I have a long history with python, recently due to I'm starting using cursor.so, I started to give a try again in python, but now in MacOS brew version.

List all installed package:

python3 -m pip list

Setuptools can be updated via pip, without having to re-brew Python:

python3 -m pip install --upgrade setuptools

Pip can be used to upgrade itself via:

python3 -m pip install --upgrade pip

List of all outdated packages:

pip list --outdated

Upgrade package one by one:

python3 -m pip install --upgrade ipython

Install via requirements.txt via proxy

python3 -m pip install -r requirements.txt --proxy socks5://127.0.0.1:6153