This happened in Zurich, Switzerland, at a self-directed learning center for teenagers who crave high amounts of personal freedom.

I created the workshop in February, and I was excited to run it because it gave me an excuse to:

• discuss three versions of freedom—physical, social, and political—and the connections between them

• use some wonderful hands-on activities I’d recently discovered through partner dance (physical freedom) and authentic relating (social freedom)

• integrate a few books I’d recently found about Hannah Arendt, Alexei Navalny, and Megan Phelps-Roper (all related to political freedom)

• explore the thorny topic of political polarization within the safety of a community that already trusts me (because I’d previously given two workshops at this center)

I also had an ulterior motive for running this workshop. I wanted to seriously address the question: Who am I to talk about “freedom?”

In other words, how am I, as someone who has experienced so little “un-freedom” in life, qualified to speak about this slippery, fraught, and historically complicated notion?

If I’m going to remain relevant to younger generations, I believe this is a question I must take seriously.

Perhaps writing Dirtbag Rich brought me here. Perhaps it was world events and shifting political tides. Regardless, I decided to address this question—both for myself and my teenage audience—right off the bat.

Below is a transcript of the first 15 minutes of How to Be Free: the most lecture-style, “sit and listen” part of the workshop, directly before jumping into two hours of playful, hands-on, and high-vulnerability activities. (At the bottom of this post I link to my full notes and slides, if you’d like to learn more about these activities or run them yourself.)

I’m sharing this to give you a sense of how I’m engaging teenagers these days, how I think about freedom as a relatively privileged westerner, and (if you read the full notes) what’s giving me hope for the future.

No Groundhog Day

Groundhog Day is an old movie about waking up to the same day, over and over—about being stuck in a loop.

The protagonist, played by Bill Murray, tries crazy stuff to escape the loop. He becomes reckless, wild, and indulgent. Nothing works.

Eventually he realizes he needs to change his whole way of being in the world. He focuses more on other people, complains less, and lets himself fall in love.

He wakes to a new day, fresh with possibility.

Do not wake up sick to your stomach

This is how too many people spend their days: waking up sick to your stomach about where they must go and what they must do.

You’ll probably be here at some point, too.

You’ll wake up feeling like you’re stuck in a loop of school, work, or a bad relationship. You won’t be sure how to exit your Groundhog Day.

Plenty of people will give you advice, but ultimately, it will be up to you—to free yourself.

Who am I to talk about “freedom”?

At the same moment I started dreaming up this workshop, I was reading the memoir of the Russian political activist, Alexei Navalny.

While documenting the corruption of Vladimir Putin’s regime, Navalny was perpetually harassed, imprisoned, and prevented from running for political office. Putin’s henchmen poisoned and almost killed him (watch the documentary “Navalny”). He recovered and returned to Russia, despite knowing that he’d be arrested. Navalny was kept in various prisons, and eventually, in 2024, poisoned again. This time, he did not survive.

Reading his book, I asked myself, “Who am I to talk about freedom?” This guy put his life on the line.

I thought of various world conflicts taking place [in February 2026]: Gaza, Ukraine, the civil war in Sudan, and the ICE events in Minneapolis.

Compared to so many others, I have experienced so little un-freedom.

Who am I to talk about freedom?

Who are any of us to talk about freedom?

Here we are at an alternative school, in a prosperous country, in the year 2026.

Without a doubt, we are the global and historical “winners.” We are safe, rich, and enjoy more freedoms than almost anyone else. If you had to be born into a random body in a random moment within the past 10,000 years—this is a pretty good time and place.

(This is well documented by the Swedish physician Hans Rosling, the Harvard psychologist Steven Pinker, the economist Deirdre McCloskey, and many others.)

So, really—who are any of us to talk about freedom?

The more free we become, the more we notice un-freedoms

This is the nature of social progress: it’s limitless. The more freedoms we enjoy, the more capacity we have to notice un-freedoms.

In my own lifetime, I saw this happen with gay rights. When I was in middle and high school, I witnessed open ridicule of gay people. That’s different today. The experience of being openly homosexual in the United States has improved massively in two decades.

After the fight for marriage equality was won, activists began focusing on the rights of a smaller and lesser-known group: trans people. Something similar happened with environmental concerns, labor rights, and women’s rights.

And while many different people drive social progress, it’s often the freest and most privileged (like the slavery-era abolitionists) who have the easiest opportunities to make a difference. Because they have resources, they can operate within existing power structures, and they can afford to take bigger risks.

So who are you, or I, to talk about freedom? We are those with the best opportunity (and the moral obligation) to discuss, understand, and fight for freedom.

Don’t obey — and have as much fun as you can

This doesn’t mean you must have the same opinion about “freedom” as everyone around you.

This is the tricky thing about “freedom”—there are many different versions of it, and they quickly come into conflict. There is no one clear path. Distrust anyone who insists otherwise.

Niemand hat das Recht zu gehorchen, wrote the philosopher Hannah Arendt, after documenting the Nuremberg trials of the surviving Nazis after World War 2. This means, “No one has the right to obey.” She wrote this in response to the Nazi officers, both low- and high-level, who claimed they were “just following orders.” They were just obeying.

Don’t obey, Arendt argued! You have the obligation to think for yourself, weigh the evidence, and form your own conclusions.

Yes, you are “free” to avoid thinking for yourself. You are “free” to do what your friends, family, or the mob demands. But this, she argued, is a path to unfreedom. I agree.

Popularity doesn’t necessarily make something right. History is not yet written. It’s not obvious how to be “on the right side” of it. The only way to know is to talk, entertain different ideas, and eventually, make a choice.

And also: this doesn’t have to be a chore! Thinking is passion—and passionate—Hannah Arendt argued. Political action is fun! Participating in public life opens a new dimension of human experience where change is always possible. Have fun, Arendt urged the student activists of the 1960s; have as much fun as you possibly can.

So who am I?

I’m someone who has tried to have a lot of fun while expanding other people’s freedoms.

I’m not a political organizer, lawyer, or armed freedom fighter. I’m glad that other people have taken these roles, because I’ve benefited from them (as have you).

Rather, when I turned 20, I became obsessed with a certain oppressed class: young people in school.

Compared to those facing genuine war, hunger, displacement, or enslavement, this might seem like a ridiculous statement. From a global and historical perspective, school is something that only wealthy and secure people can access. Why would students in school—even well-funded schools—be “oppressed?”

A few good books changed my mind on this issue, as did a closer examination of my own experience as a “successful student.”

I’ve written extensively about this transformation, but here’s the punchline: School is a prison-like experience for far too many students, one that negatively shapes their views of themselves (and society) for the rest of life.

I came to believe that the typical school experience does not create free people. It conditions young people toward a life of servitude, not self-empowerment. It involves too much “obeying,” too little independent thinking, and insufficient quantities of both genuine challenge and genuine fun.

So I dedicated myself to promoting alternatives to school: through writing, speaking, and bringing together groups of young people to experience freedom first-hand, through camps, retreats, travel programs, and small schools & centers that embrace self-directed learning.

Outdoor adventures, summer camps, and youth travel opportunities were exactly where I felt the most freedom as a young person (in the brief moments that I enjoyed these experiences, within an otherwise typical public school upbringing). This mode of education, collectively labeled “experiential education,” brought an incredible amount of growth, joy, challenge, and connection, in a very short amount of time. These are the places where I felt freedom in my bones.

(I also recognize that these environments aren’t for everyone, and were I born into a different brain or body, I wouldn’t necessarily find freedom in summer camps, wilderness, or travel.)

That’s why, for 20+ years, I’ve brought young people together in high-freedom, high-fun, and high-challenge environments, why I’ve learned and grown alongside them, and why I’ve written and spoken about my experiences.

Then, when the work is over, I’ve gone off to continue adventuring with my adult friends (mostly travel, wilderness, and dance), to continue experiencing freedom in my own way. Along the way, I’ve done a ton of reading (in history, politics, psychology, biography, and economics) to try to understand “freedom” from many different perspectives.

Long story short: I’ve been trying hard to avoid Groundhog Day, both inside and outside, for myself and others, for more than two decades.

These, I believe, are my qualifications for discussing freedom.

Freedom must be practiced

But today I don’t just want to talk about freedom with you. I want to practice it.

One of the biggest problems I had with school as a teenager was this: it was all talk, no action. Sometimes we had a field trip or hands-on project, but for the most part, “school” meant sitting, listening, memorizing, and regurgitating.

This did not feel like freedom. I wanted to feel freedom in my bones.

You’ve generously given me your time and attention, sitting and listening for the past 15 minutes. Now I’d like to invite you to act—to put freedom into practice—right here, right now, as we experiment with three types of freedom: physical, social, and political. My hope is that, by the end, you too will feel it in your bones.

</introduction>

While the rest of workshop is very hands-on (and must be experienced to be fully grasped), you can get a taste for it here:

• workshop notes (google doc)

• full slides (PDF, previewed below)

As always, your comments are welcome—critical, constructive, and supportive—both publicly and privately. And if you make a public comment that involves politics, please be extra thoughtful, in the spirit of the workshop.

❤️ Blake

[Big thanks to the Blake Quarterly readers who gave early feedback on the workshop, and to Julie for helping shape this post.]

My friend Hannah once printed this article, hung it up in her van, and read it out loud to her climbing friends. Many of them cried.

It’s also one of the foundational pieces that led me to write Dirtbag Rich.

So enjoy this, enjoy Dirtbag Rich, help spread the word—and thanks for being part of my journey!

Last summer, I walked across a high ridgeline in the mountains of California. 

Here above the treeline, off-trail travel is surprisingly easy. With a light pack, strong ankles, and a decent sense of balance, you can traverse rock and sand like a god at the world’s ceiling.

I smiled and laughed as I hopped between granite boulders, writing poetry with my feet: leap, balance, assess, leap, balance. The sky was clear, with long views in all directions. Sunshine and a cool breeze mingled on my skin. The night before, back in Lake Tahoe, a group of friends had come over—people who mostly didn’t know each other—and we’d all bonded over food, drinks, and games. I felt strong, healthy, alive, connected.

It was a perfect day to die.

At a spot where the ridge dropped off precipitously, two hundred feet straight down, I removed my pack and laid belly-down on a flat sheet of granite that jutted over the edge. 

Scooting up to the cliff, I peered down at the smooth granite shelves, jumbled boulder fields, and alpine lakes below. My head swam with a touch of vertigo.

“It would be so easy,” I told myself. 

It would be so easy to end life here, surrounded by austere beauty, rather than an ugly hospital room in an ugly city. 

It would be so easy to end it quickly, without burdening family members or the healthcare system.

It would be so easy to leave this world at the apex of life, instead of the nadir—free of disease, disability, dependency.

It would be so easy to jump from this ridge. 

I wasn’t even considering it. 

Thinking about death is really no different from thinking about life.

Here at the world’s ceiling, with my head hanging over the precipice, I conjured images of those with truly debilitating conditions—terminal cancer, incurable disease, severe paralysis—and what I might do in their shoes. 

I thought how a different society might offer such people a more beautiful way to depart this earth: something that felt like jumping from a mountain ridge on a sunny day, heart filled with gratitude, but without the painful and messy consequences.

I thought about the selfish appeal of “live fast, die young,” about the pain that suicide inflicts on loved ones, and about the folly of assuming old age has little to offer. I thought about Jack Kerouac’s lonely death from excess drinking.

And I remembered my great-aunt Lavalette, who passed away some years ago at the age of 101. 

After an independent and healthy life as a single woman, living by herself in a multi-story house, Lavalette had finally fallen and broken a bone. She recovered quickly for someone in her 11th decade, only to be shocked by the hospital bill that threatened to drain her carefully-managed savings. 

Shortly after this event, on a call with my father, she declared, “This is not how it’s supposed to be,” and announced her intention to stop eating and drinking. 

With a close friend by her side, Lavalette lasted a full week before passing. Near the end, as she drifted in and out of lucidity, my father spoke with her on the phone one more time. 

At the end of the call, my dad told her, “We love you, and we’ll see you in heaven.” 

Lavalette, a lifelong religious skeptic, replied, “Yeah, okay. Bye-bye.”

In many ways, my great-aunt’s life was ordinary. She worked as a secretary for the same company for 40 years. She raised Yorkshire Terriers and volunteered for the Red Cross. She traveled in Europe with friends. But mostly, she stayed in the same small town in Pennsylvania. 

In another way, Lavalette was totally extraordinary. She grew old in good health, she lived life on her own terms, and she ended life on her own terms.

Lavalette did what she loved, right until the moment it was time to go.

I don’t know what the next 20, 40, or 60 years will bring. 

Maybe I’ll meet someone I can’t live without, get married, buy a house, plant a garden, have kids, and become a stay-at-homeschool dad.

Maybe my body will betray me, dependency will be forced upon me, and I’ll watch some of my deepest loves fade into obscurity: hiking, running, dancing, travel.

Maybe my business will fail, my writing will find no audience, and my life will take such a bad turn that I’ll look back at the words I’ve written and marvel at their their sheer hubris, their naïve idealism.

Maybe.

I do not know the future, but I do know a few things:

If I died tomorrow, I'd be okay with that. I’ve pushed hard for love. My life is rich with memories, relationships, and few regrets. I made a positive impact on my tiny corner of the world. If I were hit by a car and had a few minutes to assess my choices, I imagine I’d feel content.

I’ve avoided many traps. As soon as I got a taste of pointless meetings, endless commutes, knee-jerk consumption, soul-sucking jobs, and other varieties of modern servitude, I tacked hard in the opposite direction. I’ve spent very little time doing things I don’t believe in.

I can always rejoin the standard path. I will not join the ranks of the corporate elite in this lifetime. But if I want to reenter the workforce and pursue a more normal lifestyle, I can. Doing what I love hasn’t meant forsaking all marketable skills.

I still have a soul. I don’t believe in immortal souls—but you know what I mean. I’ve avoided the slow death of the human spirit. I’ve retained a sense of hope, joy, and exuberance.

Something else I know: 

The more I’ve given up, the better life has become. “Doing what you love” certainly involves taking positive steps, but it’s also about what you don’t do. What expectations you discard. What you give up. 

Giving up the idea of a reliable paycheck. Giving up the assumption of home ownership. Giving up the expectation of finding a soulmate who will join you in a committed domestic existence. Giving up common notions of entertainment, consumption, and recreation. Giving up the idea of having children. Giving up the assumption that your life will continue, in good health, till ripe old age.

You may, of course still find yourself with a beautiful home, reliable income, loving partner, charming children, and vibrant health until your 101st year. 

But knowing the person you are, do you suspect that these things will come through direct pursuit—or as a by-product of doing what you love?

Has attempting to follow the standard path lead to frustration and resentment?

If so, I invite you to join me, here on the crooked path.

Prepare for the future by staying in love with life today. 🌞

We’ve spent ten years together: two solidly cohabitating (2024-2026), five on-and-off (2020-2025), and a few more flirting (2017-2019).

What an excellent long-term relationship. What a secure attachment.

Goodbye, fast trains. Goodbye, friendliest cycling routes. Goodbye Black Forest, U-bahns, cobblestone, steeples, brown bread, ubiquitous high-grade coffee, Alps, and canals.

Goodbye, peak partner dance: all those sweaty weekends in Bern, Busca, Berlin, Brussels, Toulouse, Vienna, Lyon, and Krakow, and all the lovely little local scenes that support them.

But really—goodbye to 200+ people I’ve called friends.

Nuclear families, domestic stability, and geographic monogamy aren’t my thing. I prefer to surf among one, big, chosen global family. You’re all a part of it.

I’m headed to America for a while. I’ve got people to see, roads to cycle, and deserts to wander. But I’ll be back, soon enough. How could I stay away? This is love.

❤️ Blake

The People

(in no specific order)

AUSTRIA

Andy, Eli, H, Christian, Christian, Flo, Flo, Sarah, Sarah, Marie, Lenka, Melinda, Judith, Eddie, Sofia, Alma, Nadine, Fabio, Caro, Ned, Anya, Mira, Nepo, Dana, Sandra, Sandra, Hannah, Blanka, Änna, Lucy, Kirsi

GERMANY

Jacky, Steffi, Paul, Clemens, Pablo, Piret, Jonathan, Eva, Andrea, Marco, Elena, Nine, Luke, Laura, Jules, Tonia, Lui, Luisa, Carla, Paul, Madita, Florian, Flo, Emelie, Henrik, Sandra, Pia, Veronika, Alex, Tinka, Martin, Sonia, Carolin, Susanna, Nehal, Andreas, Susi, Tabea, Tata, Anne, Cam, Maria J, Nis, Lukas, Anna, Marina, Stacey, Sina, Sarah

FRANCE

Anaïs, Celine, Jimmy, Meagan, Justine, Rolando, Ouardane, Olivier, Julie, Lou, Maxi, Ariane, David, Amélie, Marine, Amandine, Thierry, Iris, Vanessa, Carole, Axel, Lizea, Amelia, Kasia, Cécile

POLAND

Weronika, Weronika, Agata, Agnieszka, Nastya, Kasia, Joanna, Alena, Dan

CZECHIA

Blanka, Evgeniya, Míša, Zuzana

NETHERLANDS

Josine, Anouk, Anne, Nate, Jeremy, Rowena, Roos, Remy, Micha, Katz, Pieter, Naomi, Ellen, Nicky, Tjitte, Tamara, Abel, Brian

DENMARK, NORWAY, FINLAND

Liam, Fie, Rebekah, David, Anna, Biru, Iggy

BELGIUM

Tim, Emily, Lies, Arnoud, Cécile, Noémie, Laure, N, Alexi, Laurein, Xavier, Cedric, Lisa, Francesca, Katia, Freddie, Hilde, Raven, Verena

SPAIN & PORTUGAL

Fred, Alicia, Amalaia, Carole, Meg, Ivo, Marina, Fer, Elena, Jenny, Lou, Faviola, Monlam, Atenea, Ksenia

SWITZERLAND

Bea, Nathalie, Kade, Katrin, Zora, Sia, Ryan, Lea, Sinje, Tian, Tanja, Angie, Andreas, Amélie, Nicholas, Sonja, Pascal, Pascal, Mandana, Sarah, Kevin

UK

Alex, Duncan, Alec, Claire, Alain, Frankie, Genna, Malcolm, Nick, Jess, Dan, Nirjala, Charlie, Tina, Martin, Annelore, Michael, Siân, Ceri, Jeremy

ITALY

Giulia, Tommi, Flouer, Chiara, Chiara, Marco

(Those I’ve neglected to mention—forgive me!)

And I need your help.

Not just as an independently published writer who wants to expand beyond his circle, but as someone attempting to spread important ideas that have the power to shape people’s lives—maybe even the lives of your loved ones.

As a reminder, here’s what Dirtbag Rich is all about, and why you (or anyone) should care about it.

• In one way, Dirtbag Rich is my story: why I fled from “normal life” and ended up pursuing wilderness, travel, dance, and intense communal experiences.

• It’s also about others who can’t fit in: those with a severe allergy to traditional work and school, a powerful connection to nature, an undying lust for “freedom,” and the belief that we must live wildly and joyfully, right now, or risk the early death of the soul.

• It’s both practical and idealistic: explaining how to think about work, money, housing, and big costs (like healthcare, childcare, and retirement) while also living a purposeful, playful, and socially connected life.

• Finally, it’s a call to arms: against workaholism, burnout culture, entitlement, sedentary existences, and the assumption that we are but “brains on sticks.”

Dirtbag Rich is for young people of all ages. It balances my unique weirdness with universal philosophies. It’s compact and accessible, filled with short, digestible chapters and six original illustrations by (of Semi-Rad fame).

The book is intentionally self-published, allowing me to discount it, give away copies, release material into the public domain, and focus fully on spreading ideas that matter rather than earning money for a publisher.

If these ideas resonate with you, help them travel farther.

Below are the most useful and efficient ways to help spread Dirtbag Rich to those who might otherwise not encounter it.

What you can do right now

1. Pre-order the Kindle version at 50% off. It’s just $4.99 through one week after launch. There’s also a beautiful $16 paperback and an Audible audiobook that I personally narrated (coming soon). If you’re willing to purchase multiple versions—thank you!

2. Email, message, or verbally encourage others to pre-order. Pre-orders make a big difference for the book’s visibility and discoverability.

What you can do beginning March 28th

1. Review the book on Amazon or Goodreads. These platforms are where most readers will discover Dirtbag Rich. Five stars are great, but words matter more: share a few specific ideas or stories that spoke to you. Brief reviews are fine! And if you might forget—perhaps add a calendar reminder?

2. Share nice words about Dirtbag Rich in an online community, private message group, or social media. If you wrote a review, it’s easy to share that along with a brief personal note. Include the cover image to help with visibility.

3. Gift a copy to a free-spirited 20- or 30-something. While Dirtbag Rich can be profitably enjoyed by everyone from teenagers to retired folks, I believe that soul-searching 20- and 30-somethings have the most to gain.

What you can do anytime

1. Ask your library or local bookstore to carry Dirtbag Rich. I deeply believe in these institutions, and it’s also difficult for self-published books to break into their worlds. Your advocacy makes all the difference! (ISBN: 978-0-9860119-9-3)1

2. Connect me to a podcast, online show, or radio station where I might appear as a guest speaker. There are so many angles to discuss (here are a few).

3. Connect me to a public speaking opportunity along my bicycle book tour in New England, Western Colorado, Utah, California, Oregon, Washington, and BC. (Think: bookstores, conferences, climbing gyms, outdoor clubs, alternative schools, homeschool groups, or even living rooms.) I can offer bulk purchases at a discounted rate.

4. Directly subsidize me, so I can give away more paperbacks, go farther on my bicycle book tour, and say “yes” to more non-lucrative speaking opportunities. There are many ways to do this: Coffee, Venmo (@blakeboles), Zelle (yourstruly@blakeboles.com), or sponsoring a part of my new touring bicycle (write me: blakeboles@gmail.com). Every cent counts, and I promise to tell you how your money was spent!

In a nutshell

This is your chance to amplify ideas that matter to both of us.

Thank you for your support.

❤️ Blake

[Big thanks to Tim, Angel, and Six2 for commenting on a draft of this.]

Also known as the Rota Vicentina, the Fishermen’s Trail is a Camino-style route with frequent food, accommodation, and signage. Just pack a few layers, throw a grocery store lunch in your backpack each morning, walk 10-14 miles (15-22 km), find your next bed, scrounge up dinner, and repeat for 12 days.

It’s easy. It’s beautiful. It’s accessible. And you’d be crazy to walk it in mid-summer, when prices are inflated, beds are scarce, and temperatures are sweltering.

Better would be spring and fall—but there are many other great trails to hike then.

So why not hike the Fishermen’s Trail in the dead of winter, when the rest of Europe is a frigid hell, and no other easy hiking opportunities present themselves?

That’s what I asked myself last year, contemplating my next post-New Year mental-health escape. (Previous escapes have included: Spain, Argentina, Chile, Brazil, Colombia, and New Zealand.)

Initial research offered few reports of people hiking the Fishermen’s Trail in January. And many commenters said it was a bad idea due to cold, rain, and the threat of closed amenities.

But further digging revealed that January offered perfectly fine hiking temperatures (for my oft-overheated body), manageable rainfall (less than neighboring months), and no evidence of trail towns closing completely.

Another curious thing: almost everyone seemed to walk the Fishermen’s Trail from north (Porto Covo) to south (Lagos). But I wanted to start in the south (so I could fly into Faro) and end in the north (and visit Lisbon). There was no clear reason to hike southbound beyond the mere fact that everyone else went that way.

That’s how the idea of a northbound, mid-January hike on the Fishermen’s Trail was born. And spoiler alert: we did it, and it was awesome!

I say “we,” because my friend Jack—the same one who biked the Camino in a shark costume with me—had decided to join the adventure, despite me offering no plan beyond “meet me in Faro and we’ll walk for a few weeks.”

Once again, Jack put his full faith in me, resolving to make the most of whatever might happen on the Portuguese coast.

The world needs more Jacks.

If you’re planning your own Fishermen’s Trail hike and looking for hard facts—distances, finances, practicalities—you’ll find those at the bottom of this post.

But if you’re familiar with my other trip reports, you know that such details don’t get my juices flowing. It’s the human element, the unknowns, and the big questions that matter most.

Why do we—by which I mean, anyone—take adventures like this? What are we looking for? Why do we venture to far-away lands to walk along barren coasts? Why don’t we all just stay home?

These are the questions that interest me, and these are the stories I choose to share.

Enjoy the report, and happy hiking.

The Fishermen’s Trail Will Not Break Your Heart, But it Will Feed You Unlimited Sushi

When your friend arrives in Faro Airport, it will be essential that you hastily type his last name on your laptop and hold it up as if you are his driver. Because these are the moments that matter: the coming and goings, the reunions and beginnings, and the anticipations of adventures to come.

Trails are but conduits for moments like these.

A bus drops you in Lagos, and you begin walking.

The Fishermen’s Trail is well-signed. Like the little yellow arrows of the Camino de Santiago, the Fishermen’s trail is marked by pairs of little green and blue lines, painted on buildings, light poles, utility boxes, the back of stop signs, and an endless army of small wooden posts.

Almost immediately, you lose your way. But you don’t want to be checking your phone all the time to make sure you’re on the absolute, official route. This is a simple trail, and you develop a simple rule: keep the ocean on your left, horses on the right, and you’ll eventually find your way.

You buy bread, meat, cheese, apples, chips, and cookies from a mini-market and smash your first lunch overlooking dramatic cliffs. This is your life now—eating little sandwiches, with amazing backdrops, in t-shirt weather, in the middle of January—for a little while, at least.

In the second trail town, Salema, you stumble upon a sushi restaurant: well-reviewed, with honest-to-god, all-you-can-eat including sashimi for 17 euros ($20). Eventually, you’ll notice that half of the towns along the Fishermen’s trail have similar joints, all similarly priced. Apparently it’s a thing here. But this little spot, with its overflowing octopus and hyper-attentive servers, sticks with you. You don’t forget your first time.

As you settle into a hiking rhythm, your mind relaxes, and you begin to philosophize, often inappropriately: What is an “ocean” but one, big, all-you-can-eat sashimi restaurant?

But listen, life here isn’t just endless picturesque coasts and overflowing buffets—we’re working, too! Which is totally possible on the Fishermen’s Trail, since a typical day requires just 4 or 5 hours of walking.

The days are short, but longer than other parts of Europe: first light is 7:30am, and sunset is 5:30pm. Mornings and evenings are chilly (we’ll each wear multiple layers), but you’re not crazy to wear shorts and sandals. It’s a forgiving, California-style winter.

On a typical day we begin hiking around 9 or 10am. We arrive around 2-3pm. We drop our stuff, shower, and have plenty of time for emails, calls, writing, and whatever else our dirtbag rich lifestyles require of us. (Jack, who recently purchased a summer camp, considers himself “debt-bag rich” at the moment.)

Finally, before knocking off around 9pm, we book the next evening’s beds. Even though some accommodations close in January, there’s plenty of space, and pre-booking isn’t necessary. The flexibility is delicious.

Jack introduces you to a new term, friction-maxxing: deliberately adding friction to a life of comfort and building up tolerance for so-called “inconvenience.”

The Fishermen’s Trail is, in fact, an easy trail. One could quickly adjust to its comforts and conveniences. So we begin to embrace the dead-ends and brief disorientations, the trail-swallowing puddles born of recent squalls, and the barbed-wire fences that occasionally stand between us and our next beds.

One day, we munch on sardines and greens on ciabatta while hiding from the wind behind tall bushes. Then the rain begins, drives us back to the trail, and for a full half hour, soaks the westward half our bodies.

Rain and wind can, and will, conspire against you on the Fishermen’s Trail in January. But forecasts are generally accurate, if you’re willing to wait out the worst of it—and perhaps skipping an entire day to let a storm pass—you’ll be fine. Over 12 days, we hiked in less than 60 minutes of rain.

Sand-walking was another worry, but ultimately not a problem. The deepest dunes were limited to our final day (i.e., most hikers’ first day), from Milfontes to Porto Covo. If you hate walking in deep sand—as I do—just skip that day. Otherwise you’ll enjoy mostly firm surfaces with short stretches of sand, plus a handful of steep, slippery scrambles.

But you will forget the sand, wind, rain, and puddles, for they are but bumps on the parchment on your adventure. What you will actually remember, what you will etch with ink into the ridges and folds of your gray matter, are the names, faces, and fleeting moments shared with those people you meet along the way:

• the grocery store cashier from Buenos Aires who exchanges a few grinning words of Argentine slang with you

• the Dutch hiker who joins you for dinner in the ghost-town sushi restaurant, working toward a medical degree with a Master’s in ethics, who argues for compassionate euthanasia as a fundamental right

• the sour-faced woman who lets us fill water bottles in the utility sink of her closed restaurant

• the steak guy who preaches the gospel of ribeye and shakes our hands on the way out the door

• the two enthusiastic young British hikers whom we advise to turn around one afternoon—rather than continuing 4 more hours through dicey dunes and swollen rivers—whose hands we shake (inspired by steak guy) when they ultimately decide to turn around

• hard-charging, forever-smiling Adam from Slovakia, who is “definitely not high” but just has trouble understanding English, for which he compensates by smiling

• and dear Céline, a reader of this very newsletter, who kindly offers to host and feed us for a night, who laughs with us about the obscure French phrase “courage, mon ami” and smiles as we coach her 14-year-old, always-unschooled son on his upcoming, first-ever, multiple-choice exams

These are the moments that you can easily share with others. But there are also moments of quiet transcendence, dawning awareness, and subtle realization:

• watching a troop of sun-drenched toddlers run around a lawn, dragging large sticks and screaming joyfully, just after storm clouds part

• listening to Jack describe his experience of depression at the Cabo de São Vicente lighthouse, perched on a stone step, peeling mandarins together

• walking away from Odeceixe with no food (because nothing opens until 10am) to find a delightful roadside cafe, where three pastries, two coffees, and two chorizo pockets cost a total of €6

• waking to the brutal roar of the western ocean at 6am, unsure if it is the Atlantic or Pacific

• reading Desolation Angels with um pouco de vinho tinto, perched on a sandy bluff as waves crash below, as day fades to night

What else do your hastily scrawled notes and internal memory banks tell you?

What about sprinting 15km to avoid a forecasted rainstorm, and instead being rewarded with pure sunny bliss?

What about the mysterious potatoes you find embedded on the trail, evidently washed downhill from a nearby farm?

What about the next program for young adults that you scheme, with Jack as your muse—the one that might tie together everything you’ve been working on?

Or finally discovering something that you and Jack disagree about: the nefariousness of advertising?

And what is transcendence, if not a large pig walking down the trail toward you, wagging its tail like a dog, accompanied by one mule, three horses, and zero humans?

In the end, you are still you. You adore sun and movement. You love sweeping vistas, endless horizons, and language barriers. You still read books, write postcards, and get temporarily lost in pine forests.

You still wonder why so many people inhabit gray, rainy, concrete cities when they might equally inhabit clear-skied, somewhat-less-rainy, foreign coasts: walking, smiling, inappropriately philosophizing, and seeking those ever-elusive pockets of somewhat-firmer sand.

You still check your phone impulsively, addicted to the intermittent reinforcement of email and Whatsapp notifications.

You still catch yourself posting TikToks (one / two / three) atop picturesque cliffsides. (More accurately, Jack catches you.)

You are still part of the very problems that you rail against.

It’s reassuring to know that, here in coastal Portugal, on your friction-maxxed, sushi-filled, cliffside journey, you are the same person as before.

Except you’re not. How could you be? Because it’s only through moments like these that you ever ebb and evolve. It’s subtle, but it’s happening—right here, right now—as reliably as waves lap the Portuguese coast.

“The true risks of travel,” writes Kate Harris, “are disappointment and transformation: the fear you’ll be the same person when you go home, and the fear you won’t.”

Will the Fishermen’s Trail transform you? Will it disappoint you? Will it fill you up with hot espresso and delicious pastries at exceedingly reasonable prices?

There’s only one way to find out.

Happy trails,
♥️ Blake

The Hard Facts

Stages, distances, and accommodation

We mostly followed the traditional stages and routing of the Fishermen’s Trail, referring frequently to the Stingy Nomads guide for elevation change, trail conditions, and other context.

All of our accommodations were private twin rooms with bathrooms (prices indicated are for 2 people).

1. Lagos Bus Station to Luz (12km) - Club House CVL €26

2. Luz to Salema (12km) - Salema Eco Camp €45

3. Salema to Sagres (20km) - Sagres Sun Stay €48

4. Sagres to (down the road from) Vila do Bispo (18km) - Casa Nook Sagres €95*

5. (near) Vila do Bispo to Carrapateira (18km) - Casa Presente €61

6. Carrapateira to (just beyond) Arrifana (23km)** - (stayed with friends)

7. Aljezur to Odeceixe (26km)*** - Residencia do Parque €44

8. Odeceixe to Zambujeira do Mar**** (19km) - Breathe In €58

9. Zambujeira do Mar to Almograve (23km) - HI Almograve €55

10. Almograve to Vila Nova de Milfontes (16km) - MUTE Hostel €52

11. Vila Nova de Milfontes to Porto Covo (20km) - MUTE Hostel €44

*This was actually a whole studio apartment! Fancy pants.

**We followed the coastal route, not the inland route indicated by Stingy Nomads.

***Since we stayed with our friends in Arrifana, we skipped the entire Arrifana-Aljezur section (it would have been just a 7km day or a lot of backtracking). We got a ride to Aljezur and added some extra coastal walking (i.e., we got lost).

****We took a rest day in Zambujeira do Mar to avoid a rainstorm.

Costs

On average, Jack and I each spent €26/night ($31/night) for lodging, and roughly the same on food (none of which we cooked ourselves).

The bus from Faro Airport to Lagos, and Porto Covo to Lisbon, each costs under €10 (Flixbus/Rede Expressos). The only other things we spent money on were laundry and drinks (not much).

Doing it like we did, you can hike the Fishermen’s Trail in January for USD $900-1000.

A few reasons to walk north on the Fishermen’s Trail

• The sun is typically behind you, not in your face

• The first two days are short with lots of amenities, offering an easy onramp

• The final day (Vila Nova de Milfontes to Porto Covo) is actually pretty rough; I wouldn’t want it to be my first day

• The southern coast just feels a bit calmer, safe, and filled with more surfers and vanlifers—a more friendly “welcoming party” compared to the wild west coast (and its sometimes-swollen river crossings)

• You’ll cross paths with many southbound hikers, and you can give them helpful advice. (But if you’re hoping to make friends to hike with, southbound is better.)

Practical tips for northbound walkers in January

• Go with a friend, lover, or anyone else who wants to share a twin room! We encountered few hostels (with dorm rooms) until later in our hike. Going solo might mean paying for double rooms by yourself.

• If you don’t have enough time to do the whole trail, definitely start in Lagos—you’ll get the best views with minimal sand walking. Try to get to Arrifana!

• There are a few river crossings on the west coast that seem to be very tide-dependent. We lucked out and crossed both at low tide.

• Try to stay the night at Casa Nook Sagres. It was our favorite place. Their double rooms cost the same as other places. They just don’t offer twin beds, which is why we upgraded to a studio.

• The prize for “most desolate winter ghost towns” is shared by Odeceixe and Almograve 🏅⚰️ In each, mini-markets and restaurants were open, but choices were slim and hours were unreliable. Every other town had a wider selection of places to stay, eat, and buy lunch supplies.

Drop any further questions in comments, and I’ll do my best to respond. 🎣

(Also: my 2025 in Review is up.)

🇪🇺 January-March 2026: Europe

I’ll be dancing in Switzerland, walking the Fishermen’s Trail in Portugal, taking self-directed teenagers to Spain, walking some of the Camino Mozarabe (Spain), and dancing in the UK.

During this time I’ll…

• Publish Dirtbag Rich and start giving interviews (⚡️podcast suggestions?)

• Ship the first Blake Quarterly (backstory)

🦞 April 2026: New England

Returning to the USA, I’ll mount a new touring bicycle and take a wee little ride through Connecticut and Massachusetts, adding on (as time & weather permit) Vermont, New Hampshire, the Hudson Valley, Philly, and NYC.

During this time I’ll…

• Visit family & friends

• Give talks about Dirtbag Rich (⚡️suggestions for bookstores / outdoor stores / student groups / living rooms / other venues?)

• Crash with friends & strangers (⚡️maybe you?)

• Begin posting more short-form videos… reluctantly

• Give workshops at alternative schools (⚡️let’s talk)

🏜️ May-June 2026: The Southwest

I’ll box the bike, fly it to Western Colorado, and continue riding through drop-dead gorgeous Eastern & Southern Utah. The route isn’t fixed—I might add Denver or Durango—but I intend to finish in Flagstaff.

During this time I’ll…

• continue doing talks/interviews/workshops + staying with strangers (⚡️open to your connections!)

• add camping gear + start sleeping outside (making up for zero nights spent outside for two full years 😩)

• possibly recruit a cycling companion (⚡️try me 🚲)

🌁 June-July 2026: California

Hopping an Amtrak from Flagstaff to Barstow, I’ll ride through Eastern California (I-395) to Tahoe and Reno before dropping into Sacramento and the Bay Area.

During this time I’ll…

• continue doing talks & crashing with nice people (⚡️all connections welcome)

• keynote the Davidson Institute’s conference in Reno (for profoundly gifted children & their parents)

🌲 August-September 2026: Pacific Northwest

Amtrak will drop me in Oregon, and from there, I’ll continue riding/🚂ing north to Washington and British Columbia.

During this time I’ll…

• work my 16th(!) summer of Not Back to School Camp

• visit my many friends in Eugene, Portland, Bellingham, Vancouver, and Squamish—some of whom will definitely ride with me (👀🚲⚡️)

• talks, interviews, workshops, couchsurfing, yada yada (⚡️)

🐉 October-December 2026: ⚡️UNKNOWN⚡️

We’ve reached the edge of the map, folks—who knows what happens next?

• Europe will beckon. So many friends, so much good dancing!

• Perhaps all my yapping about Dirtbag Rich will open new doors.

• Maybe I’ll just be tired, ready to cease all this wandering, and finally content to settle down with a full-time job. (Place your bets, folks, place your bets!)

May your own 2026 be filled with mystery, grandeur, good friends, and spacious possibilities.

❤️ Blake

Salsa, bachata, lindy hop, west coast swing, tango, blues, shag, balboa, kizomba, urban kiz, zouk, forró, fusion, and contact improv: these are the kind of non-choreographed, fully improvised, social partner dances I’m talking about.

Why? Because partner dance can change your life, and there aren’t many people advertising this fact.

I grew up believing “I can’t dance.” Which really means, “I find dance intimidating.” None of my friends or family were partner dancers. I didn’t have a “musical ear,” and I struggled to “find the beat.” Then at age 24, partner dance crashed into my life and radically reshaped it for the better.

Here are eight reasons that learning partner dance is worth the time, money, and effort, why it’s not “what you think,” and why you—yes, you—should seriously consider giving it a shot:

1. Partner dance is a great way to make friends and connections

2. Dance is an antidepressant

3. Dance weekends are a hell of a lot of fun

4. Partner dance teaches communication and body awareness

5. Drinking and drugs, not required

6. Sexuality and sexism, not required

7. Partner dance teaches attention and connection

8. Partner dance offers profound meaning

1) Partner dance is a great way to make friends and connections

Partner dance is playful, joyful, and fun. It brings you into immediate physical contact with people you’ve never met before. Unlike traditional ballroom dance, where you mostly dance with a single person (your one and only partner), partner dance encourages you to dance with many different people. In dance classes, you rotate through multiple partners, and at social dances, light, friendly conversation naturally emerges on the edge of the floor.

People you meet in classes invite you to social dances. People you meet at socials tell you about new classes. You’re smiling, learning, and growing together, week after week. Do this long enough, and you’ll eventually get invited to do something outside of dance—and then, all of a sudden, you’ve started making new friends. Like any friendship, they require active nurturing to transcend your shared activity, but it’s an excellent place to start.

Crucially, you don’t need to convince anyone else to begin partner dancing; you can just join a class or social and immediately reap the benefits. And it empowers you to travel many places in the world and immediately begin making friends. As Russell Max Simon observes:

Knowing how to salsa dance felt like something close to a superpower. Colombia and Portugal, Ireland, Ecuador—wherever I touched down, I could walk into a salsa club, not knowing a soul, surrounded by an unfamiliar language, and immediately feel something close to comfortable. . . [The] way around a cultural divide is by joining a subculture that circumvents it.

Partner dance is also a fine way to meet possible romantic partners, because dancing with someone is like being in a little relationship together: it gives you an incredible amount of information about the person’s personality, patience, conflict style, and sense of humor (no matter their level of experience). You learn about potential compatibility in quality of touch, movement, and sensuality, in a non-sexual context, which you cannot easily do in other settings like a running club, typical social gathering, or the apps.

This is not to say that you should go dancing in search of romance. Rather, in a world where organically meeting kind-hearted strangers feels increasingly difficult, the opportunity afforded by partner dance is rare and important.

Many good people I know have found wonderful relationships thanks to partner dance. Others have deepened their preexisting relationships through dance. Dating within a dance community isn’t risk-free—a break-up can complicate your participation in a particular scene—but the risk is no different from dating within any other activity group, workplace, or friend circle.

2) Dance is an antidepressant

Therapy, medication, and exercise all fight clinical depression—but dance may be a secret weapon, as this post from scientist suggests:

While this particular meta-study has significant limitations, countless people I know will testify: the antidepressant effects of partner dance are real and powerful.

The benefits of dance are well known. It’s great exercise (without feeling like a chore), it increases flexibility, it relieves stress, and it protects against mental decline. But partner dance also fights loneliness, builds relationships, and offers a crucial source of platonic touch. We don’t need more studies to prove that “dance is good for us”—we need more reasons to walk out the door and give it a shot.

3) Dance weekends are a hell of a lot of fun

At the beginning of my dance journey in 2006, my friend Nathen gave me some important advice.

“Taking regular local classes is good,” he told me. “But dance weekends are where you really level up.”

“What’s a dance weekend?” I asked.

“A bunch of people come together to take classes all day and dance all night, for two or three days straight. The people who go tend to be pretty good—they’re the ones who are serious about learning.”

A few years later, I joined my first tango weekend in Portland, Oregon. The dancers were so amazingly good (and the floor so terribly crowded) that I spent most of the evenings just watching from the sidelines, mesmerized and content.

In 2014, I attended a blues weekend in upstate New York. I was a novice, I didn’t know a single person, and everyone was dressed in fancy vintage clothing. Despite feeling that blues wasn’t “my scene,” the classes were excellent, everyone was friendly, and I loved traveling somewhere exclusively for the purpose of dance.

Finally, in 2016, I found a weekend that spoke to me: a fusion dance “Recess” organized by a friend-of-a-friend named Justin Riley. Held at a massive campground in the California High Sierra, Recess was like an adult summer camp. Classes took place through the day, and at night, multiple dance floors emerged among the pine forest, dramatically illuminated by colored lights. Volunteer cooks (including me) prepared three meals a day, and everyone provided their own camping gear. For three days I happily wandered from my tent, to food, to classes, to food, to dancing, to shower, to tent, and repeat.

I felt like I’d discovered a nearly perfect container for combining learning, community, and dance. At Recess, the other dancers were open, playful, serious about learning, yet always willing to laugh at themselves. Skill-building and socializing held equal weight. Dressing up was optional. Various substances were present but never felt necessary for participation (see below: “drinking and drugs, not required”).

Driving away from the campground on my 34th birthday, blasting a new playlist of fusion songs, I felt totally alive. More, more, more! I want more dance weekends!

I discovered an entire ecosystem of similar fusion weekends in the US and Europe that brought me to Seattle, Oakland, Denver, Utah, Virginia, Spain, Paris, Berlin, and Washington DC. Then the pandemic happened, weekends were cancelled, and sadness reigned. When they reemerged in late 2021 (in Europe) and 2022 (in the US), I was thirsty: joining roughly 25 events over the last four years—weekends that brought deeper skills, dozens of new friends, and a handful of relationships.

Sometimes I was hosted in foreign cities by dancers I barely knew. Other times I teamed up with others to share affordable accommodation and cook communal meals. I discovered a trusting, inclusive, and high-solidarity community of fellow dance enthusiasts who adored these intense, joyful weekends.

This is all to say: partner dance isn’t just about local classes and local dances. Big, powerful, peak-experience weekends await you, no matter your preferred style—and they’re a hell of a lot of fun.

4) Partner dance teaches communication and body awareness

“Blake, touch my chest!”

The 50-year-old Argentine woman spoke with authority, so I did as she commanded.

I placed my palms on her clavicles. As she walked forward, I held the tension in my arms and walked backwards, matching my steps to hers. When she paused, I paused. When she twisted her torso or shifted weight in her feet, I followed.

The year was 2008, I was 26, and I was leading my first Unschool Adventures trip to Argentina. Ostensibly, Alicia Pons was teaching my group of teens how to dance tango, using me, for a moment, to demonstrate the art of following. But clearly, something more than tango was happening here.

“As a leader, you need to send clear signals,” Alicia instructed us. “You must know what you want and move decisively. Otherwise, your partner won’t know how to respond.”

For a moment, I felt like I was in a relationship therapy session.

“If you don’t know what you want, then stop moving. Just shift the weight in your feet for a few moments. That’s okay.” Alicia rocked back and forth almost imperceptibly; I felt the motions in her chest and moved my body to match.

Now it was a life coaching session.

“In the early days of Argentine tango,” she continued, “every man had to learn how to follow—to listen very carefully—before he could become a leader, before he could take that responsibility. Today, we have many bad leaders because they’ve never followed before.”

Now: a communication class (and political theory, too).

She released me and entered the middle of the tiny dance studio. “No matter whether you’re leading or following, you must walk confidently. Raise your arms high above your head and take a deep breath. Then keep your chest in that position as you release your arms. Feel your spine lengthen. Feel your new height. This is how you will connect with your partner in tango. Practice walking like this everywhere you go.”

The basics of body language? Alicia just summarized them.

“At a milonga (a social tango dance), it’s common to dance four songs together. If you begin dancing with a partner, you are committing to all four songs. It’s rude to leave early, but you always have the power to say no. If your partner is being disrespectful, walk away immediately.”

Finally, a lesson about consent.

For two weeks in Buenos Aires, Alicia taught my group more than just tango—she taught us how to move with confidence, power, and grace while remaining humble, perceptive, and open to feedback. Having danced, competed, and taught across the world, Alicia had an incredible repertoire of moves to show us, but she focused entirely on one lesson: communication.

What you just read is a chapter from my 2014 book, The Art of Self-Directed Learning—and it’s still my favorite way to illustrate how partner dance offers life lessons that go far beyond the floor.

Partner dance has taught me about clarity, boundaries, connection, creativity, respect, rejection, and responsibility. I’ve learned how to be strong and soft at the same time, how to listen with my entire body, how to make an invitation with only my eyes, and how to enjoy dancing with both total beginners and intimidating professionals. Some of these lessons might have otherwise required years of talk therapy. And it all started with a 50-year-old Argentine woman telling me to touch her chest.

I hope you, too, find your own 50-year-old Argentine.

5) Drinking and drugs, not required

“Don’t you need a few drinks to enjoy dancing?“ “Are all these people high?”

I’m amazed by how many assume that alcohol or drugs must be a part of the social dance equation.

Yes, some partner dance communities do imbibe: more frequently at big weekend events, later in the evenings, and among pre-existing friend circles. But in the communities I frequent, drinking is casual or non-existent, recreational drug use is rare, and most people I know are dancing 100% sober.

This is a crucial difference between partner dancing and more commonplace club dancing. We’re not just bouncing up and down with a drink in our hands, looking for someone to grind on, or trying to enter a trance state. We’re performing a fairly technical act that requires balance, precision, and careful attention to our partner. One glass of wine might help a partner dancer loosen up; three glasses are counterproductive. Dancing with someone who is clearly in an altered state isn’t fun, and it’s potentially dangerous.

We partner dancers are quite good at producing our own chemicals, thank you very much. Supplements are not required.

6) Sexuality and sexism, not required

Two more common assumptions:

1. pressing your body against someone else’s body is inherently sexual

2. “lead” and “follow” roles are inherently sexist

There’s so much to say on this topic, but I’ll emphasize this: partner dance is a fantastic way to receive platonic touch.

In a world where touch is frequently reserved for intimate partners, the simple act of connecting your hands, arms, chest, and belly to another person’s hands, arms, chest, and belly can actually reduce one’s perceived need for sexual contact. You might start partner dancing with a secret hope of romance, only to discover that platonic touch is what you needed most.

This is doubly triply quadruply true for men socialized with the belief (as I was) that you DO NOT TOUCH your friends, family, or anyone but an exclusive romantic partner for an extended period of time, with the exception of team sports and martial arts.

As the dance teacher Gui Prada once mentioned in a class about “close embrace,” which is the most intimate way to hold a partner:

The first time I embraced a man like someone I’m attracted to, my dance transformed.

As a straight man, I experienced a similar revelation: dancing with men can be just as fun (or more fun) and nearly as intimate as dancing with women.

Gender-normative Argentine Tango was my gateway into partner dance, which meant that as a man, I was assumed to lead. But I also did much of my initial learning in hyper-progressive Portland, Oregon, where I immediately witnessed many women leading, the occasional male follower, and many dancers of more expansive gender.

But the real awakening came when I entered the fusion dance world, where I learned to ask one, simple, magical question before every dance: Would you like to lead, follow, or switch? Implicit in this question were many beliefs:

• Just because someone looks a certain way doesn’t mean they want to dance a certain way.

• Just because I’m more comfortable dancing a certain role, doesn’t mean I should never try the other role.

• We also have the option of discarding fixed roles altogether and switching between “lead” and “follow” throughout a dance—or even “co-leading” (as practiced in contact improv)

So here’s the good news: partner dance doesn’t have to be sexual or sexist, especially if you’re dancing fusion, contact improv, queer tango, or swing/blues in more progressive communities.

Unfortunately, in many other corners of the partner dance world, sexuality and sexism are very alive. If you want to follow as a man in bachata, good luck finding many dance partners. If you want to lead as a woman in traditional tango, good luck finding many dance partners. If your gender presentation is ambiguous, you’ll have to do a lot more work—and risk weird looks and outright rejection—to find many dance partners. The culture is moving in the right direction, however slowly, while self-described “cazagringas” (slang for “hunters of white women”) continue to prowl the salsa clubs of Guatemala.

Despite the challenges, partner dance can be a place where you go to connect with other nice people, regardless of gender, without sexual overtones or homophobia. Great dances between people who are attracted to each other can be just great dances, and nothing more.

This is the best way to approach partner dance, in my experience: not as sexual conquest, not preening and posturing like a mating bird, but as a way to create profoundly deep, fun, and connective experiences between two people, no matter who they are.

7) Partner dance teaches attention and connection

This is a topic I’m so passionate about, I created a whole workshop to practice it. But allow me to summarize in four bullet points:

• the best partner dances begin with giving someone your full, undivided attention, because attention is the most basic form of love

• this is vitally important because today, especially with the rise of smartphones, our default mental state is one of continuous partial attention

• partner dance allows us to enter a classic flow state of optimal challenge, total concentration, and effortless achievement

• partner dance can even feel like meditation—like when dancing “microfusion”: a stationary, eyes-closed dance demanding utter attention to one’s partner and the music

The classic image of a sweaty salsa or swing dancer may not overlap with that of a quasi-meditative state of absolute focus. But it’s real. When you’re partner dancing, you’re not thinking about your phone, you’re not thinking about yourself, and you’re locked into the music and the subtle motions of the flesh-and-blood human in front of you: rare and valuable experiences in a time of constant distraction.

8) Partner dance offers profound meaning

Once you’ve achieved a certain level of security, belonging, and self-esteem in life—once you’ve climbed a good way up Maslow’s Hierarchy of Needs—what’s left to do?

You can start a family and support them unconditionally. You can dedicate yourself to a philanthropic cause, political movement, a business, or your art. You can journey inside, pursuing new truths and spiritual awakenings. You can journey outside, through foreign lands and wildernesses.

You can also… dance.

Dance is the ultimate renewable resource. The number of ways to move your body is limitless, and when you throw in a whole other mind and body—plus a vast, ever-expanding library of world music—the possibilities become exponential. Or as the dance teacher Mark Carpenter described it to me: partner dance is co-created ephemeral art, made in real time with another person, in a room full of other people doing the same.

You will never run out of ways to dance. You can spend a lifetime learning a single style or sample dozens of different ones. You can dance with people who don’t speak your language, all across the world, year after year, or at least as long as your body says, yes—please, god, more, yes!

Dance requires time and money, but no more than most other forms of recreation. It keeps you healthy and limber, connects you to new people, and teaches you timeless lessons. There’s a reason that every human culture dances.

I’ve dedicated lots of my time, money, and energy to partner dance because it’s given me so much. I’m incredibly grateful that it found its way into my life. I hope that you, too, can experience some of its magic.

See you on the dance floor.

❤️ Blake

Thank you to Frankie, Mark, Flouer, Dane, Bronwyn, Martin, Jeremy, Lui, Siân, Tata, Anouk, Tina, Nathalie, David, and Tim for commenting on a draft of this.

[Other things I’ve written about dance: Partner Dance is Magic · Notes from a Master · Saturday Night, Berlin, 3:52am · 30 Nights of Tango · Crème de la Connection]

To earn the money necessary to do these things, you must work. Yet work often means sitting indoors, staring at a computer: the slow death of the body in your most physically capable years.

What if this weren’t true? What if you could spend a majority of your time in nature, moving your body, doing that which brings you joy—while still supporting yourself financially and making a meaningful contribution to humanity?

Let’s explore.

We’re all richer, yet we’re still busy

In 1930, the economist John Maynard Keynes famously prophesied that 100 years later—approximately right now—the average citizen of a rich country (like his United Kingdom) would be eight times wealthier than one living today, working just 15 hours a week to cover the basics.

Keynes was right, and Keynes was wrong.

Most of us in rich countries today are much better off (materially speaking) than he assumed. Yet most of us still work 40+ hours a week.

How did this happen? How could we become vastly more wealthy than before and yet still find ourselves working just as much?

One reason is that the “basics” now include modern healthcare (see: hospitals in 1930), modern housing (see: construction in 1930), modern transport (see: long journeys in 1930), and modern consumption (see: food and entertainment in 1930).

Once the basics expand, it’s almost impossible to go back. In rich countries today, you can’t choose to live in a 1930s-quality dwelling or receive 1930s-quality healthcare. (You probably can’t even use a cell phone made a decade ago.)

If you drastically reduced your standard of living while continuing to earn a modern wage, 15 hours a week would be more than enough. But that’s called “living in squalor,” and we’ve outlawed it.

As a society gets materially richer, it drags its members forward in the name of human dignity. This is called progress, and it’s a rather good party. Many people die every day—crossing deserts on foot and oceans by raft—to join the progress party.1

If you live somewhere that other people are willing to die to join, you should consider yourself lucky. But that doesn’t mean you have to party the same way as everyone else.

Keynes recognized that material progress led to new possibilities for living:

Thus for the first time since his creation man will be faced with his real, his permanent problem—how to use his freedom from pressing economic cares, how to occupy the leisure, which science and compound interest will have won for him, to live wisely and agreeably and well.

The strenuous purposeful money-makers may carry all of us along with them into the lap of economic abundance. But it will be those peoples, who can keep alive, and cultivate into a fuller perfection, the art of life itself and do not sell themselves for the means of life, who will be able to enjoy the abundance when it comes.

— “Economic Possibilities for our Grandchildren” (1930)

Here’s what I believe: Keynes was more right than wrong.

You can live well today—shockingly well—on 15 hours a week of paid work. And this can be good, satisfying work. Work that doesn’t immiserate yourself or others. Work that serves both yourself and your fellow human beings.

You can join the progress party just long enough to shake a few hands, kiss a few babies, snag some hors d’oeuvres, and then ghost—disappearing into the night to sleep under a blanket of stars.

Enter the dirtbag

The first dirtbags were hardcore rock climbers in Yosemite Valley in the 1960s who camped illegally, showered infrequently, and scavenged for meals. When they needed money, they’d leave the Valley to paint houses, wait tables, teach skiing, or even take a desk job: anything to refill their coffers and get back to the big walls. They lived like bums in pursuit of the good life.

Today dirtbags come in many flavors, not just “climber” and “white male.” Some are trail runners, mountain bikers, long-distance hikers, backcountry skiers, cross-country cyclists, or endless-summer surfers. Others are dancers, slackliners, or perpetual travelers. All are passionate. All are extreme. None are what the mainstream would describe as “balanced.”

Some dirtbags live in vans, trucks, or tents. Others couchsurf, hitchhike, or stay with friends. Some do pay rent: just not very much, and not for very long. For dirtbags, full-time, full-price rental contracts lie somewhere between a luxury and an obscenity.

Many dirtbags come from middle-class security. Some come from upper-class privilege. Others come from next to nothing.

All dirtbags revere nature, movement, and thrift. All struggle to fit into conventional society. All want to be left alone to do what they love, while they also yearn for membership in a tight-knit community of the similarly obsessed.

Many who lead such lives aren’t aware of the label “dirtbag.” Of those who are aware, many don’t welcome its associations. I understand their aversion, but I like the term.

To me, being a dirtbag simply means that you’re too busy following your bliss to worry about a little dirt under your nails. It means you’re doing something right.

Dirtbagging is unsustainable, as is normal life

Unfortunately, dirtbagging is unsustainable in the long run.

Traveling, adventuring, and living close to nature is undoubtedly fun and fulfilling—until you get seriously ill or injured, need to sleep or eat better, require comprehensive health insurance, want to save for retirement, get fed up with your menial seasonal jobs, fall in love with someone who’s not a dirtbag, or start a family. Normal life and its promise of security begin to look awfully attractive when the wheels come off your vehicle or finding shelter becomes a real issue.

Unfortunately, for people like me (and perhaps you), normal life is also unsustainable in the long run.

If dirtbagging calls to you, then attempting to live normally is a brutal reminder of why you cannot accept the full-time job, the boss, the commute, the meetings, the bureaucracy, the accumulation of junk, the normalization of debt, and the never-ending postponing of life.

Your body rebels against all the sitting: at desks, in cars, on trains. Your mind rejects the barrage of advertisements and entertainments, the chorus of phones buzzing and vibrating, the endless splitting of attention. Even among friends and romantic partners, you feel isolated and alienated.

You might fit in, but you know you’re out of place. You sense that something vital is being eroded, precious possibilities are being erased, and that you are growing old at an unacceptably early age.

Despite a growing bank account, you feel neither wealthy nor secure. You feel like a fraud.

A glorious compromise: becoming dirtbag rich

Fortunately, there is a middle way between conventional existence and hardcore dirtbagging: a path I call dirtbag rich2, which I currently define this way:

a high-freedom, low-income lifestyle
filled with nature, movement, and connection
fueled by purposeful, well-paid, part-time work

In the 15+ years since I decided to pursue this path, I’ve learned much about what it takes to become dirtbag rich. I’ve tweaked, refined, and pressure-tested my ideas in the mountains of New Zealand, on the highways of North America, and among the capital cities of Europe.

Your version of “dirtbag rich” won’t exactly match mine. We have different histories, personalities, aptitudes, and blind spots. What “purposeful” means to you differs for me, and that’s okay. What matters are the fundamentals:

• working just 15 hours/week (averaged over the year) doing something that doesn’t hurt the world (and ideally improves it)

• keeping your expenses dirt-cheap (without exploiting family or government) while gradually increasing your savings

• spending lots of time doing what you love (often in the outdoors), alongside people you love

• with time leftover for creative expression, entrepreneurial experiments, travel, romance, reading, friendship, and reflection

If this sounds idealistic, that’s because it is. Dirtbag rich is an ideal. But some people do live this way today; I’ve interviewed 38 of them so far. And why trash idealism?

As Keynes wrote a century ago, it will be those “who can keep alive” and “not sell themselves for the means of life, who will be able to enjoy the abundance when it comes.”

The dirtbag rich don’t actually want to sleep in the dirt—at least, not against their will—and they certainly want to enjoy the riches that “science and compound interest” (and political activism) have won for them over time. Yet dirtbag rich is just one path toward a more humane future: a path particularly suited for those who must move their bodies through nature, frequently and intensively, in order to feel sane.

For people like us, retirement is a cult. We will not wait until 65 to do what we love, after our bodies have been compromised by decades of neglect. Vacations and weekends are not enough. We must find a way to live differently, now, before we self-destruct.

Many challenges remain:

• How does one afford housing, eat decently, cover healthcare, and possibly care for dependents, without working full-time?

• How does a low-income life mesh with the expectations of family and higher-earning friends?

• Where, exactly, does one find these mythical, part-time, well-paid, world-improving jobs?

• How can you let yourself enjoy a trail run, raft trip, or climbing adventure today when the future is unknowable, disaster may always strike, and more money = more security?

This is one reason I wrote Dirtbag Rich: because I hadn’t found a book that addressed all these questions in one place, especially as I navigated the polycrisis of my twenties. I ended up cobbling together practical advice and actionable philosophy from disparate sources, and eventually, decided to write the damn book myself.

What you’ve found above are three of the 37 chapters of Dirtbag Rich, due for release in March 2026. Right now I’m printing test copies, reaching out to fellow writers for “blurbs” (those nice little paragraphs that authors write for each other), and awaiting the creation of some original illustrations.

I’m excited to share the final words with you in just a few short months.𖤓

For updates about Dirtbag Rich, stay tuned to this newsletter or the podcast.

In recent months, whenever I publish an article, I lose some subscribers, and then I slowly regain the same number.

The Adventures of Blake has flatlined.

Other writers are noticing this too: it’s becoming difficult to retain newsletter readers.

And this makes sense—because now there are A BAJILLION EMAIL NEWSLETTERS. No one has time for all these newsletters!

Podcasts followed a similar arc. In 2005, there were ~4000 podcasts. Now there are ~4 million. At some point, you start thinking, “Wow, TOO MANY PODCASTS.” And then your reign of terror begins: Too many ads? Out! Guest I don’t like? Out! Too long / short / frequent / infrequent? Out, out, out, out!

I know, because this is me. I am a ruthless unsubscriber. I take “inbox zero” seriously. My Gmail is spic-and-span. If cleanliness is godliness, then I’m on a path to digital sainthood—or at least, basic mental health.

When a newsletter rubs me the wrong way, I unsubscribe—and I hope you do too. Life is too short for overflowing inboxes. If this newsletter doesn’t light you up regularly, please unsubscribe!

When writers talk about the “problem” of flattening readership, I wonder: Is it a problem? From the perspective of perpetual growth, it certainly is. But is this really just another form of status competition? Another way of screaming “I matter” to the universe? And perhaps, at the end of the day, about the fear of death? (At some point, everyone’s subscriber count drops to zero.)

Meanwhile, how can we measure what matters?

One approach: asking readers to “resubscribe” as a form of radically honest housecleaning. A decade ago, I had 5000+ email newsletter subscribers, many of whom joined to gain digital access to one of my books. Then I asked everyone to click a button (within a two-month window) if they wanted to stay on the list. Fewer than 20% clicked the button.

Was this a success or a failure? Absolutely a success! Because from that moment on I was cluttering fewer inboxes, paying less for newsletter hosting, and most importantly, not living the delusion that I have a Very Big & Important Email List.

That experiment helped me remember what really matters: the small number of people who really give a damn.

In 2008, WIRED Magazine founder Kevin Kelly proposed in a viral essay that "to make a living as a craftsperson, photographer, musician, designer, author, animator, app maker, entrepreneur, or inventor,” you only need 1000 true fans:

A true fan is defined as a fan that will buy anything you produce. These diehard fans will drive 200 miles to see you sing; they will buy the hardback and paperback and audible versions of your book; they will purchase your next figurine sight unseen; they will pay for the “best-of” DVD version of your free youtube channel; they will come to your chef’s table once a month. If you have roughly a thousand of true fans like this (also known as super fans), you can make a living — if you are content to make a living but not a fortune.

I love this concept, and I also don’t like the word “fan,” because it feels like a one-way street: You produce, I purchase.

Instead of having fans, or being someone’s fan, I prefer to be in relationship.

This means: the street goes both ways. There‘s a real chance of reciprocity.

I discovered Derek Sivers through his extremely short TED Talk and wonderful book Anything You Want. Then I learned that he responds to every email that readers send him. (Apparently this takes him a few hours a day, sometimes much longer.) When I first emailed Derek in 2012, he wrote back promptly, with kindness and generosity. This felt significant, because on top of connecting with his writing, now we’d connected on a different level. This small act brought me into relationship with him, no matter if he does the same with thousands of others.

Of the many writers I admire, I consider myself a “true fan” almost exclusively to those with whom I’ve corresponded or met in person.1 Because the personal touch matters. We need to remember that we are dealing with humans.

Some people make wonderful connections through Instagram, TikTok, and Facebook. But the noise on these platforms is so severe, the advertising so obnoxious, and the algorithms so fickle, that I remain absolutely faithful to the boring, direct nature of email newsletters, even as they become too popular for their own good.2

How sweet it is to receive another person’s intimate disclosures, clever analysis, careful curation, or wry observations dropped straight into my inbox, without the interference of advertisers or overlords.

I still believe in the promise of the early internet: You can just find interesting people and connect directly with them! We don’t have to market and monetize and influence each other. We don’t have to scale forever. We can use the internet to cultivate healthy connections, to people we wouldn’t otherwise know. Relationship is possible.

In the spirit of relationship, I’d like to offer you something.

Don’t worry, this newsletter isn’t going anywhere. And I’m not asking you to join a Patreon or subscription scheme. (I almost never sign up for such stuff myself.)

Rather, I’d like permission to send you something bigger than a newsletter, four times, throughout the year 2026.

Think of it as your quarterly dose of Blake-off-the-books: a story from my life on the road, a short video I create, or an essay that’s too spicy for public consumption. “Heartfelt, raw, and fun” is the vibe. And I’ll need your postal address, too, because at least one thing that I send will be physical.

What do I ask in return?

Not money—although I will let you know how you might sponsor certain projects (with zero expectation).

I only ask that you meaningfully respond to one thing that I send you in 2026—because I’d love to hear from you, and because this is a two-way street. It can be an email, postcard, video, or something else entirely. Have fun with it!

I’m excited for this initiative because it feels like a interesting way to:

• cut through the noise of “too many email newsletters”

• provide creative motivation for me + fun stuff for you

• go deeper into relationship with those who share my outlook

• maybe (just maybe) scream “I matter” to the universe ☄️

And who knows, maybe I’ll continue this beyond 2026: developing a new form of direct relating, tailored for the era of digital superabundance.

There’s only one way to find out.

To join, submit this form by December 31st, 2025:

Join the Blake Quarterly

Anxious? Avoidant? Secure?

Mine is “Existentialist.”

Discovering attachment

A dozen years ago, at the end of my first long-term relationship, my partner handed me the best-selling book Attached. We’d been caught in an “anxious-avoidant spiral,” it seemed, and we never found our way out.

I scoffed at the book’s reductionism: how could there be just three attachment styles in the whole world? But I’m a sucker for personality typing, and attachment found its way into my vocabulary. At the beginning of a new love connection, I’d wait for the right moment to disclose my “avoidance,” as if it were an incurable STI.

In the middle of my next serious relationship, one that was struggling despite addressing attachment from the outset, I consulted a therapist.

“What’s wrong with me? How can I be less avoidant?”, I asked her.

She said that I could learn to sit with my uncomfortable feelings a bit longer, to not immediately indulge the urge to escape—but fundamentally, I’m fine. I have a good life, clear values, and the desire to connect. Keep going!

So I kept going, straight through the end of that relationship, across Europe by bicycle, and into multiple sweet and loving “situationships” in recent years—until one of them floored me, and I went crawling back to attachment theory for answers.

Oh no! What if I’m actually the dreaded, lesser-known, fourth style: disorganized, combining the worst of both anxious and avoidant?

My therapist reassured me that I don’t have enough childhood trauma to warrant that label. I’m not broken, she told me, just… different. And fortunately, I seem to know what I’m looking for. I just hadn’t found it yet.

Dateblake.com

That’s when I decided to reboot dateblake.com.

I first ran this experiment in 2017. The concept was simple: I would create my own dating profile (self-hosted, far away from silly dating apps), share it with my friends (amazing people who live all over the world), and encourage them to connect me with potential matches. “If you see something, say something,” I advised, “just like the airport.”

My friends adored the concept. A few introduced me to potential matches, none of which transcended email. I ended the experiment after one year and let the domain expire.

So my expectations were modest when, in October 2024, I re-registered dateblake.com, rewrote the profile, and pitched my friends once again. And as before, just a few possible connections emerged over a year, none of which felt right, and I let the domain go. (The page is archived here.) Meeting people online feels equally alienating, it turns out, whether on an app or via personal referrals.

But despite the two-time “failure” of this experiment, it did offer a chance for reflection. When I revisit my dateblake profiles with fresh eyes, it’s fairly obvious that I’m not actually available for traditional dating.

Why? Because I’m constantly traveling and working on different projects. Because I want to cycle across countries, attend twenty dance weekends a year, and visit my friends who live everywhere. Because I mostly enjoy doing my own thing, don’t seek constant cohabitation, and would be genuinely happy to spend just half of the year in the same place as a long-term partner (assuming reliable and consistent communication).

But if we’re brutally honest, it’s because: the only thing I can commit to is my own freedom.

Enter the existentialists

[To] me, the word ‘duty’ is weighty and oppressive. I’ve pared my duties down to only one: to perpetuate my freedom. Marriage and its entourage of possession and jealousy enslave the spirit. They will never have dominion over me. I hope, Doctor Breuer, the time will come when neither man nor women are tyrannized by each other’s frailties.

—from “When Nietzsche Wept” by Irvin Yalom

My life has been shaped—to a profound and possibly disconcerting extent—by books I’ve stumbled upon. Some found me in bookstores, libraries, and friends’ shelves. One waited for me on a street corner in Brooklyn. The Amazon algorithm played a crucial role in my deep-dive into alternative education.

So it was that I stumbled upon How to Be Authentic: Simone de Beauvoir and the Quest for Fulfillment, written by philosopher Skye Cleary, just a few weekends ago—at the same moment that dateblake.com was expiring.

Until this moment I’d only known Simone de Beauvoir as the author of The Second Sex: the book that launched second-wave feminism. What How to Be Authentic showed me was that Beauvoir was, in fact, a key member of the broader existentialist movement that included Jean-Paul Sartre, Friedrich Nietzsche, Albert Camus, and Søren Kierkegaard—all of whom held unconventional beliefs about love, partnership, and commitment.

“Authentic love must be founded on reciprocal recognition of two freedoms,” Beauvoir wrote in The Second Sex. And this recognition, writes Cleary,

calls lovers to accept uncertainty and separation as the very condition of a relationship. . . . to look for joy in the distance, to welcome and to love the ambiguity, the otherness, and the freedom.

Why, hello existentialism! You’ve got my attention.

I learned that Beauvoir, like Nietzsche, distrusted the false promises of traditional romantic relationships and instead prized friendships, personal projects, and independence. But unlike Nietzsche (who never sustained a long-term romance), she still believed in the possibility of an authentic love grounded in mutual freedom.

Beauvoir practiced what she preached, enjoying a famously public and long-term open relationship with Jean-Paul Sartre—an unconventional project from the beginning:

Early in their relationship, Beauvoir and Sartre agreed to a two-year commitment, on a stone bench by the Louvre. While it was neither state-sanctioned nor enforceable, the psychological contract was strong. They wanted intimacy and freedom without the risk of decay into duties and inertia. . . . It mostly worked out for them and, after the two years, they made their commitment permanent, and theirs remained a deeply intimate relationship until the end of their lives.

Beauvoir was a famous critic of marriage, and not just on feminist grounds. She believed that “marriage’s monotony and vacuity can be metaphysically mutilating, cramping people’s freedom.” When one’s romantic partner is around all the time, “there is little space for missing and yearning,” which leads to the death of intimacy, and results (at best) in “companionship and cohabitation.”

Read more of my favorite quotes from How to Be Authentic, or just take my word for it: the punchline is freedom.

Beauvoir believes in romantic love and commitment—but only when both people care deeply about perpetuating each other’s freedom: the freedom to grow, transcend, pursue meaningful projects, “self-overcome,” and work to eradicate oppression in the name of the “collective freedom” of all humans.

Existentialism is not a complete philosophy for life. While I didn’t agree with everything in How to Be Authentic, in the chapters about romance and marriage, I found myself saying Yes, Yes, Yes. Because Simone de Beauvoir, like Friedrich Nietzsche, clearly sees the value of avoiding false promises of security (which are inherent in traditional relationships) and injecting life with danger, desire, and the recognition of inevitable death—all of which make life infinitely more precious and worthy of engagement.1

The existentialist view of love and commitment rings so true, in fact, that I now question why I would continue labeling myself “avoidantly” or “anxiously” attached when I don’t even seek the conventional, entangled relationships assumed to be most “secure” by mainstream culture.2

When someone recognizes, values, and honors my own pursuit of freedom—I like that person more, feel secure around them, and experience a genuine desire for commitment.

This is why friendship, which honors mutual freedom by default, has always worked out well for me—and feels like the foundation of true, long-term security.

This is why viewing life as a series of endless adventures—even at age 43—doesn’t feel like Peter Pan syndrome, but rather a reliable way to avoid becoming a “warm corpse, merely going through the motions of life but not living in any meaningful way.”

And this is why I’m going to start telling people—especially those love interests who I meet in the flesh, not online—that my attachment style isn’t avoidant, or anxious, or disordered. It’s existentialist. 𖤓

Book one

I signed my first—and only—book deal at age 26.

New Society, a small, sustainability-focused publisher in British Columbia bought the manuscript for College Without High School for $5000 CAD.

I had no audience, no followers, no “platform.” This was 2008, just before the social media explosion. New Society helped me get featured in a large Canadian magazine, a couple radio shows, and… that was it. The rest was up to me.

A mentor advised me to think about books as big business cards that open doors, and I took his advice to heart. With my “published author” credential I got myself invited to speak at homeschool conferences, alternative schools, parent groups, an education-focused TEDx, and a few early podcasts. (The public speaking helped launch my teen travel business, too, but that’s a different story.)

Despite these efforts, the book sold modestly. I wouldn’t see a penny of royalties for a dozen years. So when I went back to New Society a few years later with my next book, Better Than College, they offered me the same deal: $5000.

Book two

I understood their position. Light sales of a first book make a second deal unlikely. But I’d started building my own audience, I’d improved as a writer, and the book was linked to a timely topic: the college affordability crisis. This didn’t feel like progress.

At the same moment, the Amazon self-publishing system was taking off, making it easy to create print-on-demand paperbacks and Kindle e-books. Independent authors were crowdfunding their startup costs on Kickstarter and IndieGoGo, hiring their own freelance editors and designers, and tackling promotion with novel online approaches.

The self-publishing path sounded like my kind of adventure—so I jumped in, followed the pattern, learned a ton, and had a blast. Within a few months of self-publishing Better Than College, I’d already earned more than the advance I didn’t take. I experimented with giving away PDF copies in exchange for newsletter signups, eventually distributing 10,000 free copies.

The cultural timing proved correct; everyone wanted to discuss alternatives to college. Over the next few years I found my way into USA Today, The New York Times, Wired.com, Reason TV, Fox Business (watch and chuckle), and NPR affiliate radio. But mostly, I continued speaking for tiny schools, conferences, and podcasts, spreading the idea that you don’t have to go to college or high school to become educated. I felt like I was genuinely changing the world in my own, small way.

Book three

In 2014 I crowdfunded and self-published The Art of Self-Directed Learning: a short, playful, illustrated book that would eventually become my best seller, especially in international markets like India.

Much later, a TikTok influencer would spontaneously promote this book (despite misreading the title), sending sales skyrocketing (5x) for months.

Book four

After writing something so light, I wanted to go deep. I immersed myself in the research on alternative education outcomes, the sociology of “intensive parenting,” and the nature-nurture debate. I pressure-tested my ideas by writing long articles, interviewing people on my education podcast, and embarking upon a self-funded, 24-stop, alternative-school speaking tour.

The result was my 2020 book, Why Are You Still Sending Your Kids to School?, ironically published at the same moment that pandemic stay-at-home orders mandated that no one send their kids to school.

I felt intensely proud of this book for its intellectual clarity: not just the density of citations, but its impartial analysis of the alternative education world: a world that tends to looks at itself through rose-colored glasses. (“When You Get Into Unschooling, It’s Almost Like a Religion” was the title of a 2020 New York Times opinion, in which I appear. They’re not wrong.)

Researching, editing, and peer-reviewing this book felt like completing a full-scholarship, self-directed graduate degree: one that arrived with praise from best-selling authors like Seth Godin, Daniel Pink, Jane McGonigal, and Johann Hari.

Looking back at the 5-year story of creating Why Are You Still Sending Your Kids to School?, I still say to myself: ”Damn, that was one badass adventure.”

Book five

Now I’m close to publishing another book: Dirtbag Rich. It’s my first book that’s not about education, my first with heavy personal disclosure, and the first that may connect to a broader audience (compared to books about quitting school, which most people simply won’t consider).

The seed was planted in 2016 when I began writing about living nomadically. Then I got involved in a messy, passionate relationship with a dancer from Germany, complete with multiple break-ups and smuggling myself into Europe despite the pandemic travel ban. (Solution: launder yourself through the United Kingdom!) When that relationship finally ended, it cracked me open—and out poured lots of words about the “dirtbag” life that I (and many others) hold so dearly, even at the price of romantic partnership, geographic stability, and wealth accumulation.

I channeled the word-flood into a zine called Do What You Love & Die Trying, printed in 2023 as a one-time Kickstarter. Then I stopped writing my education newsletter, shuttered my education podcast, and started publishing this newsletter. All of of which, I now see, was preparation for Dirtbag Rich.

The adventure had begun. The clarity was building. But for a book with a larger potential audience, how would I get it out there?

To publish or self-publish?

A literary agent—one who’s shown interest in my writing for years—came close to working with me, and then backed away. He said the book looks great, but at 27k words, it would be a hard sell for most publishers. (I think the brevity is a feature, not a bug.)

Also, left unspoken: my platform is quite small (no viral article, big email list, or 100k followers), and my sales history is middling (~34k cumulative).

All of which I understand. And if I pitched ten brand-new agents, maybe I’d find one who wants to take a chance. But that’s not how I want to spend my next 3-6 months, followed by another 12-16 months of waiting for Dirtbag Rich to work its way through the gears of the publishing world.

’s recent article, Everything I Know About Self-Publishing, masterfully explains why the indie route continues to offer significant advantages to those who bring their own audiences (however modest) and embrace creative self-promotion.

• No, you won’t get a big advance—but you can crowdfund your initial costs, and you’ll receive 60% royalties (rather than 10%) for the rest of your life.

• No, your book won’t magically appear in bookstores—but most normal books have shockingly short shelf lives, anyway.

• No, you won’t have a publisher’s imprimatur to open doors to major media—but side doors exist (as I’ve already seen).

Some of my book’s “comparable titles” were traditionally published: Moral Ambition (Rutger Bregman), Vagabonding (Rolf Potts), and The Art of World Domination (Chris Guillebeau). Others were self-published to great success: Anything You Want (Derek Sivers), The War of Art (Steven Pressfield), and The Pathless Path ().

Listen—I’d love for Dirtbag Rich to sell widely. I want to get these ideas out there and continue changing the world in my own way. Securing a publisher might accomplish that. But with my mixed credentials, it’s likely to be an uphill battle, and I might spin my wheels for a long time… when I could be spinning them differently. 🚴‍♂️

A bicycle book tour, a fireside YouTube bootleg, and other ridiculous ideas

When you self-publish, there is no Publisher Daddy toiling in the shadows to snag you a plum review. You’ve got to make things happen. As Kevin Kelly says,

it is not hard to produce a book. It is much harder to find the audience for it and deliver the book to them. At least 50% of your energy will be devoted to selling the book.

That’s why I’m not worried about creating a beautiful, well-edited book. Been there, done that. But I am absolutely concerned about connecting to my audience.

Fortunately, choosing your own release date also lets you entertain weird and fun promotional ideas: like a nationwide bicycle book tour.

When my European residency ends in April 2026, it’s the perfect time to return to the U.S., get a new touring bicycle, and spend five months riding through New England, Colorado, Utah, California, Oregon, and Washington to see old friends… and speak along the way! Living a dirtbag life while promoting a dirtbag book—it only makes sense. I envision speaking at climbing gyms, outdoor stores (like REI), university outdoor clubs, mountaineering and hiking clubs, vanlife gatherings, tiny bookstores in mountain towns, and anywhere else I can find outdoorsy people who already know (and sympathize with) the term “dirtbag.”

Convincing venues to host me will be hard. Carrying any quantity of books on my bicycle will be hard. Shipping books ahead to multiple venues will be hard. Long-distance, multi-month cycling is always hard, especially in the arid, empty west. But is this my kind of hard? Absolutely.

Another idea: narrating the book on YouTube, next to a roaring fire, in costume.

Books still earn major respect in our culture. And also, as Kevin Kelly observes, “Books no longer have the gravitas they did, and my children and their friends are not reading many of them.”

To reach twenty-somethings raised on videos, one clearly must make videos. And while my TikTok foray was fun, I suspect that a longer, professional-quality video will let me express more nuance.

This is another massive advantage of self-publishing: you can give away your stuff for free! In this case, I could simply narrate my entire book in some entertaining fashion—like sitting next to a roaring fire, dressed in a rotating cast of “dirtbag” costumes & sets (ski bum, rock climber, thru-hiker), caption it, and put it on YouTube.

Would I lose some potential book buyers who just watch the video? Yes. Would I gain many more potential buyers, especially younger people who don’t pay attention to someone they haven’t first “met” through video? I’m confident. And would it be a lot of fun to produce? Absolutely.

What other kinds of ridiculousness could I get into?

• Geocaching copies of Dirtbag Rich along the bike tour and publicizing the coordinates?

• Commissioning illustrations by of Semi-Rad (who’s also one of my interview subjects)?

• Recruiting tour sponsors, to whom I dedicate individual bike parts? (Imagine your name + ♥️ scrawled across my front fork.)

• Serial-publishing multiple chapters here on this newsletter?

This is where self-publishing wins me over. I could do much of this with a traditional publisher—but I would be selling a book that someone else technically owns.

When I promote something that’s truly mine, start to finish, I’m willing to take more risks. I’m more playful and stress less. It all feels more meaningful and adventurous. And that’s the point of selling books, or doing pretty much anything—right?

This is how I’m thinking about self-publishing in 2026. Thanks for following the journey. I’ll have more for you soon.▪️

As a child, I gazed out California school windows as sunshine dripped from the heavens above. That was enough ass-in-seat time for an entire life.

Think of all the young people sitting in similar rooms today, their bodies prematurely crumpling, congealing, and stiffening.

Think of all the “knowledge workers” hunched over desks and perched afront laptops. Think of all the security guards, bus drivers, cashiers, and assembly line workers.

The answer isn’t standing desks or longer recess.

The answer is less school, and less work.

Run me like a Border Collie: through parks, across cities, down trails. Ask me to ford a river or traverse a mountain range. Put me on a bicycle, skateboard, kayak, or skis: anything that rolls, floats, or glides.

Give me that full-body high: the kind that follows a long day’s hike, a 10-mile run, a lake swim, a multi-hour cycle, an epic frisbee session, or an all-night dance party.

Moving till exhaustion is how I think, I feel, and I dream.

It’s how remember that I am, in fact, alive.

I type these words while standing in a kitchen, laptop on a shelf, music playing. If focused, I’ll be still for a few minutes—then I gyrate my hips, switch my weight, and stand on one leg. Sometimes I walk away, rest my eyes, circle my shoulders, and do a little dance. Maybe I’ll pace the apartment, stretch on a yoga mat, or clean the dishes. After my few hours of genuine mental effort are spent, I’ll relax on the couch with a book, take a run in the hills, or bike through the city.

Self-employment can imprison our bodies as readily as regular employment.

The point of working for yourself isn’t to replicate inhumane conditions in the comfort of your own home, coworking center, or café.

The point is to liberate your mind and your body.

Are we “meant” to constantly move our bodies? Are we “not meant” to sit at desks?

I’m weary of such arguments, even when they have a few million years of evolution on their side.

Human bodies are adaptable. Some people sit happily, all day long. If the only real alternatives are backbreaking agricultural labor or 11-hour factory shifts—as they’ve been for so many, for so long—I’d probably take a desk, too. And for those whose bodies don’t function as they wish, a desk-bound existence can spell liberation.

But for my body, my place, my time—desks are not my liberation. Ever since I received a choice in the matter, I’ve avoided them. No office jobs. No unnecessary meetings, no pointless lectures. No sitting inside on sunny days, wishing I were elsewhere.

Even when liberated, we forget to move. We get sucked into screens. We sit too long in cars and planes. I’ve neglected my body and paid the price.

I know, with absolute certainty, that movement is what I’m meant for.

So bring on the AI revolution—not the one that murders us all, but the one that eats the most mundane jobs, shortens everyone’s working hours, and liberates young people from the 19th-century classroom.

Bring on the dirtbag rich—those who deliberately choose to work less, earn less, and spend more time moving their bodies through nature.

Bring on whatever allows our inner Border Collies, Basset Hounds, Saint Bernards, and Pugs to thrive.

More runs, more walks and dances, more naps and cuddles—and less deskbound toil.

Give me that world.

Everyone wants to feel connected: friends, families, lovers, communities—and most certainly, partner dancers.

Partner dance is fun, invigorating, and a great way to meet people. But without connection, swing, salsa, tango, and other forms of improvised lead/follow dance wouldn’t be so different from a running club or climbing gym.

The first time I pressed my chest to a stranger’s chest while learning Argentine tango at age 26, I tasted connection. Years later, “fusion dance” introduced me to even deeper levels of closeness, communication, and platonic intimacy on the dance floor.

But even among such communities, I still experienced a good deal of frustration, loneliness, and self-doubt. So I eventually stopped and asked myself, “What exactly creates connection in partner dance?”

What emerged was a 4-hour workshop that draws upon my time with one magical summer camp, one amazing tango teacher, the world of authentic relating, and some of my favorite fusion workshops.

In recent years I’ve given my “dance connection” workshop to three groups of dancers in Germany. Later this year, I’ll do it again in Prague. And in just a week, I’m co-leading an entire fusion dance weekend focused on connection.

Which is all to say: I’ve been thinking a lot about connection in partner dance, and I’ve got some things to say.

Please enjoy these abridged notes from my dance connection workshop. It’s not the same as taking the actual workshop, but you just might find something to inspire your own dance, relationships, or life.

Connection and attention

• What is this thing we call connection in partner dance?

• Well, what is the opposite of a connected dance?

  • when you are (or your partner is) distracted, uncommitted, or not really “there”

  • when you are (or your partner is) obsessed with looking good, showing off, or otherwise “performing”

  • imagine dancing with someone who is constantly checking their phone, watching other dancers, or looking in a mirror

• Connection = attention = love

  • In a connected dance, my partner and I say four things to each other:

    • I see you

    • You are special

    • There is no rush

    • Let’s be children again

  • To “see” another = giving your full, undivided attention

  • Attention is “the most basic form of love” (source)

  • The opposite of full attention is “continuous partial attention”—like having an important conversation while also checking your phone

• Focus gym

  • Seeing your partner begins in your own mind. If you’re distracted or worried about looking good, it’s tough to see someone.

  • Let’s begin with focus exercises before ever stepping on the dance floor:

    • Classic guided meditation (10 min)

    • Listening to non-dance song, Adagio for Strings, while doing absolutely nothing else (10 min)

• Eye contact and questions

  • Feeling more focused? Now let’s take this state of mind and share it with a partner.

  • Find someone (dance roles don’t matter) and sit across from them. We’ll do periods of sustained eye contact followed by questions that one partner asks the other.

  • Each person has one minute to answer. Let your partner talk, listen fully, and give your full attention, then switch roles.

    • 15 seconds of eye contact, followed by: “Why do you dance?”

    • 30 seconds of eye contact, followed by: “When do you feel most connected?”

    • 60 seconds of eye contact, followed by: “What is home?”

  • By now you should be feeling the first two elements of dance connection: “I see you. You are special”.

Progressive touch exercise

• Now—“There is no rush.” How slowly and deliberately can you initiate physical connect with your partner?

• Find a new partner, maybe someone you’re curious about.

• Song: Riding the Merge Home (11 min)

  • (2min) Close your eyes and breathe. Try to align your breath with your partner.

  • (1min) Now, open your eyes. Gaze in your partner’s eyes. Keep breathing together.

  • (1min) Bring hands together as close as you can without touching.

  • (2min) Close your eyes again and try to keep your hands close without touching. If you touch, simply adjust as needed.

  • (1 min) Open your eyes and make contact, only touching fingertips.

  • (1 min) Slowly invite more touch: first fingers, palms, then forearms to elbows.

  • (2 min) Contact dance with hands/arms. Play with different speeds, pressures, parts of body. No leader or follower.

  • (until end) Lower your hands and just make eye contact.

• Song: Little Lover (5:30)

  • (1 min) Walk around in a mingle style, making eye contact with others as you pass them. Hands at your side.

  • (1 min) Allow hands to interact, just tiny finger touches.

  • (1 min) Allow hands to explore others in passing, brushing hands, arms, shoulders, head.

  • (2 min) Full freedom. Linger with a person and migrate as desired. Stop sometimes to view the people around you—close your eyes, breathe in the connection.

Negative space game

• Now, “Let’s be children again.” How can we remember to play, rather than just execute “moves?” How can we respond exclusively to the person in front of us, rather than get lost in our heads?

• Find a new partner.

• Song: Agatha (12:00)

  • (2 min) One partner strike a pose and becomes a statue. The other partner finds a way to fill the space around the first person with arms, legs, and torso. Then the second partner walks away, becomes a new statue in a new pose, and the first partner attempts to fill the space.

  • (1 min) Find a new partner. Same exercise, but now switch roles without walking away. After you fill the negative space around your partner, freeze in that position, and then your partner attempts to fill the space around you without leaving.

  • (2 min) Find a new partner. Same exercise, but when switching roles, flow smoothly instead of switching abruptly. Now both partners are constantly trying to fill the negative space around each other. When in doubt, slow down.

  • (2 min) Split up. Find two new partners and make a group of three. Do the same exercise, with each partner attempting to fill the negative space around the other two bodies.

  • (2 min) Now two groups of three join together into a group of six. Same exercise.

  • (until end) Now… touching is okay! You limbs and bodies may press on each other, beginning to feel like a “real dance.” Continue filling the spaces that appear. If you’re in the middle, feel free to remove yourself to the outside. You are free and connected at the same time.

Now, we dance!

• I’ll put on four classic fusion songs. Continue dancing as before.

• Feel free to dance with one person, two people, or more. Split and merge groups as desired. Whenever you want, go to the side and just watch for a while.

• Don’t think about looking good, leading, or following. Just give your partner(s) your total attention, and communicate silently:

  • I see you

  • You are special

  • There is no rush

  • We are children again

• Songs: Fantasy, Technicolour Beat, Down, Reprieve

David Whyte quote

Let’s discuss this quote:

Life can find you only if you are paying real attention to something other than your own concerns, if you can hear and see the essence of otherness in the world, if you can treat the world as if it is not just a backdrop to your own journey, if you can have a relationship with the world that isn't based on triumphing over it or complaining about it. . . . we put ourselves at the center of the world, strangely, by eliminating our concern for the smaller self.

—David Whyte, The Three Marriages: Reimagining Work, Self and Relationship

[long break]

The dance before the dance

• Beginning dance with the right mindset can make all the difference. How do you set yourself up for success, i.e., set yourself up for connection?

• If we could play warm-up games with everyone person we’re about to dance with, or 10 minutes of guided meditation with eye contact, followed by activities like we just did… we would all feel more comfortable!

• But what really happens is: we’re often dancing with a brand-new person, and we rush from initial meeting to full-on dancing.

• Instead of rushing, let’s explore the “dance before the dance”.

• Goal: “Instead of hearing a song, conceiving a plan, and then executing that plan—notice the environment, listen to your partner, and go from there.” (Alejandro)

Music awareness

• Yes, No, and Hell Yes

  • Early in our dance careers, we want experience, so we nervously say YES to everyone and every song. This is good! better than being timid and not learning through trial and error.

  • As we progress, we begin to know what we like, what kind of music moves us, and we become more selective. We begin to feel confident saying NO. This is good! then we can conserve our energy for a “hell yes!”

  • This also applies to a long evening or dance weekend, too: conserving energy is important, not just for your body, but your ability to pay total attention.

• When a song comes on, listen closely and ask yourself: does my body want to dance to this now? Is this a No, Yes, or Hell Yes?

• Rather than rushing into a dance, It's ok to…

  • recharge your batteries

  • witness: just soak up other people’s connection

  • take a long time to decide if you’re feeling the music, and then dance the rest of the song

• I’ll play three songs. You can dance to one, two, or none of them.

• During the other song(s), just rest, appreciate, watch others, and mind your breath. Notice any feelings of stress, rush, FOMO, or frustration that arise. Let them pass. (optional dark chocolate)

  • SONGS: (11 min): Androgyne, Pythia, Unholy

Partner search

• Sometimes you hear a song, and you know exactly who you want to dance with. Amazing! Go find that person.

• Other times you want to have a dance, but your desired partner is unavailable, or you’ve already danced together a lot, or you don’t know anyone, or you want to meet someone new. Time for a partner search!

• Different ways of searching for a dance partner:

  • The Mad Rush (scarcity mindset)

  • Playing Hard to Get (false non-neediness)

  • Open and Curious (yes, do that one!)

• Assume that your new partner has a secret ability, and it’s your job to discover it.

• Let’s take a cue from tango: the mirada and cabeceo

  • Mirada: looking at someone’s eyes to see if they would like to dance with you

  • Cabeceo: The leader looks at the follow and indicates interest with a nod of the head. If the follower also holds eye contact and nods, then the leader approaches, offers a hand, and they dance. If the follower refuses, they simply look away.

  • Activity: walk around the room and silently invite others to dance. Say yes sometimes, dance for 20 seconds, then separate and keep walking. Other times, say no.

• It can be hard to say no (and accept a no). But we must! To practice this, find a partner and line up for walking boundary-setting exercises:

  • Walking toward partner, verbally saying “no”

  • Walking toward partner, nonverbally saying “no”

Body language

• The proper goal of dance is to “create goosebumps.”

• A few small things that we do (but usually don’t think about) in the transition from saying “yes” to beginning a dance: smile, hands, and walking onto the floor.

• This is all part of the dance, even before the dance begins. So how can we be less predictable? How can we start creating goosebumps before we even embrace?

• Smile

  • what makes a smile? practice authentic and inauthentic smiling.

  • think to yourself: “I knew a secret: we’re about to have an amazing dance”

• Hands

  • how many different ways can you hold a hand?

  • how can you lead (or be lead) onto the floor with a clear physical connection, without holding hands?

• Walking onto the floor

  • what are other ways that we can lead each other onto the dance floor? miming from a distance? gently pushing (contact improv style)? finger play?

  • lead a partner across the room, find a new one, and do it again differently.

Choosing roles

• Classic question: “Would you like to lead, follow, or switch?”

• Find a new partner, and try asking this question differently. Dance a little bit, then separate, continue wandering, and do it again.

• Now—try it without words!

• “What we can create together is more interesting than my plan for you.” (Alejandro)

Initial embrace

• Something I don’t like: seeing a couple walk the floor and immediately enter into big, acrobatic movements.

• Instead of rushing in, how slowly and patiently can we enter the embrace? How much can savor this moment?

• Use the first 2:22 of To Build a Home to simply walk across the floor, enter an embrace with your partner, and make a single weight change.

• “Don’t be a single-embrace guy. Be open to different pressures and positions. Embody the emotion of the music. No robot man! No one-size-fits-all solutions!” (Alejandro)

Putting it all together

• Dance connection principle #1: “I see you. You are special. There is no rush. Let’s be children again.”

• Dance connection principle #2: “Instead of hearing a song, conceiving a plan, and then executing that plan—notice the environment, listen to your follow, and go from there.”

• Now let’s dance! I’ll put on four songs.

  • Begin with sitting/standing, being present, feeling the music. “Do I want to dance to this?”

  • Invite a partner (or receive an invitation), giving either a full “yes” or “no”. If you receive a “no”, smile and move on.

  • Enter the dance floor and decide roles in a way that feels interesting (and maybe creates goosebumps). Take your time to embrace. Smile.

  • As you dance, give your partner your full, undivided attention.

  • Dance 1-2 songs with your partner, say thank you, then do it all again.

  • SONGS: Hopeful, Aching, Como Si Na, Crush

That’s how to be a connected partner dancer—or at least, how to get started. Enjoy!

What do you do
when you don’t want to play the same game as everyone else
but you also don’t want to become a bum, nun, monk, or parasite
or end up dead in a bus in Alaska?

When most serious jobs feel morally suspect
When full-time work is a conveyor belt to burnout
When vacation allows only for recovery, not re-creation
Why contribute, why participate, why buy in?

Why listen to those who tell you to suck it up,
get serious, stop your griping, and take the damn job,
when they seem to inhabit a very different universe
and came of age in very different circumstances?

You try listening to the hustle bros
They’re clever and enthusiastic
but still pray to the money gods

You follow the full-time athletes, artists, and explorers
They’re beautiful and inspirational, with unfortunately little to say
about money, relationships, or finding work that can support lives like theirs

You try the self-care: “I’m good enough, just as I am right now”
But “good enough” doesn’t exempt you
from bills, debts, inflation, and social expectations

Older people call you talented and capable: ”don’t waste your potential”
You wonder how much of this praise is genuine
And how much validates their own questionable choices

All you really know for sure:
You can put your faith in sunrises and sunsets
Sweat, dirt, and campfire smoke
Cold lakes and windy forests
Bird calls and rocky trails
One leg in front of another
And the rare souls who speak your same language

You don’t need to become rich or famous
You just want to do good work, and not too much of it
and invest heavily in nature, relationships, and social causes

How does one do this
when anxious family, friends, and doomscroll media
tell you to play it safe?

How does one participate in “capitalism”
without losing mind, body, soul
and still purchase a goose down sleeping bag?

How does one step away from the algorithm
of “work, nest, accumulate, reproduce, retire”
and still have warmth, friends, community, safety?

Who is asking these questions
and where are the answers?

How does one survive this world? 𖤓

[I wrote this to explore the core readership of Dirtbag Rich: their urgent problems and concerns, and why my book might matter to them.]

You usually get one or the other: mountain towns without much dancing, or big cities without real mountains.

But Shangri-La may exist.

Yesterday morning I woke in Vienna, Austria. I hopped on the U-Bahn (light rail) at 8:30am and boarded two trains to Puchberg am Schneeberg, where a local bus deposited me at the base of a mountain.

Front door to trailhead: just over 2 hours.

I scrambled up a rocky ridge to a broad plateau, tagged Lower Austria’s highest peak (Schneeberg), and then ran down the other side, back to the train station.

Multiple mountain huts tempted me with food and drink along the way, but I saved my appetite for cheap chips and orange juice at the grocery store in town.

Total moving time: 4 hours. Resting time: 1 hour. Return to Vienna: 2 hours.

I’m in the shower by 5:30, eating leftovers at 6, and ready to dance by 6:30.

Vienna, like most large European cities, has a thriving partner dance scene, which includes salsa, swing, tango, contact improv, and more. If you’re open to anything, you can easily dance every night of the week.

My favorite scene is “fusion,” which creates a container for people with different dance backgrounds to playfully coexist. Just a few cities have regular fusion socials, and Vienna is one of them.

And that’s how I spent my night: dancing outside for three hours with a handful of other fun, playful, and talented dancers, before cycling 15 minutes back to my place and collapsing into bed.

If you adore the mountains but also crave dance (and similar culture), where can you go? Where is Shangri-La?

I lived in South Lake Tahoe for many summers. The mountains were amazing, but at night I craved alcohol-free social opportunities, namely dance. But accessing dance meant a long drive to Sacramento or Reno: one I’d have to repeat later that night.

I’ve also lived in many almost Shangri-Las: Portland (Oregon), Asheville (North Carolina), Boulder (Colorado), and Freiburg (Germany). Each was amazing, yet none offered a true combination of “big mountains at your doorstep” and “thriving dance scene.”

The reason for this is clear: thriving dance scenes (and most other forms of culture) require population density, which mountainous terrain doesn’t accommodate.

Yet I remain hopeful, as more potential Shangri-Las remain on my radar: Zürich (Switzerland) and Squamish (British Columbia).

Zürich is a major city, but you still see people walking through the train station with mountaineering gear (summer) and skis (winter), soon to be whisked away to the Alps by an utterly reliable (if terribly expensive) Swiss train. Just last month, I took a 2-day mountain adventure and then returned to dance the night away.

Squamish is a certified mountain town, but one with a surprising amount of dance (I’ve never been, but I’m told on good authority). Its proximity to Vancouver helps attract a critical mass, much as Boulder benefits from nearby Denver.

One final request: no driving required.

This is why Shangri-La is utopia: because now I’m just asking for too much.

What I loved about my Vienna adventure—and what Zürich and Squamish represent—are these rare, magical confluences of great mountains and great dance, without requiring a vehicle.

No late-night drives home. No battling traffic on congested highways. Just good nature and good people, a short walk, bike, bus, or train ride away.

This is what I seek. If you know where else I should look, do tell. 🌄

Some stare at their phones. Some stare into the empty space over their partner’s shoulder. Some watch their partner pick at a dinner plate.

Every now and then, a couple shares a murmur, a smile, or a nod of understanding—and then four eyes return to the void.

My friend Nate and I are hiking through a remote region of Switzerland, and the fancy hotel-restaurant is the best and only place to stop for the night. The 20-bed hiker dormitory (separate from the hotel) has plenty of space, and the restaurant is the only food for miles. So here we are: two scraggly, hungry, colorfully outfitted hikers, giddy and tired from our eight-hour walk with 1400-meter (4600-foot) ascent, perched inside an aviary of respectable Swiss couples who drove their nice cars up a nice mountain pass for a nice dinner.

The waitress asks what we’d like to drink. Nate requests Leitungswasser (free tap water). The waitress responds, still or sparkling? Nate tries again with different words and a wide, “help a brother out” smile. That is not possible. Oh, well—we’ll fill our bottles at a bathroom sink later tonight.

The meals are sumptuous: juicy meats and crisp vegetables float atop beds of creamy carbohydrates, the cheapest plates on the menu at $40 a pop.

But what’s most delicious is the conversation.

Nate and I are both Americans living in Europe, united by our love of mountains and dance. Alongside mutual friends we’ve already taken a few Alps adventures. Now we’re comfortable hiking with just each other, and we have so much to discuss: recent dance weekends, ongoing love affairs, personal struggles, future plans, cultural comparisons, the next day’s logistics, and the endlessly fascinating habits, neuroses, and sex lives of the small army of houseflies that seems to inhabit every high-altitude dining establishment in Switzerland.

We stand out in this restaurant, not only because of how we look and speak, but by the sheer breadth, depth, and exuberance of our conversation.

This is how I like it.

I like conversations that never run dry and leave us hungering for more. I like hip-hopping and flip-flopping between the practical and philosophical. I like discovering how another complex, autonomous being navigates this world. I like catching up, revisiting old threads, and recalling (over and over again) why I find a particular person so delightful. I want the endless horizon: always more to learn, share, dissect, and realize.

And I’m sure that if Nate and I spent multiple months hiking together, we would run out of things to talk about—and we could easily become one of those quiet pairs, each giving more attention to a phone, book, or internal world than the flesh-and-blood person in front of us.

This is what scares me about long-term, monogamous romantic partnership—and by extension, the nuclear family.

I recognize the trust, security, and connection that arise in long-term romantic relationships. I’ve tasted them. They’re wonderful. And they come at a price.

Every capital-R Relationship reduces the time and attention available for other relationships, most notably friendships. Every Relationship brings depth and understanding (which can encourage rich conversation), but also breeds predictability and saturation (which can discourage it).

One person is just that: one person. You can’t expect endlessly vibrant conversation from even the most fascinating person. Every fascinating eventually becomes familiar—and from there, it’s a short trip to a silent dinner table.

Why do I fare poorly in long-term relationships but thrive in temporary communities, like summer camps, dance weekends, travel adventures, group retreats, and short-term stays with friends?

Why am I more interested in a rotating cast of characters—groups and individuals to whom I periodically circle back—rather than a year-round core?

Why, following a long period of travel, visiting friends, and intense gatherings, do I feel more sadness than relief to return to the privacy of an apartment?

One answer is: quality conversation.

Which to me means: varied, deep, and vulnerable conversation.

This is why I’m happy to sacrifice comfort, privacy, and a good deal of “normalcy” to regularly access entire ecosystems of brains at camps, gatherings, and my scattered friend communities.

This is why the college environment—especially the 50- to 125-person student co-ops where I lived for years—felt so meaningful.

And this is why living alone consistently wears me down faster than living communally.

So why not try the original form of communal living?

Start a family, and you’ll always have someone to talk to!

No one ever actually said this to me, but I feel like it’s a widely held assumption. And I don’t buy it.

Raising young children limits the scope of conversation, most brutally for mothers. You have less time to talk with other adults, and when you do, it’s fragmented, and the usual topic is… children. And while some parents seem to genuinely enjoy their extended conversations with young children, I’m skeptical about my own capacity in this department. (I’ve long observed that I most enjoy children when they can wipe their own butts and understand sarcasm.)

As kids get a bit older, I think some genuinely interesting years of conversation await. After the hike with Nate, I visited an ex-girlfriend in Switzerland with a 5- and 7-year-old. They’re super fun, and I’ve enjoyed seeing their development over recent years. To the extent that you can reclaim your adult socializing during the mid-child-rearing, perhaps you can have it all. But I still fear the triple threat of isolated nuclear families, overworked parents, and the diminishment of adult friendships during the early childhood years.

Finally, teenagers. I’ve worked with enough teenagers (and their parents) to know that there are fantastic conversations to be had, but they’re inconsistent. A teen’s priority is connecting with peers, which often means going online. As I shared in my conflicted thoughts about having kids, the chance of living in a household where every family member is holed up in separate corners of the house, glued to their respective screens, feels too real.

But without a full-time partner or kids—what remains?

What remains is community. Multiple communities, scattered across the world, the solar system, the metaphorical galaxy!

What remains are the globular clusters of other adults who say “no” to standard paths and “yes” to ever-deeper conversation, connection, and cohabitation.

What remains are the isolated nuclear families who appreciate occasional visits from old friends and itinerant travelers.

No, I don’t want to live in a real commune, where individual identity and agency are erased. Nor do I endorse capital-C Communism. I like living in individualist societies. I might even agree that nuclear families are the building blocks of such societies.

But bricks need mortar. Who will be the mortar?

If your affections run wide (as mine do), and you fear the quiet death of conversation (as I do), then perhaps it’s okay to say “no thank you” to standard relationships and prescribed family constellations.

Perhaps it’s okay to continue blazing through the galaxy like a comet, appearing periodically in far-flung solar systems, gravitationally bound to all and none.

Everyone wants to stay warm in the frigid vacuum of space. You can keep it nuclear, or you can venture widely. The universe needs both. ☄️

In less than a minute, this page has the potential to say so much:

• What do you care about?

• What’s your vision for the world?

• What are you obsessed with?

• What’s your sense of humor?

• Are you trying to sell me something?

Different people have different reasons for maintaining personal websites, of course. Many professional About Me pages are brief and dry, because many people believe that’s how to be taken seriously.

Which makes it all the sweeter when someone does take a risk: by getting vulnerable, going deep, or “oversharing.” As long as they remain concise and truthful, I take such people more seriously—in appreciation of their courage and self-awareness.

Summarizing yourself in 3-10 paragraphs is hard. Impossible, in fact. You have to be selective. That’s the therapeutic part.

If you’ve never written one before, give it a shot. Write a draft, walk away from it for a day or two, and then return to read it out loud. Ask yourself: Is this a compelling story? Is it a bit boring or overly cautious? Do you hope for more (or less) drama, more (or less) detail?

This is the story of your life. You’re free to rewrite it.

If you already have a public bio, is it still current? Is a rewrite in order? Recently I peeked at my own About page, and it felt too sterile and outdated. I realized I hadn’t meaningfully updated it in five years. So I sat down and asked, Who am I today? What really matters? How do the pieces fit together? The result is below.

If you have an About Me page—or especially admire someone else’s—I invite you to share it, whether publicly (in the comments) or privately (yourstruly@blakeboles.com).

Happy writing! ✍🏼

About the temporary agglomeration of atoms known as Blake

I design adventures—for myself, for my friends, and for young people.

But designing is less than half the fun. You’ve got to take the adventure, too.

Computers were an early love, but I never wanted a desk job. Too much sitting, too many rules, too little fresh air.

I flirted with becoming a high school science teacher, but I never understood why most teachers just teach. What about the doing? Normal teaching positions (public or private) leave little time for doing the thing you propose to impart to students. Where’s the passion? Where’s the skin in the game? Young people can smell that stuff. They know when you’re just showing up, clocking in, and going through the motions. I wanted to become a different kind of teacher. So I quit my astrophysics major, designed my own course of study in alternative education theory, graduated from UC Berkeley with a degree no one ever heard of, and launched into the world without much of a plan.

I threw myself into adventure: travel adventures, wilderness adventures, entrepreneurial adventures, and creative adventures. Some alone, some with friends. These adventures brought me to new worlds and hidden communities, where I discovered yet more inspiration, motivation, and co-conspirators. The flywheel started spinning, and it never stopped.

At age 25 I started Unschool Adventures, a tiny travel company that let me earn money by exploring the world, sharing my passions and curiosities, and giving teenagers real-life freedoms and responsibilities. I hired my friends from the world of outdoor and alternative education. I almost never repeated a trip. And I only ran a few trips each year, ensuring that I’d have plenty of time left over to continue doing the thing I taught.

Around the same time, I wrote my first book, connecting the ideas of unschooling (full-time self-directed learning), adventure, and the “real world” (as symbolized by college admissions). A small Canadian publisher purchased the manuscript, and suddenly I was a published author. I started blogging, speaking for homeschool conferences and alternative schools, and making friends across the realm of self-directed education. Three more books on similar topics followed.

No one goes into education or writing for the money. Between the travel programs and book royalties, I earned enough to pay my way and save a bit each year—but only if I lived like a dirtbag.

“Dirtbag” is a term adopted by rock climbers, long-distance hikers, and others whose deep love for the outdoors leads them to take creative and extreme actions to minimize their cost of living and maximize their free time. Maybe you’ve met a dirtbag climber living out of their van or truck, given a ride to a scruffy thru-hiker along the Pacific Crest Trail or Appalachian Trail, or met someone who’s traveled around the world or lived on their bicycle for years on end. These are all dirtbags, and once I got to know a few, I realized that we’re cut from the same cloth. I’m not a hardcore climber, badass thru-hiker, or hobo hippy—but I am willing to live differently in order to avoid full-time servitude.

In my early 30s, after briefly considering the house/wife/kids trajectory, I resolved instead to double down on adventure: to have no fixed address, to migrate between the people and places I love most, and to continue reading, writing, exploring, nurturing relationships, moving my body, and working with young people in unique ways. I spent little on rent, never owned furniture, learned to cook inexpensive meals with universal ingredients, said “no” to many forms of entertainment, and said “yes” to shared housing, frequent transitions, and a minimal safety net. In 2020, I started writing about this way of living: a project that evolved into my next book, Dirtbag Rich.

In recent years I’ve dedicated my dirtbag riches to:

• Fusion dance: a form of partner dance I mostly do in Europe, adorned with Argentine tango, contact improv, urban kizomba, contemporary, clowning, and whatever other dances I’ve encountered over the years.

• Bicycle touring: very long bike rides, with or without camping gear, to visit old friends, make new friends, and experience the world at 10 miles per hour.

• Epic hikes and runs: around Lake Tahoe and the Bay Area, to the Tahoe Crest, across New Zealand, and through the High Sierra.

• Writing more vulnerably and provocatively: about my doubts regarding adventure, how I’ve made money, my conflicted thoughts about having kids, what matters in a romantic partner, worries for the far future, loving a mountain range, the beauty of trail running, and redistributing your privilege.

Now you know something about me!

Walking a Camino is like doing a long string of pleasant day hikes, each ending with a warm meal, cold drink, and real bed—without breaking the bank.

When people talk about the Camino, they’re usually referring to the Camino Francés. But there are many Caminos through Spain (and neighboring Portugal and France), all of which end in the city of Santiago de Compostela.

Just seven Caminos are popularly traveled, but all share these features:

• frequent accommodation: no need for camping

• affordable accommodation: €10-€50/night, depending on whether you’re staying in a public albergue (hiker dorm) or a private pension (basic hotel)

• frequent restaurants, cafes, grocery stores, and drinking water: the most you’ll need to carry is a sack lunch, some snacks, and 1-2 liters of water

• safe walking away from busy roads: it’s mostly pleasant rural roads, gravel roads, and nature paths, while never straying too far from a bus route or ambulance access point

• an endless string of charming towns with deep history: cobblestone and cathedrals and countryside, oh my!

• good signage: a small army of yellow arrows make it hard to get lost

Caminos, like all long walks, are excellent opportunities for reflection. What began as Christian pilgrimage routes now serve as secular or quasi-spiritual “active vacations” for soul-seekers from around the world.

The community is a big draw, too. Like the spontaneous “tramilies” (trail families) of the Pacific Crest and Appalachian Trails, clusters of like-minded and similarly-paced walkers form on the Caminos, resulting in shared meals, deep discussions, emotional support, and the occasional lifelong friend.

In 2017, I spent three weeks walking the Camino del Norte and Camino Primitivo. In 2022, I cycled the Camino Portugués and Camino Francés (occasionally in a shark costume). And in January 2026, I’ll walk the Camino-style Fisherman’s Trail in Portugal, perhaps followed by a lesser-known Camino through southern Spain.

Clearly, I’m a fan. And I can’t help but wonder: Do we have Caminos in North America? Can we have them?

The United States and Canada have incredible networks of long-distance wilderness paths, but they all require camping. Not everyone can camp, and some prefer not to. Camino-style routes bring together people of more ages, abilities, and incomes. The combination of low pack weight and frequent amenities makes multiple styles of travel possible. On a Camino, for example, I have the option to take my laptop. I can even have some nice town clothes—and gosh, regular showers—while still hiking every day! Crazytown.

The question of American Caminos feels especially pertinent because I’m getting kicked out of Europe in April 2026 (when my 2-year residency permit expires), and I already feel ruined by Europe’s endless array of accessible long-distance walking and cycling opportunities.

I need something to aspire to. Come on, America—whattaya got?

As long as North Americans have walked the Camino de Santiago, they’ve wondered whether something similar can exist back home. So I started with an online deep-dive to see what routes others have considered (or created), and then I presented my findings to three illustrious adventurers who have thought and written extensively on this topic (and each walked a hell of a lot more than me):

• Tim Mathis: author of The Camino for the Rest of Us, The Dirtbag’s Guide to Life, and a forthcoming book about American pilgrimage routes.

• Dave Whitson: author of Pilgrimage, multiple Camino guidebooks, and a forthcoming book about his walk across America.

• David Six: Triple Crown section hiker, currently walking across Oregon.

With their feedback, I began outlining the contours of the elusive American Camino.

But first, some disclaimers. There are a few good and obvious reasons that American Caminos are harder to find (or create) than those in Europe:

1. In America, the distances are bigger. Towns are spread out, population density is lower, and car culture dominates.

2. America lacks deep history. Specifically, we lack the tradition of churches and monasteries offering cheap accommodation to Christian pilgrims: the same institutions that evolved into modern-day hiker albergues charging €10/night.

3. America is expensive. The Spanish Caminos are only “affordable” from the perspective of a Canadian, German, or Australian coming from a country of relative affluence. When you hike in your own country, food and housing suddenly becomes pricier. We also have many fewer youth hostels (another tradition with roots in Europe).

4. Life on the road in America—and I’m talking more about the U.S. than Canada now—is just a bit harsher. Compared to Europe, you’re more likely to get hit by a car, assaulted in public, or accosted by someone struggling with drug addiction. We are a land of extreme diversity, which increases the potential risks for a long walk through public spaces.

With those facts in mind, here are a few routes that emerge as contenders for an American Camino.

Certain stretches of the Appalachian Trail (East Coast)

As David Six told me, when you hike on the Appalachian Trail between New Jersey and southern Vermont, you pass through towns once or twice a day, many with affordable, hiker-oriented accommodation. Route-finding on the Appalachian Trail is straightforward, and since the trail is incredibly popular in the summer months, finding community is easy.

But the Appalachian Trail is still fundamentally a wilderness trail, and you need to be ready for a surprise night out on the longer stretches (e.g., due to injury or poor conditions). The AT is also famous for its brutal elevation change. All this increases the gear, experience, and stamina requirements, thereby decreasing Camino-style accessibility.

The California Missions Trail (West Coast)

Unbeknownst to my California-bred self, the California Missions Trail (map) is a 800-mile walking & cycling route connecting the 21 Catholic Missions between San Diego and Sonoma. It’s very much under construction, and the distances seem better suited to cycling. But at least one Camino-inspired couple documented their full journey, two walking guidebooks are available, and more stories exist on the American Pilgrims on the Camino Facebook group.

The Missions Trail connects an interesting mish-mash of urban and rural California. I can only imagine the cost of paying for food and accommodation through these parts of America. (I hope you have $5k+ burning a hole in your pocket!) But this route is a fine contender for the dirtbag pilgrimage approach, which I discuss later.

The C&O Canal Towpath (East Coast)

As Dave Whitson, Tim Mathis, and many people online told me, the “C&O” is a dirt and stone path that runs 185 miles along an old canal between Washington, DC and Cumberland, Maryland. You can walk or bike it, there are plenty of amenities, and it seems virtually impossible to get lost. A bit short and seemingly repetitive for my taste, but it has history, and it’s popular enough to make friends along the way. (The trail continues to Pittsburgh on the Great Allegheny Passage, but that stretch seems better suited to cyclists.)

The Bay Area Ridge Trail (West Coast) & other urban thru-hikes

Back in 2023, I schemed and then actually did a 2-week, 250-mile hike around the San Francisco Bay Area. It was a hell of an adventure, ping-ponging between dense urbanity and surprisingly “out there” parks and preserves. I did camp a few nights, but more out of choice than necessity. There’s good signage, frequent food, and endless pricey accommodation (I mostly stayed with friends). And while I encountered plenty of other walkers, they were all day hikers.

In a similar vein, Liz “Snorkel” Thomas is developing and promoting “urban thru-hikes.” According to Outside magazine, Snorkel has hiked “60 miles through Chicago, 200 miles in Seattle, and 210 miles in Portland, Oregon . . . [and] 54 miles from Selma to Montgomery, Alabama, on the 50th anniversary of that historic civil rights march.” She also hiked 225 miles through New York City to visit 100 city parks. (Thanks for the lead, Tim!)

Whether you’re following an established route in/around/across a metropolitan area—or you’re making one up yourself—urban hiking offers a cool, Camino-style walking opportunity. Housing won’t necessarily be affordable, you’ll need to traverse some busy roads and ugly parts of town, and you won’t have any hiking partners except the ones you bring along—but you’re guaranteed an adventure.

Short religious pilgrimage walks

David Six brought my attention to the Easter Pilgrimage to Chimayó, a walk from Albuquerque to the Santuario de Chimayó near Santa Fe, New Mexico. Apparently, some people get really serious about this walk—for example, by dragging a large cross. There’s also The Way of Stella Maris in Nova Scotia, Canada, also around 70 miles and created in 2019 with the intention to mimic the Camino de Santiago. Both of these pilgrimage walks are highly organized, date specific, and quite short. It’s cool that they exist—and their brevity and actual religiosity turn me off. Give me something longer and more agnostic, please!

The Prince Edward Island Walk (Eastern Canada)

Another Camino-inspired Canadian creation, the Island Walk traverses 430 miles of non-technical terrain around Prince Edward Island. Certain stretches don’t have accommodation, so you need to get a ride or shuttle to your lodging (also true for The California Missions Trail). Beyond this fact (and the high cost of lodging), the Island Walk might be the best contender in North America. Bravo, Canada.

“We have a Camino in America, and it’s called bicycle touring.”

Apparently Tim Mathis and David Six have a longstanding debate on this topic. David firmly believes that bicycle touring is the most reasonable way to do something like a Camino in North America. Pedaling lets you cover more distance, find accommodation each night, and stay close to roads with amenities and emergency services. It’s not walking, but it’s the best our continent has to offer.

When I cycled a section of the Transamerica Trail in summer 2022, I liked the vibe. Lots of people of all ages were doing it. Cheap or free accommodation was frequently available for long-distance cyclists, including churches, fire stations, and community centers. In the empty stretches of Wyoming and eastern Oregon, camping gear is helpful but not mandatory.

I don’t want to give up on walking, but I’m inclined to believe David. And I’m inspired when I see someone envisioning the marriage of cycle touring and Camino principles (thanks Dave!).

The dirtbag pilgrim approach

Finally, inspired by two 19-year-old German cyclists I met (and interviewed) at a Couchsurfing host in the south of France, I propose that almost any long voyage can approach Camino status—if you’re willing to knock on doors.

When I met Lilli and Elena, they had already cycled across Germany, spending just €10/day on food, and sleeping with a mixture of campgrounds (cheap), Couchsurfing (free), and knocking on people’s doors and asking to camp in their yard (free). This final approach often won them a meal, a couch, or even a guest room.

Yes, yes—if you’re a pair of spunky, charming, and street-smart young women traveling through your (quite safe) home country, this approach might work. It’s not for most. But that’s where hospitality networks (like Couchsurfing and Warmshowers) come in: they’re the digital equivalent of knocking on someone’s door, with the important addition of a reference system for safety.

Using this “dirtbag pilgrim” approach, you could walk across many parts of America—including quite expensive areas, like Coastal California—and not break the bank. Nor must you constantly seek new hosts, as your previous hosts are likely to know (and refer you to) other folks along your route.

What’s most important for succeeding with this approach—beyond not looking and smelling like a complete dirtbag—is having a good, true, and compelling story to offer. Why are you walking this route? What is your purpose? What’s your situation? If you can say something like, “I’m a recent college graduate trying to reconnect with my Catholic upbringing by walking to all the California Missions, and here’s my blog/Instagram showing that I’m not an axe-murderer,” you’ll have an excellent chance of getting hosted, and probably fed, most nights of your trip. Peace Pilgrim took a similar approach for 28 years.

And this is the true spirit of pilgrimage, is it not? Many of the Spanish Caminos are now developed to the point of feeling like Disneyland, especially in final 100km to Santiago de Compostela. Knocking on doors, banking on the hospitality of strangers, entering people’s homes and friend networks: this is closer to what (I imagine) the O.G. pilgrims experienced. We all want a warm meal and comfortable place to sleep at night. The farther we walk, and the more risks we take, and the more connections we make along the way, the richer these things are. That’s why Caminos matter in the first place.

So, is there an American Camino?

Not really. Or… not yet.

But we do have compelling alternatives, most notably cycle touring. And if you’re willing to camp a little, knock on a few doors, and feel more “out there,” then a world of walking adventures awaits you.

See you on the road,
🏞️ Blake

I cannot stop traveling.

This was the past six months.

If Europe still had internal border controls, here are the passport stamps I would have racked up:

Switzerland - Spain - Portugal - Netherlands - UK - Ireland - UK - Austria - Greece - Turkey - France - Austria - Germany - Netherlands - Belgium - France - Italy - Switzerland - Austria.

Am I on a whirlwind tour? An adult gap year? A last hurrah?

Nope. This is normal.

Should this scare me?

Some of this time was work: six weeks voyaging across Greece and Turkey (with 13 teenagers in tow), plus a week and a half in Brussels (with 17 young adults).

Four weeks were spent in one place (Valencia), sharing a rental house with friends.

Of the remaining 14 weeks, I was in full-blown travel mode: living out of two carry-on sized bags, staying in one place for no more than a week, and criss-crossing the continent by train and touring bike.

I’ve got just two years to enjoy Europe as a legal resident: a big incentive to keep moving from one amazing dance weekend to the next, visiting friends (from dance / camps / couchsurfing) and the occasional family member along the way (like my mom and sister, who each came out to visit).

Staying with friends helps me afford this lifestyle. Beyond the month in Valencia (€575), I’ve hardly paid for housing in 2025.

The trains and flights and meals do add up; many are legitimate Unschool Adventures business expenses (which doesn’t make them free, just reduces my income tax).

But I can’t throw Europe under the bus. Because it’s not a phase.

Even back in the USA, I lived this way. Outside of a few half-year stints in South Lake Tahoe, California (my favorite mountain town), five months in New Zealand (because New Zealand), and a couple years in Asheville, North Carolina (for a long-term relationship), the map of my life has resembled the one above: bobbing, weaving, and bouncing across and between continents, an orgy of frenetic motion, a spitting image of digital nomadism—and one, big, fluttering, red flag, embroidered with the words: Why can’t this guy stop moving?

I’ve written before about the danger of becoming obsessed with travel, adventure, and wilderness.1 I believe I’m aware of the trade-offs I’m making in terms of maybe not having kids and sacrificing long-term security. Yet here I am, the cup already overflowing, still pouring wine into the goblet.

Why, why, why?

Maybe because short-term relationships are easier than long-term relationships. No time for bad habits to reveal themselves. No boredom or hard conversations. Just warm hellos, catch-ups, and goodbyes.

Maybe because travel represents courage, growth, and boldness. Because it symbolizes freedom, access, and privilege. Because it’s what so many people want more of, and I have so much of. Is this another form of status competition?

Maybe because I don’t like who I am when I’m stationary. A normal person without sexy stories. Someone who must witness the uglier, harder and more banal sides of life, who must confront the profound sameness, illness, and sadness of the world.

Maybe because it gives me purpose. Every animal species has its scouts and explorers. Even unicellular bacteria must migrate to survive. To travel is to have a goal, and I was indoctrinated early into goal-setting.

Maybe because I cannot stand to see the same thing every day. Unless it is a beautiful mountain range. But even then—even in the Lake Tahoes and New Zealands and Alps of the world—I eventually become saturated. To love something, I must long for it. It must feel out of reach. (“You liked me a lot more when I wasn’t available,” an ex-girlfriend once told me.) Immerse, retreat, long, repeat.

Now I’m slowing down a bit. I’m renting a furnished 1-bedroom apartment for the rest of the year. I’ll be cooking in the same kitchen, sleeping in the same bed, swimming in the same pool, hosting some of the same people who hosted me, and deepening my relationship to a single European city and country.

A certain degree of rootedness is necessary for mental health.

I’ll still travel, just not as frequently. There are still mountains to be climbed, dances to be danced, and friends to be visited. But I’ll be “home” more than away, and therefore living a bit more “normally” for the rest of 2025.

And it will not last.

Because I’m not settling down, just catching my breath.

Because I don’t think I want, need, or deserve a house of my own.

Because I may be fated to travel until death, disability, or disaster do me in.

Because my name is Blake, and I have a problem.

For organizing and co-leading this 10-day program, I earned about $1000/day.1

If I ran ten similar programs each year, I’d take home $100,000.

Instead, I run programs infrequently—a couple a year—and earn $30-40k.

Mostly, I choose to pay myself in time rather than money. Time for reading, writing, running, dancing, cycling, traveling, and visiting friends and family. Time to live a low-stress, high-connection, high-adventure life.

My next book, Dirtbag Rich, offers a deep dive into this approach. I tackle issues of accessibility and privilege, family and relationships, thrift and consumerism, purpose and comparison, housing and healthcare, entrepreneurship and retirement.

But today, reflecting on the miraculous fact that I can earn $1000/day teaching stuff I care about to young people who care to learn it, I’m cataloging all the ways I’ve earned money since finishing college at age 22.

Why? Because it’s been a long road which I’ve never properly documented. And because I wish more people talked openly about money. (I would have loved reading a post like this when searching for entrepreneurial role models in my twenties.)

Many parts of this timeline overlap. I became genuinely self-employed at age 28. I’m now 42.

Age 22: Outdoor educator & summer camp counselor ($10/hour plus room & board)

Age 23-24: Summer camp assistant director ($10/hour plus room & board)

Age 25: Ski resort market researcher ($10/hour, i.e. snowboarding 5 days a week to interview people on chairlifts for a whole winter, the closest thing I had to a “real job”)

Age 25: Summer camp cook & deputy director ($15/hour plus room & board)

Age 26: First (and only) book deal for College Without High School (CAD$5000 advance, no royalties for a dozen years, then a few hundred dollars a year)

Age 26: First 6-week Unschool Adventures trip to Argentina ($100/day—which is less than $10/hour—plus room & board)

Age 26: First of many speaking gigs at homeschool conferences (a room + few hundred dollars, which mostly covered travel costs)

Age 26: Outdoor education medic ($15/hour for one season; my final W2 income)

Age 27-29: More Unschool Adventures trips with larger groups and better budgeting (~10 weeks each year, $200-300/day)

Age 29: Crowdfunded & self-published my second book (~$3000 one-time earning, plus ongoing monthly royalties ~$200-500)

Age 30+: Occasional private coaching for teens and parents ($100-$150/hour, 5-10 times a year)

Age 30-37: More Unschool Adventures trips, slightly higher priced, with excellent budgeting and ideal group sizes ($400-700/day, ~10 weeks each year; prime saving years)

Age 31 & 37: Crowdfunded & self-published third and fourth books (each netting a few thousand dollars and increasing monthly royalties to ~$400-1000)

Age 35: Created a self-paced online course, “Launchpad” (one-time earning of a few thousand dollars, plus a few hundred each month for a couple years)

Age 36: One-time family inheritance (~$6000)

Age 37: Ran a 1-week online course, “Emailing Strangers” ($800)

Age 38-39: No Unschool Adventures trips due to pandemic; received ~$30k total support from the US government (i.e., half of what I might have earned).

Age 38: Ran a bigger, longer online course, “Self-Directed Learning 101” (12 weeks, ~$25k)

Age 40-42: The modern era of Unschool Adventures ($700-1000/day, ~6 weeks/year)

Age 41: TikTok influencer bro spontaneously promoted one of my books; sales skyrocket ($2000-3000 royalties each month for 4 months)

In summary, how I’ve made money (best guesstimate):

1. Running Unschool Adventures trips (60%)

2. Book sales—34k total sold, largely self-published (15%)

3. Online courses, speaking, coaching (10%)

4. Summer camp & outdoor education (10%)

5. One-time government/family support (5%)