Here is the payoff before the work: I plug in my YubiKey in the morning, type one PIN, and the rest of the day my authentication just happens. SSH to a server, no password. Sign a git commit, no passphrase. Pull a secret out of pass, just touch the key. One physical thing sits in a USB port and the friction is gone. Getting there cost me about three evenings of swearing at gpg-agent. Now that it runs, going back feels unthinkable. ...

I used KeePass for years. Then 1Password. Then Bitwarden. All decent tools, but every one of them felt like too much. Too much UI, too many features, too much friction to wire into the way I actually work. Every time I reached for a password I was reaching across an app boundary, and that small interruption added up. Then I found pass. It does exactly what the name promises: it stores passwords. I want to walk you through it the way I learned it, starting with the one command that hooked me, then adding layers until you can see my full setup. ...

GPG is one of those tools everyone keeps meaning to learn and never does. The docs are a wall of text, the terminology is its own dialect, and the error messages are cryptic in both senses of the word. I put it off for years myself. The thing is, you keep bumping into it. GPG sits under pass, under signed git commits, under encrypted email, under verifying that the binary you just downloaded is the one the maintainer actually shipped. If you care about owning your security instead of trusting a vendor to handle it for you, you end up here eventually. ...

For context on how my brain works, see Working with an AuDHD Brain. Here is the smallest version of my entire productivity system: task add "Write the intro" +next task 1 start That is it. The task is recorded, the clock is running, and I can see both in under a second without touching a mouse. Everything else in this post builds on top of those two lines. The stack is taskwarrior for task management, timewarrior for time tracking, and vit as a vim-style interface on top. Keyboard-first, terminal-native, plain text on disk. ...

For a long time, the cloud was just the water I swam in. I provisioned managed Kubernetes, clicked through the console, pasted a Terraform module someone else wrote, and shipped. It worked. Billing landed every month, the dashboards stayed green, and I never once asked what was actually running underneath. I trusted it the way you trust a lift in a building. You press the button and the doors open. ...