The Stopover

Journal entry from the first three weeks of my #MessinaOdyssey

It’s 5am and I’m heading back to San Francisco as a stopover on my way to Redmond, Oregon, where I’ll continue on to Bend. I’ve got 5 hours and 20 minutes of Airplane Mode to nail down my TEDx talk. The good news is that I feel pretty good and rested (went to bed by 10pm last night in Newark and it’s 11am in Lisbon, so I feel like I have more wind in my sails, even though my body has no idea what time it is). I know I have a lot to work out, but I have the pieces, I just need to cut this thing down and focus on my core message. Perhaps I’m getting confused with AI and voice computing and just need to focus on makers of the next generation of social technology (i.e. “conversational computing”), which will eventually be in everything (like how everything is mediated through the smartphone today)… Hmm, that’s a useful angle.

Anyway, I was contemplating this idea that I’m flying to San Francisco not to go home, but en route to someplace else. There are people waking up there today who consider San Francisco their home, and that was me for 14 years. But it is no longer me. And so when I think about the feelings of relief and comfort that I used to get whenever I was finally flying back to San Francisco, I miss them. I miss them now, while we’re taxiing. I don’t have a place that offers that anymore, except perhaps in myself, and with the people I love.

I realize I haven’t been gone a month, but just over three weeks in and it does feel like I’m looking at the city from the stern of a ship, chugging in the opposite direction, miles off shore, as the cityscape grows smaller and more miniature on the horizon.

It’s funny to think of San Francisco as a small place because when I was there I knew its bigness. It took about a decade to fit the entire geography in my mind so I could calculate travel times and routes to avoid in my head, especially when biking or on foot, in order to avoid climbing one of the city’s seven never-ending mountainous hills. I had a rough color-coded spaghetti map of all the destinations where the unfortunately-named BART subway system ran and had familiarized myself with some of the more useful cross-town bus lines which once intimidated me with their overlapping express routes and transfers. This maze of conveyances eventually became my capillary chariot between far-flung neighborhoods in which I built my momentary nests.

With this stopover, I’m reflecting on my former self: who was this person that called San Francisco his port of call, and what was he up to for a third of his life? Visions rain out of my mind like a stack of toppled, forgotten Polaroids, recalling not-yet-faded memories of people and friends, drama and elation, struggle and success, coffee stained cafe mornings, blurry nights and craft cocktails, and yellowed blue skies in the fall and gusty frigid foggy summer days.

And yet, I feel at peace with my decision to depart into the unknown, knowing that I lived in San Francisco well, and we both bore witness to each other’s scuffles with compromise and self-identity. Perhaps that’s the stage we’re both in right now, which is why we have to separate… For me to continue growing into who I need to be, I need to give myself space away from who I think I know myself to be — which is a person buttressed, but also lashed down, by San Francisco.

And San Francisco needs space from me, in order to become what she has been becoming for the last several years. Without this distance, we won’t be able to see each other clearly, as settled into our new skins, because our internal definitions are too wrapped in anticipation of (or anxiety about) how the other needs us to be. In other words, for each of us to have the freedom to be all of (or none of) the way the other sees us, we must let go of all expectations and see where the chips fall, wherever they may.

In this releasing, it’s not so much about losing what was, but about allowing for what is.

We are both two of a kind: refuge for lost and wayward souls, providing space and validation for those who question; and yet we are of that kind too, wayward and constantly seeking; our shelter is within.

It is not love unless it is generous, and we’ve both been generous with each other. This next chapter is about also being generous to ourselves and to shed those layers grown stale as an act of self-definition and exfoliation.

I may one day return to San Francisco, perhaps to stay. Or I may not. Neither of us begrudges the other for pursuing this needful period of sublimation, nor should the chrysalis resent the caterpillar when it emerges with wings and finds flight for the first time.

Chris eventually reads every response on Medium or you can chat him up on Twitter, send him an email, or subscribe to his seldom email newsletter. Do let him know what you think.

Special thanks to Renee Ya for her editing support.

Inventor of the hashtag. Ever-curious product designer and technologist. Previously: Google, Uber, Molly (YC W18).

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