A perspective measured in horizons


The most distant goal you can envision is like the furthest point you can see on the horizon. It might be difficult to reach, but if you commit yourself and get there, you realize it's just a starting point for some further journey.


If I were to try to take stock of my life, I'd say I'm a bit more than 2 horizons from where I was when I graduated high school.

The first leg of that journey was both difficult and chaotic. I didn't have comprehensive goals or even a very strong sense of agency; I was mainly just kind of reacting to different life circumstances, bouncing from one event to the next.

The biggest driver for me at the beginning was money. I was broke and paying for all my own expenses, and I had a girlfriend I wanted to get nice things for. I did ok working in hospital supply chain management before going to college, but it seemed like getting a degree would give me a lot more flexibility and job security, so I went.

Tuition was an added layer of expense on top of everything else, but I could get loans to pay for what I couldn't immediately afford, and I just focused on the present. I kept working while going to school; I learned a lot by switching between theory and direct application, I think. There were a lot of ups and downs in this phase but I also just got a lot of important, foundational life experience that I appreciate more in retrospect than I did at the time.

At the time, I mainly noticed how difficult everything was, and I didn't really have a sense of progress because I didn't have any real goal to measure myself against. Some time around junior year I felt so burnt out and beaten by the demands of constantly working only to shovel all my money into tuition, I started interviewing for full-time programming gigs, hoping I could just get something to pay the bills and drop out.

I got all the way through to final stages of interviewing with one public relations shop in Arlington, VA, but ended up getting turned down in what I thought (at the time) was a truly bizarre way. "You're too talented," they said, "you'll just get bored here. You're going to end up at Google or something."

At the time, that was really frustrating to me to hear. In my mind I thought: "I'm unhappy now; I need a way out of this mess, I can't just keep plugging away for years without any guarantee it'll just work out." I didn't understand why everyone just kept blindly pushing forward when it didn't seem like anything ever changed on its own. I felt like a lot of people's high hopes and aspirations amounted to magical thinking.

From 2012 through 2015 I tried to kill myself 3 different times. I didn't know how to anchor myself with hopes for a better future—to some extent, I still don't, and I think that's part of why I focus on working to improve things. I was empirically bad at suicide, though, and I was pretty good at the coding thing, so I kept up with that for a bit.

At some point towards the very end of college, I was googling a lot of programming terms for both school and work, and a coding challenge appeared within the Google search screen. I got into it, completed some problems, eventually it asked for contact info to be passed to a recruiter. That was how I got my Google internship, which paid more money than I was hoping to make full-time just 8 months prior.

That summer was great. I connected with both the full-time staff and the other interns; I had fun; I did some interesting work; I got paid.

I got a full-time return offer, negotiated it up, and when I graduated I moved to a new apartment in Manhattan. At that point, I probably had everything I could have ever envisioned myself having just 4 years prior—maybe even a bit more.

That point was a hill-top on the horizon from the perspective of where I began. From there, I would have surprised an earlier version of myself, because I did what we all have to do; I did what we're all always doing, consciously or not.

I asked myself: "Ok, what do I do now?"


A Certain Kind of Eden

It seems like you could, but you can’t go back and pull
the roots and runners and replant.
It’s all too deep for that.
You’ve overprized intention,
have mistaken any bent you’re given
for control. You thought you chose
the bean and chose the soil.
You even thought you abandoned
one or two gardens. But those things
keep growing where we put them—
if we put them at all.
A certain kind of Eden holds us thrall.
Even the one vine that tendrils out alone
in time turns on its own impulse,
twisting back down its upward course
a strong and then a stronger rope,
the greenest saddest strongest
kind of hope.

poem from Flamingo Watching (1994) by Kay Ryan


It might sound strange, but people accomplish a shocking amount without ever really meaning to.

In fact, I'm not sure our society could function without that.

Where would we actually be if every important breakthrough in technology required someone to pursuse that field single-mindedly from childhood, determining the topic of their dissertation while still in middle school? What if important novels could only be written by someone who had spent at least 15 years writing professionally, carefully honing their craft in magazine pieces for more than a decade?

I think what's much more common is something similar to the route that I took: people have some early reason to believe they're kinda sorta good at something, they practice it and get better over time, and career advancement becomes an iterative process. At some point, you look around, and you think "huh, I guess I made it here".

After reaching their own horizon points, a lot of people talk about experiencing some sort of metaphysical vertigo. It's weird to suddenly reach some summit when you only started on a trail that looked promising; you never meant to climb the mountain, you were just too stubborn to quit mid-way through.

People who say such things are over-prizing intention, though. The important question has nothing to do with what we intended or anything else about the past; the important question is not backwards looking; the important question is "what do I do now?" and we give some kind of answer to it every day, whether we want to or not.


“Let me give you some advice, Captain,” he said.

“Yes, sir?”

“It may help you make some sense of the world.”


“I believe you find life such a problem because you think there are the good people and the bad people,” said the man. “You’re wrong, of course. There are, always and only, the bad people, but some of them are on opposite sides.”


“Down there,” he said, “are people who will follow any dragon, worship any god, ignore any iniquity. All out of a kind of humdrum, everyday badness. Not the really high, creative loathesomeness of the great sinners, but a sort of mass-produced darkness of the soul. Sin, you might say, without a trace of originality. They accept evil not because they say yes, but because they don’t say no."


Vimes paused at the door.

“Do you believe all that, sir?” he said. “About the endless evil and the sheer blackness?”

“Indeed, indeed,” said the Patrician, turning over the page. “It is the only logical conclusion.”

“But you get out of bed every morning, sir?”

“Hmm? Yes? What is your point?”

“I’d just like to know why, sir.”

“Oh, do go away, Vimes. There’s a good fellow.”

Excerpt from Guards! Guards! (1989) by Terry Pratchett.


Upon becoming a vaunted Google Software Engineer, my life was not immediately replaced with one of joy. I think some part of me vaguely expected it would be — and I want to softly chide my past self for the sense of disillusionment that came over me after that, but these emotional journeys are the substance of our lives.

What came next was actually more similar to what came before than I ever would have expected.

I iterated.

I tried different hobbies, met different people, and generally just kinda flailed about, hoping I would bump into some deeper meaning I could anchor my life to. I had some interesting experiences at this point and there were definitely some real adventures mixed in, but the important thing was that I started to figure out what was bothering me.

Despite being very aware that I had (for the moment at least) stepped into some rarefied world, I did not find myself deeply impressed by of lot of my fellow Manhattanites. Whether at work or elsewhere, a lot of the people I was meeting were quite successful within their fields, but they didn't seem to feel that way—at the very least, they didn't seem to feel any obligation to others.

Having started my adult life working in a hospital, I was a bit surprised by this outlook. The baseline there was that every day on the job you had some part in a very immediate struggle of life vs. death; many people then went much further, with rich lives filled with art projects and volunteer efforts, very consciously trying to make the world a better place in whatever way was possible.

Finding myself deep within the young professional crowd for the first time, I couldn't help noticing how many people seemed to be doing so much less in their lives than the hospital folk, despite having so much more to work with. And it was "more" of everything, really — more money, more resources, more connections, probably even more time.[1]

A further surprise: most of the people in my new peer group didn't seem particularly happy, either. I begain to wonder if freedom from constraint wasn't all that important, if fulfillment came from actually fulfilling some external purpose.

A working hypothesis emerged for me that living for myself would not, in the final analysis, be a kindness to myself. I had to find something larger to connect myself to.

At some point I started actively thinking about how to build community. It started with really small things, like always going to the same bars and restaraunts—not just because I liked them but because I was aware that my support was important to them. It grew into bigger things, like starting The American Leadership Foundation.

The process of shifting my focus outwards brought me a surprising amount of clarity. I'm still ambivalent about trying to build a happy future for myself, but I'm deeply passionate about building a happy future for those that I care about, and that drive got me to similar places: trying to be careful about saving money, developing skillsets I know will be useful later, trying to build a network instead of burning bridges, etc. I never had an interest in self-improvement for my own sake, but I seized upon it for others' as I realized how inextricably linked my life was with theirs.

I also found myself becoming more competitive, which I wouldn't have necessarily expected. I still don't really care about "winning" most things, but I accept that's how certain parts of life are structured, and I really don't like some of the people who will be set up to win by default.

In short, I started to really give a damn about something bigger than myself, and that led me to being a better version of myself. The experiences I gained in that process pushed me further into my career and into more interesting places than I ever would have imagined my first year in New York.

Now I'm an executive at a venture-backed start-up, and the chairman of a scholarship foundation I founded. Said like that, my life sounds very impressive, but the truth is that these things are small right now, almost nascent. What I find meaning in is the opportunity.

Every day I work to try to make these things as real in the world as they are to me, and an increasing number of people believe I can do just that.

After walking for 2 horizons, I finally really know what I'm doing with my now, and what I will be doing for the foreseeable future.

Sometimes I wonder a bit: what comes next?

Something that's new, though: I'm actually kind of excited to find out.


I was talking to Kris Abdelmessih about mentoring recently, and the conversation ended up nudging against a question we've asked in board meetings for the A.L.F.

What is our goal in mentoring?

The official answer for the A.L.F. is something we haven't quite boiled down yet, but we generally goal on getting grant recipients to the point where they can contribute back to the foundation. We don't have any expectations or assumptions that they'll do so (we are a charity, after all), but it seems like a good goal because it requires the mentees to be both successful and have good feelings about us.

Personally, though, I think my way of thinking about it has shifted a bit recently.

I want to help the mentees to hit their own first horizon points as fast as possible, and then I want them to just keep moving.

In the same way that hitting your first horizon point is hard, it's easy to get stuck once you've made it there. It's always easy for us to feel sorry for ourselves, to feel like we can't do more or grow further or otherwise adapt or change; it's easy to feel like that no matter who you are or what stage of life you're in.

It's also easy to use up all your self-belief if you don't feel like anyone ever believed in you.

I'd like my mentees to feel enough sense of agency to keep pushing no matter what. Because that's something I feel like I can really see now, even if I couldn't before: effort matters. Things can be changed.

The whole world can be changed, it just takes work.

And I believe in the A.L.F. grant recipients, both because of who they are (as we see even in the selection process), and also because of how arbitrary the starting point for so much of the world is. They don't need a master plan for how to fix the world's problems, they just need to show up, care a lot, and try real hard.

That's all any of us need to do.

  1. A 12.5 hour nursing shift is just a starting point — hand-off can add up to 2-3 hours onto that for a full unit. ↩︎