Fifty-Year
Friends

Fifty-Year Friends

For two weeks this summer I went rafting on a river in Alaska. Fully off grid! No phone, no calendar.

Being off grid for two weeks coming from SF social life was more impactful than I expected, and I want to record my reflections. I’ve done various off grid experiences (meditation retreats, burning mans) before, but this one felt different.

In short: the depth and slowness that I felt was really inspirational, and I want to bring more of it to my daily life. On one hand, this is quite cliche, I hesitated to even spill ink on the topic. But hey, it’s cliche for a reason, so here we are.

If anything, a piece of advice earns its way into cliche status by being true for basically everyone, all the time, in a way nobody manages to resolve. So here I am, journaling about depth, with an embarrassing amount of sincerity.

The reading came back

I have wanted to read more for several years. My journal entries are laden with grief of books unfinished (or worse, unstarted).

I’d been carrying around a low-grade fear that I had actually broken something, that years of phones and frantic startup life and half-attention had done real damage to my ability to sit with a book, and that getting it back would be a long, effortful rehabilitation project.

On the river, I read voraciously, and effortlessly! Not dutifully, not as part of a self-improvement program. I fell into books the way I remember falling into books as a kid, where you look up and it’s dark out and you’re annoyed about it.

I read:

1. Dungeon Crawler Carl
2. That will Never Work (founding story of Netflix)
3. Endurance: Shackleton’s Incredible Voyage (incredible book, and also made it very hard to complain about minor inconveniences on a raft trip!)
4. Into the Wild
5. 70% of Slaughterhouse Five (plotline jumping got too excessive for me)
6. Misc essays from Substack

I was shocked with how easy it was. I loaded up my Kindle before leaving, which usually collects dust beside my bed, and within a day or two, I was really immersed. Even books I had struggled to get into during normal life I would suddenly find myself halfway through. The acclimation to “books are the most stimulating thing available, let’s just read non stop” happened much faster than I expected. It won’t be easy, but I am going to aggressively audit my SF lifestyle to bring this sort of low stimulus environment into my day to day. 

So — that was a relief. It also turned out to be the smaller of the two things I noticed out there.

The fifty-year friends

I was traveling with a group of people around seventy years old, most of whom have known each other for close to fifty years. Most met in high school. Some are married to each other, some are siblings, some are just friends. They live mostly around Chicago.

They have had full, complicated, meandering lives. Lots of fireside stories of love, divorce, career wins and losses, etc. Real life stuff! And somehow they are still here, together, on a river in Alaska, laughing together, telling the same story for the umpteenth time.

One of my larger frustrations with the SF social scene is the lack of age diversity. There’s minimal exposure to older people, and very little “respecting the wisdom of the elders”. In startup culture especially, youth is heavily prized. Disrupt! Subvert the old ways of doing things! New is always better! Which, okay, you certainly get somewhere with that mentality, but you lose a lot too.

Floating slowly down the river, surrounded by this wise and elderly friend group, I was inspired to build more “fifty year connection” community.

There’s a line on the internet about optimizing for the number of people who come to your funeral. I don’t love turning something sacred into a metric. But there’s a real thing underneath it, and I’d put it the other way around: not how many people show up at the end, but who am I building a life with now, such that showing up for each other later would be obvious?

The same appetite

At some point I realized this is all part of the same puzzle: a life of depth and thoughtful contemplation, deep connection over small talk at parties. Which, again, is painfully cliche, and yet it seems like so many of us continue to struggle with it.

The reading and the fifty-year friendships are the same appetite pointed at different things. Depth in reading is what it feels like to disappear into a novel and look up hours later. Depth in relationships, sustained across decades, is what those seventy-year-olds have with each other. Both just ask you to actually stay: to not leave the moment something newer and lighter shows up. Resist the impulse! 

So the thing I came home wanting is to be a fifty-year friend. To be the one who remembers, who checks in when there’s no occasion, who notices the version of you that’s arriving and gets curious about it instead of holding you to the version I met. It’s difficult at times: following up, showing up, saying the slightly-too-sincere thing — and I want to be much better at it than I am. I’ve lately become fond of the quote: “everyone wants a village, no one wants to be a villager”. Perhaps this essay is a bit of declaring my desire for villager status ❤️.

Integration into daily life

The honest difficulty is that in Alaska, the distractions were removed for me. That was the whole trick. Depth appeared for free because the shallow option was physically unavailable.

At home, nobody removes anything. It has to be chosen, repeatedly, against a default environment that is extremely good at filling the space. And if you never stop to plan, the default environment quietly becomes your life philosophy.

So the work is structural, not inspirational. Protect silence on purpose. Keep the books within reach. Build recurring things — the annual trip, the standing walk, the dinner that happens whether or not it’s convenient. Actually follow up. And pause, at whatever cadence, to ask the stupidly simple question: I said this mattered — am I doing it? If not, do I change the behavior or change the goal?

Mary Oliver asks what you plan to do with your one wild and precious life. I thought about that line a lot out there, mostly while being cold.

Part of my answer is people. The ones I already have, and the fifty years I’d like to spend earning them.