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  • Tim Mathis

How to travel with intention: Deciding what your trip is going to teach you

Updated: May 28, 2023

In this series, we’ve been introducing 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 the personal goal: the value of knowing why you’re doing this.

TL;DR - If you know what you’re looking for, you’re much more likely to find it.

An image of a long wharf disappearing into the horizon

I was raised in a conservative Midwestern family of small business owners, teachers, and factory laborers.

For me, it feels weird to talk about things like “setting intentions for your transformational journey.” It smacks of spiritual-but-not-religiousity and it smells like yoga class and Gwyneth Paltrow’s candles.

Well, maybe it is weird.

But so is everything else that human beings do. Green bean casserole, for instance.

You might as well do weird stuff that makes life better (also like green bean casserole). The fact is, if you’re going on a trip and you want it to be amazing, it helps to identify a specific personal intention about what you want to get out of it.

Even for Midwestern factory laborers, there’s nothing wrong with needing something from life, and if you can identify what you’re looking for, you’re more likely to find it.

So yeah, it’s only weird if you make it weird.

A story about setting intentions

Because “setting an intention” is a phrase that’s picked up some baggage along the way, I want to tell you a simple story about what it looks like.

My wife Angel and I went to Greece in 2022. We planned the trip because some friends invited us to their wedding in Athens, but I knew I wanted more out of it than just a nice wedding experience (not that there’s anything wrong with that). It was our first international trip in years. We’d both turned 40 just as Covid hit. The disease grounded us after 5 years of intensive travel and killed the small business we’d been working on. I was back employed full time as a psych nurse, talking to people all day, every day about suicide. As for essentially everyone in the world, it’d been a rough couple of years.

I needed to shake some of that off. I needed to get my groove back. I needed to make sense of all of the darkness I’d been immersed in.

So I set that as my intention for Greece.

It was a vague intention, but it was an intention none the less. I decided to make Greece an international journey meant to break out of the isolation and hopelessness and stagnation brought on by the Covid lockdowns.

I didn’t do much to address that need purposely - I just thought, “This is why I’m going to Greece.”

It seems too easy, but just having the intention meant that I experienced Greece in a specific way. Throughout the trip, my mind returned to the intention again and again as different experiences triggered reflection. I knew I needed to get a sense of direction in the world again, and to get a sense of what to do with all of this malaise. Little coincidental things pieced together to help me sort that out.

Greece is an ancient place and a lot of stuff’s happened there. I hiked up Mt. Olympus, a mountain haunted by the dead gods of a lost religion. I wandered the ruins of humbled civilizations in Athens and Thessaloniki. I visited museums memorializing forgotten conquests by Alexander the Great and millenia of Greek wars and colonization and death and humiliation. I learned that all of those beautiful white buildings in the Cyclades (which you’ve almost definitely seen on Instagram) were painted that way originally to try to fight a cholera epidemic. The dictator at the time held a mistaken belief that the white wash (which contained lime) would kill the disease.

This isn’t the only lesson you could take away from a trip to Greece, but going through those generally touristy routines, a lesson stood out to me:

Bad stuff has always happened - pandemics and wars and 40 year old men struggling to make sense of their lives. History has been shitting on people for millennia.

Modern times are just same shit, different day, but with smart phones.

There’s something reassuring in that - just recognizing your normality and accepting reality as it is. But because I intended to break out of my malaise, and not just accept it, other things also stood out.

While it’s had a rocky history (and a rocky present, for that matter), I also saw that Greece was full of old men spending their days in sidewalk cafes drinking good coffee and eating spanakopita. It was friendly tourists lounging on beaches. It was classic, delicious spiced meat everywhere. It was taxi drivers telling you stories about their family’s history on the Peloponnesian Peninsula. It was colorful churches and dramatic scenery. Greece was great music and food and wine and conversation everywhere.

The Greeks are still protesting in the streets and causing active harm by doing things like rejecting refugees fleeing the war torn countries that surround them. They’re also dancing to Laiko music, laughing, drinking too much wine and giving each other Covid. Shit happens in Greece, and has for millenia, but it is still undeniably there and human and moving on with its life.

My experience of Greece wasn’t just that shit happens, it was that life also goes on in the midst of it and even expands into beauty and happiness and fun. People keep putting together meaningful lives. They keep making art and music and babies. Bad stuff happens along the way - very bad stuff even. But what can you do but make the best of it?

It’s not that specific. It’s not that profound. But that’s a lesson I needed to absorb, and did, because I went on the trip intentionally looking for some sort of slap in the face.

Life felt sucky when I left.

I asked Greece to teach me how to break out of that.

Greece communicated simply and beautifully that when life sucks, the thing to do is to keep living.

That was the outcome of my intention.

Would I have experienced Greece differently if I’d had a different intention? Probably, I’d guess. If I were looking for reconnection with nature or an experience of transcendence, I probably would’ve approached the trip differently. Or, I probably would remember different things about the same experiences. Maybe I’d be thinking now about how all the cultures in the world have been impacted by Greece, and my own cultural roots were tied in some way to those dead gods on Olympus? Maybe I’d be thinking about the smallness of human existence in the face of history and the natural world? Who knows?

Did the trip help me break out of my funk? I think so. When I came back home I scaled back my hours at work and went to a few writing conferences. I went on a road trip, and I started planning more international trips with Angel, I started training for a half-marathon. In short, I reset after a difficult period and started getting back to living. I’m not sure I had any dramatic emotional revelations, but my perspective was gently but assertively reset in a valuable way. Greece helped me shake off stagnation and inertia of isolation and malaise and get on with it.

Greece is awesome, and I’m sure I would’ve had a good trip even if I hadn’t set any intentional goals, but travel is a bit like thrift shopping. It’s true that if you go and aren’t looking for anything in particular, you’re still likely to find something to be excited about it. But if you have something specific in mind you’ll be more likely to spot it because you’ll have your eyes open.

It’s a simple point about travel and life: if you decide to look for something, you’ll be more likely to find it.

That’s what I mean by setting a personal intention when you travel. Define what you want to get out of your trip. Keep your eyes open for it. Think about it when you feel like it. Journal or write or whatever. Just establish your mindset and define what you want to experience. The world will help you progress towards the goal.

What kind of intentions might you set?

As you’re trying to identify your intention, it’s worth thinking about the types of things that a trip might be useful for.

Another way to think about it: what kinds of problems might a GAP Month solve? If you take an intentional month away from your routine, what can you reasonably expect to accomplish?

Well, I mean, lots of things, but if you look into the history and modern reality of pilgrimage, it’s possible to come up with some specific categories of usefulness. There are at least six types of pilgrimage, and all of them are aimed at dealing with different types of problems.

I’m stealing these categories shamelessly from Dave Whitson’s book Pilgrimage: A Medieval Cure for Modern Ills. In turn, he took them from Alan Morinis’ Sacred Journeys: The Anthropology of PIlgrimage. I’m not sure where Alan got them but let’s assume he did his research since he’s an academic with a PhD from Oxford.

These categories are maybe going to reinforce the feeling that “setting intentions” is for weirdos because of all of the spiritual and/or academic language, but bear with me and I’ll translate into human-ese.

My goal here is to give you some examples to help you identify the problems you might solve, and the intentions that you might set personally.

So, I’ll list the categories of pilgrimage as defined in academic terms, and then I’ll give you the translation so it’ll be easier to think about why they might be relevant for you.

The types of pilgrimage and their purposes.

1) In devotional pilgrimage, the goal is to encounter God or earn favor with the spirits. El Camino de Santiago was traditionally this type of pilgrimage, and still is for many people.

Translation: Call it God or don’t. Classically, it’s been recognized that pilgrimage can help you experience something bigger than yourself. That helps you set your path more confidently. It helps you get perspective and clarify your values and beliefs. Pilgrimage is also useful for achieving “enlightenment” - which is just a way of saying that it helps you figure out what’s important in life, or sort out the path through some particular challenge.

2) Instrumental pilgrimage is about solving a concrete problem - like seeking a cure for illness. The pilgrimages to the Virgin of Guadalupe in Mexico and to Lourdes, France are active modern examples. People go looking for healing for specific ailments.

Translation: Pilgrimage can help people deal with actual, physical illnesses or injuries. I’m not sure it’ll actually cure you, but it’s worth a shot. More importantly, a lot of times the “cure” just means that the pilgrim comes to terms with their reality in a way that helps them suffer less. A good trip can help you move from a place of psychic suffering to acceptance and peace. A lot of people who go on walking pilgrimages on the Camino de Santiago list “physical fitness” as a goal. I’d include this here too. A long physical journey can be about getting healthy when you feel that you aren’t. A month of movement is very good for that.

3) Normative pilgrimages are annual traditions that occur at a specific time. During the Dajia Mazu pilgrimage in Taiwan, for example, every Spring, hundreds of thousands of pilgrims process a statue of the sea goddess Mazu hundreds of kilometers through the country to a specific temple near the coast. Another variation on this theme are pilgrimages that are attached to specific moments in life - like old age. In both cases, the idea is that most everyone in your culture does it at the same time - either the same time of year or the same time of life.

Translation: Pilgrimage can be used to address the need for connection with your culture. It can be participation in a community event. It can tie you in to sense of being part of something bigger than yourself - but that’s a specifically communal and traditional thing vs. something abstract like “God.” It can be a cultural ritual and a way to connect with your history and community. It’s everyone doing something together. In modern, secular America, thru-hikes often take on something like this purpose - with masses of hikers starting each Spring, walking North together on the Pacific Crest and Appalachian Trails.

4) Obligatory pilgrimage is expected to occur at some point in life by requirement. The Hajj in Islam is the most famous example. (It’s the most famous pilgrimage of any sort, actually.) Another variation on this theme are pilgrimages that were prescribed for penance or punishment by a spiritual leader - this was very common in Medieval Christianity, for instance. They’re trips that are prescribed vs. voluntary.

Translation: While your priest probably won’t force you to go on a GAP Month trip, pilgrimage has been required in religion because there’s a sense that these types of trips are effective to correct certain kinds of wrongs. That might be something you did or something that was done to you, or just something inherent in who you are. It’s a way to grind away the stuff you don’t like about yourself or get right with the world. It’s purification. You leave one person, and for some reason you come back someone slightly better. You use the time to get your shit together.

5) Initiatory pilgrimages are rites of passage into a new stage of life. The Native American “Vision Quest” tradition fits this model, as a physical and spiritual journey that young males took on upon achieving adulthood.

Translation: A trip can be a way to mark and facilitate a transition into a new stage of life. It’s not just a stamp on your passport. It’s a way to actually figure out who you’re going to be now that you’re (divorced/a parent/widowed/an adult/poor/wealthy/a college graduate). It’s also a way to move yourself beyond thought patterns that no longer serve you now that your life has changed. It’s not about becoming a new person. It’s about becoming yourself in a new situation.

6) Wandering pilgrimage: Here the goal is to wander - not to get to a fixed site. These types of pilgrimages have been completed by monks and nuns in various religions with a lot of time on their hands. You could say that this is what Jesus was doing out there in the desert for 40 days and 40 nights. It’s also often in the spirit of what backpackers get up to these days on their OEs.

Translation: Pilgrimage works if you don’t know what you need, but you know you need something. Wandering is about this, I think? Maybe what you need is openness to experience. I met a person on the Pacific Crest Trail who was “only saying yes” along the way, so they had been fried on drugs. Not setting boundaries is a terrible idea but they were hitting on a tradition there - openness to experience has a real value and pilgrimage can teach you lessons you didn’t know you needed to learn. Wandering can follow a specific route or it can involve drifting, but philosophically it’s about openness to what comes.

One trip isn’t going to solve all of your problems. Also, I’ve distilled the entire history of pilgrimage into six bullet points on a blog, so this is a gross oversimplification.

But the point is that there are certain problems that a GAP Month might be particularly useful at addressing. It might help you connect with something bigger than yourself, and this might help you set a better course in life. It might help you cope with a literal, physical problem - or make you physically healthier. It might help you connect with your community and history. It might help you get your act together or right a wrong in your life. It might help you make a transition from an old life stage into a new one. It might help you identify the problem when it feels like something’s off, and it might teach you lessons that you didn’t even know that you needed to learn.

It’s not a universal cure, but it’s a pretty solid intervention for some of life’s most complicated problems.

While I’ve divided pilgrimage into different types, in fact most trips take on characteristics of multiple categories. You don’t have to pick just one. You can have both enlightenment and stronger legs, and you can absorb new, unexpected experiences while also participating in a journey that people in your community have undertaken for centuries. Pilgrimage has endured as a practice in diverse cultures with diverse motivations because it works for all of those purposes.

How to set your own intention - in brief

You don’t have to pick one of the intentions we’ve just covered, or you could pick more than one if you want. But now you have a starting point for identifying your intention if it wasn’t set already. It doesn’t have to be that concrete - as you can see - and you don’t need to overthink it. You probably already know what your intention would be, at some level.

“Follow your gut” isn’t always the best advice, but in this case I think it is.

What’s making you interested in this sort of travel? Why do you keep reading these GAP month articles? What’s life serving up that you don’t know how to handle?

Simply put, what do you want to get out of this?

Start there, keep an open mind, and go with it. Things might change along the way, but having a set intention will point you in a specific, useful direction.

When you pick an intention, what can you expect the process of to be like?

After you’ve set an intention, and you head out on your trip, what should you actually expect?

Well, concretely, it’s like this:

Every day, toddling along you think about your problem for a while. You get sick of it and stop. Then you think about other things. Then something triggers you that is relevant to the problem, and helps you see your situation in a different light. Then you go back and think more. You have a coffee. You write down some thoughts or have a conversation about it with a stranger. You get sick of thinking about your problems and go on to something else. You’re reading a book to pass the time and when your mind is in a totally different place, you notice that the book hits on your intention. You underline a sentence or two. You tweet it out even. You go back to that problem when you have another trigger and repeat the process. After a long period of time things click together like a puzzle. At the end of the trip, you may not have all the answers - but then again, you may. At worst you will have new perspective and a new plan of attack. Or maybe you realize your problem wasn’t such a big problem at all. Or maybe it is, but you’ll realize that you have to accept it.

There’s a classic picture of the pilgrim struggling to the mountain top, finding the guru, and achieving enlightenment. I’m not sure that’s how this works.

It’s normal for people to go into these types of experiences hoping for something, then worry that they’re not doing it right when they don’t have some type of mountain top experience. Sometimes those come, and it’s awesome, but they often don’t. That doesn’t mean the process isn’t working.

No matter what intention you set, it’s best to expect something like my experience in Greece. Maybe you won’t have a single moment of revelation or Nirvana, but a series of lessons along the way will contribute to your progress. Expect something more like an experiential educational process than a ‘shroom trip or a religious conversion. Your intention will give your trip a cognitive framework and will shape the process into something productive.

Think of a GAP Month like lazy therapy or passive spirituality or embodied problem solving.

Eventually in some way or another the journey gets you through.

Your intention will help you make progress on your journey, and your journey will help you make progress on your intention.


“Setting intentions” can sound weird at the start, but it’s really just about identifying your personal goal. It doesn’t have to be fully sorted when you leave, but it helps to have something in mind. The history of pilgrimage can give you some guidance about what types of problems this sort of trip might be good for. Follow along with the types of goals that people have been pursuing for centuries. Or don’t, and see what happens. In any case, an intention will give your trip a theme and a purpose to keep you moving, and will infuse the experience with meaning and insight. Along with the other features of the GAP Month we’ve been discussing, it’ll help guarantee that the experience works. That is - and sorry if this sounds weird - it’ll make sure that the experience is life-changing.

As with all of the features of the GAP model, setting an intention is useful on its own, but it’s best done in conjunction with the other bits of the framework. If you want to read more on those, link from the menu above or go back to the GAP Month home.

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