Link Rot and Roombas

Roombas

I always say about a physical robot, the physical appearance makes a promise about what it can do. The Roomba was this little disc on the floor. It didn’t promise much—you saw it and thought, that’s not going to clean the windows.

(from https://crazystupidtech.com/2025/09/29/irobot-founder-dont-believe-the-ai-robotics-hype/ )

This quote has been bouncing around my head for the last few weeks since I read the (very good) interview it comes from.

I am finding myself increasingly frustrated by the quiet implicit promises made (and often not kept) by UI. Like a roomba, UI makes promises about what it can and can't do. It is so so so hard to get right. Especially with LLMs.

(Quick aside on my motivation for writing this, feel free to skip its non-technical and very naval-gazey)

I am new enough to the tech space, and had a circuitous enough route getting here (I'm a carpetbagger--ran my first terminal command at 29), that I think I have a unique spidey-sense for how normal people experience software. A lot of really brilliant software people frankly either never experienced or don't remember what it's like to use software every day (hours and hours of screen-time) but understand little to nothing in terms of computer science principles.

A partial working thesis of this blog is me trying to quickly jot down what I remember about using software as a normal person, because (in my opinion...) software engineering daily subtly but substantially changes your brain and how you interact with the world.

Link Rot

It was indescribably frustrating my first months of 'Deciding To Get-Into-Tech' to find dead links. I was looking at lots of free educational resources and student-created material, plus a lot of it was at least a few years old, so there was a fair amount of link rot.

I know I said just said it was "indescribably frustrating" but let me try:

I'm in my childhood bedroom, 29 years old, jobless because I'm full-time "trying to learn tech", tearing my hair out daily over the smallest things, trying and failing to find resources appropriate to my current level of skill that don't feel patronizing (looking back: I should have been more humble and focused on the "dumb" stuff that felt "beneath" me but whatever), and then I finally find something that sounds just absolutely perfect, exactly what I was looking for...and its a dead link.

It really was the kind of thing that made me think: "maybe I should just go to law school" (kidding (about law school)).

Dead links felt personal. Irrational, I know, but that's really how it felt. It felt like just such a basic thing and then to not be there was like... fuck you for trying to learn something you moron.

What I think about Link Rot today

I think:

"Link Rot" is a terrible name.

what, some random person wrote href once fifteen years ago, this magic incantation worked for years totally unmaintained, but the moment it doesn't work anymore we're mad about that???

links kinda subtly make a promise they don't keep: "click me and I'll take you to a server that works exactly the same as it did the day the programmer's fat fingers typed h-r-e-f".

its amazing that any link ever works! Let's be grateful for the vast majority that do their job. Let's focus on on those links. Let's write articles about the links that showed up to work today.

How I would explain it to the frustrated earlier version of myself:

You know how the internet is, like, not just one computer but a whole bunch of computers?

When you click an external link, you're going from requesting something (an html document) from one computer (server) that works (since it's showing you a webpage), to requesting something from another server (computer) which...hopefully that server works, too. But there are so many servers! Every day new servers come on-line and old ones break. Not every link is gonna work.

Maybe quit looking at capstone projects of bootcamp graduates from 2013? Go read the MDN docs .