Don’t get it twisted. Longtime syndicated Tribune advice columnist Amy Dickinson is not retiring. She’s leaving “Ask Amy,” the writing gig that she’s had for 21 years, on her own terms and with her own “steam.”
Although doing the job she calls “amazing” was not physically taxing — she admits to working on it while in bed on many occasions — the constancy of being a seven-day-a week sage and never really being able to step away from it has proven challenging. Dickinson is looking toward other adventures closer to her home in Freeville, New York.
“Maybe I’ll be the first advice columnist not to die at my desk,” she said jokingly. “Ann Landers (the columnist Dickinson succeeded) — they ran her column after she died. She had banked a bunch of columns. Mad respect for her, but I am not built like that.”
Dickinson will be handing the reins of syndicated column writing to R. Eric Thomas, a Black male playwright, screenwriter, bestselling author and a former columnist for Elle.com and Slate.com. His new column will be called “Asking Eric.”
Dickinson said that as someone who hasn’t ever “left” anything — a person or a job — the decision to walk away from her advice column was not an easy one, especially because people may want to frame her departure as retiring. “I am leaving, not retiring,” she said.
Dickinson’s friend Julia Keller, a Pulitzer Prize-winning former Chicago Tribune journalist and author of “Quitting: A Life Strategy. The Myth of Perseverance — and How the New Science of Giving Up Can Set You Free,” had offered her these words of wisdom: “You may run out of money, but you may not. But you know you’re gonna run out of days.”
“I have incredible ideas and goals,” Dickinson said. “I want to fulfill them.”
Dickinson’s last column will run June 30, and in it she hopes to offer what she calls “big picture” wisdom. She’s learned a few things over the years through her experiences as a single mom, as a reader of self-help books, as the youngest in her family, as a partner in a 16-year marriage whose wedding and Hallmark Channel-esque relationship was covered by The New York Times, and as a bestselling author of “Strangers Tend to Tell Me Things: A Memoir of Love, Loss, and Coming Home” and “The Mighty Queens of Freeville: A Mother, a Daughter, and the Town That Raised Them: A Memoir.”
Let’s not forget her regular appearances as a panelist on NPR’s weekly news quiz “Wait, Wait … Don’t Tell Me,” which she plans to continue.
Dickinson’s fascination with human behavior has served her readers well through the years, with some viral moments along the way, including homophobic parents and notable pranks. And it’s the connection with readers that she’s going to miss the most, Dickinson said.
The road to becoming one of the few nationally syndicated advice columnists all “started as a joke that got very out of hand,” she said.
“I had written a column for Time magazine for a couple of years, but I’d never written personal advice, Q&A type stuff. Jim Warren, who was the D.C. bureau chief at the Chicago Tribune had always said to me, ’If you ever want a job … or … be a newspaper reporter …’ But I had a young child at home and there was no way.”
But then Ann Landers died. “She died and I wrote Jim an email. The subject line was ‘Now there’s a job I’d take … ha ha ha.’ All caps,” said Dickinson. “A few weeks later, he contacted me and said, ‘We had decided after Ann Landers died, we were getting out of the game. But we’re going to launch a new column and we want you to try out for it.’”
Now, Dickinson is pivoting to opening a library in her hometown. Remember the “A Book on Every Bed” initiative she kick-started with the Family Reading Partnership 14 years ago? It encourages readers to leave a wrapped book on their children’s beds on Christmas morning, birthdays or other holidays, so kids wake up to the gift of reading. Dickinson says the library that she is creating, the Freeville Literary Society, is the next step in her childhood literacy campaign.
“I’m no Dolly Parton, but I feel so strongly about literacy,” Dickinson said. “I grew up in a pretty hardscrabble environment. But we had books and books and books, and we got them from the library. To put a book in the hand of a kid … children who already love books, love getting books. Children who don’t know about having books, these become really treasured artifacts.”
The Freeville Literary Society will have membership cards, where a person will use those old-school stamps that make the thump sound when books are being checked out.
She envisions the Freeville Literary Society being a safe place where kids in her small town of several hundred residents can visit on their bikes, after school, on Saturday mornings, by themselves, to enjoy board games, puzzles and movie nights with their families. The building she bought for the library has two sections, so she plans to rent out the other side to a grocer.
“Like every little town in the world, this is a food desert. … If kids could come in and buy a popsicle, that would be amazing. So that’s what I’m doing,” she said. “I’m going to sell penny candy. I want to be that place where you can feed your mind, rot your teeth.”
You can hear how psyched Dickinson is about creating a community hub for children. She’s going to poll the youths to make sure the grocery store sells their 10 favorite candies. She’s looking to open its doors around the time she ends her column. She plans to hold a movie series that features books made into films.
“I really wanted kids to enjoy some of the physical experiences of taking out a book,” she said. “It’s a great place to gather.”
And when she’s not opening worlds and minds with literature, Dickinson will be continuing an advice newsletter and working on a novel, one that is as close to fiction as she can get, she said.
“I’ve never written fiction before. I am finding it incredibly exciting and fulfilling. … I got a lot going on,” she said. “When I decide to come back to advice, I’ll do it under my own steam.”
Looking back, Dickinson said the world has changed since readers started asking her for advice. Early on, she made it a point to win over her haters by replying to negative feedback in ways that were “always very respectful, very measured.” She said that was good practice.
“I went into this job as a really scrappy, mouthy, reactive person,” Dickinson said. “And I have taught myself to be much more careful, measured. I think I’m a much better listener.”
And while she admits to not being perfect and making her share of mistakes, showcasing her readers’ voices in her column with her strong writing is what distinguished her columns from others.
“The thing I have learned to do, which I appreciate, is I let the readers correct me. The third letter in my column is always a reaction to a previous column,” she said. “I have learned to be much less defensive about standing my ground behind my point of view, and I have really been happy to turn part of my column over to readers who want to take issue with or want to correct me. Receiving critique has been a lesson that I needed to learn.”
Dickinson is excited about focusing on the relationships in her life. And as she gears up to “go do those for a while,” she’s passing the syndicated columnist duties to Thomas, who has been heard on a variety of NPR shows himself, including serving as a host of “The Moth” StorySlams in Philadelphia.
Thomas loves audiobooks, dinner parties and cooking; he’s still trying to perfect his bouillabaisse, he said. Thomas’ husband is a pastor with a green thumb. “I don’t really have a green thumb, but he grows the rhubarb and I make the cobbler, so it all works,” he said.
For those not familiar with Thomas’ work, he gravitates toward projects that have people going through hard things in life and negotiating the ways that all identities intersect. It’s “who you are in various places in your life,” he said.
“It’s always gonna be this mix of pathos and humor,” Thomas said of his approach. “There’s this line from ‘Steel Magnolias’ that Dolly Parton’s character says: ‘Laughter through tears is my favorite emotion,’ and that is very much how I like to operate.”
Thomas said a lot of people got to know him through his Elle.com column. “That was very voicey, fun and focused on pop culture and politics,” he said. “But, there was a certain remove to it and what I love about doing advice is that you get to have a fun, little brunch conversation with a friend, but we’re talking about things that are going on in their lives, as opposed to what celebrities are doing.
“As we’ve come out of the pandemic, I’ve been hungering for that human connection,” he said. “I want to talk to more people. So when they approached me about doing this, I jumped at it because … it was sort of like the universe was conspiring to make it happen.”
Thomas’ column will premiere in early July. He said he’s proceeding with excitement but a fair bit of caution.
“There are times that it seems a little bit daunting — the exposure — but I’m really excited that I have this kind of opportunity and that people can see that somebody like me also has something really valuable to give, and I think that’s really important,” Thomas said.
He’s already started to get questions from people through his website. “I’ve read ‘Ask Amy’ for years,” he said. “One of the things I think that’s great about the long tradition of advice that “Ask Amy” has modeled, Ann Landers has modeled before me and so many others, is that this is somebody’s compassionate opinion. I’m a listening ear and somebody who has been through a lot of different things. The thing that I’m most expert on is empathy, living life and making mistakes, which I think makes for the best advice.
“I don’t know if anybody is an expert on being a human,” he said. “It’s really helpful for me to see other people being honest about muddling through, trying to figure it out, getting it wrong and then trying again, because it allows me to have grace for myself, too.”
Thomas wants his advice column to feel like hanging out with a friend, an approach that he has taken with his many writing projects. He is eager to make more friends in this new venue, and if that means spending more time on radio or TV shows like Dickinson, then so be it. He’s here for it all: Weddings, neighbors, office drama … nothing is taboo.
“Sometimes the best advice that we can get is rooted in things that we saw, read or listened to,” he said. “Sometimes you get life coached by a Whitney Houston song: ‘It’s not right, but it’s OK.’”
Thomas says he’s a good listener and he takes the “Yes, and” improv approach. “So you say, ‘Hey, I’ve got this problem with my boss.’ And I’m, ‘Yeah, I hear you. Maybe you’re right, maybe wrong. But also maybe you want to take a look at this,’” Thomas said. “I think people started asking my advice more as I’ve gotten older, and that’s a testament to being a different kind of person, growing and maturing.”
Although Dickinson didn’t weigh in on who would succeed her, she did say it would be great if the columnist were a man, so as to reduce any confusion about whether the successor is related to Ann Landers, something that happened with her. She’s delighted that Thomas, a Baltimore native now based in Philadelphia, is onboard.
Her words of advice for anyone who wants to help others in a syndicated column: “Lead from compassion and ‘to thine own self be true.’ That has served me really, really well.”