Living Safely is Dangerous and Deadly

on European dreaming, turning 40, and killing your darlings

What’s a 40-year-old, childless man to do? Particularly one with an undying lust for adventure, a commitment to educational freedom, and some money in the bank?

Since finishing my teen program in Patagonia, I’ve been thinking hard about where to focus my efforts in 2024. Notebook scribblings include:

• Biking around Europe, giving workshops to groups of teens and/or college students, and interviewing them for a new podcast.

• Choosing one place in Europe, staying there for 6-9 months (visa gods allowing), and working deeply with one specific school or community.

• Traveling around Europe to discuss self-directed learning, getting a clearer picture of why Europeans are less receptive to such ideas, and writing about it. Also: bringing together disconnected members of the self-directed education community and creating new homestay opportunities for US teens.

• Purposefully making no plan for 2024, taking on no new commitments, remaining totally receptive to new opportunities, and committing to write about whatever happens. And maybe still biking around Europe.

You get the idea: Europe, biking, writing, education.

Why Europe? Simply put, I’m in love with it—and that love must be obeyed.

More specifically: I have friends scattered across the continent, the dance scene is thriving, housing and food are affordable, cycling routes are everywhere, public transport is ubiquitous, and the cultural/linguistic diversity still charms me.

And… because it’s hard.

Legally, it’s hard to stay in Europe. Americans are entitled to 90 days of visa-free travel in any 180-day period. Translation: you can come for 3 months, but then you must leave for 3 months. Or come for a month, leave for a month, repeat. The only way to circumvent this restriction is by accepting full-time employment (😅), getting married (😅😅), or applying for a short-term visa as a job-seeker, freelancer, or language student (👌).

These restrictions are frustrating, but they’re also motivating. When time is precious, you’re unlikely to take it for granted. A hard time boundary can make anything feel like an adventure.

For self-directed learners, it’s hard to exist in Europe. Or straight-up illegal, if you live in one of the many countries that outlaws homeschooling or regulates it to death. While Europe has many private alternative schools, few offer truly high levels of autonomy. Scattered communities of unschoolers do exist, but many are underground. And while I’ve observed delightful amounts of “free range kid” culture in Europe, the continent as a whole remains woefully committed to compulsory schooling.

I find this disappointing, but again, motivating. What would it take to stoke the fires of self-directed education in Europe? What might be possible with determined effort? For a Yankee on a bike to make a dent would require learning new cultures, laws, and languages. Hard? Yes. Riddled with obstacles? Yes. Impossible? No.

The writer Brian Doyle once asked a monk why he signed up for a life of lonely commitment to an ideal that may never be realized. To which the monk replied, “because it’s hard.”

Because I am not sure I can do it at all, he said, let alone do it well, and do it for years and years, perhaps for my whole life . . . I want to be a monk because I think that would be a very good use of me, he continued. Does that sound strange? It sounds a bit arrogant, I suppose. I don't mean to be arrogant. I want to be an implement. Something like a shovel with a beard. If I live with humility and intent, if I do what I do well and gracefully, that is good. Beyond that I cannot go.

This resonates. Why live on a bike? Why not reside in the country where I hold a passport? Why always create new Unschool Adventures programs instead of repeating the successful ones? Why not accept middle-age and settle down? Why keep trying to live this kind of life?

Because I am not sure that I can do it at all, let alone do it well.

Because I think it may be a very good use of me.

Does that sound strange?

In September I turned 40. I have no conscious baggage around that milestone. Rather, I feel empowered in a way that my Couchsurfing host in Charleston, Shawnda, once predicted: “You start accepting big parts of who you are, and you stop apologizing for them.”

I also feel a deep sense of financial ease, as my net worth is now 10x my annual spending rate. I don’t spend much, so don’t let your imagination run wild. But it is a very long runway. Without debt, dependents, a house, or even a car to worry about, now feels like the right time to take interesting risks instead of playing it safe.

One such risk I’ll soon be taking: sharing some new writing that’s more personal, vulnerable, and uncensored. (Expect a Kickstarter announcement soon.)

Another risk: letting go of my long-running education podcast and monthly email newsletter. Both have served as wonderful tools for creative expression and entrepreneurial survival since 2015, and both garner heartwarming feedback. (Last year, one mom told me that my podcast saved her family’s life!) But when I’m out of inspiration, I’m out of inspiration. Both the podcast and newsletter feel like artifacts of a previous existence, ones I must jettison to make space for the new.

Is this stupid? Shouldn’t I keep running a popular podcast and newsletter to remain in the good graces of the tech algorithms and maintain online followers? Why risk losing these audiences? Why not play it safe?

I recently finished a few books about Nietzsche. He was a complicated man with a complicated philosophy, yet there’s a reason we still remember his name—because he said things like this: “Living safely is dangerous. Dangerous and deadly.”¹

I don’t interpret Nietzsche’s advice as adolescent regression or wanton recklessness. Rather, it’s about the siren call of comfort, safety, and predictability, and the threat that such forces pose to the human spirit.

William Deresiewicz, the incisive critic of American culture, recently asked why the arts feel so boring. His answer was vaguely Nietzschean:

All the weirdness that we’re missing now, the wild originality, can only come from the activity of singular spirits: contemptuous of imitation, courageous in the extreme, obedient to nothing but the effort to achieve their vision.

I don’t consider myself an artist; I am a writer, explorer, and entrepreneur. Deresiewicz speaks to me nonetheless when he describes the importance of the “freedom to take chances: to be irresponsible, dangerous, difficult, strange.”

This doesn’t mean chucking it all, but it does mean chucking rutted routines and whatever anchors may be dragging the seabed. It also means prioritizing whichever forces conspire to produce your best work.

For the past year, this Substack has effectively served as a container for my most thoughtful, long-form writing: the kind I’ll value for a very long time. The monthly email newsletters, in comparison, are flashes in the pan. More podcasting may be in the future, but the current show no longer passes the Hell yeah! or no test, hence the need for Darwinian housekeeping.

So, bring on the 40s! With all their strangeness and difficulty! I’m clearing the decks for the next adventure. Whatever happens, I’ll write about it.

This is all to say: Welcome to The Adventures of Blake. I’ve given this publication a new name, and I’m doubling down by shuttering my monthly newsletter and inviting those subscribers to join us here on Substack. I even paid the $50 necessary to park blakeboles.substack.com on a new domain: letters.blakeboles.com. (“Letters” is a good word for what’s happening here, after all.)

I’ll keep writing my stories and analyzing the modern obsession with adventure, if you’ll keep reading. I promise that I won’t charge a dime for membership (though I happily accept coffee). Your comments are always welcome, publicly or via email. And if you know someone I should meet—whether a potential collaborator, co-conspirator, or European friend with a spare room for a cycle tourist—please connect us.

-Blake

There is a legitimate reason for this image, but I’m not telling you what it is.

Where to find me next: Eugene (late May), SF Bay Area (June), Tahoe/Portland (July), NBTSC (Aug), Berlin (Oct), Patagonia (Dec/Jan).

1. This line is adapted from Irvin Yalom’s novel, When Nietzsche Wept. For a direct quote related to this idea, see Nietzsche’s The Gay Science:

“For believe me! — the secret for harvesting from existence the greatest fruitfulness and the greatest enjoyment is: to live dangerously! Build your cities on the slopes of Vesuvius! Send your ships into uncharted seas! Live at war with your peers and yourselves! Be robbers and conquerors as long as you cannot be rulers and possessors, you seekers of knowledge! Soon the age will be past when you could be content to live hidden in forests like shy deer! At long last the search for knowledge will reach out for its due: — it will want to rule and possess, and you with it!”

(Another Nietzschean nugget, here.)