There are only two episodes remaining of Mad Men (or, in the ridiculous verbiage of TV marketing, "only one episode left until the series finale"), so I found myself thinking it might be an opportune moment to weigh in on this final half-season.
I'm sure I speak for many when I say that the recent events around the agency itself are not what I was expecting in the final stretch of episodes, but the show has always been adept at avoiding what viewers are likely to be expecting. With the agency being absorbed into McCann-Erickson, I was not at all surprised to see the characters having difficulty adjusting to becoming part of such a huge organization. It would have been too anachronistic to use Pink Floyd's "Welcome to the Machine" (Wish You Were Here was not released until 1975), but it certainly would have been appropriate.
Pete, Harry, and (especially) Ted seem quite comfortable with having been assimilated into the Borg; Roger feels like he no longer has any real purpose, but he doesn't need to work and could easily choose to slide into an early retirement. The mistreatment and lack of respect shown to Joan were unfortunately all too typical experiences for women in the business world and, sadly, women are still experiencing such things today. Don has simply abdicated, driving off in search of the elusive Diana Bauer and picking up hitchhikers going to destinations he wasn't even planning to go (I loved Roger's comment to Jim Hobart on Don's absence: "He does that").
Peggy stands out, quite pointedly, as the exception. She already has a decade of experience and is ready to set the world on fire. Watching her arrive at her new office, it's clear she's prepared to extract every possible ounce of portfolio-building mojo from her time at McCann, and she seems likely to arrive at the end of her contract as someone at the top of the profession, ready to move on and perhaps form her own agency.
Historically, acquisitions were very common in advertising (and led to the super-agencies of today), but my gut tells me Matthew Weiner does not intend to wrap up this story with his characters adrift in a place they feel they don't belong. It's just too much of a down note, even for a show that has been so focused on characters who were struggling to find meaning in life (and generally not succeeding). Therefore, I think there's a strong possibility we are going to see a time jump,
either at the start of the next episode (as usually occurred at the
beginning of each season), at the start of the final episode, or perhaps
during one or both of them.
Don knows he is never going to find any kind of fulfillment working at McCann, so I think he might decide to walk away from the business. Jumping ahead in time would allow the story to move to a point where these people could theoretically come together again in some form, or it could merely serve as a kind of check-in, giving viewers a sense of the paths the various characters are on and where they may be going. But I realize that I may be completely wrong. Like I said, the show tends to avoid doing what we think it will.