RPC3

Four years running a scholarship foundation

R Phillip Castagna — Mon, 01 Jan 2024 11:11:00 GMT

Introduction

For anyone reading this who doesn’t know me personally: hi, my name is Phillip. Most of my friends call me RPC, and if you want to be my friend then that’s something you can do too.

I’m the founder and chairman of the American Leadership Foundation, a 501(c)(3) nonprofit that issues scholarship grants and provides ongoing mentoring support to students graduating from large public high schools.

I filed the paperwork to incorporate the ALF in September of 2019, which is just over four years ago now. Building and running the foundation has been a big journey, and I feel like I’ve learned along the way; I have some hope that I’ll be able to share some of those lessons here in a way that people find useful.

More than that, though, running the foundation has proven to be important to me in a way that is hard to summarize, and I have some hope that people who read about the experience might find something in it thought-provoking.

When I filed that paperwork in September of 2019, I was 25 years old — which now strikes me as preposterously young. I could list any number of things that I might have focused on instead, not the least of which would have been my career and personal savings. I definitely wasn’t “ready” in the way that people talk about these things; I had no experience starting an organization like this, non-profit or otherwise. Everything involved in running the ALF ended up being an area of growth for me, and I’m deeply grateful for that.

There’s this quote from Garson Kanin^[1] that I think about a lot:

When art critics get together they talk about content, style, trend and meaning, but when painters get together they talk about where can you get the best turpentine.

It’s one of those vague-but-pithy framings that people use to say all kinds of things, but I like to read it as a comment about what we choose to focus on. There are all kinds of intellectual exercises you can dive into as part of your desire to better appreciate art, but the actual business of creating largely deals with concrete, definite problems. It’s surprisingly easy to get caught up in the former and not realize you’re neglecting the latter; you need to find an outlet through which you actually make contact with the world and face the challenges of reality.

For me, the ALF has been that outlet and more. Working to build the foundation has been both humbling and inspiring, and it’s brought me tremendous clarity. I don’t worry about finding meaning in my life because I don’t have the time. I worry about the annual application cycle and our students’ internships, and I don’t have the energy left for anything else after that.

There’s always more to do, and there are always things I could be better at, but I have the peace of knowing I’m doing everything I can. I don’t ever lack motivation in my main career, because I always have something obvious I can do with more money. And the lessons I learn running the ALF don’t just make me a better chairman — they usually make me a better person in the other aspects of my life, too.

It’s nice to focus on turpentine.

What is the American Leadership Foundation?

The ALF is a scholarship foundation. We issue grants and provide ongoing mentoring support to students graduating from large public high schools.

At the time of writing we’re still entirely focused on our pilot grant program (the Deo Kujirabwindja Memorial Scholarship) working with students from Montgomery Blair High School (my alma mater), but we have plans to expand to more schools with additional grants as we figure out how to best scale our model.

My original idea for the foundation was simply focused on the pain I felt the most when I was a student: money. Paying my own way through college, I was splitting my time between work and classes, and I would be frustrated by small grant offerings on the order of $500. If I had been able to aggregate a lot of those, apply in large batches, and had confidence in my odds of receiving any given one, the small face value wouldn’t have been an issue — it’s free money, after all. But I had real bills I definitely needed to pay and a limited amount of time, so I focused on work.

When I thought about that experience later in life, I wanted to set up a program that would appeal to someone in a similar situation. One that issued larger grants, paid out in lump sums, would both give the recipient a meaningful boost in purchasing power and justify the speculative effort of applying. That was the origin of the Deo Kujirabwindja Memorial Scholarship, whose primary grant recipient is awarded $10,000 just as they graduate from high school, giving them a financial cushion when they need it most and have the most time to apply.

The mentoring program grew quite naturally out of the grant program. The applications gave us a chance to get to know very impressive students that we would then financially invest in; it’d be silly to not stand behind that investment with career assistance, networking help, and so on. Even the $10,000 award of the primary grant could be easily beaten by the $12-25k a student might make in a summer at one of the more compelling internship opportunities, and those internships turn into full-time jobs and career paths.

In the spirit of figuring things out as we go, the grant program has evolved to offer secondary and tertiary awards as the mentoring program has become a more primary focus of the foundation. As of 2023, we have awarded 17 scholarship grants summing to over $60,000, and all recipients have access to the foundation’s board of directors for any help we might be able to provide.

Building a foundation

An old manager once told me that his only real job as a manager was to figure out how to fire himself.

His constant goal, he explained, was to understand all the tasks he was responsible for, create job roles that would cover all those tasks, and train other people into those roles, freeing him up to take on new responsibilities. He would know he had succeeded when he was no longer needed by any part of the organization he created.

I’ve thought about that conversation a lot over the past few years — I think that core skill of management has been the single biggest area of growth I’ve had to focus on, and I’m really grateful to have had it broken down so clearly for me.

A necessary first step is simply diving into a problem and trying to figure out what’s going on. Those early stages of understanding the space you’re operating in are fundamentally chaotic, and are filled with a lot of concrete, procedural challenges. For starting the ALF that meant learning about how to get 501(c)(3) status from the IRS, setting up some kind of process to get our first applications, getting the word out so students would actually know to apply, etc. Starting from zero, all these things just kind of hit you at once; I think the best approach is to just try to figure them out one by one.

Over time, though, I started to think about the foundation as having 3 main “parts” that we had to work on, and separating tasks into these 3 buckets helped a lot with organizing board meetings and thinking about how to budget time and energy. They are:

The annual application cycle
The ongoing mentoring program & alumni network
Organization-level concerns (governance, funding, etc.)

I’ll examine each of these pillars in a moment, but I want to pause here to emphasize the importance of the structure itself.

It’s not enough to understand what needs to be done and be able to explain it to others; you need to be able to explain it so well that the person you’re explaining it to can explain it to some third party.

That might seem like a small distinction, but I’ve found that one extra step requires an entirely different mental muscle group than what is needed for building personal understanding. I’ve also found that last step to be one of the most important for being an effective leader in this role. The foundation is a part-time effort for everyone involved — all of the board members have other jobs, and we go weeks or months between discussions depending on the application cycle. Deeply distilling the understanding of what needs to be done is essential to building continuity across those time gaps.

Creating this structure for the foundation’s activities is also how I make progress towards firing myself. A key personal goal I had when starting the ALF was that I wanted it to be more than just a vanity project, I wanted the foundation to be something that could outgrow and outlive me. That was why I took the title of “Chairman”, to act as a small cue to myself to focus on organizing things so that they could be done without me.

At this point I would say I spend about 15-20% of my time on the annual application cycle, 60-65% of my time in ongoing mentoring, and the remaining 20-25% focused on org-level concerns. That’s about what I think the long term split should be for the board, though I would hope that the time and attention paid to org-level concerns falls below 20% over time, leaving 80+% of the focus on the core work of actually helping students.

The application cycle

“The application cycle”, as a bucket of work, includes figuring out how to structure the application process, getting people to apply, and reviewing the applications received.

Structuring the application process has generally been pretty straightforward. Pretty early on we figured out a core structure that gave us pretty good signal on the applicants while being easy enough to handle a potentially large number of applications:

An open call for applicants, who must submit a written essay
Every essay is read by at least two board members who each give it a yes/no vote. Applicants with that get double “yes” votes are shortlisted for further consideration
All shortlisted applicants are asked to provide a letter of recommendation from an adult non-relative (usually a teacher, but employers etc are welcome also)
Every shortlisted essay and recommendation letter is read by every member of the board. Each board member individually stack-ranks the applicants, and finalists are chosen on the basis of ranked-choice voting.
Finalists are interviewed by the board (2 interviews, each interview with one half of the board)
The board conducts a final review that considers applicants’ initial essays, rec letters, and interviews. Grants are awarded by ranked-choice voting.

Nothing here is really new or exceptional in any way, and I’m happy leaving it like that. It’s important to be picky about where you feel like you have unique insight and really want to invest the time and energy into being innovative, because otherwise you’ll stretch yourself too thin. For the ALF I just don’t think it’s that important for our application process to be groundbreaking, especially since students are still finishing their senior year of high school when they apply.

I will note two decisions that have definitely been helpful even if they aren’t groundbreaking, though. One was using ranked-choice voting at multiple stages in the application review process. That has been very helpful both in making sure everyone’s point of view is represented and focusing conversation where it’s most productive — cases where an application causes high variance in reactions, or where there’s a tough choice between two candidates at a certain stage in the process.

The one other point I’d call out here is that our essay prompt asks students to choose from a selection of films and compare or contrast themselves with their choice of character in that film. This was a very deliberate decision to push students to write in a way that expresses their personality more while still giving them enough structure within the prompt to help their writing. At 17-18 years old, most people will struggle with writing into a totally open-ended format; giving them choices within a defined structure can help focus their thinking and actually bring out more of their personality than asking them to just talk about themselves.

With the above structure in place, reviewing the applications is just a question of putting in the time each year to follow the process outlined. We do reflect a bit each year on what went well or poorly and make some tweaks to things, but the core structure has worked pretty well and remained roughly the same for all four years.

Most of our time and energy in the application cycle bucket is currently focused on promoting the scholarship and getting students to actually apply, and I expect this to continue to be true.

Go-to-market is always harder than people expect it to be. I see this all the time professionally, of course, but I’ve been aware of the core issue since college when I was participating in student organizations.

People will have an idea — for a product, for an event, even just for a party — and are consistently surprised by how hard it is to get anyone else to notice.

The fact is, people are busy and there’s a lot competing for their attention. You can’t just mention something once and have people latch onto it; you have to introduce the idea, remind people about it, and make it easy for them to participate.

The experience can be extremely discouraging! It can feel frustrating to have to put so much effort into getting people’s attention. If you’ve already invested a lot of time and energy into an idea, the last mile of getting the word out about it can feel like an overwhelming hurdle after an already exhausting journey. But that’s not a productive way to think about things. Some problems you can’t avoid, you just have to invest into solving them.

Go-to-market is something that we’re still solving at the ALF, and will be a place where we’ll need to keep coming up with fresh solutions over time.

For the Deo Kujirabwindja Memorial Scholarship, we set up a registration process where students sign up to get the application info emailed to them, which also lets us send follow-up emails as the application deadline gets closer. The ALF website also uses Google Analytics so we can try to gauge interest and can see the effectiveness of certain outreach attempts — e.g. how many views an email from the guidance counselor’s office can send our way.

I’m happy we have these bits of infrastructure in place, but there are a few obvious areas where we could easily do more. Social media presence is a big one — at the time of writing, the ALF still has no Instagram or TikTok or anything — and we haven’t had flyers, which are how a lot of student events are shared. If I compare our outreach to that of Blair’s principal, who is prolific on every social media platform of note, I find us sorely lacking.

The mentoring program

The vast majority of my overall time working on ALF development is spent on the mentoring side.

Concretely, this has meant having regular meetings with all our various grant recipients at different times throughout the year to catch up, hear about their lives, and give input on anything they ask about.

Every board member contributes time to the program. Personally, I’m currently averaging about three meetings a month, generally lasting somewhere from 1-2 hours, with text follow ups and ad hoc discussions as needed, e.g. for certain internship application deadlines. I’ll typically talk to any given grant recipient somewhere between 2-6 times a year depending on their circumstances, with the general trend that I hear less from students as they get situated into a major and career path that they’re happy with.

Long-term, I expect the mentoring program to be the single most important facet of the ALF, though it’s also been the most ambiguous and challenging to figure out.

Like I said earlier, the entire idea was an organic development from simply having the infrastructure of a scholarship foundation in place. We identified promising students, invested in them financially… Now what?

Some things are pretty straightforward. When a student knows what field they want to work in, it’s not too hard to help them figure out what internships they should be applying for, or who someone on the board knows that might be able to help them get their foot in the door. I also feel very lucky that I was able to recruit a board from different aspects of my own life, as we have a variety of life experiences represented that translates into pretty good coverage of various career paths students might be interested in.

Helping with things like writing résumés and cover letters, doing mock interviews for internships, or figuring out good budgeting strategies are easy wins that help develop the relationship with our students while also delivering simple benefits.

What’s trickier, but still worth doing, is coaching students on bigger topics of personal development.

The cross-over points tend to be pretty obvious and intuitive. We can help students find and get internships when they know what field they’re interested in, which inevitably leads to some students asking what they should be interested in.

When you’re just graduating high school and don’t have much or any work experience, even the question of what to major in can feel vague and daunting. Some students definitely do come to us having a pretty clear plan of what they want to do and why they want to do it; talking to them, you can feel a certain level of conviction in them and realize all you have to do is support them in their vision, maybe pointing out some tips or shortcuts along the way. There are other students that benefit a lot from someone talking to them in an open ended way about different possibilities — one major distinction of the ALF vs other scholarship programs is that we don’t have any focus on students going into certain professions, which means we’re well positioned to have those open ended conversations and help people pursue anything that’s right for them.

I don’t go into any of these conversations with any set agenda in mind. I keep notes while we talk, mainly as a way to cue myself to actively pay attention, and I’ll have threads from previous meetings to follow up on, but I try to focus on these discussions being as useful of a service to the student as possible. That usually means trying to listen and be reactive to the life circumstances of the day rather than proactively lay out how they should be living their lives.

A reactive approach is especially important because of the age we meet these kids at — 18 to 22 is a period of pretty dramatic personal growth and reinvention. When we first started the ALF I was somewhat bewildered by the first cohort of grant recipients, any one of whom would be a completely different person every six months. From semester to semester it was like they were replaced by body doubles, with entirely different goals, hopes, fears, and preoccupations on their mind when we next talked. Over time, I found this to be pretty typical for their age, with freshmen being the most extreme and variance gradually reducing with age.

Even without a set agenda, though, there are definitely core themes in my conversations that come up repeatedly with many different students. Points of emphasis include:

Developing an internal locus of control
Executive functioning skills
Growing in confidence and assertiveness
Focusing on what’s important, not just what’s salient

Any one of these could be the subject of an essay unto themselves; I might follow up with separate writing on these themes if I can figure out a way to present the information in a general way that’s still useful.

One of the most interesting and most challenging aspects of the mentoring program has been the difficulty of isolating what really delivers impact in student lives. From a purely material perspective, almost all of the benefits and best outcomes stem from a very small set of the conversations I have with a student. A single conversation where I push a student to be more ambitious in what internships they’re applying to might account for all of the concrete benefit that the mentoring program provides to them.

Putting numbers to it, it’s probably less than 10% of my time talking to students that is directly responsible for virtually all of the positive outcomes. The tricky part is just that those 10% of conversations usually rely on the relationship we develop during the other 90%. Building trust and mutual understanding is fundamentally a time intensive process, but you need that trust and understanding to have a real impact in someone’s life rather than just address surface-level details.

From a personal perspective, getting better at developing these relationships has been a major area of growth for me — one I’ve found both difficult and rewarding. Talking with young people has a strange quality to it, because they’re usually able to perceive a lot more than they can express. Trying to understand their thoughts and point of view can take more effort than you put into other conversations, but they can be lightning sharp on noticing whether or not you’re putting in that effort. I’ve found I tend to have best results when I take up to 10 minutes before a call with one of them to mentally prep myself, checking back on notes from previous conversations just to clear my mind of anything I’m thinking about from my own life so that I can be fully present with them. I can take a call with one of them “cold”, especially if it’s one of the older students I already have a rapport with, but it can lead to conflict and misunderstanding if I don’t really cue myself to focus on the conversation from the start.

Of the 17 grant recipients, I’ve had my connection with 3 of them fizzle out over time. I mostly attribute those cases to inherent differences of personality — you can never get along with everybody — but reflecting on those experiences has been useful for finding ways I can continue to grow.

One small thing that’s been extremely helpful has been making a point of finding out every student’s birthday in one of my first conversations with them. I add each one to my calendar and make it a top priority to send some kind of well wishing text at least. (I do this with ordinary friends, too.) Everyone likes to be remembered, and it adds a no-pressure touch point with each student every year. Some large percentage of my happy birthday texts end up leading to us scheduling a catch-up call when a student has been busy with classes and clubs etc.

The last point that I want to note briefly here is that there is incredible variance in output with students this age. I might write more about this later, but even though we run a competitive application process that selects very motivated individuals, there can still be a big gap in efficacy between them when we first meet. A common case will be that students will get great grades and be active in clubs, etc, but need a fair bit of hand-holding when it comes to applying for jobs — usually because it’s an all-new process to them which is inherently intimidating. I can think of one student in particular, though, who literally had more than 20 internship interviews in the Autumn of their sophomore year, and whom I had to push to be more selective and focus on just the best opportunities. Truly, there is always someone who sets your personal best as their baseline.

I have some hope that, as the ALF gets older and we have a larger “alumni” pool, we can foster more peer-to-peer connections that will help these students inspire each other and bring them all up to that highest level. There’s certain things you have to see someone similarly situated do before you can believe you’re capable of them, too. I think developing more peer-to-peer support is also just generally important for making the mentoring program more scalable, as I and the rest of the board only have so many hours in a week.

The organization

I’ve tried to be as thoughtful as I can be when planning the ALF as an organization, but this is one area where time will be the most important test.

My initial focus was just on building up enough structure for us to receive tax exempt status. There’s a lot of important table-stakes stuff in there: recruiting a board of directors, putting together a core group of corporate bylaws, etc.

When you start reading about these things, though, you realize there’s a fair amount of diversity within the “tax exempt organization” umbrella. Do you want to start a public charity? A private foundation? A social welfare organization?

We ended up being recognized by the IRS as a 501(c)(3) “private operating foundation”, which has favorable tax treatment for donors (donations are deductible up to 50% of donors’ adjusted gross income, instead of the 30% limit for other private foundations) while allowing a level of flexibility in board control and fundraising that was essential for us getting started.

I’ve generally been very happy with this structure as it allows us to run the foundation, essentially, as a start-up. Instead of worrying about fundraising campaigns, I’ve been able to fund all our initial grants myself while we figure out a good working structure and answers to all the other challenges I’ve outlined here. It’s been a strategic de-risking. Now we can raise money knowing that we already have something that works, and start to make longer term plans about how to scale and grow from here.

The high level concerns remaining for me at this point revolve around funding and longevity.

For funding, we have two main options open to us. We should probably build our capabilities in both, but currently have expertise in neither. First: our structure allows us a lot of flexibility in fundraising, but we don’t actually have any organizational experience there. Second: we can carry an endowment and pay for grants through investment proceeds, but we haven’t built out that expertise yet, either. A focus in the next few years will be developing both of these skill sets so that we’re not fully reliant on either one and maintain flexibility.

I will note that one big advantage we have on the funding side of things has been our grant structure. The lump sum approach I was attracted to from a student-empathy perspective is also much easier to fund, as it removes the asset-liability matching issues that other foundations hit when they pay out grants over longer periods of time. That simplifies the endowment planning process considerably; we’ll always know how much money we have available to deploy in any given year.

Our extreme efficiency in general is helpful as well. With an all-volunteer board and outreach that goes directly through partner schools (rather than relying on any kind of advertising), our expenses outside of the grants themselves are generally pretty negligible. That’s been a win both in easier accounting and financing.

My concerns about longevity are a bit more vague but I think they’re important to keep in mind. The most pressing one is the “bus factor”: making sure that I’m replaceable. I think I’ve made progress on that front — this writing is part of that effort, even! — but I’m still less than confident that the foundation would be able to thrive without me.

One thing I’m trying to work on is delegating more of the foundation’s day-to-day work to other board members and/or looking for other volunteers to help with basic administrative tasks like keeping the ALF website updated. In a normal business setting, these would be easy things to hire for, but in the non-profit context it’s more difficult. I have some intuitive sense that, beyond having the tasks broken down, people have to have some reason to care about the organization and the mission. It’s not enough to be a great manager; you have to be a great storyteller, too. I’m still a work in progress on both points.

Concretely, we’ve just re-elected the board of directors and organization officers for the next three years. During that time I expect we’ll mainly be focused on continuing operation improvements and developing expertise in the two areas of funding I’ve outlined above. At the end of those three years, though, I’m hoping that we’ll be in a place where I can start to transition my own role further away from day-to-day operations, potentially bringing in someone new to focus on the application cycle and mentoring program — maybe one person for each. And though I’m deeply grateful to everyone on the board who has helped this journey so far, the first board seat replacement will also be an important milestone for us.

Like I said, these concerns are vague, but I think it’s important to worry about this kind of thing early.

A funny contrast between non-profit work and business is that you have a lot of different ways you can succeed in business. Your company doesn’t necessarily have to become a behemoth and IPO on the New York Stock Exchange — being quietly acquired at some multiple of invested capital can be a great outcome for everyone involved. With non-profits that’s a lot less true. You either build an institution that endures or you end up winding yourself down and dispersing the funds to other people who did. And you can’t build an institution without eliminating your key man risk.

Closing thoughts

If you’ve read this whole thing, I want to first thank you for your time and attention.

There’s a lot of heavy detail in here, but part of why I wanted to write all of this out is that I think the details matter.

For me, one of the most fascinating parts of running the foundation has been the emotional experience of it. When I started out wanting to do this, I thought it came from a very altruistic place — I wanted to give back and help kids from my old high school, what’s better than that? And I think there always was a core of true altruism in there — I stuck with it, after all. But it’s also just been a lot of work.

I’ve written with a ton of detail here because there were a ton of details I had to figure out to make any of this happen, and there are still many more challenges to face and questions to answer.

Our first cohort of grant recipients is graduating from college in 2024, and the early successes there have been a huge confidence boost for me. I feel like I’m seeing that effort come to fruition in a way that’s more deeply satisfying than I can explain. But I would feel negligent if I gave you the impression that I never had doubts. Preparing a 50 page application for tax exempt status was never my idea of a good time; trying to improve our application process and figure out how to get our applicant numbers up is always stressful; trying to show up and be my best self with every grant recipient in every mentoring meeting can be utterly exhausting, even when it goes really well.

There are still times when I get a little nagging voice in my head that asks me why I bother with any of this stuff. What am I trying to prove? Who am I trying to impress? Truthfully, I basically never interact with anyone in my day-to-day life who cares at all about the foundation. It’s not even been a helpful résumé entry for me.

But it’s not about me — that’s the point.

To the extent that it is about me, it’s about my desire to genuinely be an altruistic person and a net-positive presence in the world. That means putting in the work; that means getting stubborn, digging in, and solving real problems; that means telling the little nagging voice to shut up if it’s not going to be helpful.

If you get nothing else at all from reading about this experience, I hope you can take away something from that. You have to believe in yourself in order to be the best version of yourself.

It can be really easy to feel lost in the world’s problems like some great lake. You just have to get your feet underneath you and look for a bit of sand. Refuse to drown. Find a foothold and push.

Many thank yous to Aviva Mitchell and Claire Boston for reading early versions of this work.

He attributed it to Picasso (and that's how it's often remembered), but it probably was original to him. ↩︎

A perspective measured in horizons

R Phillip Castagna — Fri, 26 Aug 2022 01:58:44 GMT

i.

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.

ii.

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?"

iii.

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

iv.

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.

v.

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

“Yes, sir?”

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

“Sir.”

“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.

vi.

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.

vii.

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.

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. ↩︎

Towards agency

R Phillip Castagna — Mon, 18 Jul 2022 03:19:36 GMT

i.

Imagine laying out all the ideas you've ever heard into some great plane somewhere, like you're dotting stars into the night sky. Once you have everything laid out, you can step back a bit, and try to organize things.

An obvious place to start might be by trying to separate out ideas that are right or correct from the ones that are wrong or stupid.

You could put all the good ideas on the right, and all the bad on the left, and see what the balance was on each side.

If you did that, though, I think you'd find that the binary division isn't quite satisfying. Ideas can be either "right" or "wrong" in many different ways.

Imagine the variety of possible "wrong" ideas, for instance. Some are trivially wrong to the point of absurdity, like "the capital of Maryland is Calcutta". Some are closer to misleading, maybe to the point of being sinister—"crime is only wrong when other people do it".

If we looked at the universe of "right" ideas, we'd find a similar diversity of right-ness. Some would be simple, specific, and somewhat trivially true, like "my favorite color today is indigo". Some would be true situationally, or with caveats that make them hard to succinctly express, like "nothing can travel faster than the speed of light".

ii.

Good ideas have something in common with power tools: the most useful ones are at least a little dangerous, presenting opportunities to be misapplied and inviting all kinds of subsequent adventure.

Still, there are gradations here. Some ideas are more broadly helpful than others, with less danger when misapplied. Some ideas are just not that useful in a practical sense; some mental models don't pay enough rent to compensate for the space they take up in your head.

iii.

Some ideas are foundational to our worldviews; these ideas can be the hardest to immediately judge on how useful they really are.

When we reflect on really big moral, philosophical questions like "are people fundamentally good", I think we're really looking for answers that will be useful to us, personally, rather than answers that work for everyone. And I think our answers to these big questions change over time because we need different answers in the different seasons of life.

An example might be helpful to explain what I'm getting at here.

One idea in different Stoic writings—especially by Marcus Aurelius in his Meditations—is that we should expect the worst from others. To quote the 16th emperor of Rome:

Begin each day by telling yourself: Today I shall be meeting with interference, ingratitude, insolence, disloyalty, ill-will, and selfishness—all of them due to the offenders’ ignorance of what is good or evil.

I had a lot of resistance to this idea when I was first presented with it, as I felt like it reflected a rather negative outlook and seemed like it could be something of a self-fulfilling prophecy. My experience has been that when we expect the worst from others, they tend to rise to the occasion.

Over time, though, I felt like I understood something that Aurelius et al. were getting at: there's a difference between assuming a basic value in other people's lives and assuming that they'll be helpful to you in your endeavors. Assuming that people will be actively helpful to you is not just setting yourself up for disappointment, it takes people for granted when they do make an effort on your behalf.

Phrasing it like that made the idea "click" for me—I felt like I found the handle on this thing and, once I was holding it the right way, I could see how useful the concept was.

I think ideas that are the most foundational in our experience of life tend to be the hardest to convey and understand.

iv.

As a rule, I'm not really impressed by anyone at this point in my life.

People talk about politicians, celebrities, company founders, etc. as if they were superheroes stepping out of a shared cinematic universe; I generally think that if anyone was really that awesome, then the world wouldn't look like it does today.

My experience has been that there are a lot of smart, hardworking—even well-meaning—people in the world, but the big successes necessarily include a healthy dose of luck and happenstance.

The great "it's just money" scene from the end of Margin Call does a good job capturing what I tend to see in practice: wealthy, powerful people who feel like it takes all their time and energy just to keep up with systems and forces much larger than themselves.

Jesus, when did you start feeling so sorry for yourself, it's unbearable...

What, you think we may have helped put some people out of business today? That it's all just for naught? Well you've been doing that everyday for almost forty years Sam. And if all this is for naught then so is everything else out there.

It's just money, it's made up, a piece of paper with some pictures on it so we don't all kill each other trying to get something to eat.

But it's not wrong and it's certainly not any different today than it's ever been. Ever. 1637, 1797, 1819, '37, '57, '84, 1901, '07, 1929, '37, '73, and 1987... God damn did that motherfucker fuck me up good, '92, '97, 2000, and whatever this is gonna be called.

They're just the same thing over and over. We can't help ourselves, and you and I can't control it, stop it, slow it, or even ever so slightly alter it... We just react... and we get paid well for it if we're right... and get left by the side of the road if we're wrong.

As a rule, I'm not really impressed by anyone at this point in my life. But I think I have a much deeper appreciation of some people now than I once did.

When you step away from mythologizing others, you get the chance to focus on some more basic stuff. Who's making an effort for other people? Who's trying to make the world a better place, even when they realize how hard that is and how small their contribution will ultimately be? Who folds in the face of trouble, and who just takes the pain and keeps coming back for more?

Maybe most importantly: who uses their struggles as an excuse to demand more from the world, and who tries to learn from their experiences in order to help others?

I feel like these questions have been pulling me towards a richer relationship with the world at large.

v.

It's incredibly hard to have any kind of meaningful impact on the world, but I don't think that means we get excused from trying.

I also think that it's impossible not to have an impact on the people around you. It's sort of like being a parent: you can't opt-out, you only have the choice of doing your best or being a deadbeat.

When the large-scale stuff feels impossible, it can be helpful to focus on the small. Take things one step at a time, and hope you can build up from there.

I can only put some fraction of this idea into words right now, but the important part for me is focused on maintaining a strong sense of agency in life.

We all have to find ways to push through, because no one else can do it for us.

vi.

I've been feeling happier than I have been in a long time.

I feel like a lot of different narrative threads in my life that I've been developing for a while are finally starting to come together a bit.

Most importantly for me, I'm enjoying my day-to-day life more.

I don't believe meaning comes from elaborate vacations or that happiness is something you have to travel across the earth to find.

You'd be amazed at how many people can come back from a multi-week tropical vacation and be upset with the world. I've never really had money like that, but I've gotta assume it's expensive to feel that sorry for yourself.

It feels good to rack up base hits and win the game at home.

Turning points

R Phillip Castagna — Mon, 04 Jul 2022 16:00:00 GMT

i.

Something I've been thinking about lately is this idea that persistent failure can be much more impressive than success.

There's one piece of this idea that's about what poker players call “resulting”, evaluating a judgement or action by its outcome, ex post, rather than what could have been known at the time, ex ante. It's easy to pay too much attention to end results and ignore the importance of strong decision making with limited information.

But there's another, complementary, piece to this idea of being impressed by failure: most people do overindulge in resulting, and they worry too much about superficial “wins” and avoiding losses as a result. Persistent failure in a single area is a high signal indicator of someone breaking from this trend in a way that persistent success can never be.

Someone on a lucky streak in life and put off thinking about their real goals or desires for a long time, because they'll get a lot of external encouragement to just keep doing whatever it is that they're doing. Someone who gets a series of bad breaks has the exact opposite experience: not only do they deal with the personal sting of their setbacks, but people around them are likely to lose faith in that person as well. Bad news can always keep coming, and the person on the wrong end of it faces uncertainty about the future, personal disappointment, and strained relationships all at once. That person does not have the luxury of not knowing what they want; their willpower is being ground to dust as it is.

There are trivial cases in which persistent failure is unimpressive, of course. If you make a hobby of consistently attempting something—running a sub-3 hour marathon, say—but then you never make any concentrated effort to improve—e.g. you go jogging but never follow a real training plan—then you can conceivably “fail” and, by not really trying, further fail to gain anything of substance from the experience, either. But examples like that kind of prove the point: is your goal really to run a great marathon, or is your goal to get exercise and enjoy a sport in a semi-structured way? After 5 or 6 years of attempts, I'd expect most people would either admit to the latter or finally get serious about the former.

ii.

Dan Luu has a great essay noting that “95th percentile isn't that good”, which feels related here. Most people don't seek out feedback on things they're trying to get better at; more generally, most people don't take the time to make a plan for how, procedurally, they can improve at the things they care about, other than “do it a lot”. That might seem like another way to be unimpressive in persistent failure, but I'd argue for a different take: raw determination can let your surpass an overwhelming majority of the active practitioners of a skill. Adding a bit of cleverness to that seems easier (and maybe more potent) than the other way around.

One thing I routinely tell ALF grant recipients: all successful people have some part of their personality that is inherently uncompromising. It's something that structurally needs to be there, a backstop of stubborn determination that can be relied on after life has ground down the more elegant parts of you.

Finding that part of yourself is usually synonymous with finding what you really care about in life. When you find something you care about enough that you can keep failing at it indefinitely, you'll usually find a way to turn the narrative around eventually.

The techniques vary from activity to activity, goal to goal, but the general shape is the same: you get a bit more mindful of your daily practice, you solicit more feedback, you find ways to assess and reflect on your own performance, you study the greats in the field, all the etceteras.

Eventually you start thinking about the full sum of your personal experiences and look at what makes you different as a possible source of strength. Going from track & field to football sucks when you can't take a hit, but pays off when you can dust any cornerback; moving from practicing law to software engineering can feel like a huge career reboot, but you'll be a lot more diligent than any of your peers; stories like this happen over and over, taking many guises and appearing in many settings.

iii.

As someone whose career rests on architecting complicated software to do complicated things, I would say that most of life is not, in fact, that complicated.

Life isn't complicated. Life is hard. When people try to make it complicated, they're trying to avoid the inevitable part where it's just hard instead.

It would be much easier if we could find a way through the world where we never faced prolonged setbacks, every defeat was followed by a winning streak, and every disagreement was, in the end, resolved happily. I don't generally believe that's possible, though.

Some people try to chart convoluted paths that avoid any chance of backtracking, but they mostly sit still with their plotting, going precisely nowhere instead.

The simpler solution is generally the better one. Accept losses as inevitable in every game worth playing; accept failure, even many failures, as the price of every success; accept that most people won't believe in you when it's not convenient to do so, and fight to hold onto the ones that do.

Find something you can really believe in even when the world's moving against you. Cherish it; nurture it; build yourself back up; get smart; play the long game; play to win.

Everything worth saying here has been said countless times before, because it's all still true. We say it again anyway, both as a way of reaffirming the truth and as a way of reflecting on how we've embodied these greater themes.

iv.

I started a new job last week. I'm excited about the role but don't have much to say on it yet.

This essay is about new beginnings, Independence Day, and a complicated question about romance I can't pin down with words.

2022 book notes (1)

R Phillip Castagna — Sun, 06 Feb 2022 12:00:00 GMT

I try to read "a lot". As I've gotten older, I've found I really enjoy reading books as a way to unanchor myself from the churn and thrashing of thought induced by trying to stay on top of a never-ending deluge of blog posts, news articles, etc.

I don't mean to say that in a judgemental way: I've just noticed, personally, that I tend to feel worse when I'm following too many feeds of incremental information, rather than getting the chance to stay in one person's head for a while. For me, it's almost like the difference between having a real meal versus scrounging together a series of small snacks over the course of the day. The meal takes a bit more forethought and planning, but leaves me feeling much more healthy and satisfied.

I'm sure that my personally-lived experience with these things is empirically different from others', and so I'm not a zealot for the cause of High Literature or anything. That said, I have definitely noticed that it can be hard to keep a full queue of books I'd like to read next, and a lot of that stems from people just not providing rough notes on what they've read recently. So, I figured I might as well do that myself, giving periodic updates on books I've read (or re-read) recently.

Books I've read (or re-read) in 2022 so far:

The Courage to Be Disliked
Reasons to Stay Alive
The Storied Life of AJ Fikry
A Conneticuit Yankee in King Arthur's Court
A Calling for Charlie Barnes
Panic: The Story of Modern Financial Insanity
The New New Thing: A Silicon Valley Story
Next: The Future Just Happened

There is some fuzziness with the first two titles here, which I think I started again back in December, but no matter. I will also say that I'm a big believer in not just reading but re-reading books, as I usually find the content a lot more memorable upon revisiting. I know a book is really good when I don't just enjoy reading it once, but find the re-read to be even better.

On with the notes!

(re-read)
The Courage to Be Disliked by Ichiro Kishimi and Fumitake Koga
288 pages
First published: 2013

(first read)
Reasons to Stay Alive by Matt Haig
264 pages
First published: 2015

I've developed something of a taste for "self-help" books of late, due in large part (I'm sure) to my ongoing mentoring meetings with various grant recipients from The American Leadership Foundation.

Empirically, it seems that a lot of the kids have a taste for what amount to "how-to" guides on life; I've heard a few mention that they've been digging into assorted works by Cal Newport and the like. At first I think I was a bit surprised by that, but as I try to think back and remember, fleeting memories of myself doing the same kind of thing come back to me. Looking around online for "productivity tips" or something of the sort; I don't think any made a lasting impression on me, but it occurs to me that maybe if I'd found better material then things would've been different. To that end, I'm trying to read/re-read various titles in the genre to develop a good feel for what I might recommend.

The Courage to be Disliked holds up very well, and I would unabashedly recommend. Presented as a series of dialogues between a philosopher and a youth, the text presents various ideas from Adlerian psyschology, with light tie-ins to other philosophical thought (particularly Greek philosophy) and constrasts to Freudian psychology.

I had actually recalled it being more challenging/confrontational of a text than I think it really is upon re-reading — I remember being a bit surprised by the "denial of trauma" argument in particular, and thinking that was kind of edge-y. Upon review, I don't think you could consider it deeply controversial, per se; it just frames things very differently than our current cultural discourse. The "imaginary conversation" framing is still a bit clunky, but works for conveying ideas. In sum, I consider it to be a very useful book, more than anything, and would definitely recommend it.

Reasons to Stay Alive was an easy enough read, but I wouldn't necessarily consider it helpful in the way that this genre is at its best. The book is, essentially, a memoir of Haig's struggles with depression, jumping around a bit over the years in which he was struggling most.

One might consider two potential audiences for the text: people currently struggling with severe depression, and people close to those currently struggling with severe depression. The former might find themselves a bit less alone in their current feelings (though I, unfortunately, have doubts about that, as the disease tends to squash one's ability to feel that kind of human connection), while the latter might find the text helps them understand their loved one's better (which seems much more plausible).

The essential problem with Reasons, common to many personal accounts of depression, is that Haig just sort of "held on" — with tremendous support from his girlfriend-then-wife — and things eventually just kind of... got better. That is, almost undoubtedly, an honest accounting of the facts, but it's not tremendously useful for the prototypical reader in either of the aforementioned camps, as it's unclear what deeper meaning can be gleamed and supplanted into one's own life. There are some specific tips (like recommendations on novels to read), and the writing is clear and easy to plow through, even while covering a very heavy topic. There's also an overarching spirit of compassion that makes the book altogether warming to read. Ultimately, though, it's not necessarily a title I would recomend to anyone, and I do not expect I'll be drawn to re-reading it.

(first read)
The Storied Life of A.J. Fikry
by Gabrielle Zevin
first published: 2015
288 pages

(first read)
A Conneticuit Yankee in King Arthur's Court
by Mark Twain
first published: 1889
528 pages

(first read)
A Calling for Charlie Barnes
by Joshua Ferris
first published: 2021
352 pages

I might present this group as my "post-modern" block for January. Of course, A Conneticuit Yankee far precedes the other titles here as well as the entire concept of "post-modernism" (at least in name), but the grouping still makes sense to me.

The Storied Life of A.J. Fikry is an old favorite for me at this point. A widowed man loses his fortune, finds himself adopting a daughter, and rebuilding his life. Said widowed man is a bookseller in a small New England town — because of course he is — and this allows for all kinds of literary fun in the writing, along with light commentary on the state of publishing that is generally enjoyable, even if it doesn't ever seem to come to much of a point.

There are a lot of ways in which The Storied Life might have ended up too "inside baseball" or just generally cringeworthy in how prototypically writing-for-writers-and-book-people it is, but it stays on the fair side of that foul line. The story is actually delightfully structured, and you get the feeling that all the characters in it represent real, three-dimensional human beings, with gifts and faults and conflicting principles, all the etceteras.

When I first read it, oddly, I had the feeling that it was longer than it was. The chapters break sections of the narrative down into small stories of themselves, which probably enhanced that feeling.^[1] Upon revisiting, I find the book to still be satisfying, but, if anything, actually a bit short. I don't see any room for the story to be expanded further, but I still find myself wanting more. I'll have to make a point to add other books by Zevin to my "to-read" list; apparently she has another coming out this year.

A Conneticuit Yankee in King Arthur's Court is one of those books I had somehow just never gotten around to reading before. (Who knows why; go figure.) A man from late 19th century Conneticuit is transported back in time to 6th century England, hijinks ensue.

The story is enjoyable overall. I will give a special nod here to Nick Offerman's recording of the text for Audible as particularly good in a casual-adventure-listening sort of way that I could dip in and out of without worrying too much about. The tale runs a bit long, maybe — the reader is mainly being walked through a series of narrative set pieces rather than a more cohesive whole that reinforces itself — but, honestly, it's fun and fine and not everything needs to be thought to death.

Reading this book as an adult with no prior framing, the one piece that struck me the most was the complicated relationship Twain's authorial persona seems to have with his narrator-protagonist. It's a Twain book, so it's loaded with satire, but Twain has a turn poking fun at everyone here, so there will be times when main character Hank Morgan swings from the butt of the joke to being depicted as a genuinely admirable creature and then back again, all in the span of 50 pages. There's a genuine complexity there that I wouldn't have expected for a book that (as I remember it) is broadly prescribed to middle school English classes.

A Calling for Charlie Barnes has a neat connection there, as a text that's happy to both chastise and celebrate its characters — while somehow conveying the sense that it has more thoughts about the world than it cares to directly articulate.

A fictional biography of an ordinary man (the titular Charlie Barnes), as written by his adopted son — Jake Barnes, a novelist — that centers around the first man's cancer diagnosis. The narrative steps back and forth across time as Jake seeks to explain his family through their shared past, cutting back to the "present" to discuss Charlie's medical treatment or a family argument before jumping back again so that Jake can fill in more context.

The basic structure here is that of most good contemporary non-fiction writing: there's a core narrative concept that supports digressions to other places and times, and the pieces layer together in a way that never leaves you feeling stranded in a textual cul-de-sac. Since it is a novel, Ferris is able to add some extra flair — one plot point of the book comes from other family members of Jake and Charlie reading an early draft of the book they're in — but it's striking how capably Ferris recreates a certain New Yorker feature-story sensibility in the novel's structure as well as its language.

I read this book and then immediately re-read it, as it just worked on so many different levels for me. Clever constrution, complelling characters, strong prose, all the etceteras. Ferris manages that wonderful feat of looking at ordinary life with eyes wide open and finding a way to report back on those observations in a way that leaves you feeling recognized and imbued with a certain sense of meaning.

If you're a fan of This American Life, you probably know what I mean when I say there's a kind of poignant "ah-ha" moment that the show almost specializes in hitting you with — the moment where a hazy, somewhat arbitrary beginning to a story suddenly flips into something clear and quietly profound. A Calling for Charlie Barnes is a novel's worth of those moments.^[2]

(re-read)
Panic: The Story of Modern Financial Insanity
edited by Michael Lewis
first published: Dec 2008
400 pages

(re-read)
The New New Thing: A Silicon Valley Story
by Michael Lewis
first published: 1999
349 pages

(re-read)
Next: The Future Just Happened
by Michael Lewis
first published: 2001
240 pages

Prices for "growth stocks" (especially high-multiple tech stocks) started to rapidly deflate around October/November of last year; in January, that weakness seemed to spread to the broader world of equities, and the resulting anxieties about a probable bear market stoked my interest in dipping back into Panic, which in turn led to re-reading Lewis's works from around the dot-com boom era.

Panic: The Story of Modern Financial Insanity is a bit of an odd ball: a collection of newspaper and magazine stories (by a wide array of authors) written before, during, and after assorted financial crises since the 1980s. It almost undoubtedly sprang up as a way to monetize research Lewis did while writing The Big Short.^[3] But even if it's a cash grab, it's not an unwelcome one — there's a lot of meaning to be gained from the zoomed out perspective it gives as it steps through so many tumultuous market events in quick succession.

Some of the financial panics examined, like the Asian currency crisis of the 1990s, feel like vaguely refreshing topics, simply because they're not often thought about or discussed in more "mainstream"/"pop-econ" channels. The biggest surprise on this most recent re-reading, though, was realizing that the dot-com boom and bust somehow fits into that category also. Not because people don't ever discuss the dot-com era, but simply because it's been charicatured down too far for the short-hand comparisons found today to be useful.

That, in turn, led me to re-reading both The New New Thing and Next: The Future Just Happened, Lewis's two books from the era (both written entirely by him), and which I found to hold up so remarkably well that I want to do an entire essay just on them and some thoughts about the era — what's been carried over, what's been lost, and how we grapple with its "lessons" today.

Hope I have time for that soon.

Each section also begins with notes from the main character on a real book or short story, which was part of the inspiration for me wanting to write these notes. ↩︎
I'd also give a nod here to the various novels by Fredrik Bakman, which share a certain emotional sensibility with A Calling for Charlie Barnes, even if there are a lot of superficial or thematic differences. ↩︎
It was first published very shortly after the onset of the Global Financial Crisis, providing a timely stop-gap solution for content flow. It'd be another year and change before The Big Short was first published. ↩︎

Zugzwang

R Phillip Castagna — Tue, 01 Jun 2021 11:14:47 GMT

When I look back on my life, most of the memories that nag at me today aren't things I could call "regrets" in a typical sense of the word.

I think most people talk about "regrets" as things they did but understand they shouldn't have done—actions they were fundamentally mistaken in pursuing.

I've definitely done dumb things, but I try to be hold onto some compassion for the younger/dumber version of me. There are always going to be life lessons we end up learning the hard way. By understanding that our own mistakes and failures were just a natural and inevitable part of our development, we can let go of some of that inner cringe that can hold us back in the present, and (I think) learn to be kinder to others as we see them go through that same lurching growth process.

If you can't forgive the younger version of yourself for their faults, it's even harder to forgive others.

So, no, remembering various dumb things I've done in the past—looking back on past "regrets" in the way most people use the word—generally doesn't bother me much today. I try not to let myself get stuck in that mindset, at least.

The things that still bother me today, the memories I tend to dwell on, are actually those times when I was right about something important, but then found I couldn't do anything about it.

A very simple example might be when a friend of mine started a new relationship not that long ago, and it was immediately obvious to me that things weren't going to work out, and that my friend was over-committing from a place of insecurity. Well, okay—what do you do with that?

It's generally a pretty terrible idea to mettle in another person's love life directly; we all have a lot of our own baggage that we just sort of work through over time. It's also generally a bad idea to just try to "fix" people, telling them exactly what their core character weaknesses are, tempting as it might be.^[1] Usually the best we can ever do for our friends is just to be kind and supportive, and stay committed to that friendship through the ups and downs.

If there's any way to "win" in a situation like that, it's just to wait it out. There is no better salve for insecurity than persistent and enduring care.

But being able to sit and wait things out like that—that's exactly why the "thing happening with a friend" example is really too simple. When we're dealing with situations that directly affect us, waiting things out might not be an option.

Another, more intellectually honest example: any one of the jobs I've had where I felt like my team wasn't focusing on the right problems. We'll say a programming gig, to make things concrete. I look up from my computer at one point, realize our code quality sucks, we don't have a strong/cohesive vision for the product, and the individual contributors are all generally unhappy. What do you do with that?

You can try to agitate for change, but if you can't get real traction then eventually you're just someone who complains about everything and people already know how much the situation sucks; being a whine-y jerk is a good way to get fired, or at least make your teammates hate you. You can try to stick it out and hope things get better on their own, but then you're miserable all the way through, which can hurt your productivity and make it more likely that you piss everyone off and get the axe anyway. Even if you did stick it out, your whole team might get cut if things really are going as poorly as you think they're going.

Near as I can tell, your best bet in a situation like that is to quit as soon as possible. You want to try to preserve whatever nascent relationships you have there and just exit gracefully. But, speaking personally, I spent years being broke or nearly broke after high school, and so quitting wasn't an immediate option for me a lot of the time unless I had something else already lined up.^[2] The sense of entrapment in those situations can be overwhelming.

In chess, there's a game state known by the German term zugzwang, in which any move the acting player makes can only leave their position weaker. If they could just leave things exactly as they were, forcing the other player to move, then the game might play out fine, but chess (unlike go) doesn't allow a player to "pass" on their turn. You're compelled to act and can be left off worse for it.

The chess player's only recourse is to avoid getting into such zugzwang to begin with. There's a sense in which that state is only a realization of errors previously made, and the mechanics of the game force you to play through that realization.

A good chess player might recognize certain patterns that lead them to zugzwang, and proactively avoid letting themselves get caught in the same way they were drawn in before, the same way I'm now conscious of being mentally and financially prepared to gracefully exit any job that turns out to be a poor fit for me. But in life, unlike in chess, we don't start with a fresh slate and get to pick our own set up.

Something that I think about sometimes is just that I have (from what I can tell) a rather unusually fluid concept of gender. In fact, I'm a pretty strong adherent of Queer Theory, which broadly posits that what we call "gender" doesn't exist per se; rather, there are societal expectations of gender roles that we choose how to fill. That feels very intuitively real to me—much more real than more traditional (even earlier-wave feminist) concepts of gender—and I suppose that's fitting, as it seems inseparable from my lived experiences (romantic, sexual, and otherwise) as a bisexual man.

As a writer of fiction and poetry, I frequently play this a step further, "queer-ing" some character or subject of a piece by swapping their gender (or at least the pronouns) away from their real life counterpart, or even just the first image of that fictional person I had in my head.

... I don't tell anyone when I do that, and it's hard to know how I would, even if I wanted to. What would it even mean to anyone else if I did?^[3]

But the thing is, sometimes I do want to. Part of why I write is to find new ways of connecting with others, or at least to share my ideas in new forms. The thing that sucks about the really big concepts, especially many of the ones connected to core aspects of our identity, if that we are frequently too close to them to have direct conversations about them. They can act as close friends, positioned awkwardly in the middle of a conversation about them, rightfully refusing to be spoken over.

I'm still learning more ways to approach those conversations; I'm still broadening my arsenal of indirection, finding new ways to strike surprising and meaningful connection. But it's not clear to me that I'll ever find a way to say all the things I want to say, and truly be heard.

One other big difference between chess and life, of course, is that there are no inherent rules as to how we live our lives.

In chess, the game and its outcome have meaning because both players play within the standard confines of what we call "chess": the rook moves horizontally and vertically, the bishop diagonally, etc.

In life, however, we find meaning in the rules we choose to take up, the goals and restrictions we impose upon ourselves. I might never reach the perfect ease of connection with others that I want—certainly not on all topics—but it means something to me that I'm trying.

I don't look back through my memories for regrets; I look back at the tough situations I'm determined to face again, trying to find an edge I can press to my future advantage.

It's important to maintain a certain level of self-awareness with all these things in order to hold onto our core sense of agency.

One last thing I've been thinking about a lot lately—

Michael Lewis describing John Gutfreund in the epilogue to The Big Short:

"The same veneer of courtliness masked the same animal impulse to see the world as it is, rather than as it should be."

That "animal impulse" is a really essential thing in life, I think.

Lately I've been mulling over the fact that we don't have any selection criteria for American Leadership Foundation scholarships that would serve as even a rough parallel to that basic mode of operation. And that's a bit strange, maybe, because I'm not sure if it can be taught. I do think it can be learned, though, and so it's just another place where I'm hoping to figure out how to be as helpful as possible.

Almost as tempting as thinking we have some omniscient power to casually understand others that way! ↩︎
Workers on H1B visas perpetually face the same dilemma. ↩︎
"This imaginary character is actually a different gender than they were presented to you as in this writing." What? ↩︎

"This is not investment advice"

R Phillip Castagna — Sun, 07 Feb 2021 21:26:05 GMT

So there's this disclaimer that I've noticed in a lot of blogs about investing—these are blogs that discuss different companies, their future prospects, potential risks, etc. These blogs will write up all kinds of information about these different companies, then tack this statement on to the start of each post, or on to the end of each post, or will otherwise have it somewhere on their site.

What does that disclaimer say? This is not investment advice.

It's similar to what you might see from a post by a lawyer or a doctor, something saying "this is not legal advice" or "this is not medical advice". And it's kind of an interesting artifact, because it almost feels meaningless as a disclaimer, right? Andrew Walker (a professional investor^[1]) will write 8,000 words about ANGI Homeservices across three posts, complete with charts and data and consideration of different risks to the business, but he'll do so on a blog with a site-wide disclaimer that "nothing on this blog should be construed as investment advice". Who the hell wants that much information about a company from a professional investor if they're not looking for investment advice?

The distinction being made is a rather simple one, and it might seem legalistic at first—a difference in parsing words rather than in actual meaning—but it's actually a rather profound thing if you can appreciate it for what it is.

That distinction being made is between someone providing information that might help you, rather than someone telling you something they truly believe will help you, specifically. It's not (entirely) about someone washing their hands of responsibility, it's about someone acknowledging that they don't have all the context for you, your life, and everything that could or should influence your decision-making. Instead of saying "this is what you should do", they're saying "this is what I know and what I think and what makes sense to me, maybe that's something that could help you".

Something that was a real struggle for me growing up was just that I didn't have a lot of people I could turn to for advice that was really tailored to me, specifically. There's always a lot of people who want to tell you how to live your life, but very few people will ever know everything you've got going on in any given moment and be able to mold their advice to fit your actual situation. Something I'm really happy about with the American Leadership Foundation has been the opportunity to provide that kind of dedicated mentoring to our alumni, something I never really had. We even are working out plans to foster a network of mentors among that growing alumni pool that can spread that care out further and help us expand—the potential for growth there is really exciting.

But I also think there's an inescapable part of the human condition tied up in a situation we all find ourselves in from time to time: facing some unspecified set of problems on our own, looking for any advantage we can find against challenges that nobody else knows we're up against. We find ourselves cast as Lamar Allen in The Gambler, with a promising basketball career and a bad knee; we have real problems but they don't fit into predefined lines and there isn't a paint-by-numbers approach that will fix the picture for us. Those are the times I talk about when I say I want to "build the things that are there for us when no one else can be". Because when you're facing down long odds, you need every little thing you can find to improve your chances—even if it's just information from some stranger on the internet.

"This is not investment advice," because I'm not in a position to give you investment advice—I don't know anything about you.

"This is not investment advice," but maybe you'll find it interesting.

"This is not investment advice," but maybe you'll find it helpful anyway.

You can't count on strangers to fight your battles or fix your problems for you. But it's nice when they don't pretend they will or can, and it's even better when they can find something to offer that might just help you anyway.

I should note that, in addition to being a portfolio manager at Rangeley Capital, Andrew Walker is a good writer, an overall cool guy, and his blog (Yet Another Value Blog) is an excellent resource. ↩︎

Quick notes on listening

R Phillip Castagna — Tue, 20 Oct 2020 12:38:29 GMT

People share a common need to feel heard. Different people experience different levels of this need, and different people try to fulfill this need in different ways, but the core need is a shared part of the human condition, just like our common need to be able to shape our own futures.

Most people satisfy their need to be heard most often through simple, undirected conversations. Even artists, writers, and other creative types—people who ostensibly turn to those creative outlets in order to express things they can't get out through simple conversation—satisfy their need to be heard through simple discussions more often than their actual creative work. It might not be as satisfying for them, but it's a part of life and early conversations can be an important part of the creative process.

Most often, our ability to listen is the determining factor in whether or not someone else feels heard. There are some cases when the speaker will not ever be able to feel heard through normal conversation, such as when someone is depressed and their perception of an interaction is being clouded by cognitive distortions; those cases are a small minority of the total number of conversations we have in our lives. Most of the time, it is our performance as listeners that drives the "feeling heard" outcome.

The "toxicity" people associate with "venting", etc., is usually a product of poor listening. When we can effectively listen to someone else express frustration at a situation they cannot change, they will be able to let that frustration go. When we are poor listeners, people are more likely to get stuck in these more negative patterns of thought. We create truly toxic environments when we do not just bottle people in their own negative thinking, but add in our own, such that both parties complain to each other but neither feels heard. It is a mistake to only allow for conversations where "something can be done"; listening is always something that can be done.

Listening is about making people feel heard, not telling them your thoughts. Sometimes people ask for advice, sollicit feedback, or otherwise look for input in a conversation, but these are all separate needs from the need to feel heard. Sometimes those practical concerns are more pressing than the need to feel heard, but sometimes the reverse is true. Understanding what a speaker is looking for during each beat of a conversation is an important part of listening.

Listening is a skill that can be developed over time. Like other skills, it takes active, mindful practice to get better at, even when we're doing it passively everyday, but that active practice does lead to better results over time.

Once we've developed the skill of effective listening, it takes nearly zero effort to make other people feel heard. Listening is not the same thing as "showing up" for someone else; showing up for someone else means actively supporting another person, making time and space for them in your mind and life, trying to draw them out of their shell. When someone else is already willing and able to put themselves out there and share their thoughts and feelings with you, then they've already done all the real work, you've just got to catch the ball they've tossed to you. The wonderful thing is that becoming a better listener then allows us to give this gift of feeling heard more often and more freely with no drain on ourselves.

The definitive next step for further reading — Nonviolent Communication: A Language of Life by Marshall B. Rosenberg

There are core techniques used by effective listeners that can guide the active practice of listening. Different people end up with different tools here, as a natural extension of their unique communication styles, but effective techniques include:

Paraphrasing the speaker's thoughts back to them
Asking for more emotional context, e.g. "what did you feel then?"
Adding observations of the situation without evaluating it
Maintaining open body language and making eye contact

For more practical instruction I'd highly recommend Nonviolent Communication: A Language of Life by Marshall B. Rosenberg. It got onto my radar after being recommended several times by Sam Altman, but honestly I dragged my feet on reading it just because it seemed really... hippy-dippy. When I did finally read it, I regretted putting it off, as it's about as intensely practical of a manual in communication as anyone could write.

Becoming a better listener is not easy or fast but it is intensely rewarding in all senses of the word. I do not think I am a very good listener, even now, but I do think I'm much better than when I started to really care about listening as a skill, and it is something I've benefited from in all my relationships, whether they're of the personal, romantic, or business variety.

A useful book: Finite and Infinite Games, by James P. Carse

R Phillip Castagna — Sun, 12 Jul 2020 19:19:02 GMT

So, lately I've been thinking a lot about the pursuit of happiness.

There's a really good episode of This American Life about it, of course, because there's a good espiode of T.A.L. about most things. But I think it's also just one of those big fundamental themes that we encounter and re-encounter repeatedly in life and right now I find I'm in a bit of an "encounter" phase.

Wherever you go...

As of July 2020, one life lesson I've found a bit surprising is just how utterly irrelevant various life milsetones have been to my internal peace of mind. People talk about how "the journey is more important the destination" or whatever, and it's easy to just nod accept that in a general way, but I'm not sure it did anything material to prepare me for finding my own meaning in life—or even to prepare me for that odd sort of empty feeling you get after accomplishing some long sought goal.

I've been thinking about that while talking to people about their different existential dillemnas and trying to help A.L.F. scholarship recipients plan their next steps out of high school. One case I seemed to be almost uniquely distressed by was a friend who recently decided to go to law school.

Know that there are important purely-practical reasons that most people going to law school today should not be going, and that's what I was worried about at first: tuition rates are at all time highs, employment prospects are often rather bleak,^[1] and people just generally reach for "law school" as a generic "why not" thing far too often. My friend is a very practical person, however, and was able to settle all of these for his specific case pretty quickly. He then laid out an entirely reasonable seeming plan that would leave him as a well-positioned, experienced attorney in 5-6 years with a solid baseline income and interesting possibilities for future career choices.

And that was good; I was glad he had a thorough and practical plan. But I was also bothered by it, because there was just this vague nagging question whispering in the back of my head.

After 5-6 years, he'll be well established to do all kinds of work that might really interest him... and then what?

Talking with my friend about this plan, it was hard for me not to think of my own life, and my own journey through college (as an undergrad) followed by working for 2 years at a prestigious firm (Google). That path did open a lot of doors but I was also really struck by how utterly unsatisfying it all was in the end, and how most of the things I really did take satisfaction in were the incidental pieces of Life that I had to fight to graft onto this streamlined vehicle of professional respectability.

Wherever you go, there you are, as Jon Kabat-Zinn told us. When I reached whatever new phase of life met me in Manhattan, I had the feeling of someone stepping out of an airport only to realize they had no idea what to do in the city at which they had just arrived.

It wasn't my first time feeling that way, and definitely wasn't the last, but it was a particularly tough case of whatever odd syndrome that feeling of listlessness can produce.

I now take precautions to steel myself against it, and encourage you to do the same.

The useful book in question

To use the terminology of Carse, I'd say it's not uncommon for someone to find themselves excelling in some "finite game"—a game that might take years to fully play out!—only to find themselves caught off-guard by the "infinite game" that awaits them after the close of finite play.

Finite and Infinite Games by James P. Clark Originally published 1986 by Free Press (now Simon & Schuster) ISBN 0-02-905980-1

Finite and Infinite Games is a relatively short (if dense) book that explores the titular dichotomy through 101 theses. The formula here is pretty simple, but I found it immensely satisfying from my very first read. Carse will set up an example of this dichotomy—say, the difference between the theatrical (finite) and the dramatic (infinite)—make a few observations about that particular incarnation of the dichotomy, and then move on.

Some number of online reviewers seem to find this structure frustratingly repetitive, and even shallow, but I think it is a mistake to read this book looking for answers, per se. One of Carse's core ideas is that the world is always changing and so that our thinking should, too; it'd be silly, then, for him to try to outfit you with all the tools you'll need to take on a world he knows he cannot foresee. Instead of tools, Finite and Infinite Games gives the reader a set of techniques with which they can question and think about the world and apply to unknowable future situations. The repetition is important as a way of practicing these techniques while reading along, just like the practice of repeatedly tracing letters as we learn to write.

That Carse thought to structure his text like this at all is rather amazing; it almost doesn't feel like a book in the way that we normally read books. There is no real narrative or natural ordering of concepts like there is in most fiction or non-fiction. Carse just walks you through these thinking exercises—without any instruction about what he's doing!—and the result is something that feels both polished and personal like some precious stone that's easy to carry with you but holds immense value.

In addition to finding the text repetitive, though, I saw other online reviewers who found the book "impractical" for various reasons. The Times review back in 1987 had similar complaints, along with notes that the underyling ideas may not be sufficiently "original" for the reviewer's taste.

I think the Times review is rather illuminating in its self-defeat, however, as many of the "practical" concerns Kane would rather we focus on feel like distinctly 20th century issues to the contemporary reader, and his titular gripe with Carse's framing of "the garden" vs "the machine" feels almost aggressively naive 30 years later. That the framing feels much more concrete in a world where we're fully grappling with the Internet's impact on society, the unceasing danger of global warming, and whatever weird dystopian concerns Silicon Valley people have about future A.I. leaves Carse seeming ahead of his time here.

More broadly, I think the kind of rapid societal change that we've seen in the past thirty years is the kind of change where techniques—not tools—end up being much more useful guides, as we have to rethink many of the assumptions on which our tools often rely.

With all this in mind, I've recently found myself giving people copies of the book for assorted occassions. I do think you have to read it at the "right time" for it to fully click, but it's almost like a fire extinguisher: profoundly useful to have around when you need it.

A few highlights

All of these pulled from my copy of the Kindle edition, pages based on what it tells me.

It feels like I actually have most of the book marked up in some way, so it wouldn't feel fair for me to dump my whole notes file here, but these should help give most of the flavor of the text.

Page: 15

To be playful is not to be trivial or frivolous, or to act as though nothing of consequence will happen. On the contrary, when we are playful with each other we relate as free persons, and the relationship is open to surprise; everything that happens is of consequence. It is, in fact, seriousness that closes itself to consequence, for seriousness is a dread of the unpredictable outcome of open possibility. To be serious is to press for a specified conclusion. To be playful is to allow for possibility whatever the cost to oneself.

Page: 26

The joyfulness of infinite play, its laughter, lies in learning to start something we cannot finish.

Page: 26

When a person is known only by name, the attention of others is on an open future. We simply cannot know what to expect. Whenever we address each other by name we ignore all scripts, and open the possibility that our relationship will become deeply reciprocal. That I cannot now predict your future is exactly what makes mine unpredictable. Our futures enter into each other. What is your future, and mine, becomes ours. We prepare each other for surprise.

Page: 44

Deviancy, however, is the very essence of culture. Whoever merely follows the script, merely repeating the past, is culturally impoverished.
There are variations in the quality of deviation; not all divergence from the past is culturally significant. Any attempt to vary from the past in such a way as to cut the past off, causing it to be forgotten, has little cultural importance. Greater significance attaches to those variations that bring the tradition into view in a new way, allowing the familiar to be seen as unfamiliar, as requiring a new appraisal of all that we have been—and therefore of all that we are.

Page: 56

Therefore, poets do not “fit” into society, not because a place is denied them but because they do not take their “places” seriously.

Page: 69

If to look is to look at what is contained within its limitations, to see is to see the limitations themselves. Each new school of painting is new not because it now contains subject matter ignored in earlier work, but because it sees the limitations previous artists imposed on their subject matter but could not see themselves. The earlier artists worked within the outlines they imagined; the later reworked their imaginations.

Page: 93

The infinite player in us does not consume time but generates it. Because infinite play is dramatic and has no scripted conclusion, its time is time lived and not time viewed.
As an infinite player one is neither young nor old, for one does not live in the time of another. There is therefore no external measure of an infinite player’s temporality. Time does not pass for an infinite player.
Each moment of time is a beginning. Each moment is not the beginning of a period of time. It is the beginning of an event that gives the time within it its specific quality. For an infinite player there is no such thing as an hour of time. There can be an hour of love, or a day of grieving, or a season of learning, or a period of labor.
An infinite player does not begin working for the purpose of filling up a period of time with work, but for the purpose of filling work with time. Work is not an infinite player’s way of passing time, but of engendering possibility.

Page: 111

Storytellers do not convert their listeners; they do not move them into the territory of a superior truth. Ignoring the issue of truth and falsehood altogether, they offer only vision. Storytelling is therefore not combative; it does not succeed or fail. A story cannot be obeyed. Instead of placing one body of knowledge against another, storytellers invite us to return from knowledge to thinking, from a bounded way of looking to an horizonal way of seeing.

There's even a Wikipedia page for it! ↩︎

“Made in America”

R Phillip Castagna — Sun, 05 Jul 2020 00:07:49 GMT

So lately I’ve been thinking a lot about role models.

Specifically, I’ve been thinking about how it’s probably important to have a concrete idea of a generally “good” person you’d like to emulate, even if you’d like to be better than them or different than them in some way. The kind of role model that you can use as your baseline to compare yourself against, basically.

I’ve been thinking about that partly because I’m not sure I ever really had one. Growing up, I mainly recall thinking about all the things I didn’t want to be, all the people I didn’t want to be like. If you asked me who I actually wanted to be in a constructive sense, I’m not sure I could’ve told you.

That ended up being kind of a problem for me specifically because it fed into my tendency to think of myself as vaguely worthless, I think. Therapists and such will tell you that these thoughts are common in, say, the children of alcoholics, and I think I definitely got burned by a lack of perspective on my mistakes and struggles without any positive baseline to compare myself against. When you only know all these people you don’t want to be like, you just sort of end up living in fear that you’re slowly becoming them despite your best efforts.

I don’t think I ever had a proper role model. Deo Kujirabwindja (who I named the American Leadership Foundation’s first scholarship after) might be the closest, but the parallels are generally tough to draw. Starting in about high school, though, I did start to slowly build a certain sense of identity, and that can be something to lean on in a similar way. Even when times are hard, you can just focus on being true to yourself and your own identity.

There’s actually an exact moment I can remember when it really felt like that sense of self was crystallizing for me. It was in the fall of 2011, my senior year of high school: my girlfriend and I had a date to listen to Watch the Throne together. I downloaded it on my old desktop, and she came over with a big jigsaw puzzle that we put together on the floor of my bedroom, starting from track 1 and just playing the whole thing through.

The timeline in my head is a little fuzzy here, and so while I’m sure my step-father was home from prison by then, I'm only half-confident her dad was still serving out the end of his sentence in Cumberland. It had been a weird, difficult road for us up to that point, and it was actually going to be much harder from there. But there was this really nice moment there, where we were just present in my room, putting this puzzle together, listening to a rare kind of project for either Jay-Z or Kanye that was pretty much unabashed fun.^[1] It was just... nice.

I remember hitting track 11, “Made in America”, and it just immediately struck a chord with me. Even on that first listen, I knew it was kind of cheesy, but it felt like there was this hole in me the song was helping me fill. I actually got up when it was over to back up a track and hear it again.

The thing that really hit me was just this overarching idea that an important part of the American experience is not feeling like you belong in the American experience, that the struggle was an important part of life and that we celebrate the people who rise up to meet it, not those who never had to. I had sort of been walking around with this chip on my shoulder and this feeling of abandonment, but hearing this song there at that time in that almost singular space really made me feel like I was going to be able to work things out.

We don’t ask to be born, or get to choose where or when we grow up. But when I look at my life now, I’m mainly struck by how utterly improbable it all seems. I didn’t have any kind of track or discernible trajectory for most of it; I mainly got by stitching together a lot of random acts of kindness and small moments like this one, putting together that puzzle. It might’ve happened anywhere—though truthfully, I’m not sure it could’ve been anywhere else—but for me, at least, it did happen here in the U.S, built largely on what I consider to be American values.

Because I never had a real role model or a single dominating influence in my life, I’m left with this more general sense that somehow it was the country itself that raised me. And so I love this country for that, even when all the contradictions in it have probably never been more apparent. Because to me, you don’t just love someone or something for all they are; you love them for all you can see they will one day be.

It’s the 4th of July, a day where people show their patriotism in various ways and sometimes people have complicated feelings on the topic; I wanted to lay out my personal flavor in the hope that it might be useful, especially to anyone a bit younger who might be reading this. I was made in America, I made it in America, and now I’m forever committed to making America a better place, just as I strive everyday to better myself.

That’s something we can be about, too.

I still think WtT is underrated as a collection of tracks, even if the collaboration meant it never could have been a more focused concept-y album that Jay and Kanye are each known for. ↩︎

Rituals, repetition, and how we build our lives

R Phillip Castagna — Mon, 11 May 2020 02:50:34 GMT

So this is something of a new format for writing that I want to try developing specifically for this blog; it's very new and I'm super open to feedback on it, so please let me know what you think!

I have a few different ideas in here that I'm going to try to tie together, so you'll have to bear with me.

Bach and stress

The first thing I wanted to talk about was something I noticed myself doing the other week at work, as we were all in crunch mode trying to get things ready for a major deadline. Things were stressful; I was sleep deprived; everything seemed like it was falling apart... But I knew I was really feeling that weight when all I could think to do was start listening to Bach's cello suites.

Yo-Yo Ma's 1983 recordings remain my favorite, even as he's put out subsequent interpretations.

It struck me as funny in retrospect, because I realized that this was an old habit that had become a self-reinforcing ritual for me.

I listen to Bach's cello suites as I work through high pressure situations. Then, when new challenges face me down the road, I feel this itch to listen to Bach again because I associate it with working through difficult times.

As far as coping mechanisms go, this feels pretty ideal:

It's sustainable—I've already bought the CD so it won't ever cost me another dime at this point
It's a discrete physical action—as long as I can press play I can kick off the ritual, and it's hard for me to be "too stressed" to do it
It has a track record of success that I've lived personally and keep adding to

So then I was thinking a bit about what are other rituals I could develop for when times are hard, or even if there was some framework for them that could be useful when mentoring. But that felt a bit silly, really, when I had just sort of stumbled into this one, and I think most of these things are sort of organically discovered.

There's no magic to the paint-by-numbers approach, and if there's no magic to the ritual then it's just a technology—and any new technology should be at least 10x better than the baseline, or you're really just fucking around. I didn't see good prospects in digging further into the "ritual" idea, but I could tell I found the thought interesting for some reason.

Magic and the improbable

The thing that struck me as I turned over my thoughts about ritual again was that organic discovery piece—the magic.

I mean, I say "magic", but it seems much more mundane than that, of course. I'm talking about listening to music while writing code, not the moment of inspiration the led me to curing cancer or something.

When I use a term like "magic" when I'm talking to people in real life, I'll frequently get a bit of an eye-roll in return, or people will think I'm embellishing my enthusiasm to be dramatic or otherwise make a point. I'm actually being perfectly sincere, though, and I think there's a kind of "nothing is special" attitude lurking behind people's reactions that they might find value in re-examining.

Something I think a lot about is how people will you a certain idea of science to try to squash uncertainty in an inherently uncertain world. An important note here is that this thinking is not, in fact, scientific, or really even rational; it's simply trying to use the appearance of being such.

The simple mathematics of it are that there are so many tiny pieces of random chance that go into so many different aspects of our lives that it's difficult for us to not encounter something completely new to the universe on any given day.

Now, most of these novelties are so banal that people have a hard time even noticing them, but that doesn't make them any less present. Almost everyone has fingerprints, for instance, but that doesn't make them any less unique—the reality of it is that there aren't actually that many people in the world, just too many for us to reason about with normal types of intuition. But in the same way that there aren't enough people in the world for anyone to share your exact fingerprints, there aren't enough people in the world for anyone to share your exact experiences, only the outlines—and sometimes not even those!

If we can accept as a matter of literal fact that many unique things enter and leave our lives on a recurring basis, then the real question is just what feelings we project onto them. I would say making some effort to cultivate a sense of wonder is fundamentally useful in a few different ways:

It makes it a lot easier to be happy, generally, as life is just more interesting that way
It trains us to look for changes and unusual events; whether we want to change our own lives or maintain them happily, the changes happening around us are what bring both opportunity and risk

That second point, in turn, led me to larger thoughts I was having about life and work that seemed more interesting.

Creativity and industry

One mental model you could have of most human activity is that we have a set of baseline habits and behaviors that we engage with routinely, and then unusual events that shift that baseline set.

A young professional might have a normal routine but grow frustrated with a lack of opportunities for advancement at their company, say; they start taking night classes and working for their MBA, and that then becomes a new addition to their routine. Graduating will free up time, shifting that routine again, and if they get promoted upon receiving their degree then their life changes once again.

Some of these shifts in routine are internally driven (choosing to go to night classes), and some are externally driven (getting promoted). In this mental model, however, most of these shifts that we set as goals for ourselves and feel like we can control could be thought of as accumulations of routine behaviors practiced over some period of time.

The challenge, then, is two fold:

Determining with confidence what set of routines will carry us to where we want to be
Finding ways to maintain that steady-state long enough that we reach our destination

Both of these are really hard problems; in a certain sense we spend our whole lives looking for answers to these two points.

Something I've found to be useful has been to broaden that sense of wonder I mentioned before. It is useful to notice changes and novelties, but it's also important to have awareness of ourselves and what we allow to become our daily routines. Examining our everyday actions and asking ourselves if they get us to where we want to go or hold us back is an important practice.

With each new day we build another tomorrow whether we realize it or not; we'd do well to make sure we're actually building the worlds we want to live in.

One thing I actually like about the software industry is that it embraces a lot of the cyclical nature of human existence—there are a lot of company booms and busts, development will be relaxed but turn frenzied as a deadline looms, etc. We get a lot of practice living all the different parts of these cycles, at both small and large scales.

Hopefully it leads us somewhere worthwhile.

The Gambler (2014)

R Phillip Castagna — Sun, 19 Apr 2020 10:42:03 GMT

Preamble

I had another blog-type of thing before, and, oddly, the writing I had up there that got the most traffic over time was a series of posts I wrote about the 2014 remake of The Gambler, directed by Rupert Wyatt and starring Mark Wahlberg. Each post began exactly the same way, and in the series I tried to lay out the different things I loved about the movie, which got (and still suffers from) absolutely terrible reviews.

Since the content had seemingly found some unknown audience, I decided to go ahead and port it over to this new site. I suspect there's a surprising amount of value in really nailing any given niche, even when it's as tiny as this one.

What was previously a post is now separated within this text with a numbered heading. Little to no edits have been made beyond this reflow-ed structure, however, aside from some essential technical changes that hopefully won't impact anything too much.

Enjoy, and you should definitely watch the film if you haven't yet!

1. Film introduction

No one will ever convince me that the 2014 remake of The Gambler^[1] isn't the greatest movie ever made.

Don't think there aren't many people who would like to try. At the time of writing the movie stands with a 6/10 rating on IMDB^[2] and a truly brutal 44% on Rotten Tomatoes.^[3] It seems to have fared about as well as you'd expect it to if it was a film about a well-educated wealthy white male who gambles away both his own fortune and a sizable chunk of his family's—with no apparent remorse whatsoever—only to learn nothing and instead initiate an inappropriate sexual relationship with a student and escape his predicaments through a combination of rigging a sports bet by corrupting a promising athlete into throwing a game and making up the balance with blind luck in an outrageous bet... which is exactly what it is.

Jim Bennett isn't an incredibly sympathetic protagonist. As Frank puts it in the actual movie itself:

Birth, education, intelligence, talent, looks, family, money... has all this been some real comprehensive fucking burden for you?

...And to top it off, the movie is basically entirely talking! When it was (by all appearances) marketed as an action movie!^[4]

"I am of the universe, and you know what it's worth."

It's worth plenty.

The fact that the remake of The Gambler was received so poorly might actually make me love it more in some ways.

The thing is, movies are expensive to make.^{[citation needed]} Movies are expensive to make, and the major studios that make them are all divisions of publicly traded corporations that are legally obligated to try to squeeze out whatever money can be found by making them. That means limiting risk, that means making films that internationalize well, that means 3 super hero pseudo-sequels inside a shared cinematic universe every single year. Even all the way from New York, NY, we can see how Hollywood, CA changes^[5] when a Fast and the Furious sequel can make $400,000,000 in China alone and suddenly Dwayne Johnson has Jack Nicholson's floor seats for the Lakers.^[6]

The Gambler was a risk though. A genuine, honest-to-God risk that didn't even totally pay off. It's unapologetically wordy, entirely based in reality, deals with existential issues, relies on strong but often subtle acting, and has an overall sense of craftsmanship that's hard to find in major studio films. It's niche. To me, the fact that it ended up being unpopular is just a testament to it actually having a vision and not being some focused-grouped-to-hell bullshit. The Gambler takes a stand and was punished for it, but no one can ever pull a Brie Larson and ask its creators "did you make this because you believed in it or because you thought this was what people wanted?"

Wikipedia says^[7] The Gambler's director Rupert Wyatt "made his directorial début with the 2008 film The Escapist" before proceeding to actually make money by directing 2011's Rise of the Planet of the Apes---a classic Sundance-to-riches success story. I think you see a lot of Wyatt's indie sensibilities on display in The Gambler, (a friend of mine once said it's like someone made a Sundance film with a major Hollywood budget,) something which actually ties in well with its thematic content and ethos. After all, "who wants the world at their feet? It's confusing isn't it?"

A classroom full of students who don't give a fuck

The most niche thing about The Gambler (and what I love about it the most) is that it's a movie for creative people. It's for people who feel like they could yell as loud as they want and nobody cares. It culminates in Wahlberg's climactic monologue to Larson, which (personally) didn't just strike close to home for me, it cut straight to my heart:

You know there was a student—just the other day—who said that my problem (if one's nature is a problem, rather than just fucking problematic) is that I see things in terms of victory or death, and not just victory but total victory. It's true. I always have.

I mean it's either victory or don't bother. I mean, the only thing worth doing is the impossible, right? Everything else is fucking grey.

I mean you're born as a man with the nerves of a soldier, the apprehension of an angel, so lift a phrase, but there's no fucking use for it. Here? Where's the use for it? What, you're set to be a philosopher or a king or fucking Shakespeare, and this is all they give you? This? What, twenty-odd years of schooling—which is all instruction in how to be ordinary, or they'll fucking kill you—and they fucking will! ...Y'know, and then it's a career, which is just not the same thing as existence, so...

I want unlimited things. I want everything. I want a real fucking love, a real fucking house, a real fucking thing to do, everyday, and I just... I'd rather die if I don't get it.

In my experience, people tend to diverge sharply on their reaction to that speech. Some people (like me) feel like they can really relate to it... And then there's a large group of other people who are more inclined to say it's one of the craziest things they've ever heard.

There's a quote from an Eddie Huang story^[8] that I think speaks to the same kind of perception:

No matter what a stripper tells you, there are two types of people in this world. There are those who take the world at face value, keep the computers putin’, and don’t know to feel otherwise. The other type of person in this world has seen something wicked and the rest of their life is spent reconciling that vision against their existence.

I think that creative mindset (or instinct, or whatever) is both a real thing and only present in a minority of the world's population. A strong majority of people really are fine just "keeping the computers putin'", and it's always tough to genuinely feel different from everyone else around you. To that end, I would say the thing I appreciate most about The Gambler (and the thing I'd always want to bring up first) is that it feels like a genuinely very helpful movie.

It was for me, at least.

2. Aesthetics

No one will ever convince me that the 2014 remake of The Gambler^[9] isn’t the greatest movie ever made.

The first thing I always try to explain about The Gambler is that it's really a movie made for creative people. That's easy to say, but maybe not easy to convince someone of, so let's dig into it a bit more.

Maybe I enjoy the show

I remember the first time I saw the film was at an Alamo Drafthouse in Ashburn, VA—a sleepy neighborhood I didn't know at all, about a 45 minute drive from where I was living at the time. My girlfriend and I would make the trek out for occasional date nights, and I really appreciated how out-of-the-way it felt. The drive back, in particular, would usually be after 1am (late for the DMV, outside of Friday/Saturday night bars and clubs) along a nearly-empty beltway with enough time to let any given movie really sink in.

I remember making this journey back from the theater after the movie, and before I ever thought too much about why the film's themes resonated with me, I just kept thinking about how incredibly striking it was.

In a post-Loving Vincent^[10] world the "every frame a painting" adage might feel a little overwrought, but it's hard to find a single camera shot in The Gambler that isn't gorgeous. The cinematography relishes in interesting compositions that the main characters have a small presence in, along with varied, contrasting colors, and a strong sense of the environment for any given scene.

Even within the repeated setting of Jim Bennet's lecture hall, framing and lighting are manipulated to emphasize the warmth between Wahlberg's character and Larson's as well as the shared frustration with the world that connects Jim Bennet and Lamar Allan.

The creative shot composition doesn't just help the movie stand out aesthetically, either. This idea is something I want to revisit later, but all the main characters in the film are singular within their worlds, and the tendency of the movie to minimize their actual form on-screen emphasizes that.

Even in crowded scenes like the casinos, The Gambler prefers to let its main characters fall into the background of obscured shots rather than force a framing where they pop out to the camera more. The creative discipline to it is both unusual and terribly effective.

Seven days

The writing in The Gambler was just as striking to me as its visual aesthetic, and while the monologues are an obvious discussion point here, the creative discipline to some of the dialog is worth mentioning as well. Alvin Ing absolutely crushes his role, for instance, but part of that is capturing a very restrained sense of menace to the elder mobster that is Mr. Lee. His ultimatum to Bennet isn't gratuitous, he just wants his money in seven days... period.

In The Gambler the writing isn't just good in an abstract sense, it's actually good screenplay writing that gives the actors room to bring in their own energy. It might not be obvious why "I don't fucking want to do that shit" is a great line, but that's only when you haven't seen Michael Williams destroy the screen with it:

Of course, the other part of what makes the movie's writing so great are the times when it does simply go in, no holds barred. Goodman's last monologue is a great example of that—it's funny and clever while also being incredibly brazen and insensitive in a way that an actual mobster would be.

Got by talent, imagine that

I think some of what I appreciate as craftsmanship is exactly what kept The Gambler niche. What's "striking" to me feels overblown or even melodramatic to other people. Which is fine. I aim to be a man for all seasons, not all things to all people, and I appreciate others—and especially works of art—that do the same.

The sense of of a determined aesthetic present in the movie, though, is something that I think is indisputable. People might wish it pursued something different with the same enthusiasm, but the creative drive can't be waved away.

I think for creative people, though, the drive to bring a creative vision to life without compromise—regardless of what that vision actually is—is more respectable than anything else. In every field, professionals recognize other professionals before any other judgements, and The Gambler is unabashedly artsy in a way that people of the same make can empathize with.

The Gambler is for creative people, and the first mark of that is in its aesthetics and mechanics.

3. "Success"

No one will ever convince me that the 2014 remake of The Gambler^[11] isn’t the greatest movie ever made.

The first thing I tried to talk about with The Gambler is that it's a movie made for creative people, something I elaborated on while focusing on the film's aesthetic qualities. I think an unfortunate truth about it, though, is that it's also a movie for successful people—the ideal audience being both successful and creative, which is a tragically small niche.

A fairy story about a fight with a fucking monster

I linked John Goodman's excellent last monologue in part 2 of this series, but it's a really important point of synthesis for the film so bear with me while I revisit it.

It starts out with Frank brushing on his perceptions of and experiences with alcoholism—doing so, naturally, with a brutal frankness (Frank-ness?) that will continue on for the rest of the scene:

Frank

You drink? I don't remember if you drink. Of course, there's drink, and drink. I drink, but I haven't been drunk since Raegan was president.

I got a DUI, and in jail, I actually fell down and pissed my pants. You don't need to do that twice. I tell you this so you'll know everybody's been there.

Big Ernie

Everybody's been there.

Frank

Once. If you're there twice—having been there once—I can't help you...

You know, I listen to the drunks, and it's like you're listening to a fight with a fucking monster, when the actual title of the story is "I Can't Handle My Liquor," by Mr. Crybaby.

Big Ernie

Amen.

Frank

I don't know, maybe they got a problem, but fuck 'em if they do, 'cause I don't.

I really like the way this bit of dialog captures the sense of ennui that successful people can develop when they truly outgrow their past. It reminds me of Jay Z's demolishing opening bars on "Success":^[12]

I used to give a fuck;
now I give a fuck less.
What do I think of suc-cess?
It sucks, too much stress

That ennui is (I think) a strange mix of empathy and contempt; it is the "confusion" that Jim's grandfather is referring to at the very start of the movie when he asks his grandson "who wants the world at their feet?"

We all value different things. That's a fact that's easy enough to acknowledge in the abstract or on some after-school special, but a lot harder to accept in reality, especially when our own values have changed over time and people we ostensibly identify with—who have values we used so subscribe to!—can ask us why we're not happy when we have a BMW M1.^[13]

Fuck you

The Gambler is filled with characters who define their personal success on their own terms, keep their own counsel, and don't (truly) try to push anyone else to make the same choices they did.

Ed (Jim's grandfather) spent a life accruing wealth only to eschew leaving it to his (apparently only) grandson, instead trying to pass on some lesson of character.
Amy Phillips pulls her professor "into an inappropriate relationship" after seeing him in an illegal casino (where, to be fair, she works as a waitress) and even accompanies him to go gamble away the last money his family will ever give him.
Neville Baraka tells Jim (and the audience) directly that he's "not a huge fan of low company"—he's
just doing what he has to do.
Roberta (Jim's mother) is well aware that "nothing's okay", but she wants to make her own goddamn decisions.

...And on and on and on. Literally every significant character in the movie is defined by a sense of true agency that's very rare—both in narrative and in life. They make their own unique decisions based on their life own unique life circumstances, and they accept the struggles and pain as well as the happiness and success.

In some sense one could see The Gambler as a philosophically
"conservative" movie, aligned with right-wing politics and... something something bootstraps, or whatever. I think the thinking behind The Gambler is much more personal than that, though; I see the film actually as a true manifestation of Stoic thought and an exploration of the ways in which we try to live our lives beyond the confines of the hedonic treadmill.^[14]

The real divergence away from conservatism and into Stoicism is the very end—the infamous two-and-a-half minute "running scene" where Jim Bennett is finally free of all monetary obligations and he just decides to... run, all the way (apparently across town) to the home of the lovely Amy Phillips.

From what I've seen, people don't like that scene because it doesn't actually feel very triumphant. It goes on a little too long and Wahlberg's character ostensibly hasn't even really achieved that much; he's just back to zero.

Jim Bennett's ultimate success—what is (in film) normally a moment of true Triumph-with-a-capital-T—ultimately just feels like an absence of the anxiety (and beatings) that had stalked Jim throughout the rest of the film.^[15]

Which is what success really feels like.

At the end, all reset to zero, Jim doesn't want the extra cash Frank offers him, or even a ride to where he's going, because Jim has finally reached a personal position of "fuck you". Money would've been great, but Jim (like others in the film) has already "done all that", not found it rewarding, and now he just wants to start over.

In the universe of The Gambler we see first-hand that success is something we define for ourselves and how it won't necessarily feel like anything we think we've been promised.

Personally, that's a message I wish I had truly absorbed many, many years ago.

...But, hey:

Everybody's been there.

4. Character

No one will ever convince me that the 2014 remake of The Gambler^[16] isn’t the greatest movie ever made.

First, a quick recap of what I've covered so far:

The Gambler is a movie made for creative people, as seen in its aesthetic qualities---although it's also for successful people, which makes its ideal audience unfortunately small.

This link in the chain is about Jim Bennett's sense of ownership as a redeeming trait in his troubled character.

Everybody's (always) been there

So, something that I've been thinking about a lot lately is just the idea that life is intrinsically very hard, and that we aren't braced enough for that as we're growing up.

To bitch about participation trophies here would be to miss the point as much as those old after-school specials do when they explore a perverse world where all differences between people are both completely superficial and fully resolvable within a comfortable 60 minute viewing window.

What I really mean to get at is that there's an inescapable struggle in life that cannot be softened. Part of accomplishment is loss; part of health is illness; part of life itself is death. We read Dr. Seuss and muse on the places our children will go but try our best not to think of all the hardships in those journeys and what will meet them. We cannot, in fact, let ourselves get overly preoccupied with those hardships, because otherwise we would never do anything to begin with, and neither would our progeny.

No human has ever had any choice but to take chances---some big, some small—and try to figure things out one step at time, each time the results come back to us. Life's a gamble.

But still, we have a strong tendency to commit this unkindness against ourselves that express through the concept of "regret". We'll do something, live through a bad outcome from it, learn from that experience, and wish that we could have known all along without the lesson. We say that we "regret" having done what we did that made up part of who we are today, as though our lived experiences are separable from who we are.

"Regret" sucks, but the worst part about it is that as unkind as we our to ourselves, we tend to me much more cruel to others. It can be hard to not feel frustrated when people do not already know without ever learning.

The character of Jim Bennett is like a lightning rod for this emotion, and I suspect it's because he can remind us of some of the worst parts of ourselves.

I suspect, though, that realizing the strengths that are present in Jim can similarly help us find some of the better parts of ourselves.

No, I needed it...

A turning point for Jim's character comes when he realizes Amy Phillips (his love interest, played by Brie Larson) is being endangered by her association with him.

Mark Wahlberg's face at the exact moment his of his character's developmental climax.

He immediately moves to distance himself from her before fully (and finally)
launching into a plan to try to actually resolve his various mob-backed debts, something he was very notably unconcerned with before.

He is already on the hook for getting Lamar Allen to throw an upcoming game—that much was directly ordered by Neville Baraka—but Jim's approach shows immense consideration for Lamar as a person and deference to the basketball player's right to make his own decisions in life.

The discussion:

Lamar

What happened to your face, man?

Jim

A little while ago you came to me for advice about turning pro. I know it's about your knee, I know you have a feeling you have to put money in the bank, so...

I was wondering if you'd like to make a hundred fifty grand in two hours.

Lamar

Depends on what you have in mind.

Jim

Throwing a game. Can't win tomorrow by more than seven points.

Lamar

That's not throwing a game, that's winning by less than eight. Who wants me to do it?

Jim

Points at battered face

Lamar

What they got on you?

Jim

Doesn't matter.

Lamar

Man they fucked you up, and they ain't need to fuck you up.

Jim

No, I needed it. And they'll fuck you up if you need it too, you gotta deliver.

I'm asking 'cause I know you need it, it's up to you, it's your call.

Lamar

If I do this will I get you out of trouble?

Jim

No.

Key points that I think should be considered here:

First, Jim goes out on a limb to cut Lamar in on the money to be made. Note that Jim doesn't have Baraka's backing on this—he'll have to arrange his own bet on the game to fund it, all while hiding the entire exchange from Baraka—but he wants to do the right thing for the kid.

Second, while Jim does acknowledge to Lamar that Baraka's gang might try to come after him, he doesn't stress any personal risk to Lamar as a motivating factor. Realistically it seems unlikely that Lamar would be killed (or even seriously injured) without any direct interaction with Baraka or one of his people, but Jim is sure to be fully transparent about everything in play.

Third, Jim does everything he can to make himself a non-concern for Lamar. There is no attempt at emotional manipulation as Jim hides the risk to Amy, and he even tells Lamar that this definitively won't be enough to get him out of trouble.

Lamar is a key part in Jim's plan here, but Jim is taking immense ownership over the risks he's taking and refuses to put undue pressure on Lamar.

Paraphrasing a later scene, a man who takes ownership of his decisions and risks might even be more rare than a man who delivers.

Everything will start to be ok

I can understand why a lot of people would find Jim to be morally contemptible, but if you look back from the end of the movie I'm not sure that really holds up.

His absolution is to "get back to 0", having gotten out of debt and broken his ties to various organized crime syndicates, but not actually ending up with any money either. He declines Frank's invitation to take the "cream on top"—he won't even accept a ride home.

It's free money, what could go wrong?

And he achieves this "feat" through immense personal risk and having spent the length of the film getting the absolute piss beaten out of him more and more. He even gives away his Omega watch because (apparently) fuck it—or so Frank would say.

So he's spent all this time torturing himself by proxy, suffering viscerally for his various mistakes, but gets back to 0 and is strong enough to walk away, having learned from his mistakes and having found something (and someone) he wants to protect.

Can you ask much more of someone than that? Should you?

Maybe more importantly:

Can you ask much more of yourself than that? Should you?

Directed by Rupert Wyatt and starring Mark Wahlberg ↩︎
https://web.archive.org/web/20180930194141/https://www.imdb.com/title/tt2039393/ ↩︎
https://web.archive.org/web/20180930194257/https://www.rottentomatoes.com/m/the_gambler_2015/ ↩︎
That link is "supposed" to point to the trailer for the film, but it's actually the trailer for the Rotten Tomatoes viewer score tumbling down to a gentleman's 33%. ↩︎
https://web.archive.org/web/20180930203544/https://www.newyorker.com/magazine/2018/05/28/how-superheroes-made-movie-stars-expendable ↩︎
Yes, that's an Uhh Yeah Dude reference, although I wish I could find the specific episode. ↩︎
https://web.archive.org/web/20181002064757/https://en.wikipedia.org/wiki/Rupert_Wyatt ↩︎
Specifically, the Amazon original Single Asiatic Male Seeks Ride or Die Chick Published digitally 2018-05-28 by Amazon Original Stories, ASIN B078W75GKQ ↩︎
Directed by Rupert Wyatt and starring Mark Wahlberg ↩︎
The 2017 animated film directed by Dorota Kobiela and Hugh Welchman. ↩︎
Directed by Rupert Wyatt and starring Mark Wahlberg ↩︎
Track 12 off of American Gangster, one of Hova's underrated albums. Released 2007-11-06 by Roc-A-Fella Records (release B0010229) ↩︎
Ironically enough, Wahlberg's character drives a BMW 1M in the movie, not an M1. ↩︎
Stoicism is actually one of the major underpinnings of the "tech elite" today, who will often recommend A Guide to the Good Life: The Ancient Art of Stoic Joy by William B. Irvine as a good primer for the modern reader... The unfortunate part is that that's actually a really good book and the first one I would recommend, also. Published 2008-11-04 by Oxford University Press, ISBN 978-0195374612 ↩︎
Alternatively: "the absence of failure", to use Elan Mastai's phrasing from his (overrated) novel All Our Wrong Todays. Published 2018-02-20 by Penguin Random House, ISBN 978-1101985151 ↩︎
Directed by Rupert Wyatt and starring Mark Wahlberg ↩︎

Conspiracies Against the Public

R Phillip Castagna — Sun, 12 Apr 2020 15:26:34 GMT

In November of 2019, I started working on a collection of short fiction pieces focusing on relationships that I titled Conspiracies Against the Public. The original plan was to only release it physically, selling it at a wonderful "art book" store here in New York called Printed Matter, but with the COVID-19 pandemic it felt like it made the most sense to at least do some preliminary digital release.

Well, I'm happy to say that Conspiracies Against the Public is now available for Kindle (and the assorted Kindle apps) through Amazon. What follows is the first of the dialogs in the collection, to give people a feel for what the book is all about.

1.

I closed my eyes.

My head was resting on her stomach, and she was idly running her fingers through my hair. Her nails' soft sweep against my scalp sounded like the ocean. That moment: a world unto itself.

“I just don’t get why it’s a big deal,” she said.

I smiled and opened my eyes.

“You can’t fuck your receptionist,” I said.

“Why not? She’s so cute!”

I grinned, exhaled; I think my eyes closed again.

“Because you’re a rising star at your company, and the power differential of a young executive fucking the office receptionist is never really ‘ok.’ Did no one ever take a second to, like, pull you aside, have some kind of talk with you about this stuff? Like, really?”

“No, look, it’s fine: I checked on it, and she’s not even one of our employees. We contract out for reception!”

“Ok, but look, see: it’s a really big red flag here that you’ve already checked that out, you know.”

“I just don’t get why it’s a big deal,” she said.

I laughed and willed myself to stir, kissing her stomach before rolling over fully to look up at her.

She had been stroking my hair with her left hand, and still held a cigarette in her right. It was one of my cigarettes, of course—though I had told her she was more than welcome to them. Seeing her smoke felt... right. She was a captain of industry; smoking famously was part of the package.

“There’s some kind of gender-Realpolitik thing you've got going on here that I think you’re overly confident in. What’s this girl even like?”

“She’s, like… really Christian, actually," she said. She paused, thinking for a moment. "I was talking to her at one point, and she had her notebook out, and when I looked at it, it was all this writing about being happy Jesus was in her life and stuff…”

I laughed.

“What am I going to do with you,” I said. Even as I said it, though, it felt like something somebody had said to me once before.

She frowned and took a drag.

“I just don’t get why it’s a big deal.”

I laughed again.

“You’re trying to corrupt this wonderful young woman under your employ! This lovely young woman who just wants to put in an honest day’s work and love Jesus! You’re supposed to be, like, her role model, not trying to bone her!”

“I told you, she’s a contractor!”

“What am I going to do with you!”

"What kind of a question is that!"

I laughed again. I turned my head away, bowed down, kissed her stomach again, and followed that with more small kisses, meandering upwards along her body, mentally plotting a course towards her nipples. I moved back between her legs; she took another drag, and stubbed out her cigarette on the nightstand.

“When did this happen with you being bi, anyways? I wasn’t here for this development in your life,” I said. I punctuated my sentences with continued nips at her torso.

“I’m not bi, I don’t think. I mean, I definitely don’t want to say I’m bi, you know? I don’t want to have to put myself in a box like that.”

“That’s ok, I won’t ever make you.”

I paused and looked her in her eyes when I said that; I wanted to make sure she knew I meant it. She reached out, stroked my hair again, looking back into my eyes, pausing for a moment. Then she looked away again.

“Aren’t basically all women bi, anyways?” she said.

I smiled again.

“Unfortunately, no. There’s a difference between being able to find someone of a certain gender attractive and actively wanting to have sex with people of that gender, y'know. A tragically large portion of the women I've met seem to be fine with the former but not the latter…"

She looked back at me while I meandered. She ran her hand through my hair again.

“Maybe I just want to ask you about it for the same reason I like talking to you about everything else,” I said. “It feels like we can get each other, right?”

She gave me a very specific look. Then she grabbed my head and pulled me up to kiss her. I closed my eyes once again.

It was a kiss that didn’t have a duration so much as it defined an epoch. There was a before, and there was an after, but the during was not something confined enough to this world to be measured.

I leaned my forehead against hers, and I knew I was smiling a bigger smile than was truly possible.

I knew it.

“I’m going to lose you again before I get to see you again, aren’t I?” I said.

“Of course,” she said. “What kind of a question is that?”

Read the whole thing on Kindle and the Kindle apps!

Special thank yous to Lubens Besse, Allison Borko, Claire Boston, Olivia Chiu, Haneen Daoud, Gabrielle Dufrene, Aviva Jaye, Jessica Lu, and Eli Schwadron for giving input on early versions of the collection.

Content for COVID: album picks

R Phillip Castagna — Sun, 05 Apr 2020 23:05:38 GMT

So it's April 4th today, and we have this pandemic thing going on—the novel coronavirus. I'm three weeks into working from home here in NYC, and something I've been thinking about on and off has been this nagging sense that my life doesn't actually feel all that different.

I've definitely been taking a lot more time to check in on various loved ones and important people in my life, trying to find ways to free up any cash I can spare to help support various local businesses I have ties to, and really just worrying about others more in general. But I'm not necessarily feeling as much impact in my own life, personally.

I'm working from home, yes—and I definitely miss various niceties at the Facebook office—but I'm also realizing how many of my habits and routines had already been shifting to give me the mental space to work more creatively. Whether I structured my life like this intentionally or not, I was already drifting from the daily goings-on of most of the world; I already kept odd hours, had a working space at home, and had interests and hobbies that I pursued almost entirely on my own.

One thing in particular that strikes me is that I had already made very conscious efforts at some point to increase the amount of really substantive content that I was reading, watching, and listening to. In practice, this meant that I'd try to read more books and fewer blogs or news articles, watch more movies while paring down the number of TV series I was following, and look out for good albums I could dig into while dodging the random new singles Spotify would recommend me. It was never a question of eliminating those latter groups, just trying to find a way to not let them overwhelm my interest in the former.

At some point I had found that if I didn't make a conscious decision to build these substantive experience into my life, it was very easy for them to get washed out while I was dealing with my day-to-day routines, and this was a much more dangerous trap than it might seem. I noticed that really good, substantive content stayed with me in a way that was sort of hard to explain. It gave me something to think about, kept my perceptions open to new kinds of experiences, and actually helped calm me down, overall, in a way that I could only really compare to exercise—it isn't necessarily obvious in any given moment, but I'm definitely less anxious overall when I'm reading a book a week versus when I don't even open the Kindle app for a month. The danger here is the same one as exercise, in fact: if I don't stick with it, everything feels more overwhelming, and when I'm feeling overwhelmed like that it becomes that much harder to step back into positive habits.

As it is now, I feel almost pleasantly un-stuck in time. A nice thing about really substantive content is that it stands on its own, giving it that "timeless" quality. It doesn't matter if something was first published 40 years ago if it's really good, because you have this primary experience with it—it doesn't matter if it's new, it's a new experience for you. That helps you break from the habit of compulsively seeking consensus with others that can be all too easy to fall into, and focus on just appreciating your own experiences with a work without worrying about your own taste being good or bad. It also, conveniently enough, helps you get a bit of psychic distance from whatever concerns you're dealing with at that moment, and can help you keep perspective on whatever challenges you're facing on any given day, which ultimately leave you better equipped to handle them.

Because this has been so helpful for me, I thought I'd do a few posts highlighting really substantive content that's been meaningful to me, personally. The idea is to promote the overall concept, give people some pointers if they find it hard to discover meaningful stuff, and just share some work that I've really loved across my life.

I'm (somewhat arbitraily) starting with music albums. I didn't want to try to put together any kind of definitive list—even of my own favorites—because it's not about the rankings, just sharing meaning. Instead, I quickly ran through my Spotify et al, looking for albums that met all these criteria:

Albums I listen to all the way through, start to finish
Albums I've listened to at different points in my life, at least a few months apart
Albums that left me with some kind of expanded sense for what kind of music I like and want to find more of

Even without trying to be exhaustive, I ended up with these 68, and I think they cover a pretty broad variety of sounds and time periods. Hopefully there's something new in here for you, but also—hopefully—it makes you think of at least one or two albums you'd definitely put in your own list.

Year	Artist	Album
1959	Miles Davis	Kind of Blue
1963	Bob Dylan	The Freewheelin' Bob Dylan
1964	Cannonball Adderley	Nippon Soul
1966	Cannonball Adderley	Mercy, Mercy, Mercy! Live at "The Club"
1974	Parliament	Up For The Down Stroke
1976	Ryo Fukui	Scenery
1980	Dead Kennedys	Fresh Fruit for Rotting Vegetables
1980	Himiko Kikuchi	Don't Be Stupid
1980	Talking Heads	Remain in Light
1983	Yo-Yo Ma	Bach: Unaccompanied Cello Suites
1985	Kate Bush	Hounds of Love
1990	Jawbreaker	Unfun
1991	My Bloody Valentine	Loveless
1991	Nirvana	Nervermind
1993	A Tribe Called Quest	Midnight Marauders
1994	Jawbreaker	24 Hour Revenge Therapy
1994	Ryo Fukui	My Favorite Tune
1999	Mos Def	Black On Both Sides
2001	Daft Punk	Discovery
2002	The Mountain Goats	All Hail West Texas
2002	Wilco	Yankee Hotel Foxtrot
2003	Jay-Z	The Black Album
2003	Nujabes	Metaphorical Music
2004	Death From Above 1979	You're A Woman, I'm A Machine
2004	Modest Mouse	Good News For People Who Love Bad News
2004	Roy Davis Jr.	Chicago Forever
2005	Common	Be
2005	Deep Dish	George Is On
2005	The Mountain Goats	The Sunset Tree
2005	The Shanghai Restoration Project	The Shanghai Restoration Project
2005	Wilderness	Wilderness
2006	Clipse	Hell Hath No Fury
2006	Phoenix	It's Never Been Like That
2007	Jay-Z	American Gangster
2007	Kanye West	Graduation
2007	Radiohead	In Rainbows
2007	The-Dream	Lovehate
2008	of Montreal	Skeletal Lamping
2008	Vampire Weekend	Vampire Weekend
2008	Zac Brown Band	The Foundation
2009	The xx	xx
2010	The Drums	The Drums
2010	End of a Year	Composite Character
2010	Kanye West	My Beautiful Dark Twisted Fantasy
2010	of Montreal	False Priest
2010	The-Dream	Love King
2011	Destroyer	Kaputt
2011	Drake	Take Care
2011	James Blake	James Blake
2011	Jamie Woon	Mirrorwriting
2011	Wale	Ambition
2012	Breakbot	By Your Side
2012	Chief Keef	Finally Rich
2012	Kendrick Lamar	good kid, m.A.A.d city
2012	Miguel	Kaleidoscope Dream
2013	Pusha T	My Name Is My Name
2014	Jungle	Jungle
2015	Jamie xx	In Colour
2015	Jeremih	Late Nights
2015	Soichi Terada	Sounds from the Far East
2016	Car Seat Headrest	Teens of Denial
2016	Mallrat	Uninvited
2017	2 Chainz	Pretty Girls Like Trap Music
2017	Jay-Z	4:44
2017	Playboi Carti	Playboi Carti
2018	Haru Nemuri	harutosyura
2019	Toro y Moi	Outer Peace

"How to see" in 2018's The Price of Everything

R Phillip Castagna — Wed, 01 Apr 2020 03:07:44 GMT

So there's this great documentary about the contemporary art market called The Price of Everything, directed by Nathaniel Kahn as an HBO Original. The whole film is definitely worth watching, but there's one piece that I always thought was interesting—a phrase that pops up without ever being directly examined, but feels so essential to other themes in the movie: "how to see".

It first appears in a question that Kahn poses to Larry Poons early on:

The question of "how do you learn how to see?" felt very insightful at its core—over time I've noticed more and more how different people will have different immediate reactions to the same experiences. People who work in the visual arts tend to have a much richer emotional reaction to a given picture or view than the average person, and I suspect that's probably a big reason those people get into producing visual art themselves. It reminds me of Ira Glass's coaching to emerging creatives that their taste is going to be a lot stronger at the start than their actual creative ability.

This idea also reminds me of one bit of dialog in the (also excellent!) book Simon: The Genius in My Basement by Alexander Masters. The author asks the titular Simon, a bona fide mathematical genius, what "beauty" is in mathematics. Simon's reply has always struck with me:

“All I can say,” he barked, abruptly annoyed, “is that whatever nerve it was that tingled when I saw Torghatten Mountain from the boat two nights ago, it is that same nerve that tingles when I see a piece of beautiful mathematics!”

There's an intuitive feeling of "beauty" in mathematics for the people who have a certain predisposition for it. The same goes for code, incidentally—maybe even triply so. A lot of software engineers that I've worked with will sometimes have a hard time understanding why what they do is difficult for most other people, and I think it's just because they've built up such a strong intuitive understanding of code that they have a hard time remembering the journey that got them there. But they also have a strong immediate idea of what "beautiful" code is versus "ugly" code, and when I point to that it can be a helpful benchmark for them to guage the difference in their intuition versus other people's.

The second time this idea of "how to see" pops up in the documentary, it's from someone completely different (Amy Cappellazzo) which made me wonder about whether this discussion was shot before Kahn's interview with Poons or if it was just a happy coincidence:

Both Poons and Cappellazzo express this view that there are certain experiences of the world that we just either have or don't, and that we can't necessarily train ourselves into having them if we're not wired that way. In some sense that might feel kind of depressing or defeatist, but in another sense it's nice to just be aware of how rich and varied the human experience is and can be.

Understanding that variety of lived experiences is an important part of finding more richness in our own lives, I think. One of my favorite books—and definitely one of the ones I recommend to other people the most—is The Great Passage by Shion Miura, because I think it's particularly good about highlighting these differences in all kinds of ways. It's a novel about a group of people compiling a dictionary in Japan, and the narration jumps its focus from one primary character to another as it progresses; the differences between the various main characters is illuminating, but so is their task of compiling a dictionary. In order to make the dictionary as good as possible, they all have to think a lot about usages for words and how those words fit into people's lives, and it's a frequently poignant exercise:

“Well, it’s partly that.” Nishioka hesitated slightly. “Suppose an actual drifter is leafing through a dictionary at a library and comes across an entry for the word saigyo that says ‘a wanderer or pilgrim (after Saigyo, the itinerant priest-poet).’ Think how he’d feel. He’d tell himself, ‘So Saigyo was just like me! Even in the old days, there were people who never stayed put.’”

In the second clip from The Price of Everything that I embedded above, Peterson talks about apartments "on the sixth floor, the eighth floor, and the tenth floor of certain buildings". When she says that, she's moving the numbers by two floors at a time because she's talking about duplexes—ridiculously expensive two story apartments within even larger apartment buildings. She's so embedded in that environment that I expect she doesn't even think it might be a point that needs clarification, getting at Cappellazzo's early point that she's a rich person, even though she doesn't necessarily consider herself to be.

Working to keep a broad awareness of all of what's possible is something that tends to help me feel more grounded in life. The only thing I wonder about is if it's something I can give to other people, or if it's like trying to teach them "how to see".