Developer tooling accumulates like technical debt. You install something for a specific project, it stays in your $PATH, you forget you have it, you install something that does the same thing. Six months later you have three terminal multiplexers and can't remember which one has your config in it.
I started doing quarterly stack audits about two years ago. It takes two hours. I do it at the start of each calendar quarter.
The Audit Document
It's a simple table: tool name, category, when I installed it, frequency of use (daily / weekly / monthly / rarely), monthly cost if any, and a one-line note on whether I'm keeping it.
I populate the frequency column honestly, not aspirationally. "I could use this daily" doesn't count. "I did use this daily last quarter" counts.
Brew list, pip list, npm global, cargo install — I run all of them and go through the output. This is where I find things I forgot I installed.
The Questions
For each tool: Am I using it? Is there something I'm using that does the same thing? If I removed it today, would I notice in a week? If a newer or better version exists, am I on it?
The "would I notice in a week" question is the most useful one. Tools that survive it are keepers. Tools that don't are candidates for removal regardless of how useful they seemed when I installed them.
What Triggered the Last Three Changes
Q1 2026 audit: removed httpie because I was using curl and xh for the same things, and the three-way redundancy was confusion. Kept xh, removed both others.
Q4 2025 audit: switched from iTerm2 to Ghostty. iTerm2 had been daily-use but I'd been running Ghostty in parallel for two months and the only reason I'd kept iTerm2 was inertia. Removing it made the decision clean.
Q3 2025 audit: removed four VS Code extensions I hadn't used since switching primarily to Neovim. The cognitive overhead of maintaining a VS Code config I used only occasionally was real.
The Compounding Effect
Eight quarters of audits means a stack that has been deliberately evaluated thirty-two times. The tools I'm running now are all tools I actively chose in the last twelve months, not things I installed once and stopped thinking about.
This is an underrated property. You know what you have. You know why you have it. That's not a trivial thing when your environment is also your instrument.