2020, hrm. A pretty bad year by all accounts. 1.8 million dead from a world-wide plague which somehow became politicized. Our perspectives are being polarized to the point where a centrist position is effectively copping out and declaring the status-quo as good enough. I am continually ashamed for the choices of the governments in my birth country, and for the country I moved to ~9 years ago.

How does anyone strive in an environment like this?

2020 said ‘fuck your goals and plans’. We just had to deal with it.

That said in pandemic terms, Danger and I lucked out, I had moved to a stable company which did very well from the move to remote culture and Danger’s company was so new that shifting to remote was pretty straightforward, and they don’t really plan on going back. So, we had stability in a year where everyone was a buoy in the storm.

Sadly that’s not true for so many. Too many.

2020 Format

To try and reduce the overall length of writing, as it seems I become a more prolific writer each year (I guess nuance adds extra words), I’ve separated a few of the larger sections out into their own pages. Hopefully that will keep the rest of this page flowing somewhat:

Moving to LinuxCool 2020 thingsOn Polarization

A year of guilt and protestation

We opened the year with my wife receiving a legal treat which could potentially result in a court summons. Her ex-employer was threatening to sue her and her colleagues, who had also left their previous jobs with said ex-employer. It was such an american-feeling response to people leaving out of frustration with management, but it did set the 2020 tone pretty neatly. In the end, my wife + colleagues + lawyers argued that if anything, the charges should be the other way, and the case was dropped before it hit the courts. But dang, what an opening salvo for Jan 1st.

At the end of 2019, we moved to Brooklyn. Moving to Brooklyn was a mistake in my opinion. Within 2-3 months it felt like we were adding to the problem of gentrifying the neighbourhood and had started talking about moving out. We were paying a little more than before and had about 4x the amount of space, but the sense that we were spoiling an area just can’t offset residental comfort to me.

Previously we lived in the lower east side and I loved it. The lower east side had an interesting art scene, dive-bars and was basically walking (or bike) distance to everywhere I wanted to go in Manhattan. That said, we basically arrived in the lower east side, post-gentrification but I think it still had a pretty solid young punk attitude about the place. Which I guess even at 35 I still align with.

Brooklyn on the other hand is homely, spacious and well lived-in. My neighbourhood was a predominantly black borough. I get there are economic arguments for why gentrification happens (if so many people want to live near Manhattan eventually everything in transit distance will end up with Manhattan prices) but it’s one thing to think about gentrification as a concept, it’s another to walk outside and see yet more local non-white businesses being replaced with a hipster barber place run by white folks.

The process is happening regardless of whether we participate, but I’d rather we didn’t.

We got nowhere with moving out of Brookyln in the first half of 2020 year due to the NYC pandemic lockdowns, and as the protests began to take shape in Brooklyn - I felt more connected to the area, and less tied to Manhattan. I went out to join protests whenever I could, and donated to our neightbourhood’s local mutual aid group to try to contribute back to the community.

Somewhere about half-way through the year Danger and I talked about leaving America instead of just Brooklyn. She had reasons to get back to her family, and I was past the concept that the country could live up to how it portrays itself. I think America is a cruel country, which is getting worse. America may have some of the world’s richest folks, but I’d rather judge a country by the lowest someone could fall, instead of the highest they could achieve.

Don’t get me wrong, I grew up in England and I also think it’s a cruel country nowadays. I think it used to be less-so, but maybe I was young and naive.

I sympathise with the folks trying to improve those two countries, but it’s hard to not just say the financial elites won. It feels like they won a long time ago and have been making it a very unfair playing field ever since. The BLM protests in America gave me the most optimism for a non-dystopic future for the US, and so far there’s been nothing to make me optimistic for the UK. It’s hard to perceive a path forward when there are two political options, both of which get about half of the votes, which roughly equate to “The world is a zero-sum game” vs “Raising tides lift all boats”. There’s a more in-depth dive into that in Polarization in 2020.

For our new location, I pitched we should move to Denmark and Danger pitched for London, Glasgow or Edinburgh. A few discussions down the line, we settled on Dublin. Ireland is still in the EU, and on the same land-mass as the rest of her family. We moved back at the end of November, stayed in Northern Ireland till January when we moved down into the 2nd major lockdown in Ireland and the UK.

So far, for the very little of Dublin we’ve seen - mainly through dog walking, people have the feel of small town folks living in the big city, which is lovely.


We traveled once in 2020, in January coming back from visiting family we took a flight via Icelandic Air where you could stop off in the country on-route for free for up to a week. I loved Iceland, I enjoy Icelandic punk and we found some great dive-y places to enjoy. I could live there, I think.

A new family member

After the trauma of our first dog dying suddenly, we took a break from dog ownership, though we’ve almost always had a dog with us in some form. We had Oby most of last year, and Danger’s work/community meant we would have a dog staying with us at a pretty regular pace.

So, it wasn’t too surprising for me when Danger mentioned she thought she had found us a new dog. Danger’s life and career basically revolves around dogs and their training culture. She got a recommendation from a dog trainer friend and colleage that we should consider seeing a dog nearby who was a great fit for us. Meet Hayes:

Those eyes right?

We got Hayes before the lockdown, and very quickly Danger and I were both working at home full-time, so aside from us moving to Ireland - he’s had a great time with constant company. Flying him to the UK was a nightmare, we had just moved out from our apartment in NY and found out the box for him was the wrong height, which for a few hours meant we had to prepare to spend another week in NY figuring out how to buy a box that fit.

He’s very food motivated, and that makes him really easy to train. Everyone falls in love with him. You can follow him on Instagram: @outlook_hayesy.


Pre-pandemic we used to host people all the time, NYC is a fun place to visit and we can host quite a lot of folks. I also like having someone else around. Thinking about it, me and Danger have been together for roughly 10 years for that entire time we’ve probably only lived on our own, together, for about 3 years.

Obviously that didn’t happen in 2020, but the 2020 pandemic caused all sorts of complex situations for people. Over the course of the year we ended up having people live with us more permanently instead. Separately we had both of the other co-founders for Danger’s work CCA come stay for a month or three.

For a year with such low human contact, it was lovely having people over for extended time periods. They drastically change the house dynamic and our Brooklyn apartment had enough rooms that they could have their own private spaces. It gave us a chance to build stronger relationships with them and took pressure off the two of us to meet all of each other’s social needs.

Weekly Quiz

In April a friend reached out and said they were going to start running weekly quizzes via Zoom on Saturdays. Over the course of the year they ran about 30 quizzes. They’re super fun and I’m really grateful to David & Jen for running them. Our team usually battles for 2nd to last place, but we always participate. On one week we managed to end up in third, and we’ll never forget that. Here it is:


My work at Microsoft continues to be interesting, to be focused on TypeScript ecosystem-level problems and almost entirely in the open. I think it’s been super refreshing to do a stint at a mega-corp, in one sense it’s really given me a sense of how a company like this works and on the other side - it pays so well that I’ve saved up years worth of savings.

The main things I worked on in 2020 were the new TypeScript website & documentation, helped establish a single “blessed” community Discord, built out a new process for contributing to DefinitelyTyped (one of the worlds most active developer spaces), and built a system for generating web versions of TypeScript at runtime (useful for all sorts of developer-y things).

I fixed a few bugs and added some features into the TypeScript compiler, mainly through pairing with the folks who do that everyday. At first, I thought compiler work might be something I’d get into with time. A year and a half later and I’m pretty sure that deeper compiler stuff is @alloy work, and it’s probably not a long-term viable option for me IMO.

Community Work

Up until the website shipped in August, I devoted most of my spare time programming to working on the TypeScript website. Which was a sacrifice I was happy to make. In one way that helped the different Danger implementations mature, and I stopped making time for CocoaPods. My long-tail list of OSS is always generally easy to maintain, it’s like a constant hum and as long as I’m in a good mood I can usually handle all incoming requests without breaking a sweat.

Post website, I’ve relaxed my TypeScript work to a more normal pace - the normal 9-5 covering the usual needs and I’ll explore ideas in my spare time occasionally. So, what of community interest did I build out in the last year?

I shipped a game with a Microsoft friend:

I built out a plugin ecosystem for adding custom code to the TypeScript playground. This solves a bunch of problems I had when I wasn’t on the TypeScript team and helps keep the TypeScript community from splintering around different tools.

I took some time to work with the Svelte team on their TypeScript support. I took a lot of existing infrastructure, centralized it and found other people to use, improve and maintain it. For a problem like this, it really is just about coming in with a vision, making a set of decisions and doing enough to show others how it can work. As soon as it was happening, a bunch of folks volunteered and helped make it work - I worked on the infrastructure to let them do it right.


In 2020, I started to feel more wary of consolidation in technology and its pace of change - I work at a trillion dollar company, so I dig the potential for hypocracy but I’d be whole-heartedly in favour of breaking up most of big-tech. I’m burned out on the idea of venture capital, I think of it now as a quick cheat to beat competition with the goal of monopolization. I want smaller companies, I want smaller tech created by fewer people with less aggressive goals and engagement strategies. I want mature things that do less and don’t need to change so much. I’d like a more careful approach to technology.

There’s a tension here with how I actually live and work on the bleeding edge of computing which I’m not sure I can un-knot without a fundamental personality adjustment, which I don’t think I’m willing to go through with. So, I’ve taken some lighter steps forwards: avoiding buying from Amazon, switching from free Google products to paid alternatives, moving off the annual cycle of Apple software and products and I’m exploring what kind of phone suits me. I might move back to using an iPod Touch full time again.

Body work

I finished up all dental work last year, some teeth added some teeth gone. I wanted to try and fix my posture in 2020, but 2020 happened. I want to take up that idea and see a professional about posture. Danger and I also want to give therapy a shot this year, New Yorkers were always recommending it and now is as good a time as any to give it a shot.

For the first 4 months of 2020 we went very low carbs, and that did a great job of weight management, but lockdowns, apathy and convenience ended up ruining that. We’re figuring out if we’re gonna do it again for 2021.

2021 Themes

For my 2021 theme, I opted to focus on financial independence.

I’m astounded at how much money I made from one year at Microsoft. I doubled my savings in a year, and that was while still living in NYC. When we were debating moving house - downsizing was a goal. We have enough savings for about 1.5 years of living at our estimated rate in Dublin. Which provides a pretty solid amount of freedom if I choose it.

I made the call in 2020 that I wanted to start getting enough side-income to be able to choose to go independent in some form. I’m not sure about the when aspect of it, but I’m a bit more sure on the how aspects. Right now, I’ve been exploring a few potential routes, and I think it will be a bit of a balance between a few different sources of income that could happen:

YouTube - In switching from doing in-person public speaking at conferences to speaking digitally, I’ve got the pipeline for creating very high quality pre-recorded videos down pretty tight. I don’t want to become a full-time YouTuber, in part because the only way to do it would be to cater to a beginner audience and that’s not what I’m interested in. I want to deep-dive into complex and nuanced topics which rely on making assumptions of the audience.

Education Products - Think things like self-published ebooks, or pay-walled websites on particular topics. I think I’ve got a few good ideas for them, but just haven’t quite committed the time.

GitHub Sponsors - I’ve started lightly recommending folks sponsor me on GitHub, with a general sense that it’s for things which aren’t working on TypeScript. I don’t want to push this too hard while employed, because it just feels a tad disrespectful and who knows if it could be classed as a conflict of interest.

Capture - I took a problem which costs Danger about an hour at work each day and automated it. In the process, I pitched it to both Alloy and Maxim and we’re turning it into something which could generate a pretty reasonable amount of side income. We’ve not quite figured the marketing strategy, but it made it into the Zoom app store in the last few days of 2020. People are signing up.

Puzzle Box - A games project with a good friend that could turn into a somewhere between solid side income and potential full-time income, still a bit too far away to talk about though.

It’s strange that you can actually see me starting to work on these non-GitHub or non-OSS projects from October on my GitHub profile:

There’s a non-zero chance that any of these could end up being big enough to handle our expenses full time. Then I can devote more time to digging into some of the OSS I’ve been somewhat neglecting or start doing larger scale community projects.

It’s not like there’s anything negative at Microsoft or TypeScript pushing me this way. TypeScript is a great team and I have a really supportive manager. I’ve built almost everything I wanted to, and I’m still working on more things that I’m fascinated by. I just think I might be able to have that last decade of kudos / goodwill from OSS which could be used to pay maybe enough of the bills. Thanks @nayafia

I’m not looking to make any drastic changes, but I’m open to seeing where these projects lead.

Quantifying decline

Since 2017, I stopped being able to write that this has been my best year:

I used to always say “this has been my best year” and for 2017? it’s not really been the case.

Does that mean I peaked in 2016? I can’t believe that. So much great stuff has happened, and for the majority of my decisions - I’d do the same again. The state of the world gets worse but even as a buoy in the storm I can still find things to enjoy, people to love and ideas to inspire. People are still making great art, and there’s never been more access to incredible thought-provoking culture.

Part of me wishes I could have the level of optimism which Max Roser of Our World in Data has, he laments that “optimists are considered naive and without care for the problems of others”, and I wonder sometimes if more modern write-ups tend to feel a bit edgelord-y.

These posts do accurately represent my feelings throughout the year though, but how much of those memories are fleeting and not worth the long-term archival structure I provide via writing? Hard to say, either way, they were ‘ere and so was 2020.

If you’ve read this straight through, then here are those links to the deeper dives: