answer isn’t quite as simple as it may be for a standard vacation.

In fact, the answer is confusing and takes some explanation, even if I can state it in a sentence:

If you’re looking for a transformative travel experience, what you need is a destination that has a good story.

I’ll pull back for a moment and explain what I mean, because that probably doesn’t make any sense.

Pilgrimage and Story

Every place has a story. Every town came to be somehow, and every mountain means something to someone.

Some of those stories have become widely important and meaningful. The Delaware River, for instance, became important to a lot of people when Washington crossed it to take on the British (and when some German guy named Leutze painted the scene).

A way to think about all of the world’s classic pilgrimage sites: they’re all places with stories attached that a lot of people find meaningful.

Millions of people visit the Bodh Gaya and the Bodhi Tree in India because there’s a story that the Buddha achieved enlightenment sitting there.

The Camino de Santiago is the most popular long walk in the world because there is a story that God uniquely blessed a strange corner of Spain with his apostle’s remains, and those who visit can be blessed themselves. (By the way, that picture above is myself and some fellow pilgrims, only a few meters from St. James' bones at Santiago de Compostela.)

Some places are meaningful, but to far fewer people. I would imagine that there are locations in your own life that are significant to you, but almost no one else? The place where you first met your partner? Or the place where you decided to end the relationship? The location of your first job? Or the place where you celebrated your retirement? Those might be important locations for you because of the stories associated with them, even if no one else is aware.

Places take on a sense of importance to people. They represent things. It’s not just about the location, per se. It’s the story behind it.

All of that makes sense, right?

Story and Meaning

Every person also has a story. We all have a lot of stories, actually. Everyone you know has a story about you, and you have a story that you tell about yourself that defines your identity. It’s that story about yourself that is crucially important.

Emily Esfahani-Smith, in her brilliant book The Power of Meaning, said that people who self-report a deep sense of meaning in life are able to construct a coherent story about themselves and how their life fits in with the bigger picture of the universe.

Think about an electrician who genuinely loves their work and would never think of changing career paths. How would you imagine that they got to that point? They probably like the day to day tasks, sure, but if they’re really committed it must be more than that, right? Maybe their father was also an electrician who put in long hours to pull his family out of poverty and continuing the work is a way to honor his legacy. Maybe our hypothetical electrician knows that they play a key role in maintaining their town’s safety because they ensure that buildings don’t burn down, life-support systems in the hospital stay in operation, and families have access to heat in the winter. Maybe our electrician is a member of the IBEW and sees their union activity as part of a crucial movement to protect working class folks from exploitation by people with money and power. Maybe all of those things are true, so our electrician finds their work deeply fulfilling and beautiful.

Their life satisfaction isn’t just about enjoying tinkering with wires, right? Their story is that they’re carrying on an important family legacy, keeping their community safe and fighting tyranny in the process.

If our electrician wins awards or gets promoted at work, all the better. They add elements to the story - about how this has been a path that’s given them success and prosperity alongside everything else.

Meaningful, fulfilling lives are constructed from stories like this.

Conversely, life’s major crises are often points at which that story gets undermined. When something screws up the story we tell about ourselves, it can cause major disruption in our sense of meaning and identity.

Imagine that our electrician lost his job because he turned up drunk at work. Or imagine that a building burned down after he wired it. Who is he then? What’s he supposed to do now?

That’s what I mean about the story thing. As much as any other factor, the stories we tell about ourselves determine our sense of meaning in life. If they’re disrupted, it creates a crisis and drives us to do things like hire a therapist, take up cannabis or lay in bed for weeks.

Or to go on a pilgrimage.

Transformative travel and story

When it comes to travel, what you’re looking for, really, if you’re looking for transformation, is a location whose story is significant enough that it’ll impact your own story about yourself.

Another way of saying it is that you should think about going to a location that will really mean something to you.

Ideally, it’ll be a place that represents what you’re looking for from this experience (if you know what it is that you’re looking for).

That place might be an established pilgrimage destination, or it might be might be somewhere personally significant. The important thing is that you’ll have the potential to tell a different story about yourself after you go there.

This is simple enough to imagine. Here’s a hypothetical example:

Right now, the story you tell about yourself is that you’re a person who feels lost and directionless, sitting in (let’s say), South Carolina out of work.

If you play your cards right though, in one month, after the trip you’ve been planning, your story will be that you are a person who felt lost and directionless. At a moment of joblessness and crisis, you did something really remarkable, and spent a month seeking new understanding by cycling from Quito to your family’s ancestral home in the mountains of Ecuador.

These are two very different self-conceptions, and the second story might even supplant the first. You might replace directionlessness with a new sense of identity and purpose, because you might gain a new understanding of how you fit in to your family, your culture, and your history. Your shame about your joblessness might be replaced by your pride about your bravery in taking on this adventure. Your story about what makes your life meaningful might even be shifted as you gain a different understanding of where you came from and who your family is.

This is the sort of thing we’re aiming for with the GAP concept. Life change through picking a good place to go on a trip..

There are a lot of established destinations that represent things that you might be looking for, but it’s good to remember that the possibilities are endless.

Maybe you’ve gone through some deeply unjust experience, so you need to go somewhere that represent justice? Maybe your destination is the Museum of Memory and Human Rights in Santiago, Chile?

Maybe you’ve recognized that the constant barrage of biased media about Mexico has created a prejudice in yourself that you aren’t happy with, and you want to address it. Maybe a cycle tour between the cathedrals of central Mexico will change that?

Maybe life feels mundane and you’re seeking a sense of transcendence? Maybe you put together a walking circuit of sacred grottos in Ireland?

Maybe you’ve lost faith in your own culture and community? Maybe you put together a tour of significant cultural and historical sites in your home state and set out on a journey run?

The point is that after you’ve gone on your trip, you’ll have added a significant chapter to your story. You’ll experience a place that means something, and as a result your own story will be different than it was when you left.

I hope all of this makes sense. The point is that what your destination represents matters, because it will shape what you get from the experience.

What if you pick the wrong destination?

The last thing I’ll say about choosing your destination is that I gotta admit that it might not matter THAT much if you pick the right place.

This is a purely anecdotal point, based on my own experiences on the Camino de Santiago and on Cycle Route 1 in Taiwan.

In both cases, the destination was essentially an arbitrary choice that ended up being significant because the trips incorporated all of the other GAP principles.

I went on the Camino de Santiago in large part because a few friends invited Angel and I. The timing was right, and we’re always up for an adventure, so we went.

The Camino is a magical experience with all of the key elements of pilgrimage built in, but for most people through history it has represented connection with God or something transcendent. At the time of our trip, I was going through the process of leaving my faith behind, so in my mind, Santiago represented exactly the opposite of what I was looking for. The thing is, the experience worked. When I made it to the end, I felt a real sense of closure on the religious part of my life. It cemented my departure from faith in a way that I hadn’t planned or expected. The traditional rite of hugging a statue of the saint at the end felt like a hug goodbye to me, and it’s what I needed - even if many of the people around me felt like they were communing with God.

I rode a circuit around Taiwan on Cycle Route 1 because flights to Taiwan were cheap and Angel and I were looking for a place to spend our birthday month. We realized there was a cycling circuit you could complete in a few weeks around the island, so we went. It happened to be the case that there were dozens of temples to trigger reflection along the way, and it happened to be the case that the trip came at a point in life where an intention was obvious - to reconnect with the adventurous part of our personalities and to re-establish some of our lost physical fitness. So, the trip became a pilgrimage.

So I guess I should say, don’t stress too much. If you follow GAP principles, your experience will take on meaning.

There are plenty of fish in the pilgrimage sea. You don’t have to go to New Zealand if you want to develop a sense of connection to the natural world. You could spend a month paddling the waterways of your home state, You don’t have to go to Rome to develop a sense of grounding in human history. You could spend a month walking between museums and key historic sites in your own city.

I personally don’t think there are magic places in the world. The expectation of transformation matters more than the specific location. So don’t stress too terribly much.

Transformation is about the journey, not the destination.

We’ve talked about the importance of your destination, now let’s talk about how you’re going to get there.

To start, let’s just get one thing straight. The literal, physical journey matters, even if other people might present alternative visions of what makes travel transformational.

For instance, when I think of life-changing travel experiences, Eat, Pray, Love is the first thing that comes to mind. Why? It’s a good story that’s been marketed well, and it seems romantic. What happened in that book? Elizabeth Gilbert was in crisis after a divorce, so she organized a trip and spent a year between three different locations: Italy, India, and Bali. During that year she spent a bunch of time in self-reflection, focusing on specific areas of life and particular types of experiences (pleasure, spirituality and balance, if you’re wondering.). She studied under a few gurus in order to learn the ways of the world. It’s a pleasantly readable bible in the self-help retreat model of midlife crisis coping. And it was very much about the power of the destination. Not as much the journey - at least physically speaking.

Before you get mad at me, I’m not against that sort of thing. Some of my own trips have taken that form across the years - most obviously trips Angel and I took to Guatemala and Bolivia. In each case we signed up with a language school and immersed ourselves in the local cultures for a month. They were awesome experiences. There’s no better way to learn a language, and immersion is the best way to get to know a place. It’s the slow travel craze, and I’m all for it.

But since we’re aiming at transformative travel here, instead of Eat, Pray, Love, if you can I’d encourage you to Walk, Bike, or Run.

Why? Because human powered travel is the most time-honored form of transformative travel. It’s uncomplicated and reliable. I’m sure that it works.

In hiker terms, don’t get vortexed. Go on a trip that’s either a point to point or a loop.

In normal people terms, if you’re looking for transformation, pick a specific physical destination and move towards it under human power.

Or, pick a specific physical circuit and move around it under human power. Temple to temple, or town to town, or monument to monument.

In other words, (ahem) organize a Goal-directed Adventure or Pilgrimage for a month or so.

Don’t worry, you can still Eat, Pray and Love along the way if you want. (And If you want a blockbuster new-agey spiritual model for the experience, there are plenty. Try The Alchemist or The Pilgrimage by Paulo Coelho, for a start.)

And if physical or other limitations are a barrier, it’s still possible to make Drive, Train or Bus work, particularly if you integrate the other characteristics of transformative travel that we’ve been talking about.

Why human power is uniquely effective in transformational travel

You don’t have to go bonkers. You don’t have to grind yourself into the ground. You can if you want, but the point is that you should make human powered movement towards your goal a primary part of the experience if you’re trying to change your life. You can make distances as short or as long as you like, but a GAP Month is in large part about the magic of human movement.

Other than to point out that what we’re looking for is an experience of being an actual living, breathing human, I don’t think there’s one unifying reason that using your body as your means of transportation works. There are a lot of reasons, and they all work together to make a case for human power.

This isn’t an exhaustive list, but here are five of the most important.

  1. I made the argument in a previous post that what you’re looking for with this sort of experience is disruption: that is, an experience that will be significantly different from your normal day to day existence. In Dave Whitson’s book Pilgrimage: A Medieval Cure for Modern Ills, he made the depressing but undeniable point that the phrase “We sit inside” is perhaps the most concise way of describing life in the modern world. Human powered travel is a dramatic departure from that lifestyle. It’s a step away from existence defined by technology and shelter, towards a month immersed in physicality. Moving along outside on a bike or your feet or a kayak is an immersion experience in reality. The outdoors, nature, culture and history will hit you in the face on a regular basis. You’ll get direct exposure to experiences of transcendence, to discomfort, to the natural world, and to real, live people. Walking. Cycling. Paddling. Running. All facilitate that. Sailing? Yeah - it’s pretty good too. Motorcycles? Kind of. Trains? Maybe. Driving, less so. Flying, not at all.

  2. Humans are physical beings. Doing physical activity produces internal experiences. It produces endorphins and endocannabinoids and other hormones that make us feel certain ways. The relaxing rhythm of walking or pedaling or paddling leads to passive reflection. The focus on the physical allows for the background noise in our minds to quiet. Movement across time puts us in a specific physical state that impacts our mental state. In short, doing repetitive, slow human movement helps us think

  3. On a similar note, doing the same thing every day is boring, and there’s value in that. If you haven’t done something like this before, it’s hard to appreciate just how much of your time will be spent either zoning out or focusing on simple, immediate issues like how much your feet hurt, how much your shirt stinks, or how to avoid crashing into a rock. That dynamic can lead to a sense of boredom in the moment, but it’s an important part of the process. Boredom allows your unconscious brain to integrate ideas unconsciously for hours at a time, and engages you in a process of “deliberation without attention” which some psychologists believe creates an environment where epiphanies can occur, particularly when you’re dealing with problems that you’re struggling to solve consciously. Bumbling along, thinking about nothing is classically the time when people come to their most important realizations. A GAP Month should allow for a lot of that.

  4. Physical journeys, by their nature, hammer home their own lessons about what’s important in life. Adopting a lifestyle that primarily involves paddling, eating and camping along the side of the Mississippi reduces life down to the most basic requirements. Having to carry what you need forces you to reduce your belongings to the most simple needs. There’s a daily dilemma of deciding whether each thing you’re carrying is worth the weight. When you eventually sort it out, it feels like a revelation. Two lessons you’ll absorb if you do this for long enough are that a person doesn’t need much to be content, and most things you carry don’t actually make life better.

  5. Finally, overcoming a physical challenge provides an enduring sense of agency that is applicable to other aspects of life. If you can hike for a month straight, it’s not hard to convince yourself that you can do other hard things as well. It’s an objective experience that will stick, and will wire your brain to believe that you can manage whatever life throws at you. We’ll talk about this a bit more when we get around to discussing adventure as an element of the GAP Month formula.

All of that together makes physical journeys reliable. You can be sure that under an extended period of human powered movement you’ll experience deep reflection, you’ll feel both alive and uncomfortable in ways you don’t in normal life, you’ll overcome challenges that will carry lessons for life back home, and you’ll naturally absorb lessons about what you actually need to survive and feel content. While you could book a month at a retreat center in Indonesia and end up hating it, a month of physical movement even in Winnipeg is sure to be transformative and trigger revelations.


There’s a lot more to be said about the importance of the journey and the destination, but I’ve already hit you with a lot in this post, so that’s where we’re going to leave things at the moment.

To put it simply, if you want a travel experience that’s guaranteed to be transformative:

  1. Pick a destination that represents something important to you, and possibly to others.

  2. Pick a means of getting there that will change you in and of itself.

Or, in other words, find a place with a good story, and move your ass towards it.

Those are time-tested, reliable features of transformative travel.

Back to the GAP Month home.

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