Brave Enough
Letters on fear, freedom, and becoming whole.
Freedom
Do you want to be free?
Most of us are taught that freedom comes from success: Get a good job. Make good money. Then you’ll be free.
But it’s not freedom. Because to earn it, we have to trade something far rarer: our time. You can buy the car and house, but you still have to show up at 9 a.m.
I was taught something different: that real freedom isn’t about money. It’s about control.
Time and location are the real currencies.
So I spent years chasing that kind of freedom instead: the ability to work and live where I wanted, when I wanted.
This is the story of how I found that freedom — and why it still wasn’t enough.
Ambition
When I was 17, there was a word that promised to deliver all of my hopes and dreams. It was beyond grammar; it was mythological: Entrepreneurship.
It was a bright, hot Hawaiian day when I first heard it. The sun pressed its way through my windows and walls, turning my room into a furnace. I’d stripped down to my boxers to save laundry when a YouTube ad appeared: a blond guy, an orange Lamborghini, and a promise: make $20,000 a month selling products online.
He had my attention.
At the time, I was working full-time as a housekeeper, scrubbing toilets eight hours a day for $15.74 an hour. I’d come home exhausted and reeking of bleach.
I wanted the money, but I didn’t want to trade my hours to earn it. What I really wanted was freedom.
My father used to call jobs a form of modern slavery. Real freedom, he said, meant being in control of your time and location.
I believed him. If I could make money from my laptop, I could choose where I lived and when I worked.
So I dove in.
I devoured business tutorials, ordered inventory, and launched an Amazon store selling seatbelt extenders. Every $9.98 sale edged me closer to liberation, until an email arrived: Your listing has been deactivated for selling a restricted item.
I panicked. Nine hundred seatbelt extenders filled every corner of my new dorm. For months I biked packages to the post office, losing money on each one.
Still, I refused to quit. I found another product, invested my savings again, and went live. Then another email: Your account has been suspended. My appeals were rejected.
Amazon had beaten me, but I wasn’t done.
I told myself I’d learned enough about marketing to help other businesses, and cold emailed local restaurants until one owner agreed to meet. We sat overlooking a white-sand beach back in Hawai`i as I told him that I could get him more customers with advertising. He looked around at his full tables. “I don’t need more customers,” he said, “but I do want to tell our story.”
He hired me to do exactly that, which expanded into other projects.
One year later, he signed a contract to pay me a monthly retainer to manage his digital marketing.
Finally, three years after that first ad, I had steady income from my laptop.
In other words: Freedom.
The world felt wide open, alive with possibility. I thought I’d won.
I didn’t know the life I’d built on control was already turning against me.
Captivity
After signing the liberating contract, I drove to the beach to savor my victory, vividly imagining the BMW that would replace my dingy 2002 Mustang.
I walked along the shore, cherishing the warm sand beneath my feet. But as I waded out into the water and gazed upon the shore to let the moment sink in, I felt the last thing that I expected: emptiness.
I wanted to feel proud, free — anything — but instead: nothing.
I justified it immediately. It’s just because I’m still in Hawai`i. When I’m traveling the world, working remotely, I’ll feel what was promised.
This hope remained in my heart six months later as the plane descended upon Mexico City.
I wandered the city, met people, went to museums, and learned Spanish. I lived in a large apartment downtown, worked a few hours a week, and still saved money.
And yet, as I sat alone in my apartment, listening to bustling streets below, one truth pressed in on me: I’d been sold a lie.
I thought freedom meant stripping away every constraint and escaping every obligation. I believed joy would naturally follow.
But it didn’t.
Instead, I felt split — both unfulfilled by my freedom and terrified of losing it.
The same anxiety that had driven me to chase this life now powered its preservation.
My body knew it before I did: the raised shoulders, the clenched jaw, the constant sense of being on edge, waiting for disaster to strike.
I told myself it was just a matter of time, that I hadn’t used my freedom well enough yet.
I filled the emptiness with new goals, new projects, anything that would give me something to wake up for in the morning.
But no amount of motion could quiet the unrest underneath.
It would take two more years, and a monastery in the Swiss mountains, to understand what that tension had been trying to teach me.
Surrender
Night fell over Switzerland on Christmas Eve. Back home, Christmas was loud, bright, familiar. But this year, it was quiet, foreign, sacred.
Our train wove through the Swiss mountainside in the dark of night for nearly an hour before finally arriving at an isolated village with no more than a dozen homes.
We walked uphill to a dimly-lit building standing by itself: the Romanian monastery where the service would be held.
A nun greeted us at the door and told us to go around to the back, where we found a small door with candlelight peaking through the cracks. We stooped to enter a low, cavernous space no larger than a living room.
A handful of churchgoers stood quietly by the entrance while six nuns, dressed in all black, soulfully sang hymns of prayer.
I walked into this sanctuary as a man in pain. A week earlier, I’d told my father that I was blocking his attempts to contact me. It was the culmination of years of trying to repair what could not be repaired, throughout which I’d progressively distanced myself from him.
No matter what I achieved or how far I traveled, the guilt stayed with me — quiet, but unrelenting.
And tonight, it clenched me with both hands.
My chest was tight and a deep sorrow weighed on my heart as I crossed the threshold.
I had no expectations that anything would change. And yet, as I stood silently in the back of the room, feeling the waves of prayer wash gently over me, I soon felt something remarkable: freedom.
It was as if two birds had flown down and lifted a great weight from me — slowly, gently, without effort.
And in that moment I understood. The freedom I’d chased could never come from control. It could only arrive through surrender. Through trust.
Not in myself, but in something larger. In love. In life itself.
After the service, we stepped out into the night. I breathed deeply, filling my lungs with the crisp mountain air, my heart expansive like the peaks around me. I held my girlfriend’s hand as we walked down the hill in silence, savoring each other’s presence under the moonlight.
And like a butterfly landing softly on my shoulder, I felt what I had been searching for all along:
Peace.
With love,
Ryan
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P.S. If this letter made you think of someone, please consider passing it along. It means more than you know.
The Cost of Survival — On the exhaustion of living in constant vigilance.
Achievement Isn’t Enough — When success can’t fill the space it promised to.
Sometimes Normal Is Enough — On learning to love ordinary life again.
Find all of my letters at ryancombes.com.