Another HN user did a write up on Homebrew[1] that I agree with.

My main gripe is that Homebrew would regularly break my Python virtualenvs with linking errors. Meanwhile on Linux, I have virtualenvs that I created 9 years ago that still just work.

These days you might be able to sidestep that issue by not using Python from Homebrew at all, but installing and managing it with Pyenv instead.

[1] https://saagarjha.com/blog/2019/04/26/thoughts-on-macos-pack...

`brew pin python` and it'll stop that from happening.

but yeah, this is a constant source of pain, and I end up helping people at work fix it probably on a weekly basis (or more often). python bin-envs are such a hassle.

I need to run the latest Python versions, including alphas and betas, though, and have everything just work even if the system and local Python versions change under me. Pinning Python would make it difficult to contribute to CPython, or make sure my libraries work with new Python alpha/beta releases before stable versions are released.

Virtualenvs based on Pyenv's local Python installs on Linux works well, and virtualenvs that were based on old system Python versions still work even when I upgrade the system Python. This is where I'd get linking errors with Homebrew that I don't get with Linux.

at this point you're far beyond the intended use for a widely used package manager. install a stable python somewhere by hand and keep it there ¯\_(ツ)_/¯