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Finding Your Flow in the San Juan Islands

Crossing a 30-mile stretch of sea in the Pacific Northwest with a man-powered boat will make you want to throw your phone in the ocean.



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IT IS ONE of the sad realities of modern life that we spend most of our days staring at small illuminated screens. Not long after my 5-year-old daughter had taken to hiding my phone in an attempt to salvage some of my fragmented attention for herself, I was invited on a three-day sea kayaking trip in Washington’s San Juan Islands. The Pacific Coast island chain is beautiful, of course — its misty rotund peaks covered in evergreens have been drawing people to them for ages — but really, I was just looking for an excuse to let my phone die in the woods.

When I meet Tom Murphy — the owner of Outdoor Odysseys, a sea kayaking tour operator out of the San Juans — for drinks at a hotel bar overlooking the gorgeous Friday Harbor, he tells me I’m not alone, that in fact, he hopes to develop programming geared specifically toward those yearning to disconnect from technology. “Disconnecting is becoming the ultimate luxury,” he says. Murphy’s friend Tessa Lippmann has joined us. Originally from Holland, Lippmann is now the director of partnerships at NoWatch, the creators of a sort of anti-technology smartwatch that paradoxically doesn’t tell the time while using the slogan, “The time is now,” which is meant to invoke a Zen-like presence. She tells me that when she’s been on her phone too much, she feels as though it creates a film over her brain, making a barrier between the world and her so that she’s only half there. She says that bringing her teenage sons on these sea kayaking trips removes the film and gets the boys away from their phones. “It’s a chance to really be with them,” she says.

Outdoor Odysseys runs organized sea kayaking trips out of Friday Harbor, one of the more developed areas of San Juan’s islands, ranging from day trips to weeklong sea kayaking and camping excursions. My trip, a three-day journey, would cover 30 miles, which sounded like a lot, but when I asked Murphy if I should train, he laughed and explained that they regularly have folks of all abilities and ages join them and that really anyone can do it, regardless of fitness level. All details are handled by the trip leader: the camping gear, the food, the routes. Since I plan everything in my life — when and where we’ll eat, what we’ll bring, how we’ll get there — the idea of handing off this burden to a knowledgeable stranger is all too enticing.



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There are six guests in our group, including my partner Dexter and me, and a quick poll reveals that everyone on the trip, with the exception of the two of us, works in tech. These are people who love the outdoors but through fate and circumstances have chosen sedentary, abstract, and very much indoor careers, and you can tell they’re all a bit torn up about it.

Maddie Hollister, our fearless leader, is a different breed though. She is preternaturally calm, reading the tides, the currents, and the wind. She knows about knots and fathoms, teaches us how to angle our boats. Stay loose in the hips, be flexible, move your body with the wave, not against it, she says. It will pass. It strikes me as excellent life advice.

After a quick demonstration in the poorly named Smallpox Bay, we’re off. I’m immediately struck by how comfortable Hollister is on the water. She tells us to point our boats in whichever direction hers is pointing. Though she’s 10 years younger than all six of us, we cleave to her, like ducklings to their mother, whenever the seas get remotely rough. We pass by playful harbor seals and spot a bald eagle. Hollister tells us that, in reality, the bald eagle’s cry is wimpy sounding, almost whiny, so in movies, the cry is dubbed over with the screech of a more imposing bird of prey.

Later that day, we encountered our first big challenge: a channel crossing. Hollister tells us to stay in formation. It’s a large choppy swath of open water, so we need to stay visible to boats. I look over at the outdoorsy tech couple from outside of Seattle. They have brought all of their own gear, including their life vests. Earlier, when we were preparing to launch, I watched them unpack the gear with military-grade precision. Now, crossing the channel, they move exactly in sync, oar up, oar down, gliding across the water. I keep looking back at them, hoping to catch them in an offbeat moment, but it never happens; they just stare serenely ahead, oars in unflinching synchronicity. Meanwhile, apropos of nothing, Dexter says, “I see why they call these divorce boats.”

We cluster together in a group to take a break, and Hollister points to a bald island up ahead and tells us that in the ’70s, someone wanted to make Spieden Island a hunting ground and brought exotic game — zebras, mouflon sheep, and other animals. The zebras, unsurprisingly, died immediately, but to this day, if you know where to look, the sheep can be seen emerging from the fog. The island is now owned by the founder of Oakley, the sunglasses company, but no one knows what he does with it. The only visible building is a bunker, but there are rumors of something going on underground. If you land on one of the island’s beaches, armed guards will appear and ask you to leave. As we get in formation and pick up speed, heading toward Spieden, I wonder if we look intimidating, like some secret-ops mission that is going to take the island.


In the late afternoon, we land at our campground on Stuart Island, which is only accessible by non-motor-powered boat — kayaks and canoes, maybe a catamaran. Hollister prepares a gorgeous meal that includes a miso soup with some bull kelp that she has snagged along the way and a curry, followed by a cast-iron apple crisp for dessert. While she cooks, she tells us about the flora and fauna of the island. She studied marine biology and seems to know every creature and plant she comes across. The caterpillars are invasive; we should step on them. The trees are cedar and madrone, the latter of which are also called “refrigerator trees” for their self-cooling capacity. Sure enough, when I rest my palm on a madrone’s bark, it’s cool to the touch. It occurs to me that there are apps for this. Merlin for bird identification. PlantSnap for plants. There is an idea in tech development that in order to build a company, you have to identify a point of friction and eliminate it — the having to ask a human and then getting a possibly flawed answer would be the friction here. But hearing Hollister tell me, asking, the conversation that follows — so-called friction — is much more gratifying.

After dinner one night, we hike to a lighthouse on the other side of the island through forests of ferns and cedar trees. The island is a little bit spooky, but if it’s haunted, then it is haunted by benevolent ghosts. I’m told that the mouflon sheep were brought to this island too, and without predators, they’ve flourished into a flock of 200. I imagine a silent flock staring at us from the woods. We come across a gorgeous wooden building with an idyllic grass yard, which Hollister tells us is a schoolhouse—or used to be. Now there are no children on the island — indeed there are only 15 people who live here full-time — but there’s a hope that the children who grew up here will come back. There is a standing promise that if four children live on the island, the county will hire a school teacher and reopen the school. Suddenly, I can see it so clearly: my daughter running down the road past the farm and the grass landing strip, playing in the woods with friends, a little dirty and very happy. I’ve made a terrible mistake raising her in concrete-covered Oakland when we could be watching for whales from our kitchen window.

That night in my tent, it dawns on me that not only have I not looked at my phone, I also haven’t looked in a mirror. I see the phone in the bottom of my dry bag, its black screen looking oddly inert and uninteresting — it’s just metal and plastic, I think. The absence of mirrors is liberating. I look in the mirror often, and usually unkindly, scrutinizing the fall of my hair, the “elevens” between my eyebrows, even the shape of my nostrils. On the island, no one cares—best of all, I don’t care. I could levitate with relief.

On the last morning, we get in our boats, and after a few hours, we approach the channel crossing again. Without having to be told, we get in formation. I realize that perhaps now, I’m a little less reliant on Hollister, that perhaps somehow I am reading the tides myself, knowing where to point the boat. I look up at the group and see that we are now all in sync, oars up, oars down — as if we are one organism. I try not to think about it and just feel it, knowing that the thinking will mess it up. We have covered 30 miles by sea with nothing but the power of our own bodies.

On the flight home, the young man next to me with a Carnegie Mellon backpack is reviewing a document about something called Sky. Intrigued, I read over his shoulder, seeing the word “cloud,” only to realize that Sky is, of course, an app. It hits me. I’m not moving to the San Juan Islands. And I don’t really know what to do about my phone.

I think about Tom Murphy’s friend, Tessa Lippmann, and what she said about her teenage sons. I recall my own teenage years, which involved, to my mind, excruciating dinners with my parents, who asked well-meaning questions that revealed exactly how little they understood my reality. Now in my parents’ shoes with a daughter of my own, the memory pains me. Maybe if my parents and I had done something together, had shared a mission, things would have been different in those years. I promised myself that I would bring my daughter to the San Juans as soon as she was old enough. We might go through a time when I ask the wrong questions, a time when she thinks I won’t understand what she has to say, but if we move our bodies in unison, we will find our way back to each other.

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Our Contributors

Laura Smith Writer

Laura Smith is the deputy editor of Departures. Previously, she was the executive editor of California magazine and has written for the New York Times, the Guardian, the Atlantic, and many more. Her nonfiction book, The Art of Vanishing, was published by Viking in 2018.

Dexter Hake Photographer

Dexter Hake is a freelance photographer living in Oakland, California. His work has appeared in various publications such as The New York Times, California magazine, Ballena Blanca, and more. He also has numerous commercial clients in the Bay Area, mostly focused within the food and beverage industry. His favorite film is Kodak Portra 160 VC.


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