Amy D. Dickinson

Born in 1959, Amy Dickinson was raised in Freeville, a small rural village in the Finger Lakes region of upstate New York. An ancestor on her mother's side was given a land grant in Freeville in exchange for fighting in the Revolutionary War. Today the small hamlet has a population of only 500, but Amy's hometown figures so large in her life story that it is practically a main character. "I come from a place that seems to nurture two kinds of people: those who stay and those who leave," says Amy. "I grew up in a family of stayers."

Before Amy's birth, her parents had lived in a dozen different houses and farms in the area, some of which had plumbing and some that did not. They were finally able to settle when Amy's grandparents gave them a historic home near Freeville. It was an elegant house with a fireplace that was carved by Brigham Young. When Amy was seven, her mother inherited a dairy farm on the edge of Freeville. "The farmhouse," says Amy, "started as a cabin and had been added onto over many years. The rooms were small, the floors sloped, and the ceilings were low. But the barn was spectacular. We moved in and became full-time farm kids."

Amy's father supplemented their income by working on construction crews, selling paint for Sherwin-Williams, or hiring himself out as a farmhand. "Both of my parents were very hard working," she says. To help, the children worked, too. At the end of their school day, they headed straight to the barn to begin whatever jobs needed to be done. Young Amy was ambivalent about this lifestyle. The work was physically demanding, and the long winters were cold and harsh. "I did not think I was made for this life," she says. "I had an incredibly active imaginary life. I lived in my head. I wanted to be a singer, and I loved to make people laugh. I was a total showoff."

Amy's parents met in high school and neither attended college. In her memoir, Amy describes her father as "a dairy farmer, a womanizer, a brawler, a drinker at roadside taverns, and a world-class abandoner." Her mother was his opposite: reserved, bookish, and very funny. "Where my father sowed chaos, my mother craved and created stability. He was a punisher; she was a forgiver. He set fires; she put them out."

When Amy was 12, her father took a construction job in a remote town, where he stayed during the week and came home on the weekends. At some point, he simply stopped coming home. He called Amy's mother to inform her he had sold the dairy cows and that trucks would be coming the next day to take them away. Soon thereafter, her mother learned that the farm had been mortgaged and was in debt. The taxes on the property not been paid for years. Amy's mother had an auction and sold everything in the barn. A helpful neighbor paid the back taxes.

"My childhood changed overnight," says Amy. "My father's leaving and the complete transformation in our lifestyle was devastating." Before long, Amy's father remarried, adopted his second wife's children, and then left them three years later. In all, he married five times.

Amy's mother transitioned from her life as a farm wife and took a job as a typist in the engineering department at nearby Cornell University. "It was at this point that my mother rose into my full consciousness as a hero," says Amy. "Before that, she was in the background, I think taping our life together. My mother was incredibly resilient. She valued education and literature and lived a life of the mind. She loved and valued her friends and had the wonderful ability to find joy in the tiniest moments. Once she no longer had to deal with my father's chaos, she was liberated to be fully herself. The year I graduated from high school and went away to college, my mother quit her typing job and was accepted as a full-time undergraduate at Cornell. She was 48. She went on to earn her master's at Cornell and taught, briefly in the English department there. She then had a successful 15-year career teaching writing at Ithaca College."

Amy's parents' divorce was a sad and anxiety-filled time for her and her older siblings. She compensated for her deep sadness by diving into school, sports, music, and theater. Her outgoing personality took over and led her through dreams of one day making her mark. "I raced through high school," she says. "I devoted myself to every after-school activity I could find: field hockey and cheerleading through the fall and winter, and band, chorus, and the school musical in the spring." In the summertime, she worked as a camp counselor.

When it came time to go to college, she decided on Clark University in Worchester, Massachusetts, which gave her a scholarship. For two years, she basically repeated all that she had done in high school, playing varsity sports and starring in the school musicals. When a friend suggested she should go to a bigger school, she applied for and received a scholarship to Georgetown University, where she worked part time in the admissions office.

"Georgetown changed my life," says Amy. "It was much more academically rigorous, which was good. And I fell in love with Washington, D.C. It was really a good fit for me."

Amy graduated with a degree in English in 1981. Unfortunately, the economy was in a slump, and she had a difficult time finding a job. For the next two years, she lived on Block Island (off the coast of Rhode Island), where she spent her days cleaning hotel rooms and her evenings singing in a lounge. When a friend called to say she needed a roommate, Amy returned to D.C., but it was still months before she landed her first professional job with a small public relations firm. She worked at that full time but continued singing in a lounge in the evenings. "I think I could have made it as a back-up singer for someone," she says. "I am a dreamer and a schemer, but I also have a realistic view of my own capabilities. I love theater and music, but I also crave stability, which I guess comes from my father's abandonment. My goal was to have a professional career in journalism."

Eventually Amy landed an entry-level position at NBC's Washington bureau. A year later, she followed her boyfriend (and future husband) to New York, where she worked as a receptionist at the New Yorker magazine. The following year, she landed her dream job as a producer for NBC in New York, a position she held for five years.

In 1986, Amy married (her new husband was a correspondent for CBS News), and the couple moved to London for his job. When their daughter, Emily, was two, Amy's husband announced that he wanted a divorce. "My husband traveled constantly for his work while we lived in London. I was a full-time housewife and didn't know very many people. It was a very lonely time for me, and I was terribly homesick. But the end of my marriage knocked the wind out of me. I was devastated and it took me a very long time to recover. It was the women in my family who pulled in tight and helped me to do what came next."

Amy returned to Freeville with Emily and lived a short time with her sister. When Emily was three, they moved to Washington, D.C., and Amy worked part time for National Public Radio, filling in for women on maternity leave. Within two years, she landed a position as the commentaries editor for the NPR show All Things Considered. She also worked as a freelance writer and was published in publications such as the Washington Post, Esquire, and O. She wrote a column on family issues for Time and produced a weekly column for AOL's News channels, which drew on her experiences as a single parent and member of a large, extended family.

In 2003, Amy was chosen to succeed the legendary Ann Landers as the Chicago Tribune's advice columnist. She competed with nine other writers for the job, each having to write answers to a set of advice questions. They had a week to turn in their answers. Amy turned hers in that same afternoon. The editor told her she should take a full week, but Amy told him no, these were her final answers. The paper conducted focus groups to help in their decision, and the choice was unanimous.

Her column, "Ask Amy," is syndicated throughout North America and read by an estimated 22 million people each day. She is also a frequent panelist on the NPR'S popular comedy quiz show Wait Wait . . . Don't Tell Me! In 2009, her memoir The Mighty Queens of Freeville: A Mother, a Daughter, and the Town That Raised Them quickly reached the New York Times bestseller list. She wrote a second best-selling memoir in 2017: Strangers Tend to Tell Me Things: A Memoir of Love, Loss, and Coming Home. In this book, she shares her new life with husband Bruno Schickel, whom she knew as a child in Freeville, and also explores the emptiness left in her life after the death of her mother.

Not long after starting her "Ask Amy" column, Amy moved back to Freeville. She bought a small house on Main Street, next door to her aunt and near her mother, her sister, and another aunt and cousins. Amy believes that one of the best things about living in a small town is that she feels truly and deeply known. She takes pride in giving back to the community that her family has called home for generations. "At the peak of my career, I chose to leave Chicago and move back home to be near my mother and the women who helped raise me. The move changed my life and has created for me this beautiful, wonderful circle. I remet the man I would marry, Bruno, and I was brave enough to fling myself into a whole new adventure with stepchildren and a new family life. I think my story is one of connection. I'm deeply connected to this village and the people who live here."

Looking back over her career of giving advice, Amy feels privileged to have been invited into so many life stories. "I may never meet the thousands of people who write to me, but they trust me enough to share their story with me. That is total joy. I'm honored to take the common sense I've absorbed from my own life experiences and convey the compassion and humanity of the people I admire, and share these things with my audience. I did not follow a straight path to my current success, in life or in my career. I think that's what I try to impress on young people I meet. It can be very valuable to NOT know what is going to happen; to accept uncertainty, to be creative with your choices; and, if you have a pathway marked out, be willing to step off the path."

Toward the end of his life, Amy reconnected with her father. "I made peace with his regrettable choices and ruinous actions," she says. "I no longer blame him for being himself. I don't know if I would call it forgiveness, but more a letting go of my own bitterness in being the daughter of someone so hell-bent on disruption."

Amy used the phrase gob smacked to describe her feelings about being inducted into the Horatio Alger Association. "I have not received a lot of awards in my life," she says. "This is an honor, but I am equally excited about the Scholars and finding ways in which I can touch their lives. These impressive young people are strivers, as I was. They come from circumstances that are very resonant for me. I hope that any advice I will have for them will be something they can use to move forward as they pursue their own dreams."