Listen Again: Anna Sale on Hard Topics, Softer Conversations

The TODAY Show’s Jenna Bush Hager sits down for a wide-ranging conversation with Kate Bowler. Together, they share about the importance of family and intergenerational relationships (Jenna shares such tender stories about her grandparents), how they hope to let their kids make mistakes and be met with grace, and how they both (try to) find beauty in ordinary, regular days and regular problems.  In this conversation, Kate and Jenna discuss: How to model openness and empathy across difference (even when people really, really disagree) Why they want to raise their kids to be curious and independent How the love of others makes us brave—brave enough to make mistakes (and why that’s okay) Kate visited Jenna in New York City for this conversation. And Jenna is just as lovely and generous of spirit as you’d imagine. CW: fertility issues; Alzheimer’s  Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over there, too! This episode originally aired September 2023.See omnystudio.com/listener for privacy information.

Every grocery store speaker is now officially blasting “It’s the Most Wonderful Time of the Year.” And let’s be honest: sometimes it feels like a demand. The happiest Christmas music can feel like salt in the wound when life is heavy. If this season is not “merry and bright” for you, you’re not alone. That’s why many churches will hold “Blue Christmas” services next week. It’s an American tradition that says out loud what so many feel quietly: the holidays can hurt. These services dim the lights, play gentler music, light blue candles, and make space for grief. They remind us that the story of Christmas itself is no stranger to darkness—Jesus was born into a world of oppression and fear. Joy didn’t arrive because the world was perfect; it arrived anyway. I thought perhaps now, only halfway through the Advent season, it might be a good time to take a peek at the customs and traditions and plans that you’ve got on the calendar and see if you need to make any room for grief. Maybe the invitation of Advent is not to blast the cheeriest carol until we believe it, but to prepare room for joy by telling the truth. By letting sorrow breathe. By choosing practices that gently turn our hearts back toward joy without pretending the sadness is gone. What might that look like for you? A quiet walk near some city Christmas lights. A playlist that mixes Bing Crosby with a hymn that actually makes you cry. A phone call to the person who understands the empty chair at your table. Joy doesn’t demand we silence our grief. It asks us to make just enough room for God to slip in beside it. And sometimes, that tiny crack of space is all joy needs to return. Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over there, too!See omnystudio.com/listener for privacy information.

Life is painful. Period. But are there some aspects of our faith or our posture toward the world that can change how we experience it?  Father Richard Rohr is everyone’s favorite preacher of love. Love for each other. Love from God.  In this conversation, Kate and Richard talk about: How great love and great suffering can move us into a new stage of life  The spirituality of subtraction Making room for mystery of joy and suffering His secret to staying present to God Together, might we all learn when to hold on and when to let go. Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over there, too! This episode originally aired November 2021.See omnystudio.com/listener for privacy information.

We’ve all seen the Christmas pageants where Mary is very sweet and demure and she is wearing a tablecloth pulled from the church dining hall. Sometimes it’s hard to remember how much impossible courage Mary had from the beginning. She finds out that she is pregnant in a completely scandalous way. But what does this divinely-prepared, teenage girl do when an angel crashes into her life with an announcement guaranteed to upend all her best plans? She sings. But not a sweet lullaby. Mary belts out a protest song: “He has brought down the mighty from their thronesand lifted up the humble.He has filled the hungry with good things,and sent the rich away empty” (Luke 1:52–53). This is not the peace of spa music and chamomile tea. It’s the kind of peace that rearranges the furniture of the universe. That scatters the arrogant and topples the unjust. God’s peace doesn’t politely avoid conflict; it writes the soundtrack for a revolution. And somehow, Mary holds all of this—terror, disruption, and hope—in her own body. She sings peace into a world that did not ask for it, but desperately needs it. And here we are, centuries later, humming along too. Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over there, too!See omnystudio.com/listener for privacy information.

The pandemic introduced many to living with uncertainty. But for some, uncertainty has always been their norm. Actress Nikki Deloach has starred in several Hallmark Christmas movies, but her life hasn’t matched the happily-ever-after plot-lines of her characters. Nikki’s dad was diagnosed with an aggressive form of dementia and her son was diagnosed with congenital heart defects in utero… all in the same week. In this conversation, Kate and Nikki discuss how to live with constant uncertainty, how to stay open to both the terror and the beauty of living close to the edge, and how to make Christmas meaningful when hope is hard to come by.  Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over there, too! This episode originally aired December 2020. See omnystudio.com/listener for privacy information.

Well, here we are. December has arrived (shudder). And with it, the great cultural sprint: decorations, office parties, and the annual anxiety dream about whether you will accidentally forget someone on your gift list (spoiler: you will). Some of you already finished your shopping over Thanksgiving and have a freezer full of perfectly labeled Christmas cookies. (Who are you?! Come to my house and fix my life!) The rest of us are still trying to remember where we put last year’s wrapping paper. It’s easy, this time of year, to let December carry us away. The shopping carts, the streaming playlists, the endless events. Advent, though, asks us to live by a different rhythm. The early church saw this season as one of watching and waiting—not just for Christmas morning, but for the whole story of God’s redemption. They began the year not by rushing, but by slowing down. The prophet Isaiah describes this posture well: “In returning and rest you shall be saved; in quietness and in trust shall be your strength” (Isaiah 30:15). The church fathers loved this verse because it sounded like Advent: strength found not in frantic activity, but in patient trust. So maybe the invitation this December is not to do more, but to intend more. To decide, amid the cookie dough and to-do lists, that this month won’t only be measured in packages mailed or tables set, but in moments of return. Little pauses of prayer. A fat candle lit on the dining room table that makes you take a breath. A quiet reminder that God is coming, and we don’t have to hold the season—or our lives—together by ourselves. So welcome to December, friends. Whether you’re ahead of the game or already behind, you are exactly where you need to be: at the beginning. Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over there, too!See omnystudio.com/listener for privacy information.

In this conversation, Kate and Anna discuss: How conversations might engender the intimacy we need to get by Fostering the right interpersonal and listening skills it takes to approach a difficult topic (especially when you’re feeling nervous) Best practices for responding to someone’s hard news How learning to listen might bridge differences of all kinds What do we lose when we don’t talk about hard things? And what might we gain if we do? Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over on Substack! This episode originally aired April 2022.See omnystudio.com/listener for privacy information.

What happens when childhood teaches you more about survival than safety? Poet and author Nikki Grimes joins Kate to talk about growing up with profound instability—and still choosing to see beauty, feel joy, and offer forgiveness. In this moving conversation, they explore memory, trauma, faith, and the small pockets of belonging that shape a life. SHOW NOTES: Books by Nikki Grimes: Ordinary Hazards – A memoir in verse chronicling Nikki’s traumatic childhood; Glory in the Margins – A collection of Sunday poems exploring faith and resilience; A Cup of Quiet – A children’s book about the sweet bond between a grandmother and granddaughter; The Road to Paris – A semi-autobiographical novel inspired by Nikki’s experience in foster care. Poems read in this episode: Holy Architecture – from Glory in the Margins, Habitation – from Glory in the Margins Support guides: When You’ve Been Hurt as a Child, When Your Family is Complicated Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. Join us for Advent over on Substack! See omnystudio.com/listener for privacy information.

Today, we’re sharing a conversation from the More Happier podcast between Kate, Gretchen Rubin, Priya Parker, and Francis Lam.  It’s easy to get swept up in a cycle of holidays that feels more like a relentless to-do list than a source of joy. In this Celebration Roundtable, we talk about how to embrace the holidays as opportunities for intentional connection and meaning.See omnystudio.com/listener for privacy information.

Tim Shriver—educator, author, and longtime Chairman of Special Olympics—joins Kate for a tender, funny, deeply practical conversation about dignity: what changes when we decide everyone matters, how relationships (not information) do the real work, and why service is more than “being nice.” Together they trace a family story from Rosemary Kennedy to Eunice Kennedy Shriver to millions of athletes, swap hospital-and-gymnasium epiphanies, and offer a simple lens for disagreeing better. It’s an invitation to the “really real,” where joy and sorrow live together and love makes people—and communities—more fully alive. SHOW NOTES: Special Olympics — The global movement founded by Eunice Kennedy Shriver and now led by Tim. Dignity Index — A practical tool for scoring how we speak across difference, helping us learn to disagree without contempt. Unite — A bridge-building initiative founded by Tim Shriver to foster common ground and shared dignity. CASEL — The pioneering framework for social and emotional learning Tim helped develop. Fully Alive: Discovering What Matters Most — Tim’s memoir on faith, family, and the pursuit of a life that really matters. Subscribe to Kate’s Substack for blessings, essays, and reflections that hold what’s hard and beautiful. See omnystudio.com/listener for privacy information.