Mad Men creator Matthew Weiner kinda-sorta confirms my theorizing about how Depression-era generation helped create the never-grow-up culture that followed it: "One of my things is that human behavior doesn't change, but certainly the manners change, and what you're watching is the manners changing.
And I use it in every aspect of the storytelling. And it's a very fine gradation, and it's hard to do, but I think the audience felt that there was this kind of precipice, and Don feels it, too. It's not just about people saying exactly what they want. When Megan's going to follow her dreams, because that's what she wants to do, and Roger says, "My father told me what to do," and Don says, "I grew up in the '30s; my dream was indoor plumbing." We take it for granted that you can choose what you want to do. That's all part of a new generation, and very soon there's going to be a generation doing whatever it wants, and they're completely supported by the generation before them. In the Rolling Stones episode, when Don's backstage with that girl, she says, "You don't want us to have fun because none of you did." It's actually the opposite: a lot of parents really indulged their kids because of that very thing, because they grew up in the Depression."
Emphasis added. I meant to mention Don's line about "indoor plumbing" in my previous post—it's a thought that stuck with me through the rest of the season.