Trust issues (not the kind you think)

"Baby!" Colin yelled from the cockpit. "Come see. But you have to be quick."

I’d been struggling to wash dishes with the weirdly poor French dish soap that barely sudsed and refused to remove grease. I would later learn I'd been washing dishes for two weeks with hand soap.

But in that moment, I was just happy for an excuse to drop the sponge and scramble up the companionway.

My excited husband wasn’t alerting me to dolphins. Or a submarine. Or a UFO.

It was the sun—peeking through the clouds for the briefest of minutes. In winter. In Cherbourg. We wouldn't see it again for eight days.

We stood there in the cockpit, faces tilted up like sunflowers, soaking in every second of that pale winter light. And when it slipped behind the clouds again, all I could think was Right. Thank you, dear sun, for the reminder that you exist.

Living in Cherbourg during the winter requires a lot of trust—that behind those clouds, behind the rain, behind the grey that settles over the harbor like a wool blanket—the sun doesn't stop existing just because you can't see it.

I've been thinking about that a lot this past month.

We've lived aboard Pristine for a month now. If you read last month's letter, you know the champagne finally got popped and the pantry containers found their home. Since then, I've been deep in nesting mode—cooking actual meals instead of canned soup (mussels! shrimp! I love a country with more varieties of seafood than potato chips), figuring out where to stow the spare sheets, and learning which light switches do what. After five years without a permanent home, I needed this. The simple domesticity of living.

But something else has been going on beneath the surface. Something I haven't wanted to look at too closely.

I know myself as a planner. The woman who researches cruising guides, draws lines on charts, and buys books about weather routing six months before she needs them. That woman has been conspicuously absent. In her place is someone with only vague notions about what comes next. No chart lines. No guides. No grand route mapped out.

Where is she?

Wrestling with her fears, as it turns out. Because here's what I haven't told you directly, though you may have sensed it between the lines: I have trust issues. Not with Colin. With the universe.

In February of 2020, we'd prepared ourselves in every way we knew how to cross an ocean. Boat, mindset, provisions, route, plan, permits, spares, safety gear. We were ready to make the most of our precious window of health, peace, and weather.

And then Covid closed the Pacific.

Just like that, my cruising life shut down. What followed led to many good things—including my writing career—but also to dependence, rootlessness, and a long, disorienting loss of identity.

So perhaps it's understandable if my psyche is a touch reluctant to put another big dream out there in the universe. Last time, it didn't go so well.

But facing fears takes a lot of energy. So this past month, instead of planning or acting, I slept. I meditated. And somewhere deep in my subconscious, a shift occurred. It allowed me to acknowledge that I do have a deep goal.

One hard enough that I may very well not succeed.

That was terrifying to admit, because it meant this wasn't something I could approach like a task—straightforward, guaranteed, click the checkboxes and be done. It was something I had to approach like a game. With curiosity. With play. And play, I'll confess, does not come naturally to me as an adult. Play means ‘potentially fail.’

"What's the worst that could happen?" a therapist of mine once asked. "Do you trust yourself to deal with that?"

So I made myself go there with my fledgling goal. I imagined the devastation of failure. The backlash, the disappointment, the loss of respect. It wasn't pleasant.

But at the end of the exercise, I was still okay. Still alive.

We all have our hearts broken, and we all survive. Somehow, it doesn't stop us from risking our hearts again. It's huge and hard and scary, but we do it. I've done it.

When I was falling in love with Colin, there was a night I couldn't sleep. I tossed and turned until eventually he did something wonderful for a man being kept awake in the wee hours. He asked—gently—what was on my mind.

And then he listened.

What came out was this: I felt like I was on a surfboard and could feel a monster-sized wave rising behind me—this enormous swell of emotion and possibility and vulnerability—and I was terrified it could crush me.

But also? It could be the most incredible ride of my life.

And just saying that out loud made me decide. I was going to paddle into that wave. Paddle for all I was worth.

That was more than a dozen years ago. And that wave I surfed carried me here—to this loving husband, this boat, this life. This moment writing to you from a harbor in France. To writing the next Navigator Series novel that’s really opened up and started to flow.

I'm deep in the middle of A Course to Steer, channeling the real-life Ellen who inspired the fictional one—the woman who not only allowed herself to dream the impossible, but found the courage to step toward it. And the real-life Perk who risked every iota of society’s respect in exchange for something far greater.

As I write their story, I don’t feel like I inspire their fictional journey—I feel like they inspire mine.

This month, their example has allowed me to acknowledge my own impossible goal—one that risks heartbreak and devastating failure. A sailing adventure that feels like a major stretch for the current version of me.

I'm not ready to name it yet—Colin and I are still holding it close. But it's big enough to scare me and exciting enough to keep me awake at night. There's plenty to learn, practice, and absorb before attempting to surf that wave.

But then again: even Laird Hamilton didn't start as Laird Hamilton. At one point, he was a grom who got crushed. Then a kid who surfed bigger and bigger waves, stair-stepping his way up to the mountains of water he became famous for.

And that frame reminds me that there was a time, not very long ago, when even taking a sailing lesson felt so scary to me that it was nearly a step too far. 

So my job right now isn't to surf the mountain. My job is to build a staircase. One with a lot of steps.

Cue Stairway to Heaven if you’re feeling sarcastic.

But for my part, I'm starting to trust—the way I trust the sun behind a Cherbourg winter sky—that Colin and I can build the competence and confidence to paddle into the next big wave. We might get crushed, but then again, it may just be the ride of our lives.

In the meantime, I’m so glad you’re here, climbing the stairs with me.

Fair winds,

Cheyenne

P.S. What wave have you decided to paddle into? I'd love to hear in the comments.

P.P.S. If you missed it, I wrote more about crewing on a tall ship to the edge of Cape Horn here: Sailing to the End of the World.