Why Am I Doing This?

Today in crabs.

The day I asked my wife to marry me, I didn’t wake up knowing that’s what would happen that day. If I could travel back in time to the year 2000 and meet myself five minutes before I proposed, young me would have been very surprised to learn that in six minutes he would be engaged. Not as surprised as he would have been to learn what was going to happen the following year, I guess. Actually this isn’t a great hypothetical now that I think it through. Let’s move on.

A number of people have asked me some version of: “Why would you leave a lovely family and a perfectly comfortable home (“a modest two-story fixer-upper,” raves the New York Times) to traverse the east coast by foot for half a year, climbing every mountain along the way?” In order to answer that question I need to share a piece of personal lore that may at first seem unrelated, but I promise I’m going somewhere with it.

The day we got engaged we were in Europe, me and my future wife, touring Schloss Nymphenberg in Munich. Her parents are both originally German, though they met and settled in New York state, where Christina grew up. We were picking them up in Munich and then meeting her older siblings in Südtirol, the German speaking part of the Italian Alps. I’m sure there are many people who knew there was a German speaking part of the Italian Alps, but I wasn’t one of them until that trip, nor did I know there was a particularly German definition of “hiking” that involved eating a lot of bread and cold cuts and then walking a couple kilometers uphill to an alm where you were served even more bread and cold cuts, along with heaps of wurst and shots of the most potent homemade kirsch imaginable. They uncorked that schnapps bottle and we could smell it across two hundred meters of edelweiss.

But all that hadn’t happened yet. It was early August and hot and we were both dusty from wandering around the gardens of Nymphenberg, killing time in Munich before we met her parents to drive south into the mountains. I had a headache and wanted an iced coffee, so we went to the overpriced tourist cafe, which was… a tourist cafe at a Munich castle. It was fine. I got a coffee and we sat at a wire patio table. Midafternoon and the place was nearly empty. We were minutes from getting engaged. We chatted a bit. Seconds from getting engaged. Neither of us knew it yet.

In a way though, we both knew it already. We had talked about getting married in general terms. I mean we’d talked about getting married to each other, so the terms weren’t all that general. No one had said “will you” but we were in agreement that it would happen at some point. We were both eighteen when we met, freshman year of college. We lived in the same dorm, her hall was directly below mine. At a freshman mixer before classes even started I was charmed by her Doc Maartens and her long blonde hair and her glamorous stories of backpacking across Europe alone and seeing Green Day at Woodstock ‘94. She remembered a good joke I made in the game of Train Wreck at that mixer, but it wasn’t until we’d been married for more than a decade that she realized it was me who’d made it. I had to work a little harder to capture her attention than she did to capture mine.

In the six years that elapsed between the freshman mixer and that afternoon in the Schloss Nymphenburg cafe we had been together for one and half years, then not officially together for about three years because I was a callow little shit who didn’t know what I wanted, and then back together for another year and a half. In all that time, though, neither of us was closer to another person than we were to each other. We knew we would be together because we’d tried being apart and it didn’t work. That day the conversation turned to the German relatives I would soon meet for the first time, and Christina said “It doesn’t feel right introducing you as ‘my boyfriend.’ It sounds too casual for our actual relationship.”

This was the moment. I know I’m going to ask her soon, I thought, if not now then when? I have no plan, no ring, but we’re in Europe! That’s inherently romantic. We would probably want to buy the ring together anyway. And this is maybe the best conversational opening I’m ever going to get. This is the moment, just do it.

“You could call me your fiancée,” I said.

“Ha ha—” she said, than she looked at my face, and said “Oh!”

I think I said the actual words, then, will you marry me. And I think she said yes. But that part of the memory is fuzzy. What I really remember is: “ha ha… oh!” Her sudden realization that I was serious mirrored my sudden realization that this was the moment, that it had arrived seemingly out of nowhere on a day that didn’t begin with any portentous signs or omens. We secretly bought some champagne and told her parents we were engaged a few days later, in Tirol, and her father cried. Her mother told me that the first time she met me she didn’t like me, but that she liked me now. We bought a handmade engagement ring from a tiny jeweler’s shop in a side alley in Venice.

The point of this long anecdote with only the flimsiest connection to hiking is that I believe that life is essentially arbitrary, and the only trick to it is being in the right place at the right time. But no one knows what the right time will be, so you just have to find the right place and wait, staying alert for the right time to present itself.

What is the purpose of a marriage proposal? Firstly, of course, to ask the question “will you marry me?” and receive an answer. But secondly to have a charming memory and a good story to tell about an event that, whatever the outcome, divides life into a before and an after. Christina has always been a combination of amused and annoyed that the way we got engaged makes such a charming story, despite my seeming lack of preparation. But I’d been preparing for six years. I was so prepared that when the opportunity presented itself, I was able to recognize it, and I didn’t need to think about it. I could just take it.

The most truthful answer to the question of why I’m doing this hike is: I saw the opportunity, and I took it. I’ve been personally and professionally restless lately. The A.T. has lurked in my imagination for decades. Mica is the only person I think I could hike the whole trail with, and he happened to be graduating college at the right time to start southbound. I happen to have the kind of job that I could just decide to take six months off from. The kind of job I can plausibly hope to do a version of on the trail.

I can post hoc you a lot of propter hoc, and I will. But the most honest reason is that I saw the necessary pieces come into the correct alignment. It didn’t feel like making a decision, it felt like recognizing what was going to happen. The only questions I asked myself were all aimed at determining whether this recognition was correct, whether it truly was possible for Mica and I to attempt this now. I didn’t really even wonder why.

In his seminal work about one of antiquity’s greatest hikers, The Myth of Sisyphus, Camus writes of a different major life decision: “An act like this is prepared within the silence of the heart, as is a great work of art. The man himself is ignorant of it.” He’s not talking about marriage proposals or through-hiking, but important decisions are all similar. The decision to attempt this hike was prepared within the silence of my heart, during a lifetime spent in love with the outdoors. I know this isn’t a very satisfying answer, but it’s the truth, and if I can’t be completely honest what are we even doing here?

On our last practice hike, Mica told me “I just realized that you’re doing this instead of having a mid-life crisis.” I said that was a very generous way of expressing it, but he’s not wrong. I’m in mid-life, and I’m not in crisis. I think what I’m having is a mid-life opportunity.

An insightful reader asked a different but related question:

“Is this going to be some kind of limp stand-in for a proper pilgrimage? If so, you'll need a goal. A destination. Let's hear about your victory conditions. Like Hunter S. Thompson once wrote: ‘Have an objective to give your bender a theme. For instance, stalking and killing a wild pig with a bowie knife.’“

Victory conditions! This is a much easier question, because once I laid my heart open to the necessity of this absurd project, I have thought a great deal about what I want to achieve by it. My victory conditions, the themes for this particular bender, are four-fold:

1. Hike the Whole Trail

I told Christina I was going to write about what I wanted to accomplish on this hike, and she immediately said: “well first to finish the trail, obviously.” I hadn’t actually thought of that one myself, so I guess this is my version of “what do 2 and 7 have in common?” But yes, I would like to hike the whole Appalachian Trail, as near as that is possible. That’s a good, measurable goal to start with. Begin at the beginning and put one foot in front of another until the end.

2. Decarcinization: Personal

Our house is small, so for many years while the kids were little I rented an office in Portland to work at. But in the first couple years of the pandemic I didn’t use it enough to justify the cost, and then the kids were older and generally off at school all day. So I let the office lease expire, and I got into the habit of working at home. For a while I went to Portland a couple days a week to go to the gym, but then that gym closed. Now I use the tiny gym on the island. It’s convenient, but I’m always alone there too.

I have worked remotely for decades, but I used to have co-workers. We would Zoom, we would collaborate on things. For several years I traveled to New York for a few days almost every month and worked on-site at TV studios installing servers and training staff how to use our software. I had to talk to people every day. Then we moved the software to the cloud, and I didn’t have to travel anymore. Then I left that job entirely and started writing Tabs. I don’t regret starting Tabs again, but it has been very isolating in some ways that I haven’t really dealt with.

I used to crew on my best friend’s sailboat for his club’s Wednesday night races—another casualty of the first years of the pandemic, and the following years of him raising two young sons. I used to be involved in local politics. I used to see my friends more. Now I only talk to the friends in my pocket computer.

I think this is common, people get older and our social horizon shrinks. For me it was underway already, but the pandemic and then changing jobs from engineering manager to newsletter writer really accelerated it. I write at a little desk in my bedroom, and when people ask what my work day is like I tell them I spend eighteen hours a day in one small room, like I’m in prison. It’s a joke but it’s also not entirely a joke.

I feel like a crab whose shell is getting too tight. I need to molt, and expose my vulnerable blue limbs to the hostile environment for a while. I need to grow a bigger shell, or maybe just find a way to live without a shell. There isn’t a specific endpoint to this one, I just need to be out in the world again for a time, and see what happens. At the very least, I hope to meet some of the friends from my pocket computer.

3. Decarcinization: Creative

I love writing Tabs, but it takes all of my creative energy. From one perspective, this is a good thing—at least I’m actually using all of my creative energy. I’ve been a writer off and on for my whole life, but without a meaningful deadline I’m lazy. I will usually not force myself to perform the drudgery of putting one word after another. In Tabs I found a form of writing so compelling that I would procrastinate on other things to do it, and in return it has given me approximately one million words of writing practice1 and its readers have given me a good living.

But I find myself wondering if there’s more I could be doing. The internet feels small now too, like another shell that’s grown too tight. What else might I be writing, if I weren’t writing Tabs? From a professional perspective, the hike is an engine to generate material for this newsletter, where we will learn the answer to that question together, I hope.

4. I Love My Large Adult Son

An aspect of family life that I don’t think gets enough attention is how difficult it can be to make the transition from parent and child to two adults in an grownup relationship, and how much intentionality that takes on both sides. My kids are incredibly cool and delightful people. I want to be friends with them when they’re grown up, and Mica is the first to reach that point. So I want this trip together to become a foundation for both of us on which we can build a new relationship as adult friends. I want to be there for some of his first steps out into the world, and I want him to see me struggle and fail and get up and try again. I want to help him along and I want him to see how much he helps me along. If this is the only one of these four goals I manage to accomplish, it would be more than worth it.

We leave for Millinocket this coming Sunday, the 30th. I will have one more post for you Wednesday, and I hope one cued up for Sunday, but after that I think I’m going to leave a gap for the first two weeks, as we climb Katahdin and hike the hundred mile wilderness.

Thank you so much for joining me through all of this meandering scene-setting. Have you liked the newsletter so far? I mean, let’s face it, you’re down here at the very bottom reading the paid membership pitch, so I think we both know the answer to that. Please join at one of our trail-themed paid tiers to ensure you receive all the rest of it.


1  This is legitimately my best estimate for how many words of Tabs there have been in the combined six years of its first and second runs, which is kind of mind-boggling. That’s like, ten novels worth? I feel like I should be better at this by now, tbh.

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