The Side Eye app icon: a square tomato giving you side-eye

I just shipped Side Eye. It’s a pomodoro timer that floats on top of your computer windows and watches what you’re doing. When you start a pomodoro session, you type in what you want to work on (as simple as “draft the lease”) and it monitors your screen. Whenever you’re off-task, it turns red and urges you back to work.

The Side Eye floating window on task (dark, green check) and off task (red, with I'm on task! and Go for a walk buttons)

You can download it here.

It’s free to download and open source, although it uses about $0.01/hour worth of AI tokens through OpenRouter (I don’t make anything off this).

Over time — especially as you correct it when it wrongly flags you — it learns more about how your tasks are related and it gets better and better at classification.

From a privacy perspective, it only uses “zero data retention” providers and does its best to redact any sensitive information before it leaves your computer, but I would still advise you to be careful with anything that sends contents of your computer screen off device.


When Jev came out, I wanted to think of something to build using it — and Side Eye had been on my backlog for quite awhile and was a perfect fit.

Side Eye uses a cascade approach, first hitting Jev with minimal information (which updates near-instantly), and falling back to adding more info and eventually inspecting a screenshot of your screen with Deepseek’s latest Flash model. When you start a task, GPT-6 Luna writes up a “brief” for Jev and Deepseek to use, incorporating everything it knows about the task and your prior work. All of this feels incredibly snappy and is remarkably inexpensive.

I also had fun animating the menu bar icon, which blinks occasionally and gets angry when you’re off-task…

Let me know what you think!


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