How Did This Gen X Columnist Become the Queen of the Millennial Misfits?

Three years after TIME magazine cover story dubbed Millennials “lazy, entitled narcissists,” there’s been an avalanche of evidence suggesting the opposite. They are working more jobs (and unpaid internships), earning more degrees, and are arguably more generous with what little time and money they do have than any generation before them.

And yet it’s hard to find a Gen-Xer, let alone a Boomer, who sees this group for what it is: treading water in a choppy sea of existential anxiety. Aside from a cogent 2015 piece by Fareed Zakaria for The Atlantic, Millennial defenses have been almost exclusively authored by those under thirty, a viral island of misfit toys demanding they get their due.

Enter madcap agony-aunt “Polly”—a.k.a., Heather Havrilesky, who, at 46, somehow seems to get what so many other full-blown grown-ups can’t. “From my vantage point,” she says in a recent article titled “It’s Never Been Harder to Be Young,” “it looks tougher to be a young person today than it has been for decades.” Recounting her years of advice-giving on her blog, The Awl, and New York Magazine’s The Cut—much of it to a 20-something audience—she swaps tired Gen-X naysaying for an attitude much more nuanced and humane. “Many of our basic assumptions about Millennials—that they’re spoiled and entitled, that they’re overconfident in their abilities, that they’re digital natives utterly unconflicted about privacy and social media and living much of their lives online—are wrong.” 

Wittingly or not, as “Polly,” Havrilesky has heralded a new age of advice uniquely attuned to a Gen-Y ethos, now lusciously hardbound in How to Be a Person in The World, a collection of mostly new columns. To one 25-year-old’s letter that The New Yorker’s Carrie Batten recently dismissed as a “parody of privileged millennial ennui,” Havrilesky responds with respect and sincerity. “I second guess myself all the time,” says the advice-seeker, signing off as “I Don’t Know.” “Will I ever know and be certain about something? Will it ever just click into place and I’ll know?” “I don’t always know either,” admits Polly, approaching her reader on equal ground. “Part of what I like about giving people advice is that I never fucking know how I’m going to pull it off.”

And yet she does, time and again, her converts crossing generational rifts. But while on The Awl and The Cut she’s often fielded questions relevant to a crowd her own age (mid-life career crises, parenting, a sibling with terminal cancer), How to Be a Person clearly targets those just learning how to be adults. Of the 32 letters published in the book, only a handful come from 30-somethings, and not one comes from anyone older than that. Attending the New York City book launch in July was like squeezing into a rock concert;  crammed to capacity with young bodies, the basement event space of Word bookstore in Greenpoint, Brooklyn, pulsed with pathos, laughter erupting across the sweaty crowd. No offhand X-er references to The Blue Lagoon, Miss Piggy, or Modest Mouse could jostle Polly from her throne.

In many ways her appeal debunks the peskiest Millennial stereotypes. For those eager to lament the younger generation’s shrinking attention span, Havrilesky’s rambling scrolls serve as a salient rejoinder. Even calling her a “columnist” feels a bit off—the term suggests a tidy stream of vertical text, whereas Polly riffs often breach 3,000 words, closing in a series of soulful imperatives that resemble a foul-mouthed Pema Chödrön. “Let there be darkness,” Havrilesky implores at the end of her 25-paragraph tract to the aforementioned “I Don’t Know.” “Get down on your knees, and crawl through the dark. Crawl and say to yourself, ‘Holy GOD, it’s dark, but just look at me crawl! I can crawl like a motherfucker.’” In another, seven-page screed to a glum Millennial, Polly makes anecdotal pit stops for everything from misconstruing Gwendolyn Brooks’s “The Bean Eaters” in tenth grade to the bossy birdsong of the eastern towhee.

In the process, does she answer the young person in question—whose outlook on life and growing older has grown woefully nihilistic? Not entirely. But existential questions are, for all practical purposes, practically unanswerable. What today’s young people seek—and deserve—is the semblance that someone older (and maybe wiser) hears them and deems them worthy of reply. The fact that Havrilesky gets away with such prolixity speaks for her audience’s appetite for epic answers to their epic questions—questions ever more pressing in a time in which both their romantic and job prospects can be more than murky. For the lucky ones who will go to college, their high school days often serve as little more than efficient grooming centers for standardized tests and pre-professional degrees. Lump in the decline of the more introspective liberal arts and the incredible debt that most face after college, and Big Life Questions are not only something Millennials are likely less prepared to handle, but surface with ever-greater urgency. In this context, who has time for indulging in deep conversations about the meaning of life, let alone their own meaning in life?

Unlike columnists present and past—the prim didacticism of Abby, the flamboyant sass of E. Jean, the wry neologisms of Dan Savage—Havrilesky’s endless cache of idiosyncratic personal narratives serve to speak not only for those who’ve ever felt lonely or aimless, but often to those young readers most pressured to feel that these emotions should be concealed. Havrilesky not only takes Millennial fears seriously, but comically placates with pop cultural references (e.g., Kanye, Paris Hilton, Game of Thrones) and casual expletives more common to Millennial everyday speech than the mama-bear counsel of Cheryl Strayed, whose retired Rumpus column “Dear Sugar” proves the most natural Polly comparison. Like Sugar for Strayed, “Polly” is a platform for Havrilesky’s literary persona as much as it is anything, and both share their personal histories as a means of empathizing. But while Strayed’s past is so rife with trauma that many might not relate, Havrileksy’s recollections (drunken 20-something tomfoolery, penning awful poems at a San Francisco temp job), however tinged with heartache, lack the extremity that drove the former to leave everything behind and go “Wild” on the Pacific Crest Trail.

And while Sugar followers on the whole are a blameless bunch upon whom no small shower of Bad Things has befallen, Havrilesky’s are often all-too-aware that they’re actively wrecking their lives. “I’m in my mid-20s, and I’ve developed a pattern of getting involved with attached men,” starts one such missive in How to Be a Person, concluding with the pithy “if you just struck out all the men, it would be clear that I’m a good person.” Where Strayed might call this reader “sweet pea,” Havrilesky shoots straight from the hip. “Instead of asking, ‘Why do I keep putting myself in these situations?’” urges Polly, “I think you need to ask, ‘Why do I choose to spend time with assholes and break their girlfriends’ hearts?’” Her bluntness is only later somewhat softened with “You don’t have compassion for other women because you don’t have compassion for yourself.”

Such compassion for the self—which Havrilesky advises we “bathe in” whenever possible—is the crux of Polly’s credo, but for readers wary of borderline-Calgon mantras (likely a large cross-generational swathe), her “you-do-you” exhortations are balanced with a penchant for all-caps self-abasement. Rather than telling us what to do from the stance of “I know more,” Havrilesky responds with “been-through-it-too” emotional largesse.

In one 2013 response on The Awl to a woman in her early 30s (“Sad About Stuff”) who already feels “past her prime,” Polly responds, “I still remember hearing ‘Sexy and 17!’ on the radio the day I turned 18. I thought, Oh well, I’m not quite as sexy now. How sad! I WAS A FUCKING TODDLER, BASICALLY, and I was mourning my lost sexiness.” For every spoonful of empathetic Sugar, Polly adds a dash of Swedish bitters, though not always in that order. “Just shut the fuck up and listen for a change,” she tells another young Awl reader prone to grilling any man romantically interested in her. “You’re charismatic and engaging and smart and pretty. Try to stop being the best, the most confident, the toughest, the most incredible, and try being just another human being in the room.”

In a column on The Cut from 2015, Havrilesky mines her own college diary for a metaphor that could apply across generations, but perhaps speaks most to Millennial alienation. “Every single page of that journal is a testament to how out of place I was. I was a radish tossed into a sack of potatoes, trying hard to imitate a potato. ‘Why do these potatoes act like my bitterness and zing are a pain in the ass?’ I’d wonder. ‘Who doesn’t love the almost-too-sharp taste of a Raphanus sativus? Am I going crazy?’” As “radishy” as Havrilesky may have felt at Duke in the early ’90s, just imagine how much easier it is to feel “out of place” growing up around the sackfuls of social-media spuds today. But by championing her own bitter zing, while acknowledging that it’s not for everyone, Polly lends permission to anyone—young, old, or in between—to find and be our genuine selves amidst the relentless pep of Facebook feeds and Twitter GIFs.

In this way, for all the youth-centrism of her new book, Polly’s persona effectively serves as a bridge between generations. To say that Havrilesky tills only Millennial turf would do a disservice not only to the broader appeal of her voice, but also suggest that the problems endured in one’s 20s and 30s magically disappear upon full adulthood. Like any radish or “sensitive, aggressive weirdo” reader of hers, Polly “contains worlds” (another common refrain), and these worlds can’t always be slotted into a neat generational categories. How to Be a Person may resonate most with vexed, neurotic young people, but its central message that “flaws become you” is worth repeating—with gravitas, with F-bombs—until we all embrace it.