Henderson grew up, the youngest of three siblings, in a happy home in Phoenix, Arizona. Her paternal grandparents lived in the small town of Hartford City, Indiana. Just about every winter, to escape the Midwest cold, they’d visit for a month or two, usually staying in the Henderson house. Young Abby was not into it. She was a quiet kid whose parents both worked, so she relished the time after school when she could hang out at home by herself. Her grandparents disturbed that peace. Her grandmother, waiting for her when she returned from classes, always wanted to hear about her day—and Abby resisted the attempts at connection.
Now she regrets it.
“The biggest regret is that I didn’t hear their stories,” she told me in an interview. But that has altered her approach to her own parents. Sparked by this regret, she and her siblings bought their father, who’s in his seventies, a subscription to StoryWorth. Each week the service sends an email that contains a single question (What was your mother like? What is your fondest childhood memory? And—yes—what regrets do you have?). The recipient responds with a story. At the end of the year, those stories are compiled into a hardcover book. Because of the poke of If Only, she said, “I seek out more meaning. I seek out more connection. . . . I don’t want to feel the way when my parents die that I felt about my grandparents of ‘What did I miss?’?”
Abby says this ache helped her to see her own life as a puzzle with meaning as the centerpiece. “When people around me say ‘No regrets,’ I push back and say, ‘If you don’t make mistakes, how are you going to learn and grow?’?” she told me. “I mean, who makes it through their twenties without regrets? The bad jobs I took, the bad dates I went on.” But she eventually discovered that every time she had a regret, “it was in part because I was trying to remove meaning from the equation.”
One of the traits Abby remembers about her grandmother was her otherworldly baking skills, especially the pies she regularly served for dessert. “If all you’ve ever had is flavorless pie, you’re going to think pies are ‘meh.’ But once you’ve had my grandma’s strawberry pie, there is no going back.” For Abby, there’s a metaphor lurking in that baking tin.
“My life is more flavorful because of my regrets,” she told me. “I remember the bitterness of the taste of regret. So when something is sweet, good god, it’s so much sweeter.” She knows she’ll never get the time back with her grandparents. “It’s a flavor that will always be missing,” she says. Collecting the stories of her father, which she wouldn’t have done without the prod of If Only, helps. “It is a beautiful substitute,” she says.
“But it isn’t a replacement. Nothing will fill in that flavor. I will spend the rest of my life with a little bit of a gap. But that’s going to inform everything else that I do.”
* * *
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When we handle it properly, regret can make us better. Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning. The problem, though, is that we often don’t handle it properly.
WHAT ARE FEELINGS FOR?
At some point in its pages, nearly every popular book about human behavior wheels out William James, the nineteenth-century American polymath and Harvard professor who wrote the first psychology textbook, taught the first psychology course, and is widely considered to be the founding parent of the field. This book will now honor that tradition.
In chapter 22 of his 1890 masterwork The Principles of Psychology, James contemplated the purpose of the human ability to think. He proposed that how we think, even what we think, depends on our situation. “Now that I am writing, it is essential that I conceive my paper as a surface for inscription,” he wrote. “If I failed to do that I should have to stop my work.” But in other situations—suppose he needed to light a fire and nothing else was available—he’d think of the paper differently. The paper itself has infinite variations—“a combustible, a writing surface, a thin thing, a hydrocarbonaceous thing, a thing eight inches one way and ten another, a thing just one furlong east of a certain stone in my neighbor’s field, an American thing, etc., etc., ad infinitum.”
Then he dropped an intellectual grenade that reverberates still today: “My thinking is first and last and always for the sake of my doing.”[20]
Modern psychologists have affirmed James’s observation, while shaving off ten words in the service of pith: Thinking is for doing.[21] We act in order to survive. We think in order to act.
But feelings are more complicated. What is the purpose of emotions—especially unpleasant emotions like regret? If thinking is for doing, what is feeling for?
One view: Feeling is for ignoring. Emotions aren’t significant, this perspective holds. They’re mere annoyances, distractions from serious matters. Better to bat them away or cast them into oblivion. Focus on the hardheaded, eschew the softhearted, and you’ll be fine.
Alas, stashing negativity in your emotional basement merely delays the moment when you must open the door and face the mess you’ve stored inside. Blocked emotions, writes one therapist, can even lead to “physical problems like heart disease, intestinal problems, headaches, insomnia and autoimmune disorders.”[22] Burying negative emotions doesn’t dissipate them. It intensifies them, and the contaminants leach into the ground soil of our lives. Consistently diminishing negative emotions isn’t a sound strategy either. It risks turning you into Professor Pangloss from Candide, who when dealt one catastrophe after another simply declares, “All for the best in the best of all possible worlds.” Minimizing techniques like At Least counterfactuals do have their place, as I’ll explain in Chapter 12. They can soothe us, and sometimes we need soothing. But they can also supply us with false comfort and strip us of the tools to address cold reality, becoming a downward-facing dogma that undermines decisions and blunts growth.