Deep Dive with Susan Cain on Longing

Author Susan Cain, who first reframed introversion for millions of readers in Quiet, turns her attention to something even more universal: the strange, aching beauty of knowing that everyone we love, we will someday lose. Kelly talks with Susan about why sorrow might be one of the most uniting forces we have — and what changes in us once we stop running from that truth. They also discuss Susan's bestseller Bittersweet, on sorrow and longing, and her new children's book, Lucky and Norman: Saying Goodbye Is Bittersweet, written by three generations of the Cain family. It's a conversation about the particular kind of happiness that only comes from accepting how fragile everything actually is, and why the ache might be worth it.

Kristina Phipps wrote this exquisite, poetic eulogy to honor her mom Ann Emanuels. Ann's love for beauty and her affinity for the natural world shone through in her garden, where she loved to spend time. She saw a world to be seized and not squandered and would pack more into a day than seemed humanly possible. Perhaps more than anything though, Ann viewed the world as a place that should be savored - like a plump peach warm off the tree - and she made sure to impart that valuable lesson to her three daughters. (Previously aired)

Kelly shares a piece by her friend Arianna Huffington ("Self-Discovery Is Our Strongest Drive" - New York Times, June 17, 2026) about the drive underneath all our other drives—the pull toward meaning that shows up in our hardest losses and our most exhausting successes. It's a reflection on what psychologist Abraham Maslow called transcendence, and what it means to keep growing toward the truest version of yourself, even when the world tells you success should be enough.

Kelly sits down with Jim Collins—the bestselling author behind business classics Good to Great and Built to Last—for a live conversation recorded on stage at Sixth & I in Washington, D.C., about his new book, What to Make of a Life. For over a decade, Collins studied 34 exceptional people, from astronauts to Supreme Court justices to rock stars, matching them into pairs who faced the same defining turning point in life and tracing how each person navigated what came after. They talk about the "cliff" moments that split a life in two, the disorienting fog that always follows, and why the advice we get from people who love us often says more about them than it does about us. It's a conversation about trusting the parts of yourself that don't come with a plan, and why some of the most meaningful chapters of a life can show up decades later than expected.

Amy Zuckerman shares a remembrance of her late father Harry “Wes” Westlund. Wes was a special man whose dream of becoming an Air Force fighter pilot was taken away just days before he was to receive his wings, due to a heart murmur. Amy says that although her dad lived his entire life under the threat of a heart defect, he had no issues at all with his capital “H” heart. He was a loving, caring and kind man who made all around him feel comfortable and welcome. (Previously aired - created for Father's Day in 2023)

Kelly reads an essay she wrote several years ago about dropping her daughter off at college—the last box unpacked, the last goodbye said, and the strange quiet that follows. It's a reflection on the myth of ownership in parenting, and what it actually means to raise someone only to watch them walk away — unstoppable.

Most people run from danger. Raymond Ansotegui spent a decade running toward it. In this episode of our Great Coaches series, Kelly talks with a retired rodeo bullfighter about what happens when your job is to step between a thrown rider and an animal the size of a car. Through stories about learning to read personality in a bucking bull, finding connection in the most chaotic moments and understanding when getting closer is actually safer than staying back, Raymond reveals lessons that reach far beyond the arena. This conversation explores commitment, presence and the strange grace that emerges when you stop trying to control everything and just learn to move with what's in front of you—whether that's a 1,800-pound bull, an addiction or a father slipping away to Alzheimer's. (Previously aired)Raymond's organization is petriCORE Compass: https://petricorecompass.com/The aversion therapy program Raymond mentioned is the Schick Shadel Hospital which stopped providing behavioral healthcare services as of June 30, 2022.

Kelly recently found an old letter (hidden away in a closet in Bozeman) that she had written to her mom, way back in 1991. It’s good to look back sometimes at old letters and half-finished journal entries and be reminded of who we were - and who we wanted to become. (Previously aired)

Every piano, every oil painting, every scrap of silk is proof of a 150,000-year collaboration between human hands and the raw materials of the earth. Kelly shares a speech she wrote for the OneGreenThing Forum in Bozeman, MT, making the case that art isn't separate from nature—it's the clearest evidence of our dependence on it.

As part of our Great Coaches series, Kelly talks with Ali Truwit, who went from Yale Division I swimmer to shark attack survivor to Paralympic silver medalist in just over a year. Two days after her college graduation, a snorkeling trip in Turks and Caicos ended with Ali losing her left foot and part of her leg as a result of a shark attack. What followed wasn't just a physical recovery but a complete reimagining of identity, guided by coaches who understood that rebuilding Ali meant helping her see what was still there, not what was lost. (Previously aired)Please check out and consider supporting Ali's non-profit: Stronger Than You Think . https://strongerthanyouthink.org/