Cassidy Williams

Software Engineer in Chicago

Cassidy's face

See ya, 2022

Man, 2022 was a year of extreme highs and lows, probably the most extreme I’ve had… ever.

It’s kind of hard to look back on all of them, because there’s so much to really think about. Which is not unique to me, but still. I’ll break it down and see how much I can process until midnight strikes in… 1.5 hours.

Work things!

Phew so work had some changes this year. At the end of 2021, I decided to leave Netlify, mostly due to burnout and wanting to explore tech education more.

And so, at the start of this year, I ended up joining Remote as the Head of Developer Education and Experience to do that for realzies. And, ya know, on paper, that role was pretty perfect. I had a ton of autonomy, I had kind coworkers, and I had time to spare to work on side projects that had been sorely neglected. I genuinely enjoyed hanging out with a lot of the folks there, but at the same time… I was kind of on an island. A lot of the work I was able to accomplish and put out in the world (like Remote Connect and Devs For Ukraine and the engineering blog) was reliant on me getting busy people to work with me on something “extra” outside of their day jobs.

When people inevitably had to put off the “extra” (particularly as the economy started to buckle a bit), I was very… bored. I would still work— I’d always figure out how to fill in the time with something— but I was very regularly faced with, “this is awesome Cassidy, perhaps we can do this someday,” and I was getting impatient with it. I job interviewed a few times, without ever really finding a good fit. I acknowledge I am wildly privileged to be able to have had this experience, and I’m grateful for it, but that’s what was going on!

Meanwhile, in April, I started part time work at OSS Capital! I had been in chats with them since I worked at Netlify, wanting to work with them, but not quite ready to take the leap into being a full-time founder yet. For OSSC, I joined as a Portfolio Partner for Developer Experience, meaning I was advising the portfolio companies from a dev rel perspective (helping with hiring, strategy, making introductions, that sort of thing), and I also helped out the team on technical things too (like the website)! I genuinely enjoyed doing that gig, and I actually proposed joining them full time, but the timing wasn’t quite right. In November, they sadly had to lay me off (amongst others), but I still maintain a good relationship with them and hope to do more work with them in the future.

I still love advising companies! When I left Netlify, I stayed on as an advisor, and I also joined Centered and Plasmic as an advisor this year as well. Being able to help companies grow and offer my perspective is something that’s relatively low lift, but high impact, and it’s really rewarding… which leads me to where I ultimately ended up at the end of this year!

In the summer, my friend Lilly (who is the CEO of a startup Contenda that I’ve been advising since they started) started to float the idea to me about joining the company full time. It was super appealing, but I had to think on the timing and how it might work out. The more I thought about it though, it was a no-brainer. I knew the team well, it was a product I cared about, and I could make an impact at my day job (which was something I was missing dearly). So, in September, I joined Contenda as CTO full time! It has been chaotic and wonderful all at once, and I’m so happy I joined such a great group of people building something awesome.

Personal things!

So many things happened, gosh, so many things! My sister got married, I traveled internationally for the first time since March 2020, I saw family, I saw friends, I got LASIK, my cousin got engaged… I loved being with people I care about this year. I also experienced a close family loss, which was deeply devastating, but it brought our family together to mourn with each other.

I also… got pregnant!! This has been probably the most grueling physical experience I’ve ever had (so far). I’m due in the Spring, and I have been shaking my fist at the state of research in women’s health pretty dang regularly. But, my husband and I are thrilled (and so is the family), and she’ll be a very loved baby!

Side project things!

Outside of the busyness of job things and the personal life going every which way, I’m happy with my various projects this year!

First of all, my weekly newsletter crossed its 5th year anniversary! This is one that is very near and dear to my heart. I probably spend most of my side project time on this one, and the fact that we hit that milestone and folks are actually reading it is really exciting for me. I love getting to help people with coding problems and staying up-to-date, and also love that it keeps me actually reading articles instead of leaving infinite tabs open.

In other newsletter… news… (heh), we crossed 150 issues of the Stack Overflow newsletter! I’ve been helping the team write it ever since the newsletter started back in 2019, and it’s been great to see it grow. I also joined as a regular host of the Stack Overflow Podcast! I had been speaking on the show regularly for a while now, but it’s been fun being able to consistently chat with the other hosts and guests.

Speaking of podcasts, I started The Dev Morning Show (at night) podcast with my friend Zach and LaunchDarkly! It’s been a blast working on that show and speaking with such cool people.

I spoke at a few events this year, outside of the ones I mentioned above at Remote, like GitHub Universe, and All Day Hey! I admit I didn’t speak as much as I have in the past, but it was kind of nice saying yes to less and being a very happy audience member. I will say though, I spoke at my first in-person event (a local meetup!) since the pandemic this summer, and it was incredible. I can’t wait for those to come back more and more, I loved it!

I did a good chunk of writing this year, too, enough that I rewrote my blog so I could try to consolidate posts right here on this website (how meta). I wrote some articles on, for LeadDev, for The GitHub ReadME Project, and also a bunch just for myself that I haven’t published publicly. I’ve talked before about how I like to use Obsidian for my note-taking, and it’s really helped me write more consistently, whether I publish or not!

Code-wise, I rewrote the website for Cosynd (this is a project I’ve been working on for more than 6 years now), I started updating todometer, and I built some random demos on my regular livestream, too (like Better Security Questions and a pi memorization game and various open source contributions).

Keyboard-wise, I finally (finally!) got DSA Scrabble keycaps to go live!! I first designed those back in 2017, released V1 in early 2018, and I’ve been wanting to bring them back ever since. It was a labor of love to get everything re-designed with the new branding and licensing, but it happened! I also shipped a free email course to teach people about mechanical keyboards in general.

Also, not really a side project but something I’m happy with, I read 10 books this year! It’s not a lot by any means, but I’ve been wanting to build my reading habit back, and it’s a start. Similarly (kind of), I’ve been playing a lot more go recently, and I do think I’m getting better, and hope to hit some goal rankings next year.


Anyway, 2022 has been quite the year, and I feel so grateful and blessed to have made it through and be where I am today. Who knows what 2023 will bring? Thanks for reading so far. As a reward, here is a joke: What do you say when you see a vegetable that’s awesome, but not too awesome? That’s rad-ish!

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