How do I upgrade my openssl? A symlink isn't working for /usr/local/bin/OpenSSL
If you run

brew info openssl


you will have the answer :


  This formula is keg-only, which means it was not symlinked into /usr/local,
  because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries.
  
  If you need to have this software first in your PATH run:
    echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile