What Peggy Olson Has Taught Me About Doing It My Way

As Mad Men’s most important character turned 30 this week, she’s become the poster girl for making difficult life choices.

One of the pleasures of watching Mad Men has always been reveling in just how much has seemingly changed: We don’t allow our kids to play with dry-cleaning bags anymore, or leave our picnic litter at the park, or smoke at the doctor’s office. Or at least we don’t think those things are OK — as Mark Grief pointed out after Season 1, “beneath the Now We Know Better is a whiff of Doesn’t That Look Good.” The drinking, the smoking, the lack of seat belts — there’s something darkly appealing about living without (those) boundaries.

Mad Men also allows us to think about how far we’ve progressed in terms of racial and gender politics: 40 years later, we have black receptionists, and sexual harassment laws would prevent something like Joan’s behind-doors deal with Jaguar.

But that’s a simplistic reading of both the show and the audience’s reaction to it: Narratives that reproduce the past are always, at least in part, commentaries on the present, and one of the many devastating realizations prompted by the last six and a half seasons of Mad Men is that racism, sexism, and homophobia may no longer operate on the surface of most of our everyday interactions, but that doesn’t mean they’ve disappeared. They’ve been sublimated, swallowed up by the rhetoric of a post-racial, post-feminist, post-gay America in which everyone is equal and free to choose what makes them happy.

Which is, of course, bullshit — as anyone who’s tried to exercise that “freedom to choose” in a way that doesn’t fit with the status quo can testify. Not conforming to gender expectations, being “too” gay or “ethnic” or unruly, even choosing, as woman, to not want the things — children, marriage, etc. — that all women “should” want. Women’s liberation may have granted us entry into the workplace, but there are still expectations of what our lives outside the office should look like. You should try to “have it all” — the spouse, the family, the beautifully kept home, and the job — or, at least in the eyes of society, you might as well have nothing at all.

I knew when I queued up this week’s episode that it was going to make me feel some sort of way: In the last week, I’d taught my last class as a college professor, said my good-byes to dozens of students, and flown across the country to start what can only be described as an entirely new life in New York. But I also knew that this was the second to last episode of this Mad Men mini-season, and Matthew Weiner loves nothing more than a dramatic, if subtle, buildup to finale. There would, in other words, be emotions — especially since I was also watching on the eve of my 33rd birthday, which I was spending in a new place and with a new job. But I couldn’t have anticipated just how precisely “The Strategy,” and Peggy’s place within it, would resonate with the specifics of my own experience.

To watch Peggy Olson in the current seventh season of Mad Men has been to watch a woman suffocating under this realization. After the May 18 episode, we know that she’s been silently anticipating, and then suffering through, her 30th birthday, and everything that such an arbitrary number tells her she should regret.

As she and Don Draper hash out a new campaign in Peggy’s office, clearly mirroring the events of the classic Season 4 episode “The Suitcase,” almost exactly four years before, Peggy tries to figure out how to make the mother in the ad match the women she’d encountered while doing research in the Burger Chef parking lots — not some glossy image of 1955. “Moms want Burger Chef because it’s an answer to a crisis,” she explains. “What if Mom’s coming home from work?” When Don scoffs, “What’s her profession?” it’s telling — his ex-wife Betty didn’t have a job, and his current wife Megan didn’t have kids. Any familial crisis has been of his own making, wholly unsolvable by a bag of burgers.

When Peggy rebukes him (“You are surrounded by all kinds of mothers who work, Don”), he takes a different tack: The image of a mom solving the “crisis” of trying to balance a profession and a family is “too sad.” Or at least too sad for an ad, which is another way of saying too close to the way that people actually experience life, as opposed to the way that they’ve been trained to think they’re supposed to experience it. Because as Peggy explains, the happy nuclear family of their first ad pitch doesn’t actually exist anymore. The daughter’s pregnant; the son’s been drafted — or they actually just look like Don’s own family, which is to say fractured and imperfect but still, at bottom, trying to figure out an approximation of love.

But the complexities of life have never translated well into a 30-second ad, which is why most advertising aims for the broadest and most legible of sentiments. Indeed, what distinguishes Don’s genius work is its ability to get at emotions that are even slightly more complex: the bittersweetness of the Kodak pitch, or the childhood nostalgia of the Glo-Coat ad.

Peggy’s been selling the dream so long, she’s bought it as her own reality — or at least that reality to which she should aspire. As far back as the Season 1 pitch for Belle Jolie, she’s excelled by putting herself in a subject position different from her own: the girlfriend desperate to “mark her man”; the mom, popsicle in hand, offering to “break it, share it, love it”; even the Mohawk Airlines pitch —“What did you bring me, Daddy?” — had her taking the position of the doting daughter of a well-to-do father, as opposed to finding him dead of a heart attack at the age of 12, which was her reality.

She’s risen to copy chief at Sterling Cooper & Partners on the skill of her self-sublimation — her ability, in other words, to empathize with people who live lives that she does not and, in the process, tell them what they should want. But that’s a misreading of the job: You can become a good copywriter by ventriloquizing others’ desires, but the only way to become a truly great copywriter is to figure out a way to articulate your own desires in a way that resonates, even with people who aren’t like you.

And that’s what Don’s done all along. There’s a reason he uses his own family photos in the Kodak pitch, and why his Hershey confession in the Season 6 finale could have functioned as an amazing anti-advertisement. Even the idealized desires of Heinz (“Some things never change”) articulate the real, embodied yearnings for plentitude, emotional and financial, amidst the lack of his youth.

So when Peggy asks him to show him how his mind works — to share, in essence, his genius — he gives her the same advice he’s been modeling all along: “You can’t tell people what they want. It has to be what you want.”

It’s a quietly revelatory moment. Peggy doesn’t suddenly come up with the solution to the ad, or even tell Don that it all suddenly makes sense. But so many of us have had moments like that one, however subtle, when we realize that we don’t have to want what everyone else does, or what everyone else thinks that we should want. That trying to match your desires to a vague notion of the ideal is exhausting — and you can, in fact, listen to what your mind and body seems to be yearning for instead of battling to shut it up.

Peggy, of course, started listening to that voice nearly 10 years ago. When she came up with her first tagline; when she came back to work after her pregnancy; when she told Pete, “I could’ve had you. I could’ve shamed you into being with me. But I didn’t want to… I had your baby, and I gave it away.”

She “wanted other things” — her career, a life that didn’t include a forced marriage, a resentful husband, and a set of in-laws who would predictably despise her — and so she made a decision that was unpopular with her mother, her sister, and her priest.

For many years, that decision — and other bold ones like it, including leaving her mentor for a better job offer and dating Abe — made Peggy feel awesome. Here was a woman, still in her twenties, a copy chief at an up-and-coming ad agency, with a boyfriend who may have been weird and radical, but absolutely adored her.

But Don and Ted altered that trajectory. By masterminding the merger of SDCP and Cutler Gleason and Chaough, Don effectively brought her back under his oversight; by falling in love with her, Ted not only derailed her relationship with Abe, but introduced a palpable alternative, an alluring version of the domestic ideal she thought she didn’t want.

That’s always the worst: When you’ve made up your mind about your life and your happiness in it, but something comes around to persuade you otherwise. That’s why Peggy’s been so edgy and agitated this season — she thought she’d gotten past all the “this is what you should do” bullshit. But the lingering presence of Ted, the condescending shuffle of her new boss Lou, the unwanted control of Don, even the ever-presence of Julio, her neighbor who, as Tom and Lorenzo noted last week, is just about the age that Peggy and Pete’s child would be — they’re like a bizarre version of the Greek chorus, constantly reminding Peggy that she made all the wrong choices.

Peering into so many station wagons all over rural America for Burger Chef may have been the catalyst of Peggy’s breakdown, but it certainly wasn’t the root cause. When she asks Don, “What did I do wrong?” it’s not that she wants the face of the harried mother we see in the first shots of the episode, or the station wagon, or even the kids. She wonders why the path that she chose, the path she thought was right, has turned wrong. Because it’s one thing to be an incredibly successful career woman at the age of 30, confident in yourself and your abilities — but it’s quite another to find yourself, in Pete’s words, relegated to being “just as good as any woman in this business,” forever floundering under the mediocrity of men like Lou.

When Don offers Peggy a tissue and tells her she’s “doing fine,” she smiles, looks down, wipes her eyes, and returns the tissue. Or, put differently, she accepts his pity and concern and uses it to restore herself, creating the framework for the pitch that actually articulates her desire: a place where you could break bread, without television, and anyone you were sitting with, that was your family.

Each of the three parts of that pitch speak volumes of Peggy’s actual desires. She wants to “break bread,” not in the traditional way of her Catholic youth, forever shaded in shame, but in the mode of true fellowship: a community of interest, feeling, and care. She wants a place without television — not only because it’s a way to avoid talking to each other, but also because television, and the media messages, whether nested in advertisements, the news, or the banal sitcoms dominating the air, tell her, over and over again, that her decisions were the wrong ones. And she wants it to be OK that whoever she’s sitting with, no matter who they are, can be her family, because for Peggy, family isn’t an exponent of blood relation, but respect, loyalty, and compassion.

It’s easy to understand why Peggy didn’t feel addressed by Frank Sinatra’s “My Way” playing on the radio while she and Don worked. Sinatra was able to do it “his way”— and without regret — because he was a straight white male, and every decision he made, even the most callous and ill-conceived ones, were validated and, through the lens of history, redeemed. Sinatra had the privilege not only to do it his way, but for other people to celebrate it: By the late ‘60s, the mythology of his eternal cool had already begun to take form.

But Sinatra was, by nearly all accounts, an unmitigated asshole. He came to loathe his early image, with its bobby-soxer appeal, and he neglected, abused, and cheated on nearly all the women in his life. He was a draft-dodger and a self-confessed “18-karat manic depressive.” And, according to lore, he hated “My Way,” especially after it became his calling card. He may have done it his way, but it was much darker and marked with more despair and self-doubt than the melody and lyrics let on.

Which is precisely why the song is so fitting for a Don and Peggy slow dance: They both did it their way, but they’re plagued by the same doubt and regret, the fear that “I never did anything and that I don’t have anyone.”

The beauty, of course, and why this moment, along with so many others in Don and Peggy’s history, will remain crystallized in our memory, is that Don and Peggy have each other. It’s not a romantic relationship, nor, I’d argue, is it precisely paternal. It’s friendship, but the sort that comes from seeing someone who sees you clearly. Peggy may not know the secrets of Dick Whitman, but unlike Anna or Megan, he doesn’t mythologize her and render her distant. And the only person who knows as much about Peggy is Pete — who, not coincidentally, is the only person who gets to come along to break bread at their perfectly broken family Burger Chef family gathering. The most important relationship in Mad Men isn’t rooted in passion, or romance, or even homosocial bonding, but the fruition of friendship.

I’ve always loved the relationship between Don and Peggy, but it — and, more specifically, Peggy’s fear — spoke to me in “The Strategy.” I’m three years older than Peggy and, by some accounts, have accomplished far less: I may have a Ph.D., but I most certainly do not own my own home, nor do I make the equivalent of $140,000 a year. All of my friends from college are married and have at least one child. And, as I move across the country for the fifth time in seven years, there are moments when, like Peggy, I’m curious if, looking back at my life, I’ll also wonder where I went wrong.

But think back to the end of Season 6, when Peggy stood, in a magnificent pantsuit, dominating Don’s office. Or the firm resolve in her quavering voice when she told Pete that she wanted other things. Like Peggy, I’ve made decisions because they felt right and made me feel strong and intelligent and valued. But that doesn’t mean that watching every rom-com and television show that isn’t Broad City doesn’t tell me that if I’m not doing those things with a family and a spouse, I’m doing them wrong. Or at least not perfectly, which is hard for any type-A woman to hear.

But unlike a rom-com, Mad Men refuses to give neat solutions to messy questions. The salve I felt watching the episode on the eve of my 33rd birthday had nothing to do with catharsis, or even reassurance — because Peggy’s life isn’t perfect, but neither is Betty’s, or, for that matter, the lives of any of the women (or men) on the show. When Don says that “the job” is “living in the not knowing,” he’s referring to life: Even if your life does match the picture on the television screen, you’re just as unsettled as the person working their best to do the opposite. There’s a difference, of course, between living in the sort of profound disturbance that afflicted Ginsberg and Peggy’s periodic ambivalence. The first destroys life; the second is the way you can tell you’re alive.

What Peggy gives me as I turn 33, then, isn’t a role model so much as a representation. I never see myself, and my life choices, represented in a way that isn’t nested in a narrative of necessary reform: career woman finds love, softens heart, reconsiders life choices. Like Peggy, I don’t ever want to be one of those women who lie about their age, or who wallow in lack and shame instead of plenty and deserved pride. And like Peggy, I’ll continue to break bread and find family, in its ever-variant guises, where it feels most genuine and nurturing. If Peggy and I and anyone else doing it their way can heed those maxims, living in the not knowing may, however gradually, morph from something that saps happiness into something that fuels it.






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