[Note: more personal content]

My self-retrospective for 2020. Mostly for me, but I’m publishing it here - because why not? You may find it useful.

# First, a few unstructured thoughts

On Learning

This was my first year outside of the education system. The previous twenty-one were motivated by one commandment: “learn”. Whether school, hobbies, or work, the yardstick of success was “well, did you learn something?”

Externally, that expectation is now weaker - after all, I’ve entered what society expects is the “doing” phase of one’s career. Internally, however, my expectation hasn’t changed. School is ending, but my learning won’t be.

At the same time, however, I’m starting to question if Optimizing for Learning should always be the top priority. There are other good outputs - such as impact to the world or personal benefit - and this year, I made decisions that put them below learning. I wonder if that’s always going to be the right choice: When’s the time to put Execution above Learning, or Investment below Payoff?

The phrase “I’m still learning!” may be dangerous, because it sounds so virtuous. I’ll always be able to put myself in places where I’ll be learning. So the question becomes: When, if ever, is learning no longer the highest virtue?

It’s not a dichotomy, but it is a balance, and I’m figuring it out.

On Doing

Until March of 2020, I believed extended time to myself would mean I’d read a hundred books, get super jacked, and hit a new level of clarity. Given that it’s been 9 months since lockdown - and I haven’t read through a library, haven’t changed my fitness substantially, and remain just as confused - I longer believe that.

Prior to March, my justification was my environment: “I’m distracted”, or “I don’t have the time”. Those justifications were clearly excuses.

I think the takeaway is this: If I’m waiting on something, it’s because of me. Do it now, or it won’t happen.

On “Being an Adult”, whatever that means

I spent 2020 alternating between traveling (pre-COVID), living at home, and living in Airbnbs for about a month at a time. All were extremely transient. Since the timeframes were, so short, I didn’t invest much in my routines, habits, living spaces, or community. I suspect many of these define “being an adult” - so maybe I haven’t made the transition yet. But that’s totally fine. Putting off “adulting” has been fun.

On Stagnation and Growth

This year was contradictory.

On one hand, many things didn’t change. The number of new, meaningful friendships I made was probably <10% of the number the year before. I’m ending the year in a similar place to where I started it: Haven’t moved to California yet. Haven’t figured out a permanent living situation. Haven’t become an “adult”.

But at the same time, this year was extremely interesting. Paradoxically, even though I spent 9 months of the year “locked down”, and 7 months in a “routine”, full-time job, this was arguably the most eventful year of my life.

# How I spent 2020

  • Graduating from college (end of December)
  • Traveling through Asia (January)
  • Traveling through the USA, sleeping on friends’ couches (February)
  • Writing and working on personal projects (January - March) - such as this and this. One made the front page of HN!
  • Lockdown with my family (March)
  • Starting a non-profit (helpinghands.community) (March - May) - launching a product hackathon-style, growing the org to hundreds of people, evolving culture, press, and product as we completed tens of thousands of deliveries
  • Almost co-founding a startup (March - May) - building a prototype, evaluating a seed investment + cofounders. Ultimately chose not to; the reasons are another essay.
  • Working at a startup - my first full-time job! (June - December) - evolving strategy and product definition, experiencing tactics of a growing company, doing product work for the first time
  • Airbnb hopping in Utah, Colorado, and Washington (July - December)

# Ten general things I learned this year

These aren’t all novel - many are things I’d already been told. But this year hammered them home.

1. Focus is everything.

In organizations. In personal life. In relationships. In everything.

In organizations: I’m convinced every organizational issue I saw this year could have been avoided with clearer focus - whether that was product focus, decisive leadership, or clarifying culture. My corollary theory: 80% of organizational overhead is just trying to break down problems into five-minute chunks, and get one person to focus on each chunk.

In personal life: This year, I was most unhappy or most confused when I couldn’t identify my priorities - when I couldn’t focus. This was also when I got the least done.

In relationships: COVID forced this. By raising the stakes of interacting with others - through implicit Zoom awkwardness, or calculated risks from meeting in person - my social interactions became more deliberate. That made them more meaningful.

2. Narratives are irrationally important. They need to only weakly correlate with reality.

We overvalue stories. Projects we work on need to fit into a broader narrative. Our job needs to fit into the narrative of our life, and our life needs to fit into the narrative of our world.

This is somewhat nonsensical. Sometimes, things can just be objectively good - without needing to fit into a broader picture. But it’s human nature to hope that they fit into something larger.

The surprise for me this year was learning how little these narratives/stories need to reflect reality. A compelling narrative - unsupported by facts - is often enough to sway action! Whether it’s a disingenuous media interpretation of recent events (and wow, there were many this year) or a not-so-clean co-founding story that’s been reframed as a deliberate causality, this is everywhere.

I think this is really why dysfunctional organizations heavily rely on secrecy: secrecy allows for forming narratives that abstract away the details. On the flipside, transparency without a narrative can be dangerous too: if you’re an organization that prides itself on full transparency, it becomes obvious when you don’t have a narrative - and your org starts to fall apart. If you’re a country that encourages individuality, but is losing its sense-making apparatus - where institutions are breaking down and conflicting stories are everywhere - you lose the unifying narrative, and you get chaos. (See: USA 2016-2020.)

3. Good things almost never come from indeterminate sources.

A productive organization, innovative technology, or meaningful relationship - but really, any good thing - is always traceable to the deliberate actions of a single person or a small group.

Our postmodernist era indexes too much on emergent behavior (ex. markets, statistics, luck). I still think emergent behavior is an optimizer, but I now more strongly believe that improvements are fundamentally traceable.

Progress does not come from indeterminate sources. The “economy” is not a well society can drink from indeterminately. Companies cannot be counted on to always “innovate”. Instead, progress comes from deliberate planning.

Organizationally, I think there’s a stage - usually a function of organization size - where groups of people go from determinate to indeterminate optimism - where they can’t coherently pinpoint the source of their good fortune. This change is almost never good.

4. Culture requires deliberate investment, and it’s extremely important.

No amount of process can beat a well-designed culture.

My theory why: every organization has unwritten rules. One can try to enumerate the rules - this is what we’d call “process”. But at a growing organization, there will always be more unwritten rules than enumerable ones. So it’s higher leverage to instead set the meta-rules - the rules defining the interpretation of the unwritten rules. This is “culture”. In the ranking of leverage points, process touches the lower-ranking factors, but culture touches the higher ones.

5. Who you know > what you know - but it’s not really that simple.

Here’s the thing: you can’t get to know people unless you know things that those people can relate to. I think this reconciles the “business networking paradox”: the reason networking meetups don’t work is because jumping the gun to the “who you know” without the “what you know” to connect them first is soulless.

Relatedly, the best mentors I had this year weren’t the ones that taught me things directly - they were the ones that guided me towards what I should learn.

6. Holy sh*t, organizational overhead grows quick.

This was the first year I worked in groups larger than a few people - first, with my nonprofit, then, by joining a company. And damn, overhead scales quickly. With smart people, I suspect overhead scales with the square of an organization’s size - and with less talented people, it’s even worse.

Others have argued this better than me, so I’ll just cite The Mythical Man Month.

7. Don’t underestimate the power of a simple tweak to what’s in front of you.

Being around people has historically been my forcing function for change. But since that wasn’t as accessible this year, when I look at what most changed my habits, it wasn’t exciting stuff. It wasn’t epiphanies or deep reflections. Instead, it was the dumb stuff.

Disabling notifications from appearing on my lockscreen. Creating a single calendar event to force a check in with people. Laying out the exercise mat the day before.

This is reassuring - I can make huge changes with simple actions!

8. If you don’t measure it, it won’t improve.

It’s clear why this is important procedurally: measuring something focuses one’s attention and creates accountability. But I learned a more powerful reason this year: defining a measurement forces you to define the problem - and you can’t solve problems you haven’t defined yet.

Everything can be measured. If you can’t measure it, that’s not a problem with the problem - that’s a problem with how you’ve defined the problem.

9. Learn what you’d like to do now, not what you think will pay off later.

The learnings that paid off in 2020 were not things that I thought would be valuable at the time I learned them. Rather, they were the things I liked doing at the time that serendipitously worked out.

When choosing what to learn, don’t worry about what will have better “payoff”. Instead, pick what you enjoy more.

I think there are two reasons this works. The first is that we’re bad investors - what we think will be important is often not. The second is that you tend to do better at things you like - and thus the investment is more likely to be a meaningful one.

10. The decision is much less important than the following through.

Without getting into details, I likely spent 10% of this year agonizing over personal and career decisions. But looking back, I worried about the decision only before I made it. I haven’t spent a second thinking about them afterwards.

What has turned out to be important is following through on the decision I made - committing to it, and taking the steps to carry it through.

# Five things I learned about myself this year

  1. Life-consuming things make me happier than “balanced” things. I’d rather work 16 hours a day on one thing than 4 hours a day on four.

  2. I don’t regret decisions. But I do regret being indecisive. So I should agonize less over picking.

  3. I shouldn’t be afraid of free time. When I have free time, I spend it productively. The first five months of this year were completely undirected, and I wish I’d spent longer. The caveat is these need to be large chunks of free time.

  4. I work best on things I have the largest stake in, regardless of their size. I’m more passionate as the founder of something small than the supporter of something large.

  5. What I do is highly dependent on who I’m around. Moreso than I realized.

# Places I lived

Places I stayed five or more days. Not that meaningful, but interesting - I moved around a lot. Each could be an essay.

  • Taipei, Taiwan - January
  • Kyoto, Japan - January
  • Tokyo, Japan - January
  • Austin, TX (college apartment) - January-March
  • San Francisco, CA - February
  • Palo Alto, CA - February
  • Ann Arbor, MI - February
  • Atlanta, GA - February
  • Austin, TX (parent’s house) - March-July, November-December
  • Draper, UT - August
  • Moab, UT - August
  • Fraser, CO - September
  • Salt Lake City, UT - October
  • Shelton, WA - December

# Priorities for 2021


Sort of meta, but I spent 2020 too scatterbrained. Focus is my most important tool, and I want to rebuild it. This’ll look like:

  • Eliminating distractions - both at low-level (such as on my phone) and higher level (# of projects I’m taking at work).

  • Consuming longer-form content - books, podcasts, albums, textbooks.

  • Diving deep into one thing instead of cursorily investigating several.

I’m won’t be prescriptive about what I focus on - what’s more important is the metagame.


Who I’m around influenced me the most.

  • Meeting new people, more regularly.

  • Being more intentional about who I spend time with and why.

  • Maintaining relationships. Tactically, setting timers to regularly check-in.


Somewhat of an excuse here, but COVID screwed this one up. So I’ll need to get back on track.

  • Diet, primarily. Turns out it’s hard to eat lots of veggies when you’re only in a place a month at a time.

  • Mindfulness / meditation. Pairs with focus.

  • More intense exercise.