The Don Draper Dilemma

Mark Radcliffe can relate to Dick Whitman’s urge to escape his native clay and transform himself into “Mad Man” Don Draper.

The season premiere of Mad Men is upon us this week, and fans are all a-flutter—especially we New Yorkers, who’ve been surrounded by the much-discussed ad campaign. Those of us who were fans of the show recognized it instantly, and saw it as a powerful, magical and memorable allusion to the series. But those of us who are still haunted by 9/11 saw nothing other than “the falling man” and were plenty offended. Here’s what I find so powerful and hypnotizing about this image:

It’s of a man falling.

JD Salinger said it best, years ago, in The Catcher in the Rye: “The man falling isn’t permitted to feel or hear himself hit bottom.”

But he’s perfectly dressed.

And he’s completely relaxed.

There’s not a sign of peril anywhere in his body.

Yet, he’s falling towards certain tragedy.

And if you’ve seen the series, it can only be about one guy:

The enigmatic, illusive, charming, and yet self-destructive Don Draper.

He’s at the center of a series full of characters all living in denial, to one degree or another.

Whether it’s the gay art director, Sal Romano, who conceals his true self in order to be accepted in a corporate world, or the ambitious Peggy Olson, who conceals her accidental pregnancy and gives away her child in order to protect her career, or countless others, every character is being pulled in two divergent directions.

And in that sense, Mad Men isn’t about advertising at all.

It’s about the battle inside us all, between who we are and what the world would prefer us to be.

Do we conform to what conventional society expects of us? Or do we triumphantly sound our barbaric yawp on the hilltops of the world, perhaps to be exalted, but perhaps to be kicked in the gut and rejected as a misfit?

Don made his choice a long time ago when he faked his own death in the Korean war, abandoning his born identity of Dick Whitman and assuming the name of Don Draper.

His hunger to reinvent himself was so strong that he resolved to never see his family again. He leaves the farmland and moves to New York City. Gets a job charming customers into buying new high-end suits at a haberdashery. Soon he’s deftly maneuvered his way into a job as a writer at an ad agency, where he eventually becomes Creative Director.

But soon his desire to reinvent himself takes on a dark side. He gets so good at “selling” himself that he can fool anyone. He pretends to be a faithful, all-American husband by day, but cheats on his wife by night with the secretary. Or a school teacher. Or a client. Or a colleague. Or a stewardess. Or another secretary. Even his colleagues have no idea who he “really is.” They may respect him, but it’s not because he’s warm, open-hearted and welcoming. They fear him. It’s hard to tell where his loyalties lie.

Yet he’s the quintessential realization of the American Dream: we can make ourselves into whoever we want. Screw where you came from; imagine what you want to be, pretend to be it, and go out there and become that idea as best you can. And if anyone judges you, ignore them.

But by “conning” people, he sets up a tragic pattern; he’s unable to stop pretending. When he’s married, he acts like he’s single. When he’s got one foot out the door, he pretends he’s devoutly in love. When he’s tracked down by his estranged brother whom he clearly loves, he pretends he doesn’t know him because it would tear his “reinvented life” to pieces.

We watch him continually conceal his true self in order to “get ahead,” and wince as his star rises but his soul is in free-fall.

And I have to admit, as much as Don’s various deceits horrify me, I can relate to his urge to escape his native clay and transform himself. I grew up in a family devoted to the sciences, to rational careers like medicine and teaching and getting an MBA, the safe, professional equivalents of life on a farm. And yet, I always found more insight into the human condition through the novels of Kurt Vonnegut and the songs of the Indigo Girls than I did from the properties of physics, math and chemistry. So off I went.

I left New England behind much like Don left his own hometown, and eventually lived on the West coast for a decade, devoting myself to a life in the arts–music, writing, film, fiction, advertising, and the like. I reinvented myself, too. And found it convenient to ignore my past.

And while I’m happy with my life in the arts, it hasn’t always been easy. Or profitable.

There are plenty of days I wonder if I should have just kept it a lot simpler and just become a damn lawyer, for crying out loud. Why couldn’t I have just stayed on the farm?

My family might have preferred it that way, too, judging from the awkward questions they sometimes ask about what the hell I actually do for a living.

And even as I live my life in the creative arts, there are temptations to “sell out” here, all the time, too. Ones that aren’t exactly the purest expression of my creative instincts, but would pay a lot more. Or take less time. But require more shots of whiskey at night’s end.

So the thing I relate to with Don is the notion of temptation. If you’re ambitious, and want to live the biggest life you can, there are always shortcuts to success nearby, where if you’re willing to conceal the truth a little bit, you can “get ahead.” You can get the promotion. Make more money. Beat out the competition. Sleep with the girl you hope your wife won’t find out about.

But sooner or later, you have to ask yourself: are you actually becoming someone “better”? Or are you just becoming someone you no longer recognize?

Because the problem with ambition is that it can blind you to the truth about yourself. JD Salinger said it best, years ago, in The Catcher in the Rye: “The man falling isn’t permitted to feel or hear himself hit bottom.” That’s Don, whether he knows it or not.

And it could be any of us, too, if we’re not careful. Don’s life serves as a reminder: There’s a thin line between re-inventing yourself and lying to yourself.

And if the way you’re going about it requires you to keep your secrets stashed away in a box and always keep a bottle of booze close at hand?

You better hope you packed a parachute.

Because the ground is approaching fast.


—Photo Shahram Sharif/Flickr

About Mark Radcliffe

Mark Radcliffe is a writer living in New York City. He has a weakness for bourbon, jazz and girls who can drive stick. You can read more of his essays here: and

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