Что-то там было не так, поэтому мне помогло удалить / переместить все установленные библиотеки для Python 2 и 3 от brew и запустить снова (и с этого момента использовать только virtualenvs):

крипт на Python не работает с:

Traceback (most recent call last):
  File "./inspect_sheet.py", line 21, in <module>
    main()
  File "./inspect_sheet.py", line 12, in main
    workbook_name=workbook_name,
  File "./google_sheets.py", line 56, in __init__
    self.login()
  File "./google_sheets.py", line 46, in login
    self.client = gspread.authorize(credentials)
  File "/usr/local/lib/python2.7/site-packages/gspread/client.py", line 335, in authorize
    client.login()
  File "/usr/local/lib/python2.7/site-packages/gspread/client.py", line 98, in login
    self.auth.refresh(http)
  File "/usr/local/lib/python2.7/site-packages/oauth2client/client.py", line 598, in refresh
    self._refresh(http.request)
  File "/usr/local/lib/python2.7/site-packages/oauth2client/client.py", line 769, in _refresh
    self._do_refresh_request(http_request)
  File "/usr/local/lib/python2.7/site-packages/oauth2client/client.py", line 795, in _do_refresh_request
    body = self._generate_refresh_request,_body()
  File "/usr/local/lib/python2.7/site-packages/oauth2client/client.py", line 1425, in _generate_refresh_request_body
    assertion = self._generate_assertion()
  File "/usr/local/lib/python2.7/site-packages/oauth2client/client.py", line 1554, in _generate_assertion
    private_key, self.private_key_password), payload)
  File "/usr/local/lib/python2.7/site-packages/oauth2client/crypt.py", line 162, in from_string
    from OpenSSL import crypto
  File "/usr/local/lib/python2.7/site-packages/OpenSSL/__init__.py", line 8, in <module>
    from OpenSSL import rand, crypto, SSL
  File "/usr/local/lib/python2.7/site-packages/OpenSSL/SSL.py", line 118, in <module>
    SSL_ST_INIT = _lib.SSL_ST_INIT
AttributeError: 'module' object has no attribute 'SSL_ST_INIT'

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