My goals for 2021, interesting lives, and other considerations

5 January 2021
5 Jan 2021
West Lafayette, IN
15 mins

Every year, I set 10 goals for myself to set myself on the right direction in work and personal life. Since the same post from last year was popular, this post is a look back at how my 2020 goals went, and some thoughts about my goals for 2021. This post starts with some high-level thoughts on planning life, but you can also skip straight to my review of 2020 or my goals for 2021 if you want.

In every complex system, there are two sets of rules: the rules that everyone thinks describe the system, and the actual rules by which the system really works. In software, we call these two rules the “specification” and the “implementation”. In writing, there is the “standard grammar”, but great authors bend and change the rules in their writing. In anything with many moving parts, there is a big gap between how most people believe things work, and how they actually work. The sheer complexity of big software systems and human language and life can be overwhelming, so we make things easier on us by having a simpler model in our minds, constrained by a smaller set of rules.

Life itself is my favorite example of a system with this duality. Growing up, we learn the “standard grammatical rules” of how to live a good life. We get these rules engrained into our minds by seeing how other people around us navigate life, and hearing stories of role models passed around in the communities around us. Because we learn these faux-rules of life early on, it’s easy and natural to color within those lines for the rest of life.

But there are two interesting things I’ve observed about these rules we grow up with.

First, the “way life works” can be dramatically different for people who grow up in different communities. Just like there are differences in British and American and Aussie and international flavors of English, there are differences in the “rules of life” perpetuated by lineages of Silicon Valley tech workers and Midwestern families and Asian immigrant parents and European millennials. This difference is interesting, because it suggests that there’s more to understanding life than just the way you’ve always understood it growing up, no matter how you grew up.

Second, the people I think have lived life to the fullest have often straddled the gap between these agreed-upon, “common” rules of life and the actual rules, what’s actually possible. Hundred Rabbits lives on a boat, sailing around the Pacific and writing open-source software. Neri Oxman served in the Israeli Air Force and studied medicine before pivoting into architecture, and now leads pioneering research at the MIT Media Lab. George Hotz, who initially gave me seeds of this perspective on life, is a college dropout who rose to notoriety with iOS jailbreaks and is building a self-driving company in the open.

When I say “live life to the fullest”, I’m not talking about a measure of success, but rather a measure of fulfillment. To me, success feels uni-directional. You set a few goals, and you aspire to them. But fulfillment for me is also about breadth and color, about taking advantage of all the opportunities life presents to experience all the facets of it. This is why I set 10 goals instead of 1 or 3 every year. There’s so many things I want to try out and experience, and setting a single goal feels like selling myself short. We can live fulfilling lives without fitting into any particular conventional model of success. It’s a different measure of life, and one that I find more inspiring.

If the common rules we believe about life limit us, why do we carry these rules with us? We believe the things we do about a good life because, like any simplified mental model, it makes things easier.

A Venn diagram, inner circle reading 'How you're supposed to spend youre life' and outer circle 'What kinds of lives are really possible'.

When we venture outside the conventional, there are more opportunities for interesting experiences, things like sailing around the world, taking gap years or dropping out, working in an unconventional industry. But these are offset by the risks you accept when you venture outside the common rules of life. When you venture off trail, your hike might get a lot more interesting, but you better make sure you have hiking boots and know what you’re doing.

One of the common rules we have about life is “high risk, high reward.” For opportunities with disproportionate rewards, there are disproportionate risks. It’s a good rule of thumb, but like all rules of thumb, I think it oversimplifies the truth. Most things people consider “high risk” are really just “ways of navigating life that people around you haven’t done much.” This is obvious when you realize that what people consider “high risk” depends on how they were raised, and what background they come from.

Instead of thinking about a risk-reward tradeoff, I like thinking of planning life as a game of exploration. What kinds of lives are possible outside of the ones you’ve grown up knowing? If any of them appeal to you, how can you venture off trail safely without making a dumb mistake?

Computer security researchers are deeply familiar with the gap between the written and the unwritten rules of a computer system, because their job frequently involves stepping into that gap, exploring the unknowns of a digital territory and poking strategically for vulnerabilities and incongruences. But they don’t just poke and prod until they hit some jackpot while avoiding the risk, they depend on a combination of strategies and knowledge about the system they’re studying to explore safely.

As I step over into 2021, I’m thinking about how I can smartly explore the gaps between the written and unwritten rules of life safely, going off-trail for interesting experiences without getting lost. No matter how you grew up or who you spend time with, it’s human nature to simplify your inner model of your life, to make it easier to understand. To compensate, you can be constantly exploring. In that exploration, I hope to get a higher-fidelity view of the ways I can spend my life, both on and off the trail marked on the map.

Looking back at 2020

I started out 2020 by taking a break from school to work and travel for the first half of the year. My travel was cut short by the pandemic, and my work changed, but the goals still pointed me in the same direction through the year. Here are the ten I set for myself in January 2020, and how I fared.

  1. I wanted to start a startup with a mission to help young makers and creatives, and to reach small profitability. This didn’t happen, partly because I didn’t have any ideas I felt particularly committed to, and partly because I didn’t dedicate much time to this particular goal. Having this goal on the list did push me to have lots of conversations about education and community building with interesting people, which I appreciated.

  2. I also wanted to bootstrap a small passive income source or lifestyle business, probably by either selling content or with a small software service. I didn’t meet this goal either, but I think I had some opportunities to with a few projects that garnered a lot of attention. When those opportunities came up, though, I prioritized pursuing other interests with my time instead of focusing on making money, which I think made sense each time.

    A passive income source feels more attainable today than it did a year ago, though, thanks to the efforts I made in 2020, and I want to carry this goal forward.

  3. I wanted to either publish a book, or release 50 videos. This didn’t happen, but is happening! In 2020, I started researching and working on a book about building lasting communities, pulling from the many, many conversations I’ve had with community builders and founders and my own experiences running and thinking about communities. I started working on this in the second half of the year, and didn’t want to rush the process, but I hope to have something to launch in 2021.

  4. I wanted to launch at least five big, major side projects. I wanted many of these to be non-technical, because I want to get better at organizing events and pulling together people to do something bigger. I think I exceeded this goal, building a bunch of interesting side projects from ray tracers to compilers to Twitter clients, many of which are written in a language I created myself. I didn’t do as well pursuing big non-technical side projects, and I’d like to improve there in 2021.

  5. Every year, I commit 3% of my income to charitable giving. This year, my 3% went to the ACLU,, Black Girls Code, and the Equal Justice Initiative.

  6. Because I started the year with big travel plans, I planned to live for at least a week in 20 different cities. Obviously this didn’t happen due to the pandemic, but I did hit 10 places! I spent a week in Los Angeles, Boston, New York City, Kochi, Edinburgh, and London, and spent less than a week in Chicago, Glasgow, and Reykjavik. There were many things that made 2020 special, but for me, this round of trips definitely played a major role, and I’m looking forward to completing the rest of the trip post-pandemic. Given the circumstances, I’m going to count this goal as half-met.

  7. I wanted to create and share 50 pieces of creative work. In 2019, I had slowed down in my blogging and neglected my wishes to draw or make more music, so I wanted to push myself to be more consistent in 2020. I think I met this goal with flying colors, writing, making and recording music, drawing, and creating random other hacks in 2020 shared on this blog and on

  8. I wanted to read and then write about 30 books. I read 23 books cover-to-cover in 2020, and I wrote about a few of them. In retrospect the writing portion was mostly there as a way to hold myself accountable, which I didn’t end up needing. I didn’t meet this goal, but I think I improved a lot here, and I want to continue this trend into 2021.

    Because you might be asking: of the books I read in 2020, I’d recommend Exhalation by Ted Chiang, The Defining Decade by Meg Jay, The Diamond Age by Neal Stephenson, Never Eat Alone by Keith Ferrazzi, and Behind the Beautiful Forevers by Katherine Boo.

  9. I wanted to build a more consistent exercising habit in 2020, so set a goal to run 500 miles. I failed pretty badly on this one, and I can blame the pandemic, but I don’t think that’s a great excuse. I’m going to try this again in 2021, and try to be more consistent.

  10. I wanted to host 20 events and gatherings to connect interesting people I knew to each other in 2020. I didn’t hit 20, partly because of the pandemic, but I did organize 10 gatherings of various sizes, including a few in-person and a few online events around side projects, machine learning, and community building. I think I pointed myself in the right direction with this goal, but didn’t follow through very well.

In my evaluation, I met about half the goals I set for myself in 2020, which I think is good – not bad, but not great. I think the goals were good and well-designed, but I focused too much on getting better at my strengths, and didn’t spend as much time on pushing myself on new skills or where I was weak.

On the bright side, another year is upon us, and I can try again.

My goals for 2021

My yearly goals are less about things I need to do and more about pointing myself in the right direction, picking the orienteering stars by which I want to sail for the rest of the year. Because of that, they’re usually good reflection of the distance between where I am today, and where I’d like to be. I check in with these goals every few weeks to see if I’m moving in the right direction, and re-set if I’m not.

Where I’d like to be hasn’t really changed all that much since the start of 2020, so the goals I have for myself also haven’t changed much since 2020. I’ve made progress in many of them, so this year, they became more specific and polished, but I’m carrying many of my goals from 2020 forward, because they still reflect the directions in which I’d to move this year, too.

Like the last few years, I have 5 work-related goals and 5 goals related to personal growth and life more broadly.

  1. I want to build three passive sources of income that I’m happy to work on. This might be through creating more content, or with a software product, or something else entirely. I don’t want to limit myself here to only ideas that are viable startup ideas, but encourage myself to turn more of my ideas into projects that can teach me about growing businesses and help me earn some passive income.
  2. I want to publish a book, probably the one I’m currently working on, about building lasting and resilient communities. I’m drafting it at the moment, but there’s a lot I still need to learn about editing, working with a press or publisher, and telling the world about it. I care about publishing a book not so much for the book itself, but because I’m curious about the process, and it seems like a great way to make myself research and think deeply about a topic.
  3. I want to build and launch 5 major technical side projects, just like last year. But this time, I want to do more projects that push me to learn something new. It’s easy for me to build interesting projects that use the same technologies I’m used to, and I’m sure I’ll do a lot of that in 2021, but I want to push myself to learn new technologies and explore new areas like artificial intelligence, blockchain technologies, iOS development, and operating system development.
  4. I want to build a community I’m proud of. The wording here is very intentional: I’ll measure my success by how much I’d want to participate in the community myself, and by the quality of the individual connections people find in the community, over its size or impact in raw numbers. I think all great communities start out as robust, small groups that last, and I want to learn more about community building by bootstrapping one this year seriously.
  5. As I’ve been doing every year, I’m committing at least 3% of my income to charitable giving.
  6. I want to create 50 pieces of creative work this year, at least half of which isn’t writing. I enjoyed pushing myself to be creative in 2020, but biased too much towards writing, which I think is the “easy option” for me. I want to spend more time making music and art, writing longer-form pieces, and maybe even photography.
  7. I want to read 50 books, half fiction, half nonfiction. One-a-week seems like an easy number to hold myself accountable to.
  8. I want to learn a new language (or polish up on my German to be fluent again). Languages are ways to understand a world through fresh new perspectives, and over time, I find myself appreciating more and more other people’s ability to think across backgrounds.
  9. I want to run 500 miles through the year. Simple, but I wanted this for myself last year, and failed pretty miserably. Maybe second time will be better!
  10. I want to host or organize 20 different events or gatherings to connect interesting people I know and make space for good conversations. This is another carry-over from 2020. I want to improve my skills of organizing small meals or get-togethers, because I find it enjoyable and valuable when I do it well.

One item tragically missing from this list is a goal about traveling more, missing for obvious reasons. But one of my big personal lessons from 2020 was just how much I enjoyed traveling, going to new places and meeting new people without pretense or agenda. I’m looking forward to a time when that can return to this list.

These are my goals for 2021, for the next 360 days.

Sometimes people ask me how I try to follow these goals throughout the year. I have a version of these goals noted in my notes app and linked on my phone’s home screen, and every couple of months, I’ll set a reminder on my calendar to check in on the goals to see if I’m headed in the right direction, or if I need to re-evaluate how I’ve been investing my time and resources.

As I’ve worked through my process of defining these goals this week, I noticed that most of this year’s goals changed very little from last year – they point me in the same directions, sometimes with a loftier bar to meet. Since my goals are a reflection of where I want to go, I think this is a sign that I’m converging on a clear idea of who I want to be, and more sure of the direction I’ve been moving.

Someone asked me today where I see myself in a few years. I don’t know. Unlike people in some career paths with inflexible timelines, I have the luxury of being able to plan my life more spontaneously in yearly increments, and I don’t take that spontaneity for granted, because it gives me the freedom to discover who I want to be incrementally, year by year.

I did respond to them with this:

I look around my day-to-day life and try to find things that I really enjoy doing, and things I enjoy less. I try to make myself a future where I get to spend more of my time doing the things I enjoy, and less of it with the things I don’t.

For me, 2021 is just another small step towards that future.

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