How I've Made Money
without a normal job, for 20 years
I just finished running another young adult program: this one focused on learning the skills and attitudes necessary for long-term, independent world travel.
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):
Running Unschool Adventures trips (60%)
Book sales—34k total sold, largely self-published (15%)
Online courses, speaking, coaching (10%)
Summer camp & outdoor education (10%)
One-time government/family support (5%)
Beware entrepreneurial success stories! Clean numbers (like $1000/day) don’t reflect the messy reality of budgeting, liability, and unknowable external variables. Nor does it reflect the years of lowly paid (or unpaid, or costly) investment that someone puts into a business before it’s profitable.
Here’s a list of every program I’ve run, in case you’re interested.
awesome piece. i did a similar exercise with my income inspired by IRS report that shows your income for your life from their perspective. to write it from your perspective tells a fascinating version of your life. i found it interesting to try to calculate how many hours i worked per year. a parallel writing exercise was to map out all the places you have traveled and lived.
as an entrepreneur for the last 25+ years it is hard to explain the work that goes into conceptualizing, founding and runnnig a business to a person who has only worked for others. especially when you have a business built on your reputation as an educator and thought leader for decades like yours. it is easy to get caught up in the end result of $1,000/day or huge net worth or passive income without understanding the investment to get there. there are many incredible books on the topic but in my experience a small percent of people are cut out for staying the course for something to mature into full form.
if people form good money habits and keep their "day job" until business has stability it is possible.
keep inspiring and giving examples of what is possible. it is one of the highest forms of education.
This is a refreshing breakdown on a topic that’s usually saturated by extreme success stories (ie how I started a business and scaled to a million dollars in 3 months using AI). I’m so sick of those kinds of posts and videos. Thanks for showing a more humble approach.