Cassidy Williams

Software Engineer in Chicago

Cassidy's face

Buh bye, 2023

As the great philosophers of Smash Mouth once said, “well, the years start comin and they don’t stop comin,” and 2023 was one of those years. Similarly to how I recapped 2022, I’ll do my best to break down one of my most life-changing years yet!

Work things!

I’m still having a blast as CTO at Contenda, where we’ve done a pivot and are working full time on our app Brainstory now!

Pivoting was a hard transition, I’ll admit. We had originally built a product that quickly turned your videos, podcasts, etc. into blog posts (and other forms of written content), and let you compose a bunch of those things together. I really loved it, but with the release of GPT-4, tons of our work was suddenly not a competitive advantage anymore. Competitors were launching faster than ever, and sales were simply not closing. We had so many enterprise sales calls and we kept getting riiiight up to the finish line without ever crossing it, and it was really, really discouraging.

So, while we were trying to figure out how to salvage our work, we started building “mini-apps” on top of our API. I thought it would be cool for folks who didn’t have existing content be able to record it in the browser, and we would transform it from there. That spawned a bunch of products like an app that helped high school students talk through their college application essays, a productivity app that helped you take notes as you studied, a Dungeons & Dragons character sheet creator… it was really fun, but we had to figure out our direction. Brainstory is what bubbled to the top from all of our learnings, and our users… loved it.

We realized that Brainstory wasn’t just a “mini app” on top of our API, but a really valuable product for brainstorming ideas and getting feedback. We started dogfooding it by using it for prepping for our All Hands meetings, I used it to write some conference talks and blog posts, and we’ve even used it for meal prep and planning for hard conversations. The more our team used it and shared it and enjoyed it, the more we realized that we had to make it our flagship product, and that’s what we’re working on today!

Outside of that work, I’m still loving advising companies! I’m still advising Netlify, Plasmic, and The Sukha Company (formerly Centered), and I did a stint for Wix, and I recently started advising Chainlink as well. It’s been really interesting doing this for such different companies, especially in a weird economy where everyone’s trying different things to get through it and succeed.

Personal things!

I think the big, giant, massive, huge thing that really took over my whole year was having my adorable baby Nadia this April! Words really can’t describe how intense birth and recovery and parenthood has been. I did try though by writing about my c-section experience and my mindset changes and postpartum depression and schedule changes this year.

Nadia is 8 months old now, she started crawling this week and pulling herself up to stand (!), she says “mama” (but only when she’s hungry, ugh), laughs all the time, and truly the cutest thing I’ve ever seen. Our rhythm is constantly changing as we figure out childcare (so expensive!!! Like, for good reason, but ahh!!!), navigate sleep regressions, and watch her little personality grow. It’s hard, it’s so hard, but she’s worth it (and I cannot emphasize enough how good it is to feel like she’s worth it. Postpartum hit me so hard this year, and if you or someone you care about is struggling, please feel free to contact me if you need someone to talk to).

Even with late pregnancy and a baby, we did get to travel this year, where we saw family and friends both around the country and abroad! I don’t know if I’ll ever travel as much as I did pre-pandemic, but it’s nice to be able to see places again outside of our little corner of the world.

Something else that’s been genuinely lovely is just how many close friends we’ve made this year. So many kind, generous people came to us when I was struggling with the baby, and our community in Chicago is truly wonderful. I love living close to family here, and the fact that I’m within walking distance to both family and friends is the icing on this year’s cake!

And even outside of Chicago, the internet friendships are going strong, and y’all are probably the ones who are actually reading this blog, heh. I’m so grateful to all of you being there when I would be typing out my woes and live-streaming my rants. And sharing memes, of course.

Side project things!

This year was a super fun one for projects. I blogged both at the beginning and end of the year about just how much I was committing to GitHub. I really had a great time shipping things!

First and foremost, as always, my weekly newsletter is going strong! We crossed the 6th year anniversary this year, and it’s still my biggest labor of love for the tech community. I love seeing people jump into the coding questions and liking the articles, and it makes my day every time when people say they like reading it! I actually let go of the reins a little bit this year: I got a sales team for sponsorships. It was harder than it should have been to decide I needed help, but now that I don’t have to do sales calls and booking and invoicing and copy edits etc etc, I have so much more time for actually writing the newsletter!

In other newsletter news, we crossed the 200 issue mark with the Stack Overflow newsletter! I’ve been helping them write it ever since it started back in 2019, and we’re going strong. I was a regular host of their podcast for most of the year as well, but with restructuring things I’m now more of an occasional guest, heh.

And speaking of podcasts, we finished season 1 of The Dev Morning Show (at night)! I absolutely loved recording the show with my friend Zach as my co-host, and talking with incredible guests. We’re on the hunt for a sponsor for season 2 so we can record again, so if you or someone you know might be interested, let me know!

In terms of writing, I tried to blog a bunch here, and also on (where I was one of their Top 7 authors of the year!), but I admit I am working on being more consistent. Most of my writing time these days is during nap times and mostly on my newsletter, unless I can squeeze out a post here and there. I’m hoping to write a lot more in 2024!

I’m also hoping to livestream more in 2024, as well. I had a good weekly cadence going pre-baby, but as one can imagine… it’s not that easy to stream when you’ve got one of those. I have a feeling I might struggle with being regular on stream, but I’m going to try!

This year, my coding side projects were really, really fun. I made AI Ipsum, a dummy filler text generator with a dash of AI. I also updated my Obsidian theme, Cardstock, to the latest versions of the app! I did a bunch of random scripts and demos and maintenance in between these projects, but the two that I’m particularly proud of are Thirteen Potions (which is a game I made for my first ever game jam, build log here), and a jumbled word search game, Jumblie! Jumblie started as a project for a video series (more info here) and got popular enough quickly that I’ve been actively maintaining it for a few months now! I’m not sure what will come of it, but I love word puzzles, and it’s really exciting for me that others like the one I made.

And finally, not really a side project but I’m including it anyway, I’ve been actively playing go almost daily! I participated in my first in-person tournament, and I hit my goal ranking this year (6k, for those familiar)! I would love to make it to 4k in 2024, but… we’ll see about that!

There’s more side project things that I’m sure I’m forgetting, but I’ve kept my GitHub Stars profile fairly up-to-date if you wanna look there at various podcast episodes and things I’ve made for now.


Gosh, 2023 has been quite the year. I’m so grateful to have made it through some really intense lows, and to have seen some spectacular highs. I have a feeling 2024 will be a funky transitional year, but I’m all for it.

Thank you for reading all of this! Here’s a joke for you as a reward: What do you call a bee that lives in America? A USB!

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