Jack's Camp Friends Newsletter |
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First off → Campminder is how we’re running camp this summer. Background checks, reference checks, getting everyone in the system before summer starts. And sending logistics emails to make sure everything is humming. Check out Campminder and tell them Jack sent ya.
Second off → This is a newsletter for summer camp pros. But every once in a while, someone comes along who thinks like summer camp, but doesn’t work at summer camp.
Blake Boles is one of those guys.
He’s created a life (and job) taking summer camp ideals (namely: the things that make camp awesome) and pushing them out into the “real world”.
Blake’s written all about it in his blog and his new book Dirtbag Rich: High Freedom, Low Income, Deep Purpose.
And now, he’s writing about it here as well. For anyone in the camp game, this is a must-read.
Blake, take it away.
Hey everyone, it’s Blake. I’m the guy who wrote Dirtbag Rich, which Jack calls the “single best book for camp counselors to read when thinking about their career.”
Did Jack say this because he and I rode across Spain in shark costumes in 2022 and hiked through Portugal together in January—and I’ve accumulated an insane amount of material with which to blackmail him, unless he says really nice things about my book?
Yes and no. Mostly no.
Jack and I think very similarly about life. We struggle to find a single topic on which we deeply disagree. (We did find one: advertising. I’ll let you guess which one of us is the corporate shill… and also more financially successful.)
What Jack and I both decided in our mid-twenties was this: Working at summer camp is awesome, normal jobs are mostly terrible, and if “growing up” means sacrificing the playful, energetic, pro-social spirit of summer camp—then we want none of it.
The thing is, you can’t be (and probably shouldn’t be) a camp counselor forever. Admin positions are limited. Buying a camp is an amazing dream, and also an extremely challenging one. (Jack, do you know anything about this?)
So what do you do if you:
- love camp
- love working with kids
- love the outdoors
- …and also want to move forward in life?
That’s what I was asking myself at age 25, after I’d risen through the (very few) ranks of a wilderness camp in California and started working at another camp for homeschooled teenagers in Oregon.
Outside of summer, my life was a mess. I could easily land jobs in outdoor education, but I would flee as soon as the season ended (and sometimes earlier). I tried taking more “normal jobs” in education, outdoor recreation, and food service—and I fled those, too.
Why did I flee? Because I was ruined by camp.
Camp jobs were the only jobs I reliably held, because the model worked so well for my brain, body, and spirit:
- Work really freaking hard alongside people you like—for just 9 weeks, after which you’re free as a bird
- Feel like you’re making a real difference in the lives of young people
- Save virtually all the money you earn
- Along the way: get fit, get a tan, make amazing friends, and walk away with more emotionally resonant memories than you might create in an entire year of “normal life”
HOW CAN REGULAR JOBS COMPETE WITH THIS??
If you’re like Jack and me, then… they can’t.
You’ve got to go all-in.
But this doesn’t necessarily mean staying in the camp world.
It means discovering (or creating) an economic livelihood that shares the same positive features of working at camp—while putting you in the driver’s seat.
There are many ways to do this. In Dirtbag Rich, I profile dozens of people in their 20s and 30s who have found their own magical balance of time, money, and purpose: writers, guides, sailors, artists, nurses, teachers, speakers, consultants, photographers, programmers, and event organizers.
Jack’s in the book, too. I mention how he used his engineering background to become a part-time communications facilitator for manufacturing executives: a position that gave him the time to scheme his next big move in the camp world.
(And if you haven’t heard our full interview, listen in: it includes super actionable advice for soul-searching, early-20-something counselors.)
As for me, I ended up merging my summer camp experience with my passions for world travel and alternative education, resulting in a travel company called Unschool Adventures. Since 2008, I’ve taken groups of teenagers on 4- to 8-week-long adventure programs and learning retreats: my own little, quirky, camp-style experiences for quirky, delightful teens who aren’t restricted by the academic calendar. (The first trip: six weeks in Argentina to learn Spanish, tango, and the art of independent travel.)
Running Unschool Adventures has let me:
- Work really freaking hard alongside people I adore—for limited periods of time, after which I’m genuinely free
- Feel like I’m making a difference in the lives of young people who don’t go to school
- Save virtually all the money I earn (at a higher rate, since I’m the owner) while also paying my co-leaders fairly and keeping program fees reasonable
- Create emotionally resonant memories on a regular basis
- Remain sufficiently “time wealthy” to pursue my own adventures, travels, writing, and most recently, learning to partner dance. (I literally type these words from a castle in the UK, amidst a 5-day dance camp for adults. For the record, I am 43 years old.)
Remember, Jack and I demonstrate just two ways to become “dirtbag rich.” There are so many more.
Does becoming dirtbag rich require thinking entrepreneurially, whether or not you’re self-employed? Absolutely. Does it require a taste for risk and an appetite for uncertainty? Yes and yes. No one said this path is easy.
But if you’re following the “AI will eat our jobs” discussion, you already know that thinking far outside the box—not just waiting for “the right job” to appear—is a virtual prerequisite for economic survival.
If you run a summer camp, you’re relatively immune to the threat of technological displacement. AI agents aren’t going to teach a group to play Gaga or gracefully resolve a conflict between feuding 12-year-olds anytime soon.
But the young adults and 20-somethings who work for you—the ones who won’t be counselors or program directors forever—face some very serious challenges. Like brewing thunderclouds threatening to cancel swim period, their own quarter-life crises loom on the horizon.
These passionate, energetic young people are seeking guidance, just like I was at their age. But once you’ve been ruined by working at camp, it’s hard to take most career advice seriously—because most people just don’t “get it.”
Well, I believe I get it. Because I’ve lived it. And that’s why Jack calls Dirtbag Rich the “single best book for camp counselors to read when thinking about their career.”
Thanks for reading my little guest post. Dirtbag Rich came out on Saturday, and I’m super proud of it. If you’d like to grab some copiies for your staff, I’d be honored—and I’ll happily offer a bulk discount if you write me with the special code “JackLovesAdvertising”.
❤️Blake