To a Pilot, with Love

Peterson Conway
8 min readJul 17, 2023

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The two towers looked like metronomes tethered and put to rest. The far end disappeared like time into an unknown whiteness

To a Pilot, with Love

It was her first birthday we would celebrate together — the relationship not yet a year old — so a certain measure would be taken of it. The month prior she organized a trip to Sun Valley, planting a flag it seemed, as we celebrated my own. We traveled easily and its simplicity opened to an expanse new lovers find easy to fill.

So when it came my turn, I remembered the old saying: where you put your time is a good indication of what’s important to you. This birthday was meant to say I had a plan. Sun Valley may have required of us only hiking boots and change of clothes for dinner, but for her birthday, I was taking her to the mountains of my childhood and I would pull out all the stops.

“Ask her to marry you!” a rugged, if not whimsical friend urged.

Smugglers, Monastics and Yogis

We departed off a small airstrip among the vineyards of Sonoma. My mother and her childhood sweetheart, engaged 50 years ago that same Saturday, drove us down the eucalyptus lined road after brunch to see us off. Our destination was a remote monastery deep in the coastal range of California.

I had the childhood of parents that were smugglers, monastics and alternating yogis. It was colorful if not exactly planned out. That kids tend to be reactionary to their parents and upbringing, it should be of no surprise I turned out to be a pretty boring bean counter.

“Honey, I’ve landed planes on aircraft carriers and briefed two Presidents” I joked. “I can make those trees”. Hundred foot obstacles loomed at the departure end of the small runway. Kelsey seem to be understanding my need to both calculate and overstate the extremes. She preferred simplicity.

On an early date Kelsey shared a private wish she had, to volunteer in the hospice care of elderly monks. “Ram Das said that all we are are doing is walking one another home” she said. I shook my head, waving off these thoughts together with the trees, and went full power.

We cleared the obstacles without problem and climbed through the edge of a lingering marine layer just off the Marin Headlands. At 1500' I called up Oakland Center. The fog ebbed, the city appeared, and our radios came to life:

“N24201 you are cleared through the San Francisco Class Bravo Airspace. Remain west of the Golden Gate Bridge and west of the Woodside VOR”.

A half enshrouded bridge seemed to connect land to the heavens.

“Everything has a lifespan” Kelsey said looking outside her window. “The Buddhist say that every day we must contemplate our own death.” She had a way of the taking the infinite and putting it your hand like a single drop of rain. What might seem dark to others was mischievous and ever more valuable to her. “Let the fact that you could die right now determine what you do next” she said, cracking a smile.

We passed overhead the bridge midspan, low enough to see a crew on the north tower. I wondered if it was true that the painting of the bridge was a continuous cycle, and that the workers below would just turn around and start again at the beginning. If this took a year, I thought, the bridge could be seen as a horizontal measure of time.

“A friend is leaving us his open-top jeep for the last stretch” I said, disclosing the next leg of the trip. “It’s at the airport. No better way than to experience those mountains.”

Language is our Homeland

We set our course south down the coast. Our radios grew quiet. Kelsey seemed pensive. I was glad to be rid of the communication load of the Bravo airspace, so I steered us out just over the water and pulled back our power. Kelsey opened a book she had on her lap, a collection of poetry called “Little Things” by Julia Carney.

“Language is the only homeland” she read out loud. I thought about this as the engine whirred and the sea extended off our right side, to a concluding white line separating two blues. Beyond the reach of radar, and left to our own comms and navigation, I felt that familiar loneliness that comes with freedom.

Planning is not my strength. This weekend would require multiple cars, mostly on account of taking a plane, which we didn’t really need. We would be dependent on others, and if truth be told, I was chasing ideas of how things should go as much as I was chasing how things were in the past. I never thought to ask Kelsey what she might want. I had spent much of my childhood in and around those mountains and was now building up expectations. Compared to her well planned trip on my behalf a few weeks earlier, this was starting to look like a Roosevelt safari to East Africa. All in the name of visiting a monastery.

“For everything thing you have done before and want to show me, I want to do at least one new thing neither one of us has done” she said, as if giving me a pass already.

Too Much Freedom Is Imprisonment

Ravaged by succession of wildfires and closed officially since 2019 from the pandemic, our destination was even harder to get to than usual. Tassajara is owned and operated by the San Francisco Zen Center. It’s the strictest monastery outside of Japan, and I had built up much expectation, telling Kelsey we had a rare personal invitation to join the skeletal resident community keeping the place going. It‘s only about 10 miles from Big Sur, but over 4 hours by car — the last hour of which is on a road that is closed more often than it is open. I thought I would use the plane to shorten the trip. “I think it’s just because you want to fly” Kelsey said, knowing that I was complicating an already ambitious trip.

A Bad Plan is Better Than No Plan at All

There is no tragedy in this story, no lesson to add to your checklist. We landed south of Monterey and transferred our bags, cooler and the dog to the jeep. I wrapped Kelsey up in a blanket — it was now afternoon — and we started the two hour drive into the mountains. By this point I could tell I had a plan with too many moving parts. And I was slipping, still trying to make everything perfect.

We reached the summit of the dirt road. Seven miles to go, all downhill. Tassajara sits in a remote and nameless valley, its closest neighbor known simply as Lost Valley. The Ohlone word means “a good place to store meat” a fact probably lost on the vegetarian practice of the monks. But heaven bless their bread!

“All languages are my love languages” Kelsey offered, as if at first hesitating. We looked out upon the succession of ridges separating us from the sea. The jeep sat ticking, and momentarily we were still. “Touch, time, gifts, language — they all have a place”, she continued. “But the greatest gift you can bestow on a friend is laughter. After that, it’s time. Like just sitting with someone.” She waited, perhaps letting that sink in, before asking: “When was the last time someone just sat with you?”

I started the jeep back up . We may have looked the part of safari with the canvas bags piled up, but now we were just dusty and uncomfortable. Kelsey suffered through it gracefully, pointing out the yucca stalks and the soaring raptors that seem to be following us along the ridge line.

Eventually we came to a rolling stop at the gates of the monastery. The monks had left them open with a small sign that said Peterson/Kelsey Stone 3, a reference to our assigned cabin. The sun was setting early on account of a valley that didn’t run east to west, but pitched a dog leg at the hot springs. This gave the collection of buildings a crowded and dark feel. We respectfully bowed to the shuffling monks, finding our room the last on the banks of the stream.

What’s wrong, Kelsey asked. She could tell I had set about to the mental accounting, adding up what was in front of us versus what I had perhaps envisioned. “Relax. It’s just the comparative mind”, Kelsey said, trying to return me to the present. “Plan your work and work your plan” my mother’s voice went in my head.

I now think the best plans are written together. Milan Kundera said this in the form of music: “When we are young, we write one another into each other’s musical compositions. But as we get older, those compositions are more or less complete”. Relationships need moats. Plans are their drawbridges. Asking questions like, how will this affect us? What kind of experience are we seeking to have? Will it bring us closer?

The tradeoff of spontaneity versus plan is also part of the plan. We agree that there will be surprises. “All attempts to limit connection will succeed” my own Zen teacher used to say. If communication is our homeland, it is also our defense. Who gets let in? What does each opportunity mean as we seek to just be with one another?

Tassajara in its dormant state reminded me of a bridge that needed constant painting. The elements relentless, the cycles ever upon us. I had to let go of seeing it in the magic of childhood and accept that it too would change.

Why fool ourselves with a plan, I asked Kelsey, frustrated. Isn’t life just a messy thing?

She put her feet in the cold creek, and threw a stone into the shallows. As if considering my question through spreading rings, she answered. “Perhaps, but starting off with a plan is to start off together at least. A bad plan is better than no plan at all.”

A month later she would be pregnant.

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Peterson Conway
Peterson Conway

Written by Peterson Conway

I'm a pilot, writer and headhunter. I build the early teams of companies commonly associated with the so-called PayPal mafia.

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