You should consider upgrading via the 'python -m pip install --upgrade pip' command.
Then, when you try :
$ python -m pip install --upgrade pip
/usr/bin/python: No module named pip
Thank you Guido!
Fortunately, googling got me
$ pip install -U pip
threw out a tonne of errors about permissions (this is Cygwin), but seems to be working okay..
$ pip --version makes me happy
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