As a child in the early Nineties, I looked forward to reading Ask Ann Landers, the syndicated advice column that appeared in the Chicago Tribune my parents had delivered every Sunday. Like conversations overheard in public places, the letters offered little glimpses into otherwise unknowable people’s lives—and the then-unfathomable state of adulthood.
At some point my parents ended their subscription, and this peephole shut. But soon enough I was an adult myself, with a desk job at which I always kept minimized a browser window to open during my down time, and I picked up my old habit in the new form of Cary Tennis.
Tennis wrote Since You Asked, a Salon column whose heyday I’d situate in the mid- to late aughts, though perhaps that’s just when I was most into it. (His tenure lasted from 2001 to 2013, and he still answers letters sporadically on his personal website.) I loved Cary—which is how he signed off—partly because he wrote so frequently about the problems of people like me, young, feeling directionless, thinking we were stuck in situations we rightly or wrongly saw as dead ends. His long, discursive answers treated these problems with great care and gentleness, leaving me with a sense of relief that lasted at least an hour or two after I’d finished reading.
My interest in advice had shifted away from other people’s problems and toward Tennis’s writing, which often felt pertinent to my life even when it was dealing with an issue I didn’t have. “If you’re 25 and sitting in the bedroom of your parents’ house, hear this: We need you! The planet is melting down,” he advised in one rousing column. “Get out of your goddamned houses and change the world.” Though I was 26, and had been on my own for five years, it felt like he could have been talking to me.
“Cary Tennis has resurrected the advice column into a relevant, even thriving, literary form,” declared Siobhan Welch in a 2008 review. “He is the Anti-Dear Abby, with a style more reminiscent of an essayist’s ruminations than the pat responses usually found in print.” Dear Abby and Ask Ann Landers (written for decades by competing twin sisters) shared a practical sensibility that had dominated the form since the Fifties and still imbues a large swath of online advice. Here’s what you should do, they would say. Now do it. Tennis was less prescriptive and more tentative, urging readers to follow their impulses, to nurture their talents, to trust themselves. And he deployed comforting clichés with a rare combination of self-awareness and seriousness.
Since Tennis began writing his column, this essayistic style of advice has gained in popularity—adopted, notably, by writers like Cheryl Strayed, who from 2010 to 2012 authored the widely read Dear Sugar for the Rumpus; Kristen Dombek, who started writing the Help Desk for n+1 in 2013; and Heather Havrilesky, who in late 2012 launched her Ask Polly column at the Awl and then moved to New York two years later.
Earlier this summer Havrilesky put out a collection of these columns as a volume titled How to Be a Person in the World, and last month Dombek published The Selfishness of Others: An Essay on the Fear of Narcissism, which is not a itself an advice anthology but does offer a lot of implicit suggestions about how to see other people and yourself. “When it comes to the vital essayistic subject of What It’s Like to Be Alive in Our Time, Kristin Dombek is one of the smartest and most thoughtful writers out there,” writes Elif Batuman, in her blurb.
What It’s Like to Be Alive in Our Time (and, usually, In Our Pocket of the World) is a topic Dombek shares with Havrilesky, whose advice the Awl branded as “existential.” Like Tennis and Strayed, they aim to make an art of their vocation. Eight years after Welch praised Tennis for his literariness, Jessi Klein opined this summer in the New York Times that Havrilesky’s work embodied “a new type of advice column, and dare I suggest, a new literary genre.”
Dombek and Havrilesky, even more so than Tennis and Strayed, write advice that is essayistic in the original sense of the word—not so much a linear argument as an attempt at understanding. They make the examination of their own lives and those of their correspondents into the same project, drawing on personal experience to inform their answers.
In her Slate review of How to be a Person in the World, Katy Waldman likens Havrilesky’s writing to “a deep working through of vulnerabilities one yearns to see as universal.” But in an inversion of that literary cliché about plumbing your own depths to find something of broad appeal, the columns’ widening of scope can make them feel very narrowly applicable. Unlike traditional advice columns, “literary” advice tends to include general directives (“change the world”) or horoscope-like predictions (“this is your life, and it’s going to be big and bright and beautiful”) that masses of readers can adapt to their own problems.
Moreover, it is written in such a personal way that you can be forgiven for thinking the “you” they’re addressing is actually you. This specific yet intentionally generalizable use of the second person puts the reader more squarely at the center of the writing than mere identification with a literary character might. “You are kind and smart already,” Havrilesky writes in one representative column. “You are enough already.” You—I—close the tab so relieved, momentarily believing it is true, even if it is not.
While novelists or memoirists or poets might merely hope a reader takes something from their writing beyond a literal understanding of the words, advice artists go one step further. Just as they use reader questions as prompts for their writing, readers are explicitly invited to use the answers as prompts for living, ways to get unstuck from old, unhelpful truths and latch on to the truths we need. It’s a reciprocal, participatory literature that calls to mind Sheila Heti’s 2012 novel How Should a Person Be?—and not just because How to Be a Person in the World reframes that question as a directive.
Heti has an interest in self-help, and How Should a Person Be? remixes many of the ingredients of useful advice: fiction, friendship, and a bit of therapy. It began as a project that eventually grew into two separate books, the other being The Chairs Are Where the People Go: How to Live, Work, and Play in the City, which Heti co-wrote with Misha Glouberman. The Chairs Are Where the People Go was marketed as a self-help book, but like How Should a Person Be? it is written entirely in the first person. Both are based on recordings Heti made of her friends, and the reader is helped, in both cases, by watching other people think through how to live.
Heti’s novel seems designed, in part, to fill in the middle of the Venn diagram that would link self-help and literature. On the one hand, though helpfulness is a valuable property of literature, it is not a criterion against which reviewers and publishers tend to officially measure “literary” value. “Authors write with the hope of helping readers and themselves—by untangling emotional, intellectual, and existential problems,” Heti has written. And yet, “interviewers seldom ask authors, ‘How is your book meant to help people?’ (Instead, they ask the impossible, ‘What does it mean?’)” On the other hand, a lot of self-help books are too narrowly focused to offer real assistance with problems of the “emotional, intellectual, and existential” varieties, making them poor substitutes for other types of help and other types of books. If one reads them instead of “reading things that add to one’s cultural knowledge and association and therefore one’s freedom,” Heti has said, “one is driven further into the self.”
Many of Dombek’s and Havrilesky’s columns seem designed to fill the same gap—to help you without driving you further into yourself. “So much of our psychology has turned to ‘self-help,’” Dombek writes. “But what of ‘other-help’? Why isn’t other-help our most popular genre of ‘literature?’” In another vein, to another letter writer, she suggests that the “witnessing of another’s life with genuine pleasure, even or especially when its different success might threaten your own personal philosophy of life—I’ve been thinking this is true friendship, or a part of it.” Havrilesky, similarly, tells Weird Girl, a woman who has difficulty finding partners who appreciate her aggressively offbeat persona, to “accept that the so-called ultra-normals out there are far more complex than you give them credit for.”
However many characters it can accommodate, though, a literary advice column has room for only two protagonists: the columnist whose personal experience informs it, and you, the reader, written into the story by proxy.
If Havrilesky, for example, feels you are in the wrong, she will tell you so explicitly, but only after she has made a sensitive and concentrated effort to understand the complexities of your situation. Even during a satisfying takedown of an advice seeker who wants to cheat on his less-than-libidinous wife, Havrilesky pauses to note that “she needs to adjust her expectations that sex can only happen when she’s totally in the mood. Sometimes you get in the mood by going for it.”
If Havrilesky feels you have been wronged, though, she tends to declare—like the most steadfast of friends—that those who are responsible can be safely dismissed (unless, perhaps, they are your parents). “These people are irrelevant,” she writes to one advice seeker. “They are everywhere, and they don’t matter,” she writes to another. She makes you the center rather than part of a larger whole, tempting you to think that your hurtful choices and blinkered views are the only ones worth exploring in depth. This temptation runs against the grain of the empathy Dombek and Havrilesky would have their readers cultivate, but it is responsible, I think, for some of the genre’s appeal. I, certainly, am not immune to it.
For precisely this reason, some observers have dismissed Havrilesky’s readers as “young creative types living in large coastal cities and struggling with romantic self-doubt or career ennui,” in the words of one reviewer of How to Be a Person in the World. Against which critique Havrilesky recently mounted the following defense:
A passion for artistic or creative endeavors, wanting more from your career, feeling like something is missing in your life—are these shameful and embarrassing things for a person to be concerned with? Sure, at a time when people are dying in the streets and starving and drowning in the sea trying to escape oppressive regimes, such relatively minor-seeming concerns can incite eye-rolling. But everyone under the sun has their particular problems, whether those problems unfold in economically developed countries or not.
With the last line she echoes Teju Cole and others who have argued that the concept of first-world problems is false and condescending in its implication that those with few economic resources don’t also have lower-stakes desires and anxieties. But from the broad observation that “everyone under the sun has their particular problems,” Havrilesky extrapolates the possibility of universal solidarity: “Stand up for your right to happiness. Stand up for the rights of all people to be happy. These two things are not as removed from each other as this fucked-up, stupid world would have you believe. These two things are one and the same.” This assertion seems more unworldly than the letter writers she is trying to defend, who are often—as she points out—all too conscious of their social position, and of the ways their pursuit of happiness might actually harm other people.
In an installment of the Help Desk from a couple of years ago, Dombek reflects on one of the many ways that Havrilesky’s trickle-down vision of personal fulfillment is not borne out by reality. To Bank-robbin’ in Brooklyn, a man crushed by his need to do wage labor, she writes:
I suspect that for most of the members of the upper 10 percent, and even the 1 percent, the real story is … it is the system that is exploitative, and they have chosen to fight for a position in that system that is the only way to have a kind of personal power that should be everyone’s right. Do you think that if they weren’t so scared of falling into our position, so many people would choose to work in finance, for example, an industry built, in large part, on preying on the debt of others?
But this vision, too, emphasizes the intersection of incommensurable truths, glossing over the conflict between the interests of the banker and debtor within the exploitative system that binds them.
Havrilesky and Dombek suggest in these cases that we are all in this together—sometimes at the center of the world, sometimes against it (or against an irrelevant bloc of “other people”), but never legitimately against one another. Even as they celebrate the differences among people, they occasionally play down the differences among people’s interests—a flattening tendency rooted, perhaps, in the genre’s privileging of generalizable counsel for “problems one yearns to see as universal.”
Advice columns that don’t use universalizing literary tactics have more room to talk about conflicting interests. Zahira Kelly, for example, uses her New Inquiry series Dear Marooned Alien Princess as a platform to critique existing power structures. Her advice to those near the top of these hierarchies systematically turns the focus back toward those on the bottom.
An alternative tactic—favored by Cary Tennis and used from time to time by the other advice artists—is to put correspondents’ problems into perspective, reminding them of their privileges while at the same time reassuring them. “Unless you lack sufficient whiteness, you can hitchhike to California drenched in blood like a serial killer and some nice young person from Brown will give you a film job,” Tennis wrote to an unemployed Harvard graduate living in their parents’ basement, too scared and depressed to leave. “If you lack whiteness, it’s going to be harder. You’ll have to show your Harvard diploma.”
In the end, Dombek and Havrilesky often ask you to look up from the page and train your attention on what you have to do. Like Tennis’s letter to the stranded twentysomething, many of their essays conclude with valedictory calls to action. “You’re not done yet; it’s time to get to work,” Dombek tells a Hollywood screenwriter who has failed repeatedly to write anything they feel proud of. “Search out and gather around you people who will look at you and say, ‘Try harder,’” she writes to another. “What matters is you, all alone at your desk at five in the morning,” Havrilesky tells an aspiring comedian and writer stuck in a dead-end job.
These instructions demonstrate an implicit awareness that their advice might become, for readers, a form of procrastination—that by reading it we are only ever preparing to deal with whatever problem (Being Alive in Our Time?) inclined us to start reading.
In her letter to the Hollywood screenwriter, Dombek says the “fundamental wish of a writer” is “that it can happen somehow without your having to do it.” This might also be the fundamental wish of a person, which would explain why we are so attracted to exercise that doesn’t feel like exercise and questions we can answer by not answering them: Should I have a career or a baby? Can I be accepted and be myself? What am I waiting for?
To the extent that Dombek’s and Havrilesky’s responses insist on the futility of any search for a satisfactory answer, they acknowledge the advice they offer is only a beginning. Now, at 33, I read these columns infrequently, but that is in some small part thanks to their success at starting a relay of which they can only run the first leg. “In the moment when we would most authentically help,” Dombek writes, “we might also be learning to write fiction. You’re getting to the bottom of things. You’re the truth of the world. Sometimes we must wish on behalf of the other. It is up to them to find out if the wish can be true.”