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  • Tim Mathis

The DIY Pilgrim: A checklist for transformative travel based on age-old pilgrimage principles.

Updated: May 28, 2023

In this series of articles about the GAP Month, I’ve pulled together core concepts to help you, dear reader, organize a travel experience that will almost definitely be life-changing. GAP stands for “Goal-directed Adventure or Pilgrimage,” and it’s a model based on both personal experience and the long human tradition of pilgrimage. There’s a lot of time tested stuff here.

It’s a lot to read though, so in this post you’ll find the tl;dr distilled essence. It’s the “to do” bits, which you can use as a checklist for building your own experience. It includes links to the other articles and some key outside resources to get you there.

If you haven’t read it yet, I would recommend at least checking out the introduction to the series for context, but think of this as your DIY pilgrimage checklist.

Here it is, concisely, what you need to do to organize your own GAP Month.

And FYI, if you want to read more on any of the topics, full articles on each subject are linked in the headings.

A pilgrim cat sitting on El Camino de Santiago

A key characteristic of transformative travel is that it’s disruptive. It interrupts your normal flow and gives you enough distance to look back on your life from an outside perspective. Time is a big part of what creates disruption. It’s not a magic number, but a month is a reliable amount of time. It can be longer. It can be shorter. A month is good though.

Use a month away as an intentional disruption if your life feels stagnant. Alternately, if something big has already interrupted your life, use a GAP month as a way to process. The key is to give yourself the time and (literal or figurative) distance needed for change.

I haven’t personally written much here about the practicalities of saving and getting the time off work, but I do cover that sort of thing in The Dirtbag’s Guide to Life.

Here are some links to things other people have written on the practicalities of organizing time away:

  1. How to ask your work for extended time off, from the Harvard Business Review

  2. How to budget for extended travel, an excerpt from The Adventure Travellers Handbook by Nellie Huang

  3. Logistics for long-term travel from the Journal of Nomads blog.

  4. An excellent Complete Beginners Guide to International Travel by That Travelista

  5. Nomadic Matt’s How to Travel the World on $50 a Day is a classic practical book about this sort of thing.

When you’re thinking about impact, the key thing isn’t how exotic or extreme or distant your destination is. It’s the story you tell about the place. Your destination should be a place that means something to you, or represents something you’re seeking.

And when you’re thinking about your means of travel, the key is to see the journey as the key to the process. It’s not just about where you’re going. It’s also how you get there. Classically, pilgrimages involve a long walk along a specific route or towards a specific location. In the modern world, you can customize, but there are solid physical and psychological reasons to incorporate a significant amount of human-powered travel, beyond just tradition.

  1. When you’re considering where you’ll go, and how you’ll get there, think about what you want to accomplish on this trip. Think about the type of place that you’re drawn to. Think of what will be realistic within your timeframe, level of fitness and budget.

  2. To make it a bit more straightforward, pick a route that’s already established. Use this existing list of pilgrimage routes, long trails and destinations.

  3. You can also DIY your own route, of course. Pick a place to go, and pick a human powered means of getting there.

Adventure, by definition, is the act of stretching yourself. It’s taking on a challenge that you’re not sure you can overcome. It’s risk, effort, excitement, and the unknown.

It’s also a way to make sure that all of this is something you’ll enjoy. Adventure is about fun.

  1. When you’re planning a trip, think about what sort of challenge you’re going to take on. How can you create a situation where you’ll have to push boundaries you haven’t pushed before?

  2. To answer this question, you might ask yourself how you want to grow. Is the key physical, personal, or cultural?

  3. You might also ask yourself what actually sounds like fun. A long cycle trip? An immersion experience in a foreign culture? A circuit through your local mountain range?

For resources on physical and mental preparation for this sort of experience, Adventure Ready by Katie Gerber and Heather Anderson is the gold-standard.

If you know what you’re looking for, you’re more likely to find it. This is probably why, classically pilgrimage involves some sort of specific, conscious intention. While historically these sorts of intentions have been wrapped up in religious concepts and language, they don’t have to be.

GAP travel is likely to help people who are dealing with a variety of personal challenges. Pulling from the history of pilgrimage and research on modern pilgrims on the Camino de Santiago, people go on pilgrimage with roughly six different types of intention. You might think about whether your trip fits into any of the following categories:

  1. Are you looking for transcendence or enlightenment. In less spiritualized terms, are you trying to sort out what to do with your life or get your act together? Are you trying to figure out whether or not to quit your job? Are you trying to connect with something bigger than yourself? Do you want to learn something about yourself or the world?

  2. Do you have some kind of health or healing goal? That could include coping with a new diagnosis or getting fit enough to do the things you want in life. It could include a desire to finally start to address addiction or unhealthy habits.

  3. Are you going because you want to connect with nature, culture or history? Maybe life feels artificial and shallow and you’re looking to place yourself within a bigger context.

  4. Are you going for “penance?” That is, are you going to right some sort of wrong, or figure out how to correct an area of life that feels off? That could incorporate struggling with grief, loss, or trauma.

  5. Are you going as a rite of passage? That is, are you going in order to transition from an old situation into a new one? Graduation or an empty nest or loss of a job or retirement?

  6. Or, are you just wandering? Are you not sure what you’re looking for, but know that it’s something? Maybe this is just about openness to experience. Maybe it’s about stepping out of a comfortable inertia “to shake the sleeping self” to quote a book title by Jedidiah Jenkins.

Set your own intention for this trip. Don’t have to stress too much about it. Just follow your gut.

The word “ritual” can strike of magic or religion, but it’s also a psychological trick to mark out a particular life experience as special and create a sense of meaning around your trip. Integrating your own rituals into your experience will help facilitate and cement the transformation you’re looking for.

Designing your own rituals maybe isn’t intuitive, but you can draw on some time-honored


  1. Bring along a book to read devotionally during the trip. That is - a book with a specific focus on pilgrimage, or on your destination, that will add a sense of meaning and purpose.

  2. Pick “sacred places” to visit along the way - places designed for reflection like temples, museums or historic monuments.

  3. Organize some small ritual to start the experience, and again to finish it. Could be as simple as signing in and out of a trail register, or organizing a before and after gathering with friends.

  4. Journal daily

  5. Wear something that will outwardly identify that you’re on a significant journey.

  6. Bring along a “votive offering” - something that you’ll leave behind on the trip to represent the transition you’re making.

I know all of this can seem weird. I won’t tell anyone about your rituals if you don’t.

For further resources, Casper ter Kuile’s The Power of Ritual is an excellent, non-sectarian introduction to rituals for the rest of us.

If you’re the academic type, check out Ellen Dissanayake’s What is Art For?

Every pilgrimage is personal and individual, but every pilgrimage also involves and impacts your community. A key part of making sure that this experience is wholistically transformative is to think about how you’ll involve your friends and family, and the people you meet along the way.

  1. Think about inviting other people along during your training and preparation process.

  2. Recognize that, even if you’re going solo, you’re going as a representative of a community. What might that mean in your situation?

  3. Think about how you’ll talk about what you’re doing with people you meet along the way during the trip.

  4. Make a plan for how you might report back to friends back home during the experience. Social media? A blog? Postcards or letters? Photos or video? You don’t have to do any of these, but if done correctly it’s possible to make this a rich experience for your community, not just yourself.

  5. Consider how you’ll share and debrief the experience afterwards. You could prepare a public presentation. You could write or create art. You could simply organize an informal gathering among friends.

The full articles in this series will give you more ideas and rationale for using GAP Month principles to DIY your own transformative travel experience, drawing on centuries of pilgrim experience. For simplicity’s sake though, if you follow the guidelines in this list you can put together an experience that will be reliably life-changing.

For one last shameless plug, when you get back, if you’re interested in applying some of the lessons of transformative travel in your day to day life, check out The Dirtbag’s Guide to Life. It’s my book, birthed out of years of reflection on these sorts of experiences.

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