*Every week, Wired takes a look at the world of Mad Men – and the period of American history it examines – through the lens of the latest media campaign of the Sterling Cooper *Draper Pryce advertising agency.

Have you ever been experienced? Don Draper has. Given his bafflement by the Beatles' 1966 psychedelic masterpiece "Tomorrow Never Knows" last season, it's unlikely that the creative heart of Sterling Cooper Draper Pryce had been feeding his head with Jimi Hendrix when he settled on the phrase "an experience" to describe his stay at the Royal Hawaiian. (He did so twice: once to his department and once to the client.)

But there was certainly a purple haze of some kind or other in the air, in case the prominent use of that color throughout the double-sized Season Six premiere "The Doorway"–from Hawaiian flowers to Joan Harris' dress–didn't tip you off. It was "this state," as he told the hotel reps, that he attempted to capture in his ill-fated ad: a state of mind, a state of being. The reason the client balked, of course, was that the state Don was looking for was oblivion.

"Hawaii: The Jumping Off Point" went the tagline, superimposed over a drawing of discarded shoes and jacket, a noose-like tie, and footprints leading off into the surf. Roger supplied the A Star Is Born reference, but anyone who'd, well, watched Mad Men Season Five and experienced its non-stop cavalcade of suicidal imagery, leading up to an actual suicide, knew exactly what Don was selling here. We'd seen it earlier in the episode, as he stood staring out his office window, the white noise of the sea erasing his worries.

Contrast this with the pilot episode of the series, where Don's afternoon nap was soundtracked by the explosions of the Korean War. His Hawaiian sojourn was a rare opportunity to do nothing—to "shed his skin," drift from sensation to sensation, allow himself to disappear completely into the soporific, sensual haze of booze and sex and dope and food and color and warmth. No need to kill or be killed, lie or be lied to. No needs at all. "There is no man."

Don may still stride around like a square-jawed man out of time, no matter how many joints Megan Draper fishes out of her bikini bottom for him to smoke, but his idea here was very au courant. (Being current in his work is something he both takes seriously—he rejected an ad based around a groom carrying a bride across the threshold as "Paleolithic"—and tries to calibrate precisely, similarly rejecting popular, played-out cheap shots at hippies.)

Couching the concept of his ad in the perceived wisdom of non-Judeo-Christian spiritual practices also puts Don quite in line with countless proto-New-Agers of the day. And not quite a year before Don tried to turn nothingness into a tourist attraction, acid evangelist and counterculture guru Timothy Leary unveiled his famous saying "Turn on, tune in, drop out" at the Human Be-In in San Francisco. What else is Don advocating if not a similar, albeit squarer and more expensive, act of liberation through abandonment?

Don Draper (Jon Hamm) - Mad Men - Season 6, Episode 2 - Photo Credit: Michael Yarish/AMC

Don's ex-wife Betty has her own first-hand experience with a jumping off point in this episode, when Sally's magnetic, talented friend Sandy runs away to the Village, and thence to California (unwittingly following in Don's footsteps from his lost fortnight a few seasons back). Like the no-man from Don's ad, Sandy sheds her skin on her way out, in the form of the violin she leaves behind in the squat Betty stumbles across.

But Sandy's jumping off point represents not only a state, but a path she's chosen to follow; it's active, not passive. The rise of the counterculture to a level where even wealthy suburbanites know it exists has given young Americans a new option, where previously there had been only the success/failure binary the despairing violinist describes to Betty. With the trail well and truly blazed by countless kids before her, Sandy sees a way to avoid squandering her fleeting moment, and jumps for it.

Of course, the condition of the squat Betty visits, and the intervening decades of stories we've heard about free love's dark side, from Manson and Altamont on down, force us to reckon with the darkness in this idea as well. It takes some pushback from the Royal Hawaiian reps for Don to take ownership of this element of his pitch at last: "How do you get to heaven? Something terrible has to happen."

Don's eye is still on the nirvana at the end of the tunnel, though freshly be-bearded Stan Rizzo instead puts the emphasis on the end: Yes, of course the ad makes you think of suicide, and "that's what makes it so great." That ultimate erasure can be thrilling—though as Pete Campbell learned in the very first episode, "the death wish" is a tough sell to clients. Roger's approach to selling death in the form of cigarettes, ignoring it, may have made the copy less sexy, but it made the product more sellable.

Yet there's one erasure, one non-man, in this episode that was just right, Goldilocks style. Peggy is faced with an expensive Super Bowl ad campaign for headphones she can no longer use, because the phrase "lend me your ears" is now linked in the mind of the public to American G.I.s cutting off ears of their Vietnamese victims. Ironically, Peggy solves the problem by cutting away at the framing of the footage, until just the star's face, expressive but mute, remains. "It always takes a crisis to sell work this good," her boss Ted Chaough tells her; he's likely referring simply to having to start from scratch on an ad that's mere weeks from debuting, but the underlying atrocity hasn't gone away.

And insofar as the entire counterculture is a response to America's depredations on itself and others, the point is far broader than either of them realize: To get to heaven, something terrible has to happen.