“It's your life. You don't know how long it's gonna be, but you know it's got a bad ending. You have to move forward. As soon as you can figure out what that is.”
I think Freddy Rumsen is the one character where I actually buy “It’s the ‘60s” as an excuse for his casual sexism.
Despite all his “sweethearts” and “honeys” and “princesses” when speaking with her, he actually does treat Peggy Olson as a fellow copywriter and gives her the same advice he would anybody else. It’s camoflauged in the condescending language of a man talking down to a little girl, but the actual content is always on an equal level.
Including telling her to leave SCDP and leverage it into a better job at a different agency.
Even back to the beginning, he was the one who first recognized her potential. Despite Don’s self-aggrandizing claim that he is responsible for everything good in Peggy’s life, it was Freddy who brought her in for the lipstick campaign. And again for the next one. Who pointed out her brilliance to the others and stuck up for her when she was still ‘just’ a secretary.
He can’t escape the conditioning he was raised in so his tone and style treat her like a lesser, but unlike everybody else it really does seem to just be conditioning. Don and Pete and Roger have all internalized it and need to have their shells shattered from the outside before they accept Peggy, but Freddy came to it naturally.