We asked, Amy Dickinson answered: Columnist starting new chapter in Upstate NY

Amy Dickinson

Freeville, N.Y. — Amy Dickinson was driving through her hometown in Central New York last fall when she saw a for sale sign hanging on an empty, one-story building in tiny Freeville.

The building at 24 Main St. stood on a street full of memories, next to the old village hall where Dickinson’s grandmother once ran a little lending library.

Dickinson pulled over and made an offer to buy the building. An idea that had percolated in her mind for a long time bubbled up into sharp focus:

Freeville doesn’t have a library. Dickinson would open one to bring books to the village.

She knew then it was time to end “Ask Amy,” the syndicated column she had thoughtfully penned for the Chicago Tribune since 2003. It was a decision Dickinson had been wrangling with since her advice column turned 20.

“I thought, ‘Well, maybe I’ll be the first advice columnist not to die at her desk,’” Dickinson said. “What would that be like?”

Dickinson was hired to write an advice column for the Chicago Tribune after longtime columnist Ann Landers died in 2002. She came to the job after an impressive career as a reporter that included working as an NBC News producer, an NPR editor and a Time magazine columnist.

Determined to make the column wholely her own, Dickinson wrote long answers to readers’ longer-than-average questions. She responded thoughtfully to queries about everything, from whether people who hold doors open for others forfeit their place in line to painful questions from parents and grandparents struggling to accept LGBTQIA children. Often, Dickinson recommended books.

When she started writing “Ask Amy,” Dickinson and her daughter moved from Washington, D.C., to Chicago. After her daughter went to college, Dickinson moved back to the small village she’d grown up in to be with her mother before she died.

Dickinson has deep roots in Freeville, a village of 457 people about 45 minutes south of Syracuse that her family has called home since 1850. Her family can still be found throughout the community, including in a historic home Dickinson said her great-grandparents built in 1860.

As a kid growing up on a dairy farm, Dickinson said she couldn’t wait to leave Freeville. But after living in London, New York and D.C., she said she now appreciates the “world-class” beauty of CNY.

“The waterfalls, the abundance of fresh water,” Dickinson said. “I learned to swim at the base of a waterfall. I didn’t know how amazing that was.”

Amy Dickinson

Returning to her hometown also brought Dickinson a storybook-worthy love story: Dickinson reconnected with and married Bruno Schickel, a well-known builder who grew up on a neighboring farm. (“I promptly tumbled into a Hallmark Channel plotline when I fell in love with and quickly married a man I’ve known since childhood,” Dickinson wrote in the column where she announced the end of “Ask Amy.”)

As her well-loved column hit its 20-year anniversary, Dickinson started to ponder her exit. She said she turned down the Chicago Tribune’s offer to reduce her column from seven days a week to two; she didn’t want readers to think she was sick or being replaced.

At 64, she’s ready to enjoy a hard-earned break from unending deadlines. Dickinson is also pursuing a new, fulfilling venture: The Freeville Literary Society, her very own lending library.

And so if you ask Amy, she’ll tell you: She didn’t retire. She quit.

“I’m leaving. I’m a quitter,” Dickinson said last month during an interview inside the future Freeville Literary Society. “And after 21 years, that is definitely the right choice.”

But Dickinson isn’t done with words. She wants to pen new books and rework a children’s book she’s already written about her dog, Molly. And eventually, she said she again plans to answer readers’ questions and offer advice on her Substack.

“I could write longer. It could be more involved. I can use not-suitable-for-work language,” Dickinson said. “So I think it will be doing that. But I haven’t decided.”

After all, there is no rush: For the first time in her long career, Dickinson is not on deadline.

Books for Freeville

When Dickinson pulled over and bought a building last fall, her husband was excited for her. She said he always has a vision and used his experience to help turn the long, dark bowling alley-like structure into a bright space.

The right side of the building — which has space for two businesses — is home to the Freeville Literary Society. (Dickinson hopes to open the society to the public when school starts back up in September.)

It is filled with vintage touches that feel straight out of an old-fashioned library: Benches from Immaculate Conception Church in Ithaca and shelves from the shuttered Virgil Elementary School. A desk built in 1935 and a stove that once heated Dickinson’s childhood barn. A tabletop card catalog and a bronze desk bell.

The Freeville Literary Society will offer books for readers of all ages. Dickinson said she will put her eclectic collection of self-help, crime, poetry and children’s books on the shelves. She also hopes to leverage her contacts in the publishing industry to help the collection grow.

The experience will be analog, Dickinson said: She’s having a stamp made and will offer library cards. There will be no Wi-Fi.

Amy Dickinson

The Freeville Literary Society will have puzzles and games. Dickinson plans to get a license to show family-friendly films. And, eventually, she aims to sell candy, a lifelong goal for the writer with a sweet tooth.

Members of the Freeville Literary Society can also expect to see a furry mascot when they visit: Molly, Dickinson’s friendly dog, whose adorable face is adored throughout Freeville.

The other renovated half of 24 Main St. remains open and is intended for a grocery store, another amenity missing from Freeville. (Dickinson’s dreams of Byrne Dairy occupying the space and selling ice cream.)

Dickinson is determined to help Freeville. It’s a goal she shares with and her husband.

Schickel is building Freeville Cottages, a village of colorful tiny houses, to attract young families to the village. Bringing books and a grocery store back to Freeville is also part of the couple’s goal to make the village an attractive place to live.

“We are really making a very deep commitment to this place. And it’s not because it’s all we know,” Dickinson said. “It’s more because it’s all we love.”

Amy Dickinson

Amy Dickinson

Amy Dickinson

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