Havrilesky - How to be a person in the world: ask Pollys guide through the paradoxes of modern life

In the fall of 2012, I pitched an existential advice column to The Awl, a website that publishes smart, original takes on modern culture. At the time, I was a regular contributor to the New York Times Magazine, writing mostly essays about pop culture, and I had a column called the Best-Seller List in Bookforum. Id spent seven years as a TV critic for Salon.com, Id written a cartoon called Filler for Suck.com (the Internets first daily website!) for five years before that, and Id answered advice letters on my own blog as early as 2001.

But this was something new. Id never dished up advice to a wider audience. When The Awls co-founder, Choire Sicha, said yes to my idea, he made it clear that the column could be anything I wanted it to be. But what did I want it to be? Obviously, I had all kinds of outspoken, sometimes unwelcome advice to offer friends, family, and complete strangers alike. Id been handing out unsolicited advice for years. But did I want the column to be funny? Did I want to use the column to rail against the scourge of passivity and avoidance in modern relationships or to address our cultures burdensome fixation on constant self-improvement? Did I want to sneak in some commentary on troubled friendships, Kanye West, weddings, rescue dogs, luxe brands, commitmentphobic men, property ownership, the artists life, pushy mothers-in-law, or Game of Thrones?

As it turned out, I wanted to do all of these things, and eventually I did. But when I was sitting down to write my first weekly column, I just felt scared. Who do I think I am, giving other people advice? I thought. Im not qualified for this! I dont have it all figured out. What the hell am I doing?

Ive been asking myself that same question every week for four years now. And when Stella Bugbee, the editorial director for New York magazines website The Cut, approached me about taking my advice column over to her site, I wondered what she was thinking. Sure, this meant a much larger audience for Ask Polly and more money for me. But did she really know what she was signing on to? You know my column is three thousand words long every week, and half of those words are fuck, right? I asked her. Somehow, this didnt scare her off.

I dont always feel qualified to guide other people to a better life. As a writer, even when Im sitting down to start a book review or a cultural essay, as Ive done professionally for years now, the blank page mocks me. What could you possibly have to say? it asks. When are you going to give this up and do something useful with your life? The blank page can be a real asshole sometimes.

Still, nothing I do brings me more happiness than writing Ask Polly. Im not always sure of the right answer for any letter, whether someone is dealing with depression and anxiety, a go-nowhere job, a series of not-quite boyfriends, or an overly critical parent. But I do know for certain that when I reach out as far as I can to another person, using my wordsmy awkward, angry, uplifting, uncertain, joyful, clumsy words (half of which are still fuck)some kind of magic happens. There is magic that comes from reaching out. I dont believe in many things, but I believe in that, with all of my heart.