It was surprisingly easy to wake up at 4:30 in the morning. Well anyway, it was easy enough to wake up when Iris gently shook my shoulder to point out my buzzing, beeping cell phone on the night stand.

Through the living room windows facing south, San Francisco was utterly dark, the street lamps of the Excelsior neighborhood twinkling on the hillside beneath the crest of MacLaren Park. In the dimmed light of the kitchen, I spread extra chunky peanut butter across a lightly burned piece of toast and drizzled golden drops of California honey from a plastic bear over slices of a 20-cent banana from Central America. A Nespresso machine forced steam through a little plastic capsule and into my favorite espresso thimble, a miracle of capitalism, a peril of convenience.

Various layers of spandex and nylon covered most of my body. The pre-dawn air was cool on my legs, but not uncomfortably so as I pedaled slowly up O’Shaughnessy overlooking Glen Canyon to the right, a refuge for the city’s controversial coyotes. Just after 5am, the sky was already turning a lighter shade of blue to the east above the bay. Sutro Tower was enveloped in morning fog with the top three prongs stretching upwards like zombie fingers with satellite dish warts.

I timed this year’s trip so that it would start on the solstice and end on my birthday. Each solstice, my local cycling club organizes “the longest day” ride, and this year they would pedal up to the Russian River and back down, 170 miles in total and about 10 hours of continuous riding through San Francisco, Marin, and Sonoma counties. The rough equivalent of a marathon in cycling is a “century,” 100 miles of pedaling in four to six hours depending on your speed. This was nearly twice that, an ultra marathon on a bicycle. I would join them for the first half to Cazadero, just north of the Russian River, nestled under a canopy of old redwoods along Cazadero Creek.

There were 20 of us and we were to meet at sunrise, 5:48am, on the south side of the Golden Gate Bridge. Around 5:30, I pedaled by the Conservatory of Flowers in Golden Gate Park and I was suddenly overcome by hyper-sensitive wakefulness. All week I had struggled to wake up before 7 to beat the morning commute to the office, half-listening to NPR with puffy eyes and a cloudy mind. But here I was, alone in the quiet dawn of the empty city, its greedy sci-fi speculation still dreaming, and I felt wide awake to its beauty, its possibility, the way it has always attracted weirdos and hustlers and mavericks, people who don’t fit in, not even with one another. I was excited about the day ahead, all the beauty and suffering that awaited.

As we set off into the sunrise, I remembered a conversation I had heard recently between the journalist Ezra Klein and the developmental psychologist Alison Gopnik. We divide our lives between exploiting and exploring, Gopnik suggested. Exploiting is everything we do to extract utility, to earn a paycheck, save for retirement, pay off the mortgage. Exploring is what we do without purpose. I make it sound like she’s merely describing the difference between work and leisure, but it goes deeper than that. Exploiting is how most adults live our lives, constantly in search of achievement, reward, and recognition. Exploring is how young children (and adults on psychedelics) spend their time, exploring the world around them with curiosity, sometimes fantasizing, other times paying focused attention to the small details we take for granted.

The novelist Karl Ove Knausgaard describes this difference of experiencing the world vis a vis his young daughter:

I thought about something Vanja often asked, about why grown-ups never played. She couldn’t grasp that we found it tedious, and the conclusion she drew was that in that case she never wanted to grow up. Life was running around and laughing, playing with long-maned plastic ponies and little Japanese figures with big eyes, swinging on swings, spinning on carousels, climbing in trees, splashing in wading pools and pretending to be a whale, a shark, a fish. Not sitting in a chair reading a newspaper, looking serious. Or, like now, sitting still at a table and talking, with long pauses in between where nothing was said and no one did anything.

You would think that cycling 100 miles is the epitome of exploit, an activity in search of achievement and recognition. But for me, it’s the closest I get to the childlike wonder of fantasizing in the backyard on a lazy summer afternoon. There is no purpose to cycling such long distances, other than moving forward and observing what passes you by. In fact, the reason I train throughout the year is so that I can enjoy such a seemingly long, strenuous activity without pushing myself too far into discomfort.

Or so I thought. It wasn’t even 10am and we had already cycled more than 65 miles. My hamstrings were beginning to tighten at the coffee shop rest stop across from the farmers market in Tomales. I had already eaten a croissant and an energy bar, and now I was munching on a tuna fish sandwich. Typically, after 65 miles of riding I an close to returning home. But I still had another 30 miles to go and the rest of the riders were just over a third of the way done.

Ian, a soft-spoken and chivalrous Brit who has been living in San Francisco for the past 25 years, put his water bottle between his knees while he removed his gloves. Oops! Out squirted an ejaculation of Gatorade into the air and splat on the concrete. Patricia, who is active on Twitter and helps women in Silicon Valley battle the tech sector patriarchy, let out a playful ‘whoa!’ “You’ve already got your #metoo tweet of the ride, Patricia,” I joked with some trepidation, but it was received with the warmth and humor with which I had intended. Cycling long distances entitles both men and women to escape the social taboos that usually cause shame. We blow snot rockets, we fart, we adjust our genitalia as if we were merely sneezing. A recent ride organized by a group of women in Santa Cruz was endearingly called the “kitty crusher” for the genital hardships of an entire day sitting atop a narrow saddle.

Nothing builds solidarity like shared suffering, an esprit de corps. As we continued north toward our next stop, an easy-to-miss taco shack in Occidental, I thought of Sebastian Junger’s book Tribe, about why soldiers return home only to miss war. Against an ideological enemy like the Nazis, war creates purpose. But more than that, it is the experience of overcoming hardship with other human beings, of depending on others for your safety and survival, and the unspoken gratitude that permeates silently when you return unscathed.

A group of cyclists riding together is called a peloton, from the French word for platoon. And that’s how it feels, like a platoon of soldiers or a pack of wolves spreading out in search of something. Our bikes are within inches of each other, sometimes mere centimeters, as we travel 25mph down a country backroad.

We had been cycling for 85 miles and it was just past noon when we arrived to my turnoff, Cazadero Highway. I waved enthusiastically to a chorus of farewells and good lucks. I felt like I was departing from a group of close friends, even though I had only met the majority of the cyclists just six hours earlier.

Grateful for a morning of intense solidarity, now it was time for some solitude. Cazadero Highway was completely shaded by a canopy of old growth redwood, and it felt 15 degrees cooler than the main highway under the midday sun. I pedaled along slowly, contently, listening to the trickle of the creek and the occasional wind blow through the pine needles. Part of exploring is novelty, experiencing something for the first time, trying to understand a new landscape or person or piece of art uncolored by previous experience. This was my first time in Cazadero: cabins perched up on the hill looking over the creek, little kids, pale skinned and dark skinned, all immigrants from one time or another, splashing together in wading pools of the creek, while their parents looked on, segregated by the color of their skin. When I came upon stretches of road that were recently paved, the slick tires of my bicycle rolled along in total silence.

I had another five miles to go until my bed and breakfast, and I became lost in my thoughts. I was thinking about the similarities between exploring on a bicycle and exploring online, or what’s left of exploring online. I was thinking about a book excerpt I had read a few months earlier by James Vlahos about the implications of search transitioning from a list of text-based results on Google.com to a single oracular answer from Alexa or Siri or Cortana. Exploration on the Internet used to be intoxicating; I still remember the miracle of using Google Earth for the first time, zooming in on the planetary marble in space. A curious question would lead to a list of results: magazine articles, blog posts, Wikipedia pages. My time spent online was driven largely by my intentional curiosity.

Around 2014, that began to change. What I read and watched was now based on recommendation, whatever came at me via some social stream or group chat. There was always more to read than time to read it — and the more I read, the less I remembered. On several occasions I would spend an entire Saturday morning reading articles that I had saved throughout the week based on others’ recommendations. Then over lunch, my wife would ask me what I was reading about all morning and I could hardly recall. The most honest answer would have been that I had read a bunch of random and disconnected articles recommended by people I rarely see.

In his article for Wired, Vlahos describes how we’re in the midst of another transition in how we discover information. By next year, it is estimated that half of all searches will be spoken. Kids growing up with Alexa are used to asking it questions and receiving the one answer in response. They are not used to sitting down at a computer, typing in a few keywords, and following a trail of websites about the history of Cazadero, which then leads you serendipitously to more reading about Fort Ross, a 19th century Russian settlement, and then somehow to an entertaining public letter by a Sonoma County Supervisor to the men-only members of exclusive Bohemian Grove.

From 2000 – 2015, the dominant medium of the Internet was hypertext: connected, descriptive, explanatory, and introspective. It was a hell of a lot more interesting, at least to me, than 90s television. But that was just a moment in time. We’re now returning to an oral and visual culture where good looks and charisma are what count: YouTube personalities, Instagram models, and celebrity podcasters. Few people have the time or interest to read texts like this one. And I’m not a talented enough thespian to perform it on YouTube or via podcast. The culture passed by my communication capabilities and I failed to adapt, a useless scribe in the age of the printing press.

Like Neil Postman, I think we underestimate how our culture informs how we experience the world, how technology influences culture, and just how dizzingly fast all three are changing in a very short period of time. The person I am now is only one version of me, embedded in a culture and surrounded by the technology of the day. I would be a different me if I grew up in China, or was born in the 17th century before photography or film. Hell, I was a different me before the smart phone and social media.

I arrived to “downtown” Cazadero, a single block of general store, hardware shop, and Catholic church. At Cazadero Supply, a man in his 60s with a thick mustache and giant hands inflated my tires and sold me an extra tube for my bike as a matter of precaution for the next two days of desolate riding. Across the street I ordered an iced coffee and turkey bacon avocado sandwich at the general store. “I should probably pay the extra dollar for the home-smoked turkey, right?” It wasn’t really a question; it was an invitation for the cashier to talk up the turkey, or describe how often they smoke it. With a blank face, she responded, “it’s up to you.”

I took my sandwich with me and checked into my creek-side cottage at the bed and breakfast. My intention was to read a novel with my tired feet cooling off in the creek. But as soon as I connected my phone to the Internet, I was sucked into an attention black hole of social media and group chats. My body and mind were exhausted and the switching between so many apps on my phone was making me even more tired, but I wasn’t able to put the screen down. Two hours went by until, disgusted with myself, I turned off my phone and went for a late afternoon walk along the creek. During their conversation, Gopnik and Klein observed how it is usually when we are the most tired that it is most difficult to resist our phones, an endless cycle of tiredness and distraction in place of intention and exploration.

Back in my cottage, I kept my phone off for the rest of the night, played a CD by Natalie Cole on the old-school stereo, and read my novel while sipping from a mini bottle of red wine procured from the general store. Everything was perfection.

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