Twenty-twenty

1 January 2020
1 Jan 2020
West Lafayette, IN
17 mins

For the last few years, I’ve been setting ten goals for myself every year. This post is partly a continuation of that – my ten goals for 2020 – and partly an announcement I’ve been waiting to share with the rest of the world for the last month.

This post – my first story of the 2020’s – comes to you in four parts: the past, the now, the future, and the far. It’s a little longer than my usual post at around 3500 words, so I’ve linked the sections below, for your reading convenience.

  1. Part one: a review of my 2019 goals
  2. Part two: the decision I’ve made about how I’m spending my 2020
  3. Part three: the goals I’ve set for myself in 2020
  4. Part four: the decade ultimatum, a dream for my 20’s

Part one: a review

At the beginning of 2019, I set out ten goals for myself. I want to take a moment to reflect on them and see how many I’ve completed, before moving on to this year.

I wanted to bootstrap a business that was cash-flow positive, that could serve as a major side project and a source of passive income. It didn’t happen, partly because new, unexpected opportunities came up from which I thought I’d learn more than just trying something on my own, and partly because I didn’t have any burning ideas I wanted to turn into a side-business. I still want to build a bootstrapped business of some kind, where I can determine the way I work and what I build, but 2019 wasn’t the year for it.

I wanted to meet at least three new and interesting people every week. I remember the first week of 2019, not really knowing how I’d get this done, just cold-messaging people on Facebook. As of January 1, 2020, my virtual notebook of people has 196 stories from 196 people, many of which have become friends or team members today. Putting myself out there, I learned to be a better listener and a better storyteller (though I still have a long way to go), and learned how writing, building projects, and sharing what I’m working on with the Internet can help get other people excited about the things I care about. I saw how the people I met ended up being the best part of many of the projects I worked on in 2019, and how those same projects brought other people into my life. Putting myself on a deadline for going out and having meaningful conversations with new people is, by a mile, the most impactful and insightful goal I set for myself last year.

I wanted to either release an album, self-publish a book, or publish 50 videos on the Internet before 2020. As of Christmas Eve 2019, I released my first improvisational piano album, Memory Palace, to the world, to much lovely reception, for which I’m so thankful. This almost didn’t happen – I didn’t have concrete plans about how I’d pull this off until early December – but I strapped myself down during the last couple of weeks of school, and put something out there. It’s not perfect. There’s lots of little mistakes in the performance, it’s not a live acoustic recording, and I’m not satisfied by the musical variety in the album. But it’s a starting point. Like writing, I believe the only way to improve is to keep putting your work out there. There’s hopefully more music to come in 2020.

I wanted to donate 3% of my before-tax income to charities. This is a tradition I’ve kept up since 2017, when I first started having an income from my work. I love this way of thinking about giving because it rewrites the question in your head from “Should I give to this cause?” to “Which causes deserve my contributions?” which I find is a much smarter and more educational way of thinking about charitable giving. This year, my donations were split between the ACLU, Project for Awesome, and Teach for America. In particular, Teach for America is new on my list this year, but I’ve heard enough stories about how TfA have changed the lives of both teachers and students, that I felt compelled to support them this year.

I wanted to create fifty different pieces of writing, art, music, and other creative work I’m proud of. As of today, I’m sitting at 31/50 between my music, writing, podcasts, and artwork, so I didn’t meet this goal. This is particularly disappointing, because my big theme for 2019 was to work on technical projects less, and explore and exercise more of my creative side. The flaw in this plan, I think, is that technical work is very concrete – ship this feature, fix this bug, put out this release – and creative work is very nebulous. It’s difficult to calendar-block time for creating art or writing, because creativity comes and goes, and I create when I feel compelled to create. This is something I plan to keep working on through 2020.

I wanted to build and release significant projects using a bunch of different technologies. I would consider this goal a broad success. I didn’t learn everything I wanted to learn; still on my list are Rust, iOS Development, and machine learning tools like PyTorch. But I learned Go by building a programming language, learned the joys of TypeScript and GraphQL at Repl.it, tried my hand at C programming, learned the ins and outs of web UI frameworks while building Torus, and am currently maintaining a Rails codebase with Hack Club Bank. I shipped some of the most interesting and ambitious technical projects I’ve worked on, and even grazed the front page of Hacker News, more than once. More importantly, I’ve stopped feeling like I’m reusing the same designs and tropes over and over again in my projects.

I wanted to have some proof-of-concepts or sharable results in a more academic, research-heavy project. This didn’t happen. I learned that research is a task that requires unbounded, focused time. Unlike a coding project or a blog post, you can’t allocate time slots in a calendar to “research” or “think about” a problem, and then expect it to be solved. Within the way I currently organize my life, it was difficult to fit in time to spend thinking deeply about research-oriented questions. I hope to come back to this in the future, but I’m not sure how to change my circumstances so this is more viable, without sacrificing how I currently work best.

I wanted to read more books, and less essays and articles. This was mostly a failure, and I didn’t read nearly as many books as I wanted to. I don’t really have excuses here, since I really just prioritized producing over consuming, and making things over reading. I think the way to fix this problem is to specifically allocate time in my day to read. I’ve also gotten the advice that audiobooks are helpful as a transitionary tool, but I like to take notes when I’m reading, so I’m not sure how helpful that will be. Nonetheless, my reading list is long, and my time is a little more open this year, so I hope to do better.

In addition to the eight from last year’s post, there are two goals that I didn’t mention then.

I wanted to travel broadly. This was a less measurable goal than the others, but I’m satisfied with the places I visited this year. I visited LA and New York in the spring, lived in San Francisco for the summer, fell in love with Portland at XOXO Festival in September, and made a stop at Boston and Cambridge in November. Given that I was in school, I don’t think I could have done much better, but I’m also going to be more structured about the places I have opportunities to visit in 2020.

I also wanted to start a business related to the big problems in the world I care about – how students learn, and more evenly distributing educational opportunities. I didn’t do this, but mostly because I found another organization doing work that was achieving similar things: Hack Club. I’m hoping I can contribute more to Hack Club and towards my mission in 2020 than I was able to last year. I also wanted to be financially independent, and although out-of-state university tuition holds me back, outside of that, I’m now living 100% on my own earnings, which I consider a big win for my freedom.

Of the ten goals I set at the beginning, I’ve completed six – in my book, anywhere between 5-7 is neither terrible nor amazing, but right in the middle. That’s also how I felt about this year for me.

I wanted 2019 to be a year where I spent more time doing creative work I enjoyed and meeting new and interesting people to do that work with. I wanted to stop being focused on external validation, and focus instead on how I felt about the work I was doing, and the days I was living. Though I still biased more than I wanted to on the technical side, 2019 was a good year by these goals, and at its end, I’m at a good place to start a new decade.

Part two: the decision

From January 2020 through August, I’m taking a temporary leave of absence from UC Berkeley to join the Hack Club team full-time and travel around the world, living and working remotely from a different city every few weeks.

In between hitting the milestones and the goals, I hit some rocky points this year. Learning from it, I’m shifting some of my plans for 2020. It’s what ultimately led me to the big decision.

For the last semester, trying to balance my work at Hack Club with coursework, Cal Hacks, Dorm Room Fund, and other obligations I had in the normal course of life, I burned myself out pretty badly in October and November, to the point where it was affecting my ability to do even things I loved doing, like programming and writing. I lost my motivation to make anything or follow up on responses and responsibilities. I fell apart on my obligations where I had stepped up before, to the detriment of the teams I was with. During this time, I stopped shipping side projects or sharing any writing, and generally retracted to filling my time with YouTube videos and naps and not leaving my room, which then made me feel worse about not doing any of the productive things I normally do.

I got worried that the big ideas with which I had entered the year – making more things, being more creative – were just going down the drain while I was being an incapable potato just barely doing the minimum to get by. Whenever I met new people, I’d get introduced as “the side project guy” or they’d ask about what projects I was working on next, and I’d feel awful that I wasn’t doing anything. What used to be the thing I was about, was being a reminder of everything I was failing to do. All this sent me into a spiral I don’t ever want to repeat again.

Luckily, with the help of some friends and some hard decisions to dial back and reset some of my commitments, I’m at a better place today. But this meant that I couldn’t just try to repeat what I tried this fall. I shouldn’t try to work and study and take care of myself all at once. I had two options ahead of me: leave school for a bit, go all-in on work that makes me feel alive; or leave work for a bit, go all-in on coursework that interested me and pulled me back in.

I spent the overwhelming majority of my time deciding whether, after already having taken seventeen months off of school three years prior, I wanted to take another hiatus. It would push back my graduation, interrupt my coursework, and generally remove me from the steady-state of life I’ve lived for the last couple of years.

Having already pushed school back once doesn’t make this any easier. The same costs still matter, and the potential upside looks different each time. But this time, like last time, what finally led me to a decision was that school will always be here, when I return next semester, or perhaps even the semester after. I have two years left at Berkeley, but the best time to learn isn’t now, it’s when I feel most motivated and hungry to learn. And that wasn’t now.

In the two years since my gap year, I’ve formed a more mature understanding of my decision to interrupt school the first time, and what I gained and lost from it. Lately, as I talk to more friends who are about to graduate about the idea of interrupting school, I heard the same strains over and over. There’s no rush to get out of school and into the real world – you don’t get a prize for getting there sooner, and you don’t get a second chance at an undergraduate career.

I firmly believe that the best time to learn is when you feel compelled by your curiosity to learn everything you can, and the best time to go back to work is when you feel compelled by your creativity to build new things.

And as I write, at the beginning of 2020, I want to create more than I feel hungry to learn in a structured, formal setting.

So. I’m not dropping out, but I am taking another break, hopefully for just a semester, to focus on building and making, working with all the brilliant people I met last year.

But while I am taking a break from school to work, I also wanted to make the most of that absence, so I’m not going to be staying in Berkeley for all of it, or even most of it. The first half of this year will be filled with new places and punctuated by trips back home to reset and refresh. This brings me to my decision.

From January 2020 through August, I’m taking a temporary leave of absence from UC Berkeley to join the Hack Club team full-time and travel around the world, living and working remotely from a different city every few weeks.

I’ve used the same overarching philosophy to make large, life-scale decisions like this for many years now: at any moment, seize the opportunities that align best with work that excites you and mission that meets your heart, and the dots will connect in the end. I don’t really set goals or plan for events in timescales longer than a year, because I don’t want to be tied down by who I thought I would want to be months or years ago; I work on what gets me out of bed every day, and somehow, they’ve pushed me into some fun opportunities over the years that connect in a sensible narrative in the end. I leaned on this belief to take a gap year after high school, to work on all the projects I’ve shipped this year, and to join Hack Club’s team last semester.

I’m leaning on that same belief to take another chance this year, and I’m so excited to share more about where I’m going next, and what I’ll be working on, soon.

Part three: the goals

Despite the unusual plans this year, I’m still setting myself the usual ten goals for 2020. As before, they’re a mix of achievable, ambitious, and probably-impossible. I enjoyed living by my 2019 goals, so many of them are carried over, with tweaks where I felt they were useful. In no particular order, here are my ten for 2020.

  1. I want to take a startup-style scalable business with a mission to help students, and get it to profitability. This is in all likelihood going to be Hack Club Bank.

  2. Carrying over a missed goal from last year, I also want to bootstrap a profitable, small lifestyle business that can become a source of stable side income, whether through writing / publish content or running a small business operation on the side.

  3. Another carry-over from 2019, I want to either publish a book, or release 50 videos I create. If I write a book, it’ll probably be about hacking, side projects, creativity, and my conviction in the importance of building digital and community infrastructure for the next generation of students and makers.

  4. I want to build and launch five big, major side projects. Here, I don’t want to be limited to purely software, though software is my bread and butter. I think projects like XOXO Festival and Parametric Press are amazing, and would love to try to pull in more of my creative side as well. I also want to learn new languages and tools like those oriented towards machine learning and computer graphics, and I want to get better at low level systems software development with Rust and LLVM, and operating system development with Linux. I also had a lot of fun live-streaming my open source development last year, and I want to do more of that this year.

  5. A mainstay every year by now, I’m continuing to commit 3% of my pre-tax income to charitable giving.

  6. I want to live for at least a week each in 15 different cities.

  7. Another missed item from 2019, I want to create and share 50 pieces of creative work. This can be anything from video and drawings, to compositions on the piano, to writing, photography, and whatever else I feel like making. I just want to expand the scope of my creative output and practice doing a broader variety of things.

  8. I want to read and write about at least 30 books I’ll read in 2020. These will be shared here, on this blog.

  9. I want to run 500 miles. This isn’t an ambitious goal for some people, but I haven’t gone out much to exercise recently, so for me, this is going to be a good challenge, and won’t immediately scare me into not even trying.

  10. I want to host or organize more events where I bring new people together. As I met new people in a bunch of different places last year and got more comfortable in social situations, I learned that one good way to have more meaningful conversations and meet more cool people is to bring people together and host events. Whether it’s a birthday dinner or a community event with a venue, I want to be more conscious and active in my efforts to create more of these kinds of memories for myself and the people around me.

Unlike last year, where i shared an abbreviated version, this is my full list. These are the exact goals I’ve also jotted down in my personal notebook, and the goals I’ll be checking in on every couple of months as I track my progress. It’s both exciting and intimidating to see all the numbers at zero today, but hopefully not for long.

Part four: the decade ultimatum

Ten million people.

Last year, as I was setting my goals for 2019, I also set a ten-year visions for where I wanted to be, and at the start of a decade, it seems fitting to reiterate it to myself.

I don’t know much about where I’ll be in 2030, and I don’t want to speculate uselessly, but there’s one piece of it that doesn’t feel nearly as nuts as it did the first time I wrote it down. In the next ten years, I want to have touched the lives of ten million students. Through something I made myself – a software product, an essay, a video, a company – through something I built myself, I want to have opened up a new opportunity or a new direction for ten million people around the world trying to learn what they want to do with their talents.

I don’t really know how to get there. That’s why it’s not a goal. But I don’t think I need to. Instead, I’m going to keep working on projects that tip the world in the direction I want it to lean, doing work that makes me feel alive with people that inspire me to be curious and excited about what’s next. I want to spend 2020 being a little more fearless about the person I’ve become confident to be in 2019.

Happy new year.


If you enjoyed this piece, you might also enjoy my next post, Time spent thinking deeply is not wasted time.

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