It is All an Adventure

A young man named Oliver and his cat, Phoenix, captured the hearts and attention of millions of people recently. He arrived in Hawaii on May 24, 2025, after a solo sailing journey that began in Oregon and lasted 26 days across open water. His story is one of those rare, modern-day folk tales that pierce the dismay of our times; that gives a flash of hope that we desperately need. Diagnosed with a rare spinal condition that threatened paralysis, Oliver chose to radically redesign his life. He sold his things, bought a used sailboat, taught himself to sail using YouTube, and—most importantly—he actually fucking went. He set sail with a cat and a dream and a toolkit of courage that most of us spend our lives talking ourselves out of. As he says in his Instagram bio, “there are no rules.” 

Coincidentally, one of my closest friends ended his last week of formal work and started his first week in what he calls retirement mode, which, to be clear, does include a lot of golf (he loves it), but it also includes a deeper reorientation of time, energy, and attention. He’s not checking out, he’s checking in. He’s shifting from grinding to growing, from chasing to choosing. A different kind of adventure. One with fewer meetings and more meaning.

And all of this is happening as I spend my final week living in Austin, Texas, after eleven years of love, grief, friendship, and growth. My departure isn’t dramatic, but it is sacred. It’s the end of a particular chapter. One that shaped me more than I realized. One that taught me that place is a teacher and that roots sometimes need to be pulled up for the tree to grow taller.

Arriving, ending, leaving, starting, adjusting. It is all adventure.

As Cody Johnson sings in the song “The Fall”:

The ride is worth the fall
The fall was worth the smiles
The smiles were worth the tears
Tears were worth the miles
Miles were worth the pain
Pain was worth it all
It’s all worth this life
Life is worth the ride
The ride is worth the fall

(Songwriters credit: Bobby Pinson / Jeremy Stover / Ray Fulcher)

For many years, I didn’t consider myself a brave person. I thought bravery belonged to other people—soldiers, first responders, activists, risk junkies. I saw myself as scrappy, resourceful, maybe stubborn—but not brave. But then a somatic therapist helped me understand that I had been brave for as long as I could remember. She helped me access and reinhabit memories from my childhood and young adulthood, not with nostalgia, but with new eyes.

Like the time I read The Great Escape and convinced my younger siblings to help me dig a tunnel underneath the road near our house, so we could sneak out at night. (Spoiler: not successful. We got caught. I’m still convinced we could have pulled it off.)

Or the time I was the last kid picked for pick-up touch football during sixth-grade recess. I was placed in a made-up position called “stand over there.” One day, I stepped up to block Todd Chavez—a much bigger, much faster kid—and ended up with a black eye, a mild concussion, and an unexpected trip to the doctor’s office. For one day, I was a hero and even Chavez was impressed.

Or when I watched the original Red Dawn and became convinced the commies were going to invade rural Oregon. I organized my siblings and built hideouts around the ranch, created makeshift weapons out of cycle saw blades and sticks, and stashed canned goods stolen from my Aunt Vickie’s pantry in various “food caches.” (Side note: kinda feeling the same thing these days, except now it’s the Red Hats I think we might need to be ready for.)

The list goes on. I don’t say this to flex. I say it to remind myself—and maybe you—that it’s all an adventure. And now, I’m standing at the edge of a new one: moving to Mexico City with Virginia and Andre. Planting new roots. Expanding our second home base in Portland. Saying yes again. Saying yes differently.

All of these adventures came with some spectrum of negativity, sometimes as a dark cloud of violence, sometimes as the subtle residue of old trauma. But I’ve come to learn that, at least for me, that edge of fear or discomfort is often what makes it an adventure. It’s not about being fearless, it’s about doing it anyway. Moving toward, not away. Like I’ve said for years, courage almost always trails action. We don’t wait to feel brave. We act, and the bravery catches up.

And if you’re going to live this way—adventurously, consciously—then learning how to manage your mind is non-negotiable. Especially for those of us who are trauma survivors, neurodivergent, or both. Here’s the paradox: those same traits and experiences that make us sensitive, that make life feel like too much, are also what make us adventurous. We have a high tolerance for the unknown. A knack for disruption. A desire for meaning that borders on holy. But that same wiring can also do deep harm. It can trick us into thinking we’re adventuring when we’re actually self-destructing. It can make dysfunction feel like destiny. That’s why this work—this reflection, this responsibility—is vital.

In reflecting on the idea of adventure, I’ve noticed a few patterns that keep repeating themselves:

• Like I wrote in last week’s essay, you have to learn not just to find the Crease, but to live in it. That’s the thin line between what is and what could be. The sweet spot between order and chaos. That’s where the real shit happens.
  

• Be smart and be prepared. Or, put another way: don’t be stupid. If you check out Oliver’s story, you’ll see that he didn’t just buy a boat and wing it. He spent month learning. Practicing. Studying. Building. Same thing for my friend who just retired. He spent the last decade designing this season of his life. There’s a fine line between courage and destruction, and too many people romanticize the idea of leaping without looking. That’s not brave, that’s being a fucking idiot. Adventure still requires discernment. It demands that you respect risk, build skills, understand the terrain, and take care of your future self. Preparation doesn’t kill spontaneity, it fuels it. It gives your wildness a container.
  

• The universe provides the opportunity, but you still have to do the work. Grace may open the door, but you’ve still got to walk through it, often with scraped knees and a half-broken flashlight. There’s a natural law in that, a sacred arithmetic that I’ve witnessed time and again: Opportunity + Effort = Provision. Not provision like a jackpot or a magic windfall, but the kind that shows up as just enough gas in the tank, just the right person at the right time, just enough clarity to take the next step. The effort part isn’t just about grinding, it’s about aligned, intentional movement. That equation is old as dirt and reliable as gravity, but most people skip it in search of hacks. Don’t. Honor the God math.
  

• You have to take ownership of the design of your life. Yes, fate plays a role. So do genetics, luck, and the messed-up systems we’re all swimming in. But that doesn’t excuse us from design thinking. Design thinking is about constraints, tradeoffs, and creative problem solving. It’s the practice of treating your life like a living prototype, something to be iterated, adjusted, tested, and redesigned. It starts with radical honesty: Where are you now? What’s working? What’s not? Then it invites curiosity instead of panic. Design thinking asks you to treat problems as invitations and limitations as creative catalysts. You try things, you learn, you adapt. It doesn't demand certainty, it rewards exploration. Applying this to your life means letting go of the myth that clarity must precede movement. Instead, you move forward with what you know, test what’s possible, and refine as you go. It’s not perfect, but it’s alive. You can’t wait for clarity. You have to design your way into it.
  

• And you have to develop systems thinking. Especially if you want your adventure to be sustainable, not just one dramatic “hold my beer” moment. Systems thinking means seeing the bigger picture, not just the isolated parts, but how they influence and interact with each other. It’s understanding that your choices, patterns, relationships, and environments are all interconnected. In systems thinking, you stop asking, “What’s wrong with me?” and start asking, “What am I part of?” Take Ernest Shackleton, for example. The man didn’t just brave Antarctica. He coordinated complex rescue operations, managed team morale, rationed food, and adapted plans daily. That’s not just courage. That’s systems thinking.  That’s adventure with a strategy.

The adventure always begins inward. Not with plane tickets or packed bags, but with questions. Real ones. Sacred ones. The kind that strips you down, not to shame you, but to reveal what’s real beneath the performance. Questions that aren’t designed to be answered in a hurry. Questions that make you pause, squirm, wonder. These are the soul’s breadcrumbs. They show up in quiet moments, often when something is ending or beginning, or when both are happening at once. These questions aren't meant to close a loop. They're meant to open something wider. They help you make peace with not knowing. They help you reorient toward what actually matters. And if you’re paying attention, they don’t just reveal who you are. They help you remember who you’ve always been.

Questions like…

• Who am I without any social labels, titles, or credentials?

• What do I truly want, not what I’ve been told to want?

• What am I willing to give up for that?

The best parts of life don’t come with a tour guide. So sell your shit. Buy a boat. Learn to sail. Rescue a cat. Do your version of that. Find your way to say yes.

Because in the end, it’s all an adventure. And the ride is worth the fall.