After 20 years of working with teenage unschoolers, I’ve reached a shocking conclusion:
UNSCHOOLERS
ARE
DIRTBAGS
(respectfully)
The same goes for many unschooling parents, too.
Grown unschoolers, too.
Dirtbags, the whole lot of them!
"I Beg Your Pardon, Good Sir"
Don't worry, I like unschoolers. That's why I keep working with them.
And even though I went to conventional public schools, I consider myself an honorary unschooler -- because I'm also a dirtbag.
Remember how the dictionary definition of "unschooled" doesn't line up with reality?
unschooled (adjective): not educated or trained
The same goes for the dictionary definition of "dirtbag":
dirtbag (noun): a dirty, unkempt, or contemptible person
"Dirtbag," much like "unschooled," is a derogatory term that's been slowly reclaimed since the 1960s -- a term of resistance to an oppressive institution.
For unschoolers, the institution is school. For dirtbags, it's work.
A Brief History of Dirtbagging
The first dirtbags were hardcore rock climbers in Yosemite Valley 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.
YOSEMITE VALLEY: ORIGINAL DIRTBAG HABITAT
________
.-' _ _ '-.
.' _( )_( ) '.
/ / . . \ \
; \ ^ / ;
| .---'-----'---. |
; / CAMP NOW \ ;
\ | "work later" | /
'._\____________/_.'
inventory:
- 1 dented mug
- 2 bruised shins
- 6 granola crumbs
- 1 deep sense of purpose
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, sailors, slackliners, or perpetual travelers.
And even though most dirtbags are obsessed with spending time in nature (hence the dirt), many artists, musicians, writers, and entrepreneurs are honorary dirtbags -- because they, too, are pursuing a high-freedom, low-income, and high-purpose life, off the beaten path.
Some hardcore 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.
All dirtbags are passionate. All are extreme. 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. None are what the mainstream would describe as "balanced."
π§ Sidequest: pick a dirtbag subclass
Choose one (or three; nobody checks): [ ] The Granite Goblin (climber) [ ] The Asphalt Nomad (bike-tourer) [ ] The Moss-Witch (trail runner / forest creature) [ ] The Van Alchemist (turns parking lots into home) [ ] The Ocean Wanderer (sailor / surfer / salt-based lifeform) [ ] The Night Campfire Bard (artist / musician / writer) [ ] The Social Dirtbag (dance-floor creature; high in hugs) core stats: creativity + resourcefulness + anti-status immunity + a suspicious relationship with laundry
Dirtbagging : Work :: Unschooling : School
Unschoolers are those who don't fit into the institution of school. They prefer to blaze their own trails, learn and grow on their own terms, and prioritize passion, curiosity, and mental health over conventional definitions of "success."
Dirtbags are those who don't fit into the institution of work. They prefer to blaze their own trails, learn and grow on their own terms, and prioritize passion, curiosity, and mental health over conventional definitions of "success."
It's not a perfect analogy, because dirtbags are adults who pay their own way, while unschoolers are typically young people supported by their parents. But just like unschoolers (of all ages), dirtbags are creative geniuses at avoiding the laundry list of so-called "non-negotiables" that society demands of them.
JOHN MAYNARD KEYNES
"Economic Possibilities for our Grandchildren" (1930)
predicting the future with confidence
_____________
/ \
| we'll only |
| work 15 hours |
| per week |
\_____ _______/
\/
.-""-.
/ _ _\
| (o)(o)|
| __ |
| (__) |
\ -- /
___/|____|\___
/ | | \
/_____|____|_____\
/ || \
/ || \
||
___||___
/ || \
/ || \
||
(it can be true -- if you live like a dirtbag)
Dirtbags cover their costs with as little work as possible: often 15 hours/week or less (averaged over the entire year). Some work seasonally and intensely. Others develop niche skills that translate into high hourly wages. Others have fairly normal jobs (like nurses and school employees) with abnormal contracts, allowing them to take large chunks of time off as needed.
They're thrifty, resistant to "keeping up with the Joneses," and crafty about navigating the costs of healthcare, childcare, college tuition, and eldercare -- often through low-cost alternatives, relocation, or selectively harnessing government subsidies.
No, not everyone can be (or wants to be) a dirtbag. Just like not everyone can be (or wants to be) an unschooler. But that's not the point.
The point is that some of us simply don't fit into "the system." We can either complain about it, or we can do something about it. Unschoolers and dirtbags are both trying to do something radically different -- and that unites us.
You Really Don't Have To
At age 20, I had an "a-ha" moment.
I was in college, studying physics and astronomy, thinking about becoming a high school science teacher, when I stumbled upon a few books by teachers who had quit the profession out of frustration with the US education system. Like intellectual cocaine, the words in these books electrified me.
One of them, written by a New York City middle-school teacher who earned Teacher of the Year three times before quitting, captivated me so completely that I dropped everything and spent three days poring over it.
Within a few months, I decided to abandon the traditional teaching path and petitioned my university to let me create my own program of study: one that would let me study radical alternative schools, self-directed learning, and something called "unschooling."
I convinced two professors to sponsor my plan, and the administration approved. I graduated with an obscurely titled bachelor's degree that commanded little value in the marketplace, but that didn't bother me. My mind was on fire.
The lesson I took from my deep dive into alternative education was this:
YOU DON'T HAVE TO.
You don't have to go to school to become educated. You don't have to get a fancy degree (or possibly any degree) to find good work. You don't have to play by all the rules that feel so clear, compelling, and non-negotiable as a child.
You can opt out of a very large, seemingly essential system, and your life will be fine -- and possibly much, much better.
_________________________
/ \
/ I really don't have to? \
/_____________________________\
\ ^__^
\ (oo)\_______
(__)\ )\/\
||----w |
|| ||
Prior to college, I had been a winner at the game of school. I graduated near the top of my class and was admitted to a well-regarded public university. But in truth I never quite fit the mold.
Middle school and high school always felt like some sort of weird social experiment, holding chamber, or jail sentence, replete with tall fences, warring gangs, and campus police. What were we doing here? Why was the school day structured like this? Why did we have to learn this and not that? Why did students treat each other so badly, and when they did, why did most adults look the other way? There were no answers.
So when I started working with teenagers who opted out of the school system, we connected. In almost any other setting, most of these young people would have been labeled ADHD, socially anxious, neurodivergent, or oppositional-defiant. I found them hilarious, creative, authentic, and gloriously weird.
We connected because none of us felt like we belonged in that great homogenizer called school. We connected because we questioned the value of a major institution that most others embraced. And we connected because we knew that the monolithic commandment of childhood -- YOU MUST GO TO SCHOOL -- was actually a fiction.
If this was the case, then what other "musts" might be fictions?
π The Hydra of Musts
__ __ __
/ \/ \/ \
| MUST MUST |
| MUST MUST |
\__/\__/\__/
||
||
_||_
/____\
Must we start college at age 18?
Must we earn more than our parents or "keep up" with friends?
Must we own homes?
Must we spend our lives inside a climate-controlled room,
sitting in a chair, staring at a glowing screen?
Must gender dictate our social roles?
Must we get married, have kids, be religious, not be religious,
"use our education," maintain an online presence, or stay in one place?
As I entered my twenties and questioned ever-more "musts," I sensed my universe expanding.
I hailed from a fundamentally conventional background. My Californian parents, each middle-class transplants from New England, were open-minded but not deeply norm-questioning. My dad read the Wall Street Journal and took pride in the successful food-processing business he had built. My mom had me at 22, my brother at 24, a divorce from my dad at 26, and returned to college to begin a career in human resources.
My suburban upbringing was filled with computers, skateboards, video games, shopping malls, and Magic: the Gathering cards. No one in my young life nudged me down a radical path. Left to my default settings, I probably would have become a tech geek living in the San Francisco Bay Area who hiked on the weekends.
take the side trail
|
|
v
it changes your whole map
Instead, here I am on this strange and wonderful path: working an average of 15 hours a week for almost two decades, with friends around the world, adventures under my belt, money in the bank, and a spirit that remains fully alive.
I'm here to tell you, as a few ex-teachers once told me, that you don't have to play the same game as everyone else. You can throw your own party. You can have a life where you wake up and decide what you want to do, every day. You really can.
Are You Dirtbag-Curious?
If you might be a dirtbag -- or you're feeling dirtbag-curious -- then I encourage you to find a copy of my new book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose. (This article includes excerpts from the book.)
Dirtbag Rich shares the stories of dozens of people I interviewed (all free to browse) from across the dirtbag spectrum, including parents, homeowners, nomads, younger people, older people, super outdoorsy people, and less outdoorsy people.
Unlike my previous books, Dirtbag Rich is not specifically about unschooling or self-directed learning. But at the same time, that's exactly what it's about.
UNSCHOOLERS β DIRTBAGS (same spirit) (different institution) (shared refusal)
Because unschoolers are dirtbags, and dirtbags are unschoolers.
- We're both trying to escape oppressive institutions.
- We're both optimizing for mental health, autonomy, and fun.
- We're both trying hard not to worry about what others think about us.
- And we're both focusing on the little voice that says: "this is clearly what's right for me -- I just need enough courage, creativity, and resourcefulness to make it happen."
Maybe, one day, we might even see new definitions in the dictionary:
unschooled (adjective): educated through consent-based, self-directed learning
dirtbag (noun): a passionate, creative, and resourceful person who refuses normal work
Wouldn't that be an amazing world? π
π Parting Thought
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* . . .
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/\ /\ /\
/ \ / \ / \
/ \ / \ / \
/ \ / \ / \
/ /\ \/ /\ \/ /\ \ .-.
/ / \ / \ / \ \ (π₯π₯)
/__/____\______/____\____/____\__\ `-'
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~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~
~~~~~~~~~ ~~~~~~~ ~~~~~~~~ ~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~
~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
. . . . . .
. * . * . *
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* . . *
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. . . . . . .
the path exists -- just not on official maps



