I use `pip install --user pipx` to install pipx, but I think a better option when using homebrew would be `brew install pipx`. With the latter, doing a `brew up

I use `pip install --user pipx` to install pipx, but I think a better option when using homebrew would be `brew install pipx`. With the latter, doing a `brew upgrade` should keep python and pipx in step. EDIT: Thinking about this some more, doing `brew install pipx` would keep pipx from breaking on brew upgrades, but I guess your installed scripts would still fail if you upgrade from Python 3.N to 3.N+1. So the only solution, I think, is to keep around all the versions of Python you use, assuming you don't want to upgrade all your scripts when upgrading Python. I use pyenv to manage Python versions rather than Homebrew, and this seems to avoid the issues you're having, because the Python version used to install whichever tool via pipx sticks around until I explicitly uninstall it.