Managing Python based applications is made easy with pipx. But I dislike installing pipx via a pip user install, as it results in two python utilities managing packages. So, instead I let pipx manage it’s own updates.

Here’s how we can do it on a Debian system:

1. Install python3-pip, with:

   $ sudo apt install python3-pip
   

2. Install pipx:

   $ pip install --user pipx
   

   Didn’t we want avoid that? Yes! We’ll clean this up later.

   Note the installation output for the packages that were installed. In my case, they were: pyparsing, click, userpath, packaging, argcomplete and pipx.

3. Ask pipx to install itself:

   $ pipx install pipx
   

4. Now, we can clean up pip:

   $ pip uninstall -y pyparsing click userpath packaging argcomplete pipx
   $ sudo apt uninstall python3-pip --autoremove --purge
   

   If you are obsessed like me, you can also clean up the site packages directory. Only do this after verifying that it is empty.

   $ rm -r ~/.local/lib/python3.9/site-packages
   

   In my case, it was safe to remove ~/.local/lib.

5. As there already was a pipx in ~/.local/bin from the pip install, pipx doesn’t create a symlink in ~/.local/bin when we did step 3. We need to manually do this:

   $ ln -sf ~/.local/pipx/venvs/pipx/bin/pipx ~/.local/bin/
   

That’s it! Now we can manage packages with pipx, like:

$ pipx install neovim-remote

Upgrading all packages is trivial:

$ pipx upgrade-all

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