Selling Books Isn't About Making Money

how I'm thinking about self-publishing in 2026

Selling books isn’t about making money—it’s about opening doors, intellectual clarity, changing the world, and adventure.

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.”

Holding the first copy while holed up in my friend’s yurt in Western Colorado, March 2020

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.

Kevin Kelly’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 (Paul Millerd).

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 Brendan Leonard 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.▪️