There is a particular kind of courage that most of us never test. It is not the courage of standing on a stage or launching a company. It is the courage of standing at the edge of everything you know — every expectation, every security blanket, every carefully constructed identity — and choosing the bicycle instead.

Nathaniel Allenby made that choice. And in doing so, he didn't just escape the rat race. He dismantled the cage from the inside and built something entirely new with the scraps.

Purposelessness: The Shadow Prison Nobody Names

When I asked Nathaniel what made homelessness on a bicycle look like freedom, his answer bypassed every cliché I expected. It wasn't wanderlust. It wasn't rebellion against capitalism. It was purposelessness — the suffocating void of not knowing why you exist.

Before the road, Nathaniel had been on a trajectory toward American politics. When that dissolved, he found himself playing video games full-time, hollowed out by the absence of meaning. Then a best friend extended an invitation that would change everything: a voyage with no money, no plan, and no guarantee of survival. What they found was that the emptiness wasn't the end. It was the doorway.

This resonates deeply with something I navigate every day. As someone who has battled dissociative identity disorder and lives on the autism spectrum, I know what it feels like when the world's systems weren't designed for you. The shadow prisons are real — and the most insidious one isn't fear. It's the emptiness of a life without purpose. Nathaniel stared into that void and chose to pedal through it.

Dumpster Diving as Strategy: What Society Wastes Reveals What It Values

Living on less than $800 a year, Nathaniel learned to eat from what the world threw away. Most people see dumpster diving as rock bottom. He saw it as intelligence gathering — a raw, unfiltered education in what our systems actually produce and what they discard.

His diagnosis was clear and prophetic: we are living inside radically inefficient systems that are not serving mankind. They are outdated. They are archaic. And we are watching them malfunction on a global scale in real time. This is not the rant of a dropout. This is field research from someone who lived outside the machine long enough to see it from every angle.

The Kindness of Strangers: A Radical Survival Hack

We are taught stranger danger from birth. Nathaniel survived by doing the exact opposite — trusting strangers across ten countries and thirty states. And the results are staggering in their consistency.

One story stands out. The day after Christmas, somewhere along a French river freezing over in real time, Nathaniel pedaled without stopping to eat or use the bathroom, rotating each numb hand into an armpit every ten minutes to prevent frostbite. When he finally found a tiny village center, nearly every café was shuttered. A homeless man on a bench — who had already picked through the garbage for his own lunch — offered to share what he'd found. They broke bread together. They shared a cigarette. They exchanged directions.

That experience became the first chapter of his book, The Cycle of Kindness , placed out of chronological order because it captured something more important than any timeline: the proof that when you show up openhearted and vulnerable, the best parts of people almost always emerge.

Sneaking Into Castles: Life as a Video Game

Nathaniel and his best friend didn't just survive the road. They gamified it. They turned defunct buildings into levels with hidden objectives and time challenges. They snuck into castles with real security guards — one watching from outside while the other got a self-guided tour. They were, as Nathaniel puts it, practically modern-day ninjas.

The point wasn't the trespassing. It was the skill acquisition. Every uncomfortable situation they navigated gave them new strengths, new attributes, new resilience — like a real-life RPG where growth happens exclusively outside the comfort zone. These experiences armed them with the ability to handle what most people spend their lives avoiding: the unfamiliar, the uncertain, the frightening.

Robbed in London, Befriended by an Ex-Con: The Paradox of Safety

The journey wasn't all wonder. In London, a group of fifteen-year-old thieves robbed them, and one threatened to pull a knife. Nathaniel caught it immediately and stood his ground. The very next day — in the most leery, untrusting mindset of the entire trip — they met a man who had just been released from prison. A man who told stories of violence. A man who then bought them food, shared drinks, hung out in a park until past midnight, and harmed no one.

The lesson Nathaniel drew is one I carry in my own bones: our preconceived notions about what is safe and what is dangerous are wrong more often than they are right. The people I was told to fear — different religions, different genders, different communities — were the ones who showed me the love of God when the people I was told were heroes were the ones causing the most pain.

Fear Is a Tactic, Not Just an Emotion

Nathaniel delivered what I called the best sermon I've ever heard without preaching. His core message to every listener: seek information outside of how you already look at things. Our internet algorithms are force-feeding us content that ingrains our existing worldview, driving further division, isolation, and polarization.

He referenced Machiavelli's The Prince — not as an intellectual exercise, but as a field manual that remains more relevant than ever. Fear is not just something we feel. It is a deliberate instrument of control, wielded by governing bodies for centuries. Divide and conquer works. The antidote is deceptively simple: talk to people who think differently. And when you do, listen without judgment, because judgment physiologically shuts down the creative centers of the brain.

Cirque Quirk: Building a Creative Economy That Serves the Artist

Nathaniel founded Cirque Quirk , a circus entertainment company that flips the standard creative economy on its head. Instead of extracting value from artists, he built a company that hires high-quality performers to do what they love — at events, fundraisers, corporate functions, and celebrations worldwide.

His simplest business principle: fail forward. Learn from mistakes and get better. His hardest lesson: letting go of control. After running the company solo for eleven years, he hit a ceiling. As he put it: if you want to go fast, go solo; if you want to go far, go with a team. Now, in a major transition period, the choice is clear — innovate or fail the community he's built. Because stagnation doesn't just hurt the founder. It hurts every creative depending on that platform to match inflation and build a living.

He referenced Jim Carrey's famous Maharishi University commencement address: you can fail at what you don't love, so you might as well take a chance doing what you love. Nathaniel has been living that philosophy since he was twenty-eight, and the company he built proves it works when paired with relentless adaptation.

Laughter in the Darkest Places: Clowns Without Borders in Zimbabwe

When Nathaniel traveled to Zimbabwe with Clowns Without Borders, he performed for children who had never seen a white person before — let alone a juggler or a puppet. The initial reactions ranged from shock to fear. But when the performances began, something shifted at the physiological level. Children who arrived withdrawn and guarded cracked open into laughter and wonder.

The feedback repeated itself show after show: people said they had been so consumed by fear that they forgot what joy felt like. That feedback didn't just validate the work. It radicalized Nathaniel's commitment to humanitarian service. When laughter can remind someone that their humanity still exists beneath layers of trauma, you are no longer in the entertainment business. You are in the liberation business.

The Cycle of Kindness vs. Into the Wild: Why Connection Beats Isolation

Nathaniel's book The Cycle of Kindness has been compared to Into the Wild — but with one critical difference. Chris McCandless died alone. Nathaniel survived. The divergence is philosophical: McCandless sought escape from a culture that failed him. Nathaniel chose to remain part of the culture so he could change it from within.

His vision extends far beyond the book. Nathaniel is working toward an app concept — a platform structured like TikTok but inverted. Instead of ego-driven "look at me" content, it would incentivize random acts of kindness and turn the camera outward to capture the impact those acts create. When we show people cracking out of their shells and gaining joy through someone else's generosity, he believes that will be infinitely more powerful than the attention economy we are currently drowning in.

The Tattoo That Changed Everything: Radical Honesty as Liberation

When asked why he left the messy parts — the sex, the drug experimentation, the adversity — in his book, Nathaniel reframed the question entirely. It's not perfectionism that kills connection, he said. It's the mask that perfectionism forces us to wear. When we only project the shiny, curated version of ourselves, we deny others the permission to be real.

His turning point was visceral. He had been lying to his own father, and the dishonesty was corroding their relationship. When he got matching tattoos with his best friend — Veritas across his chest (truth, honesty, integrity) and Aequitas across his back (equality, justice, balance) — he could no longer look in the mirror and live the lie. That physical inscription became a psychological contract with himself to live transparently. The energy we spend worrying about other people's opinions, he argues, is energy stolen from our ability to actually live.

Teaching Children to Trust in a Paranoid World

With two daughters and a third child due in August 2026, Nathaniel is translating his philosophy into parenting practice. He teaches his children to believe in the goodness of humanity while trusting their intuition. He models the behavior of kindness toward strangers. The family practices forgiveness actively in their home — not as an abstract concept but as a daily discipline.

On Christmas Eve, he brought his daughters to a homeless encampment to deliver 650 pounds of food. Before they arrived, he set expectations: these people won't look or sound like us, they may not have access to basic hygiene, and that doesn't make them less than equal. His daughter now references that experience regularly and tells the story to others. It has become part of her identity — proof that modeling matters more than lecturing.

If the World's Mayor Gave You One Law

When I asked Nathaniel what single global law he would enact to foster human evolution, his answer came without hesitation: outlaw war.

His reasoning was as practical as it was idealistic. If we stop fighting each other as a species and redirect those resources, we have enough capacity to clothe, house, feed, and educate every person on the planet — and still have resources left over to become an interstellar civilization. The infrastructure of war isn't just morally destructive. It is the single greatest bottleneck on human progress.

The World Nathaniel Is Building

Twenty years from now, Nathaniel envisions a world of loving kindness operating at scale. Not a utopia scrubbed of difficulty, but a civilization with greater emotional maturity, personal responsibility, and ethical standards. A world where people can choose to be afraid but aren't forced into fear by systems designed to profit from it. A world where the creative class is supported, not exploited — he cited Ireland's experiment with universal basic income for artists, which generated a GDP increase that exceeded the investment.

His call to action is simple and resonant: if you don't want to create your own cause, join someone else's. Be part of something you're proud to leave as your legacy. And remember — you cannot fill someone else's cup when yours is empty. The work starts with you.