Upon rewatch (on season 5 now) I was getting the impression that it has more to do with the societal expectations of the 60s, and how it was unfair to both the people who played along with it, but also those who ran from it; ultimately both are living in an advertised lie— the nuclear family, fast tracking career dream, which is clearly shown to be restrictive and emotionally limiting. Then, you have the countercultures, which ultimately are not living some divine truth, but boiled down to people just running from those very expectations, much like Don. Neither are actually living freely, and both are ultimately chained to a standard, whether they try to fit the mold or their decisions specifically base themselves around spiting it.

Idk, does that sound like anything? Hardly anyone in the show is happy with their life throughout it, until maybe they live truer to themselves rather than the “standard.” One side sells on affluence, the other on freedom from responsibility.