But what did Don traverse across to reach this new beginning?
Much like in Dante, Don literally goes through every outlet imaginable until he stops and reaches this "true path" – also hinted at in the poster.
Among the most obvious outlets that Don goes through are women. The unseen woman (aside from her nightgown-covered arm) that Don is grasping in the poster may be Megan or Betty or even Sylvia. But the obscured identity highlights that for Don women have been interchangeable commodities — in fact, in the closing episode, both Betty and Megan wear nightgowns reminiscent of the poster.
Don also tries escaping through drinking – at least, until he attempts to give it up after knocking out the preacher in the final episode.
The preacher scene is pivotal, however, in that it is not only about drinking. It implicitly groups all of Don's addictions together. In it the ballad "Band of Gold" plays in the background just as it does in the opening scene of "Mad Men's" pilot. In that scene, Don has a conversation with an African-American server that on its surface is about smoking. Don smokes Lucky Strikes while the server smokes Old Golds. But in reality that conversation – by linking the server's Old Golds to a wedding ring (the song's so-called"band of gold") – is about their relationship to women and, indeed, all of life. The server's perspective – much like the preacher's – stands for stability. Don, however, is a "Lucky Strike" man in every sense of the word: in his relationship with women, drinking and life itself.
Indeed, the series pilot explicitly connects Don's addictions to what the firm's psychologist calls the "Death Wish:" the desire to seek death that is repeatedly symbolized in "Mad Men" by smoking.
And sure enough, at the close of this season, Don experiences his own version of the "Death Wish."
The show's writers leave little doubt what Don's desire to move to California ultimately represents. Listen to Don tell it to Megan: "…I realized, it's gotten out of control. I've gotten out of control…But I've realized something else too, I don't want to be here anymore." (Italics added.)
To her question of "What would you do out there?" Don retorts: "…It would be a chance to open my own shop. Small team, desk, windows, and sunlight…the ocean."
So that the meaning of "the ocean" is clear. This scene immediately follows Pete Campbell learning that his mother was lost at sea.
To further drive home the point, the hotel that Don stayed at in Los Angeles was the "Vista Del Mar." When Don almost drowns in the pool, he is saved by Roger Sterling, in a Navy-style coat yelling "man overboard".
(And indeed, while underwater, Don of course, pauses for a smoke with his alter ego from the season opener, Private Dinkins. There's that "Death Wish" again).
Just look at how Don imagines the Pacific in his suicide-tinged ad for Sheraton.
But as Private Dinkins tells Don, "Dying doesn't make you whole." And Don ultimately chooses not to "escape" to the Pacific.
So what does start to make Don whole?
The season seems to throw out the possibility that it's Jesus. Jesus, in fact, is an ever-present figure in this season, from the opening shot of Megan's torso, which is very evocative of Christ on the Crucifixion.
Peggy, later on, stabs her boyfriend Abe in his side with a spear (very Roman soldier-y of her), to which he yells, "Jesus".
And yet, as Don tells the preacher, "Studies show that Jesus had a bad year." More than that, Don is unwilling to stomach hypocrisy in the preacher who tells him, among other things, that Martin Luther King wasn't a true believer.
At the end, it isn't conventional religion that saves Don, it's a different kind of father-son relationship.
Ultimately, the road to recovery for Don has less to do with anything external. It comes back to what is authentic to him: his real past and a future represented by his children.
In telling the truth about his childhood, Don begins to move away from the world represented by the season poster, with its multiple, conflicting, and overlapping Dons, to a world where – to steal from his Hershey pitch – "the wrapper looks like what is inside."