kelley robinson

Overengineered side projects

May 15, 2026

One of the biggest things that AI coding agents unlock is the ability to turn side project ideas into shippable realities. What used to take several nights and weekends of dedication, fighting with configuration, and learning random APIs can now be a functional prototype in hours if not minutes. It’s made me think about the ideas that have been in the back of my mind that could now just exist with a few well-described prompts.

I’ve thought about building an app that makes it easier to share tools and equipment with my neighbors. That would be pretty straightforward to build: a small DB, invite only user logins, reservation windows, no payment needed! But I could also walk across the street and knock on the door to see if I can borrow the post hole digger I saw them using the other week and chat about the best time to transplant my irises.

I’ve thought about building an app to create a shared grocery list with my husband. The existing ones I’ve tried all have dealbreaking flaws and that, too, would be pretty straightfoward. Organize lists by store, by season, by aisle. Add recurring items, never forget the frozen blueberries again. But I could also use a scrap piece of paper on the refrigerator and have another opportunity for us to inventory the pantry and communicate about our schedules.

This is the problem that Nilay Patel so aptly coined as software brain, or “when you see the whole world as a series of databases that can be controlled with the structured language of software code.” The obvious problem to a lot of us is that “people aren’t computers, and they don’t live in automatable loops that can be neatly captured in databases.” But that’s not obvious in Silicon Valley, especially because so many people have gotten rich off of (or watched their friends get rich off of) modeling humanity through databases.

So when I revisited the idea of building an app to manage delivery schedules for a local meals on wheels type non profit, I was left with the same dilemma I faced 4 years ago when I was first involved in the project. This would be far easier now, but still not straightforward. As anyone who has done volunteer management can tell you no amount of software can replace the desire for people to feel heard and valued, especially when that volunteer time might be their only socialization for the day or week. As Patel points out:

“It is a failure when you ask people to adapt to computers. Computers should adapt to people. Asking people to make themselves more legible to software — to turn themselves into a database — is a doomed idea.”

I’m not saying that building overengineered side projects is a waste of time, I still giggle at the hackathon project I once saw that delivered a pizza to a random location and then called you an Uber to that spot. I’m sure the people that built it had fun and learned a lot. I once built an entire food blog from scratch and learned a lot about JSON-ld, React, and why everyone should stop bitching about recipe developers who share their life stories in a post.

Rather I’m saying that we might not want to blindly applaud this kind of development. Many of the power players in the industry would love if you never had to speak to another real person again and I think that’s making us all a little insane. I can hear the protestations of the efficiency these side projects unlock but I’m skeptical. Some of the best things in life simply can’t be optimized, think cultivating friendships or reading a good book (so maybe it’s no wonder that we’re seeing more loneliness and less reading).

After using the heck out of Claude Code at work I bought a personal Claude Pro subscription a few months ago. I’ve built some silly things but have yet to build anything truly useful and that’s okay: the neighbors are still happy to lend me a hand, I sometimes forget the blueberries, the volunteer schedules still get made. I still seek improvements in many areas of my life, some even involve software! But I’m also so much more content since I’ve accepted imperfect systems and have patience for more of the messy realities that come with being a person.