⭒ 2025 Review and Lookahead: A "Graduation" Every 5 Years

Today marks exactly a year since I've graduated undergrad in May 2025. I remember on this same Friday last year, I was upstairs at the Cohon Center, getting fitted for my cap and gown. Time really does fly! Too! Fast!

I find some comfort in the rhythm of a school setting, that you go through a 4-5 year long wandering of sorts (a figurative, existential sort of backpacking), and by the end of this 4-5 years, you "graduate" onto the next stretch of trail.

I like that this backpacking is lightly charted in some way, that every so often, you mark off the next waypoint in front of you.

In school, these waypoints are portioned out into the segments we know as Fall, Spring, and Summer. I liked that each segment was 15 weeks; it's short enough that you can see the end of it from the very first week, yet not too far into the future that the horizon collapses into a sludge of abstraction.

My Habit of Waypoints

When I was in school, at the start of each of these waypoints (Fall, Spring, Summer), I would write down a flurry of questions that I hoped to answer by the next waypoint. Then I would go down the list and pick one guiding question as my north star for that stretch. (Often it would be difficult to pick just one, so I had a hard-and-fast rule to not have more than three intents/pursuits.)

By the next waypoint, I would go over the "north star" questions I had from the previous waypoint. More often than not, I'd arrive at the next waypoint having wandered far from where I thought I was headed. The beauty of school was that chasing one question would surface many others, and I'd find myself arriving with very different interests than I'd set out with.

When I graduated, I assumed this habit would quietly die. Without the natural pressure of the ticking clock that's the semester system, I worried I'd drift, swallowed by what I can only call the tyranny of structurelessness.

A "Graduation" Every Five Years

In my final year of college, I read Becoming Trader Joe, and in it, Joe Coulombe, the founder of Trader Joe's, writes five-year plans for his grocery store enterprise.

I was inspired by this and realized I could continue my habit of marking waypoints in my own way.

So I decided to mark every five years as a graduation of my own making. Since I graduated in May 2025, I was delighted that the years count up cleanly, 2030, 2035, 2040, each a commencement of sorts. And within each five-year stretch, I'll continue marking my waypoints Spring, Summer, Fall, with the seasons as semesters, and the five years as a figurative degree.

By 2030, I look forward to decorating my graduation cap with the people, places, and pursuits that marked this first stretch of postgrad. :)

A Call for Names

By the way, I need a better name than "postgrad" for each of these five-year chapters. Postgrad will last fifty years; it names a negation of an era, not an era in and of itself!

My high school chapter had a name because it was a place, as did my college chapter.

I'd like my five-year chapters to have names too. Maybe it's the name of the place I'm living in or the place I work, or maybe it's a theme I only recognize in retrospect upon "graduation." I haven't settled on one yet.

If you're doing five-year chapters of your own and have thoughts, I'd love to hear them too.

Lookback: "Freshman Year" of Postgrad (May 2025-2026)

Adorably enough, I actually did write a plan for my "freshman year" of postgrad, when I was approaching graduation in my final year of undergrad. I will quietly keep that copy of my plan to myself and put a shorter (though not terribly short, hah) summary on here.

The short answer is that I came out of undergrad knowing I wanted to head in the direction of "research or startups," with a couple asterisks. So if you approached me as I was graduating and asked me what I wanted to do, the super shorthand answer I'd give you was,

"I want to do research and startups."

But that doesn't quite cover the full story; I think, the truer yet harder-to-explain way of putting it is that I was trying to become an independent researcher.

Finding the Label

Ever since my first SWE internship, I had this sense that the label SWE didn't quite capture what I wanted to do with my life. That if I were to make SWE my means of living, I'd want to have produced something meaningful outside of it too.

This was not for a lack of love for the discipline; I'd loved programming since I was a child, making silly things for the joy of it, and I was sure I could handle the technical work. But I knew I'd feel like I lived an incomplete life if I never produced anything beyond my SWE duties.

The label I eventually landed on for myself was "independent researcher", after finding my inspiration in a community of writer-creator polymaths who learn and build for the public. What I meant by that was something like an anthropologist but more hands-on, someone who embeds in communities, tries to understand what people want, builds things for them, and writes about how those systems work.

There's no job posting for independent researcher (nor would I have been unhinged/brave/financially fat-FIRE'd enough to take that route), so I translated it into terms I could apply for.

And so, I translated this into the socially legible shorthand, "I want to do research and startups." Research, because your job is to investigate things. Startups, because you're close to customers, building things for people, navigating human systems and technical ones at once.

Work, Regardless of Container

"Research and startups" is awfully broad as a goal. I saw these things, research and startups, and the institutions associated with them, as containers in which to do my work, that were interchangeable in some sense. My work was work for something bigger than myself regardless of where I did it, characterized more by how I moved through it than by which institution's name sat above it on a résumé.

So I liked the label, "independent research," and it felt right because I could do it regardless of what container I did it in. I could very well hold a 9-5 job and pursue the questions that mattered to me, and I could very well be in grad school, a startup, or a research lab doing the same.

I think there's a tendency to reduce people to the company that they work at, or the school that they're pursuing their degree at, if they even have a degree at all. One thing that unsettled me for some time was how easily I could be reduced to a one-liner, and how much this one-liner could matter for acceptance into the circles closest to me - friends, family, romantic relationships, etc.

What gave me peace with it, eventually, was that I realized that one-liners are as much for other people's convenience as they are for mine. They're a way of helping someone orient towards you before they know you. I still happily answer where I work and what I studied even if it's not the full story, and I stopped silently bracing for whether my answer would hold up under audit as "adaqueately legible" or "adaqueately ambitious" depending on who was sitting across from me.

Still, I do hope to find a container (a lab, a startup, a nonprofit, a ...?) where the one-liner is the same as what I am, where what I'd put on a résumé and what I'd write in my journal are largely one and the same.

Looking Ahead: "Sophomore Year" of Postgrad (May 2026 – May 2027)

Floor: ML Systems at Standard Kernel

I call this the "floor," since by virtue of this being my job, it already has momentum and accountability. Even if nothing else on this list gets done, this is the one that comes first.

I recently left my job at Meta in security to join Standard Kernel, a seed stage startup founded by friends. My goal for 2026 is to onboard and contribute as meaningfully as possible, so I can be qualified to mentor new hires and pay it forward.

Goal: independent research interest

I call this "goal" since this would not happen without active self-discipline; no one is waiting on me to do this.

Complete one experiment in a research area I'm curious about that's adjacent to what I do. The details are hashed below and will be revealed in my 2027 post, since I have this superstition that I'm less likely to jinx quieter goals.

sha256: fb23e049e7f357cb6c94415ff24e97ff4e6f91b1c04605aa0fc4b396637907ac (revealed May 2027.)

Ambient: lifestyle goals.

I call these "ambient" since these fill whatever space the other two leave behind. The only thing standing between me and these are couple of free weekends.

[] Ship Electric Catan with my team, DigitalFlock (Open Sauce '26)

[] Make one home-cooked app or explorable explanation for a local org

[] Learn five dishes with slightly more ceremony than I'd bother with for myself. Left to myself, I eat anything with protein and a vegetable, but most people have strong opinions about food. So this is for everyone else. :p