Ten Things I'm Glad I Did in my 20s
in search of freedom, purpose, and adventure
Run away from a life that isn’t working
Indulge my obsessions
Learn to work incredibly hard
Build skills, then start my own thing
Earn more but keep spending like I’m 22
Don’t let friendships die
Exploit my body
Become a better communicator
Dance in partnership
Read, write, repeat
1) Run away from a life that isn’t working
At 24, I was a mess. I quit almost everything I started. Whenever I accepted a new job, I looked down the road and saw a life of repetitive servitude. A wave of panic overtook me and I fled, often without giving notice.
The “right thing” to do was swallow my discomfort, grow up, and commit to a single job, place, and person. Instead, I ran away to South America.
For three months I hugged the spine of the Andes, traveling slowly southward on the gringo trail from Ecuador to Argentina. Forehead pressed to the window of long-distance buses, the fog in my brain cleared, and I started to see a different, less conventional path: one that would help me escape my samsara, begin committing whole-heartedly, and move forward in life.
Sometimes, in the choice between fight and flight, flight is right.
2) Indulge my obsessions
As a teenager, I was obsessed with snowboarding. I dreamed of living in mountain towns, riding every day, and becoming an instructor. Backpacking was another obsession: I salivated over the Pacific Crest Trail, getting lost in the Himalaya, and summiting every nameless, jagged peak I encountered in the Great American West.
In your twenties, it’s time to put away childish things. Hobbies should take a backseat to work. Save your obsessions for the weekend, vacation, or retirement. This advice works for many; it did not work for me. I had serious itches that needed serious scratching. To move forward, I needed to put the spine-tingling feeling of being alive on the tip-top of my to-do list. So I lived in mountain towns, taught snowboarding, hiked on the Pacific Crest Trail, and parked my car along obscure roads to climb nameless peaks.
Some of these experiences were amazing. Others disappointed. Soon enough, I didn’t lust over powder days or thru-hikes. I was content to move on. To temper my obsessions, I needed to indulge them. Denying or deferring them would have only made the itching worse. The best way out was through.
3) Learn to work incredibly hard
The one job I never quit was also the hardest job I ever held.
At age 20, I returned to work at the wilderness summer camp I attended as a child. Jim, the camp’s founder and director, was the supreme leader of this little hermit kingdom in the California Sierra. His word was the law. Tall, strong, charismatic, and multitalented, Jim worked night and day to create a profound camp experience while also maintaining a decaying mountain lodge. All he asked from his staff was total competency and an insane work ethic to match his own.
The first week, Jim almost fired me after I gave myself a break from raking pine needles to read 100 Years of Solitude. Later, after I skulked away from a construction project to sleep in my tent, he sat me down. “Either you learn to work incredibly hard here, Blake, or you leave.”
Part of me wanted to escape this quasi-dictator and his gulag of pine trees. But a bigger part admired this larger-than-life, Indiana Jones figure from my childhood. Jim worked harder than any of his staff despite being 30 years older. He believed that his camp was changing the world by nurturing positive attitudes, personal leadership, and nature awareness. And if you played by his rules, he was ready to teach you everything he knew—which was a lot.
So, I submitted. Following the example of past instructors, I began asking “what else needs to get done?” instead of looking for escape hatches. I became the first to volunteer for unsavory tasks, like boating our trash across the lake at night. I learned how to roll a kayak, gas a generator, console a homesick camper, and orienteer in the backcountry. As my taste for challenge grew, I received more responsibility. The next summer I returned, worked my butt off again, and loved it even more. Eventually I became Jim’s assistant director.
Without a hard-ass mentor like Jim, my inclination to flee discomfort and indulge obsessions might have slipped into solipsism. Instead, I learned that with the right combination of place, purpose, and community, I can work very hard.
4) Build skills, then start my own thing
Outdoor education was fun, but the pay wasn’t great, and I didn’t always want to be someone else’s employee. How could I break away, earn better money, and enjoy more creative control?
I played with starting a test prep service or becoming a personal chef. At the same time, I kept developing my wilderness guiding credentials by becoming an Emergency Medical Technician and Wilderness First Responder. I started working for another camp, one focused on connection rather than adventure, where I bonded deeply with the community.
Then I ran away to South America: an experience that taught me so much that, as soon as I returned to the U.S., I applied to work as a South America gap year trip leader. I came close to getting that job, but ultimately got rejected. That’s when I knew I had to start my own thing.
I’d learned from two amazing camps and many outdoor programs. I had the skills and credentials to safely take young people abroad. I was connected to a new community of teenagers (from the second camp) who hungered for adventure. All I had to do now was take the leap. Together with a coworker, I created a 6-week itinerary for a teen trip to Argentina. We reached out to our communities and eight young people enrolled. All of a sudden, I had a travel company!
On the very first Unschool Adventures trip, I earned about the same as I would as an employee. A few years later, after learning some tricks of the trade, I was earning three times as much, while running exactly the kind of programs that interested and suited me.
By my late twenties, I had successfully escaped the low pay and limited creative control of the outdoor education field. I was doing my own thing, on my own terms and my own schedule. I had begun reclaiming the time of my life. Nothing would matter more than this.
5) Earn more but keep spending like I’m 22
While I was started earning progressively more, I still wasn’t making anything like my friends with full-time professional jobs. Compared to them, I remained low-income. But that mattered little, because of how little I spent.
When I finished college at 22, I owned just some books, outdoor gear, and a used car. I paid minimal rent, never wanted a house, and took emergency-only health insurance. Thankfully, I had no college debt. My disposable income went to food, gas, and books. “Entertainment” mostly meant reading, writing, hiking, seeing friends, and low-cost travel.
These facts stayed consistent throughout my twenties. Happily, I never developed more refined tastes. Every extra dollar earned became a dollar saved. Even as I made dramatically less than my peers, I saved dramatically more, translating into less stress and more time for adventure, contemplation, and relationships.
6) Don’t let friendships die
One reason I didn’t pay much rent is that I frequently visited people. College and camps had given me a wide network, and I had family on two coasts. Between seeing friends and family, running my teen travels programs, at working at summer camps, only 3-6 months remained for me to stay put and actually pay rent. I found a number of affordable spare rooms to rent, often with divorced or widowed older women.
But more important than saving money was saving relationships. The friends I made in college, camps, and travels were dear to me. We had shared intense, memorable experiences. To let these connections fade felt like a crime. I saw how many people in their twenties ended up losing touch with friends from earlier in life. It didn’t just happen to parents or those who entered serious relationships. Keeping friendships alive seemed hard for almost everyone.
I resolved to combat disconnection by dedicating big parts of my year to visiting and staying with my homebound friends and family. In the periods that I did have my own place, and I invited my friends to visit. Sometimes I organized week-long gatherings in my favorite places, like Lake Tahoe, cross-pollinating my friends from different parts of life.
The magic of compounding interest is that small, early investments can transform into bigger, future rewards. This is true of both money and friendship. Investing early and often in my friendships paid off, big-time. If I must choose between limited money and excess friends, or excess money and limited friends, the choice is clear.
7) Exploit my body
exploit - verb (/ɪkˈsplɔɪt,ɛkˈsplɔɪt/)
make full use of and derive benefit from (a resource)
Now that I’m 41 and cannot fully rely on my body, I think to myself: Thank god I did so much physical stuff in my twenties and thirties.
Hiking, swimming, trail running, slacklining. Sleeping on unpredictable surfaces while camping and couchsurfing. Long wilderness backpacking trips and cross-country cycle trips. These are a few of the ways I desperately wanted to use my body through out my twenties, and the idea of saving such adventures for post-career, post-parenting, or post-anything was unthinkable. I felt compelled to attempt certain intense adventures while they remained physically accessible to me. Anything else seemed like some kind of early death.
While it’s certainly possible to maintain a functional body into one’s sixties and beyond, the best life hack for big adventure remains: be young.
Attempt your grandest physical challenges in your twenties or early thirties. Don’t assume that your body will always work as it does today. Go, now! Such were the internal commandments that bounced around my twenty-something brain, and for them, I am grateful.
8) Become a better communicator
During my five years at the wilderness summer camp, I learned how to become an effective coach and leader. Camp director Jim, a prolific consumer of psychology and pedagogy literature, showed us how to teach using only positive instruction (“do this” rather than “don’t do that”), give constructive feedback, employ charismatic body language, and tell a captivating story to a large audience. He trained us in therapy-style reflective listening, making “I” statements (as opposed to “you” statements), and asking probing, open-ended question.
At the other camp—the one focused on feelings and connection—I learned a whole different kind of communication. Grounded in Marshall Rosenberg’s Nonviolent Communication and something called Radical Honesty, this camp encouraged self-awareness, emotional literacy, and vulnerable sharing. Every day I would run a “check-in” with a dozen teenagers, and every evening I would check-in with my fellow staff. Many workshops involved empathy, perspective-taking, and personal disclosure. And at the end of every session, campers and staff alike received “appreciations”: a flood of positive, heart-warming statements about they “showed up” and contributed to the community.
The wilderness camp taught me vitally important ways to communicate as a traditional teacher and leader. In the raw emotional department, it could fall short. The connection camp taught me vitally important ways to be present, notice my feelings, and elicit vulnerability. In the raw achievement department, it could fall short.
Between the two, I discovered a happy medium: the ability to talk with pretty much anyone, anywhere. I soon felt equally at home talking with individuals and groups, liberals and conservatives, softies and hard-asses, and everything in-between.
Gaining practical, universal, real-world skills like these, I’d later realize, is something I desperately sought in my twenties. Most normal jobs didn’t do this. So when I did stumble upon the rare people and places that did, my patience for normal jobs dried up. That’s probably why I quit so many of them.
9) Dance in partnership
As a teenager, I thought “dancing” meant (1) bouncing up and down at a concert or party, or (2) performing a rehearsed choreography. Either way, dance never came naturally to me. I considered myself hopeless. Little did I know of the third way—improvised partner dance—and its life-shaping potential.
On my first group trip to Argentina, partner dance entered my world in the form of a spicy 50-year-old tango teacher named Alicia. I tell the story best in this chapter (free) from my book The Art of Self-Directed Learning.
Learning tango in my twenties created a rock-solid foundation for picking up other forms of dance later. Now I can go to most major cities in North America and Europe, plug into a community, make new connections, and have a great evening.
10) Read, write, repeat
When I felt bored, listless, or disconnected as a child, I turned to books—my oldest companions. This relationship deepened in my early twenties as a series of books altered the arc of my studies, turned me bohemian, encouraged me to work for myself, and showed me how to travel forever. Like the friendships I refused to sacrifice to the altar of “real life,” I knew that I absolutely must keep reading.
Parallel to reading was writing, which I started doing for myself (rather than academic assignments) around age 20. Whether journaling by hand, typing angry essays about education that no one would, or piecing together my first book (on that same fateful trip to South America), writing became my default way to spend my free time, wherever in the world I found myself.
As William Deresiewicz has beautifully argued, reading and writing are the original “solitudes” that enable us to think for ourselves. More than anything else, this is what I wanted from my twenties: to somehow lead a life I could call my own. The choices I made continue reverberating today.✷
[I’m working on a new book for twenty-somethings. Keep your eyes peeled. -B]