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Software should work for users

…but it often doesn’t. This was one of the themes of the Software Should Work conference I attended this week. I met several people and had my mind expanded in so many different ways that I won’t be able to unload all my thoughts in one fell swoop. Perhaps eventually I’ll be able to roll up my thoughts on the conference as a whole, but for now I’m going to focus on just the very first talk by Andrew Kelley because it set the tone for the rest of the conference. It turns out I have a lot to say; as the great Benno Rice once said: “I know this may come as a shock to some of you, but I have opinions.”

Antecedent

A week before the conference, I was unsure if I wanted to go. On the one hand, the slate of speakers was super impressive and it’s hard to beat a conference that was right near where I live. On the other hand, my dear friend, Keenan was unable to attend, and so that left me feeling alone, obligated to make my own impression. I eventually signed up, I am very glad I did so. It was good to demonstrate to myself that I can do things on my own.

The night before the conference, I was in Saint Louis for quarterly planning for work. My anxieties about how the conference might go was top of mind. what tools should I bring? a full laptop? or something lighter? I ended up going with my little red binder/notebook and my tablet, and that was more than sufficient. But more than anything else, I was concerned about attending a conference with a bunch of smart people in the audience and on stage, but not being able to feel connected to the people there and letting Yet Another opportunity slip through my fingers. That of course did not happen 🙂.

In the morning of Day 1, during registration, my concerns were somewhat validated because the lobby was bustling with conversation. I just found a quietish corner and made myself appear busy by setting up the day’s schedule in my notebook and trying to get a feel for the rhythm of the schedule. However, after the first few talks, there was enough to talk about with the nearby attendees that there was no cause for concern from then on.

“Don’t Take the Black Pill” by Andrew Kelley

What a great way to begin this conference. It took a bit for this to sink in, but I went into this conference black-pilled in ways I didn’t perceive. I am not immune to propaganda, ya know? I was initially pretty unimpressed with this talk because it felt like a “yeah I get it, there’s a huge and insurmountable challenge ahead of all of us and success is far from guaranteed,” which is why it was a good thing that this talk came first. It met me where I was at, and served as a stepping stone for the following talks.

A little bit about me: I found out around the beginning of 2025 that I’m transgender. fun! Up until that point I had been involved in various trans communities, especially on the internet, just by subconscious self-sorting, I suppose. I noticed this pattern of self-sorting a decade before understanding its essence; my provisional explanation was that maybe I just was like… really practicing solidarity with trans folk, for some reason. I had understood early on that I was queer in some fashion, but struggled to get a foothold on anything more detailed than that. I was scared to assert I was any particular thing without knowing it in my heart first.

This came to a head on election night November 5th, 2024 when it was announced that Project 2025, a political project created by some of the most contemptible people alive, was going to go into effect. This flipped a switch in my head from “yeah I’ve got time” to “it’s now or never.” Over the next year and a half, I came to realize I had a huge amount of work ahead of me. I was in Plato’s Cave, and the light of my emotions blinded me at first. However, each small taste of success (and estrogen) made it easier to keep going.

On the other hand, through equal part paranoia and part rational assessment of the situation, I found it really hard to be excited about the future. Going to this conference at all, but especially this talk helped me understand this bleakness for what it is, and what I can do about it:

Probably the biggest difficulty I’ve experienced in my transition, outside of the constant threat of mistreatment, is trusting my feelings, especially when my feelings lead me down black-pill type paths.

This all feels very tangential. Well here’s the thing, I don’t actually know if I’m supposed to be a software practitioner. At least that’s what I’ve been telling my coworkers about how I feel about my career. That’s not a good sign, right? A big lesson from my ongoing transition is that being in touch with my feelings is everything. So I tend to think now I should discard the question of whether I “should”, and instead focus on whether I want to. Framed this way, it’s clear: programming computers is fun and rewarding! Life has a funny way of preventing me from seeing that sometimes.

For example, I am constantly stubbing my toe on the fact that, in 2005, when I first learned about the internet and what computers were capable of doing (anything you told them to do), I assumed that there would be a smooth progression towards solving coordination problems, social media would be good and effective, and all these little bits of technology we’ve been inserting into everyone’s lives would play nice and be able to talk to each other. Holy shit, has the reality of the last 21 years not gone that way. It’s easy for me to be cynical and say we’ve managed to regress the internet (just look at the state of social media these days). What possible positive effect could I have on the situation?

I now think that’s a wrong way to look at it. I have all these projects that are cool, but I’ve not attempted to share them. Everyone associated with this conference has little projects that I think are cool too. I’ll have to dig into them in due time.

My manifest:

That is all for now. I have much more to say, but this is already pretty long as it is, and I gotta hit publish at some point.

Closing remarks

I would be remiss to not mention all the wonderful people that made this conference a delight. Thank you to Isaac Van Doren for putting all this together and being so thoughtful as to host it in my hometown 😁. CoMO is a beautiful little midwest city and this event makes me even more proud of it. (Shameless plug for True/False Film Festival, which is another important-to-me cultural event that takes place downtown.)

It’s been a real treat to see all these cool projects that I didn’t know about (since the internet has a Library of Babel–style discoverability problem). Check out the conference website, which fans out to so much cool stuff.

Thank you to Imran Iqbal, David Kotval, and Malek Necibi for engaging and sometimes mind-wrinkling conversation about the talks.

Further reading