My Z News

Amy Dickinson doesn’t think herself a know-it-all, and she doesn’t pretend to be. That’s why she’s so good at her job.

She’s been a popular advice columnist for “Ask Amy” for more than a decade. She’s funny, self-aware and more open than you’d ever expect. Her responses to personal letters reach millions in syndication throughout the U.S.

But what makes her qualified to give advice? She’s just like you and me.

“I have a bachelor’s degree in English literature,” Dickinson laughs. “But aside from that, you might learn I have five children, I have grandchildren, I’m a stepmother, I was a single mom, I grew up in poverty … I’ve really been paying attention.”

Dickinson is part of a crop of modern-day advice columnists who follow in the grand tradition of people like “Dear Abby” and “Ann Landers” — pseudonyms that entered people’s homes in the 1940s and ’50s and quickly became family legacies and national institutions. But as we hurtle deeper into the Internet age, today’s most popular columnists — from “Ask Amy” to “Dear Sugar” to “Dear Prudence” — are entering the field in totally different ways. And they’re all evolving the advice column for a contemporary audience hungry for intimacy and tough love.

In this letter, Dickinson lets a woman have it for not inviting her sister out, simply because her sister didn’t fit in and wasn’t an avid churchgoer:

Dear Sad:

First, let’s establish that I agree with your sister: You are a horrible person.

Obviously, you can do whatever you want and associate with — or exclude — whomever you want, but you don’t get to do this and also blame the person you are excluding for not “fitting in.”

The only way your sister would ever fit in would be for you to make room for her. You are unwilling to do that, and that is your choice.

But her being upset is completely justified, and you’ll just have to live with that. Perhaps this is something you could ponder from your church pew, because despite your regular attendance, you don’t seem to have learned much.

Today’s columnists aren’t trying to be experts; in fact, they’re transparent about their flaws. At the end of the day, that might be their greatest qualification.

Prepping to take calls on Thanksgiving tomfoolery for @onpointradio #butterballhotline pic.twitter.com/W4NgeqxlPc

— Amy Dickinson (@AskingAmy) November 26, 2014

Dickinson had a variety of jobs before she became one of the foremost advice columnists in the nation: NBC producer, freelance writer, TIME columnist focused on family living.

When that column discontinued, she applied to take over “Ann Landers,” the popular Chicago Tribune advice series run by the late Eppie Lederer. To stand out from the hundreds of unsolicited applications, Dickinson wrote sample clips and became the clear favorite for the job. The Trib ran her first column on July 20, 2003.

Her first decision: no pseudonym. She admits attaching her real name to the column was a little self-serving — she thought it would make her harder to replace — but she also felt it would help readers connect better.

“That choice to be transparent at the start really eliminated a lot of other decisions I would have to make about creating a persona, hiding behind that,” she tells Mashable.

It wouldn’t be the only difference. Dickinson also chose to forego her own staff, unlike Lederer. She opens her own email, chooses her own letters and handles all her own administrative tasks. Her Tribune email address receives between 200 and 300 messages per day, and that’s not counting her Gmail, Twitter, Facebook and Tumblr, where anyone can contact her. There’s a huge backlog, of course, but she wanted to remain easily accessible.

“I’m digging for gold,” she says.

Technology does more than help people reach their favorite advice columnists — it can transform the format altogether.

Enter Emily Yoffe, a long-time Slate contributor who became the third “Dear Prudence” in 2006. Like Dickinson, Yoffe had a legacy to uphold — her predecessors were Herb Stein, head of Nixon’s council of economic advisors, and Margo Howard, also known as Ann Landers’ daughter.

Despite the big names before her, Yoffe held her own and helped usher in new ways to give advice. In addition to her weekly Thursday column, she participates in live chats twice a week and records video responses. Of the 400 letters “Dear Prudence” receives in a given a week, Yoffe responds to about 20 across the various formats.

For her Thursday column, Yoffe can pick a letter, think about it and call an expert if she needs to. She has time. On Mondays, though, speed is crucial. If the live chat isn’t moving, people will click off. It’s a different kind of pressure.

Conversation is an increasingly important aspect of today’s advice columns. It’s the focus of the new “Dear Sugar Radio” on WBUR, which revives The Rumpus‘ popular “Dear Sugar” column in podcast form. The writers Steve Almond and Cheryl Strayed, each of whom wrote the column at different times, have returned to it together.

“We want, at the center of it, to have this deep, serious and sometimes funny conversation,” Almond tells Mashable. “Around that, you don’t know what’s going to happen from week to week. And we don’t know either.”

While Strayed, perhaps best known for her memoir Wild, really cultivated “Sugar” and brought it to success, Almond created it. He suggested a “really good, no-bullshit advice column.”

“On the one hand, I wanted to give people advice, but on the other hand I felt, as I think any good advice columnist should feel, ‘Well, who am I to act like an authority on anything, the mess I am?‘” he says.

Almond, who also writes advice for WBUR’s “Heavy Meddle,” envisioned Sugar as a woman in her 30s or 40s who had seen a lot of life: “Not stiff and starchy like ‘Dear Abby’ and concerned with etiquette, but concerned with things that people really struggle with inside.”

He wrote the column for about a year, but admits it wasn’t much good. After reading her work, he wanted Strayed to take over.

Strayed had several reservations: it didn’t pay; publishing your opinion on the Internet is an invitation for controversy; she didn’t know the format very well, aside from “Dear Abby” and “Ann Landers” growing up; and, like Almond, she wondered, “Who am I to be giving anyone advice?”

But she was up for the challenge. “I had no idea it would take me where it did,” she says.

Strayed developed a cult following as Sugar between 2010 and 2012, later publishing her favorite columns in the book Tiny Beautiful Things.

“I think it succeeded because I was so sincere. I really just wrote what I thought to be true … I positioned myself as somebody in the mud with the letter-writer, trying to grapple with the question,” she says.

Strayed started off anonymous, but she always knew she’d reveal her identity.

“Being anonymous actually allowed people to see me. They saw everything but my face. I wrote openly, nakedly about myself in my column … If you read the work attached to my name, it’s no less honest or naked. People thought the anonymity made me brave, but that wasn’t the case,” she says.

So she wanted to step out from behind it, and also to claim it, since the column showcased some of her best writing.

Image: Todd Williamson / Invision for Fox Searchlight/Associated Press

Now, after years of hiatus, Strayed hopes “Dear Sugar Radio” will mirror the natural way we all work out our problems — talking with friends, partners, coworkers. Except now you can listen to it on your way to work. It’s intimacy delivered directly to your ear.

When asked which topics readers want to discuss next, most reply with progressive issues.

Dickinson is currently getting a lot of questions about marijuana use, as legalization and regulation become more common. “Ten years ago, I would just say, ‘Well, it’s illegal, so that’s that.’ Now I need to think in a nuanced way about marijuana use,” she says.

She’s also getting questions from and about the LGBTQ community. She mentions one letter from a mother trying to help her transgender child feel more comfortable. A decade ago, Dickinson might not have gotten that question. The Tribune may not have even published it.

Columns like Lindsay King-Miller’s “Ask a Queer Chick” on The Hairpin are starting to fill that space, fielding a variety of questions from the LGBTQ community.

“There’s a bit of a gap in terms of life advice for LGBTQ people,” she tells Mashable. “Sex and dating are things you don’t necessarily learn about in school or from books. It’s more common to pick things up from your friends, your big sister, your older cousin … There’s more opportunity for empathy,” she says.

She takes a page from the book of “Dear Sugar” — that tone of “I care about you and I’m in your corner, but you need to get your shit together,” she says.

Image: Mashable, Christopher Mineses

For modern-day advice columns, that seems to be the recipe for success. It isn’t a stuffy paragraph or horrific advice for ’50s housewives. Advice columns are like personal essays wearing a different outfit.

We’re in the thick of this revolution, with new ones popping up all the time (see: Haruki Murakami). The advice column might be more relevant than ever, as readers let their guards down, and columnists do the same.

Dickinson is telling me about her father. They’d been estranged for a long time, but she recently decided to start visiting him at his nursing home.

“I’m the only visitor he has, because he’s kind of an asshole,” she says over the phone. “But I have a lot of time to think when I’m on that four-hour commute through the deep woods of Pennsylvania: Am I trying to repair this? Can I repair a relationship I didn’t ruin?”

I’m sitting on a couch in a small conference room at Mashable‘s New York headquarters — my head back, feet up, pen and pad idle in my lap. I’ve forgotten where I am, forgotten this is an interview for my job. I feel the urge to jump in, to empathize, to talk about my own family’s history of estrangement.

It isn’t until a meeting breaks, right outside the glass door, that I locate myself and it hits me. Dickinson is answering one of my questions through the lens of her own life, her own struggles, and completely draws me in. I want to hear more from her. Hell, I trust her. And that’s how this works.

“This is what it’s like to be on the planet right now,” she continues. “Nothing’s perfect. This is not the perfect life of somebody who knows everything. This is the life of somebody who’s really still trying to figure it out.”

window._msla=window.loadScriptAsync||function(src,id){if(document.getElementById(id))return;var js=document.createElement(‘script’);js.id=id;js.src=src;document.getElementsByTagName(‘script’)[0].parentNode.insertBefore(js,fjs);};
_msla(“//connect.facebook.net/en_US/all.js#appId=116628718381794&xfbml=1&status=1&cookie=1″,”facebook_jssdk”);_msla(“//platform.twitter.com/widgets.js”,”twitter_jssdk”);

Read more: http://mashable.com/2015/01/19/advice-columnists/