Here's a quick and easy way to upgrade all outdated pip/Python packages on a computer. It worked for me on Ubuntu 16.04, and looks like it will work on Mac and Windows too.
Save a list of Python packages to a file:
$ pip freeze > pip_frozen.txt
Then run this command (which might require
sudo on some systems) -- it will upgrade every Python package listed in that file:
$ pip install -r pip_frozen.txt --upgrade