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"I sat there with them and realized I had no story to trade. Not a faded one. None." - Ken Woodward With the election less than two weeks away, I caught myself asking how those knuckleheads could vote that way. Underneath it: I would never do that if I were them. It starts with an observation from Jason Pargin about a particular question that is often misinterpreted and a couple others that sound alike. What would you do? What would you do in my shoes? What would you do if you were me? I tell the story of my turn from straight-ticket Republican to bright blue, and the six months in 2016 when new friendships showed me how little I understood about lives I thought resembled mine. Drawing on Melissa Harris-Perry’s Sister Citizen, Thomas Nagel’s idea of moral luck, and research on deep canvassing, I ask how much credit I can take for changing, and what I owe the people who pay for a vote. It closes with sonder and a question: What don’t I know about the life behind this choice? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"A statement claims to be finished, and that claim is exactly what time comes back to audit. A question never claimed to be finished." - Ken Woodward Some ideas arrive like lightning. Others crawl. In 2016, one of my slowest ideas began with a turtle in John Steinbeck’s The Grapes of Wrath. Ten years later, it’s still walking. This episode explores a new study on the “Aha! glow.” Professional writers and physicists logged their most creative ideas, then rated them again six months later. The physicists’ flashes of insight held up. The writers’ faded. The quiet ideas grew in both groups. I revisit my year of daily questions, where the statements aged and the questions didn’t. I also return to Hank, an 85-year-old I nearly walked past during my walk of every street in DC, because I’d already decided he had little to say. Along the way: submarine navigation, the cocked hat, and why one bearing is never a fix. The question I’m carrying: What answer am I trusting because of how it felt when it arrived? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

" Real curiosity, untethered, unsoftened, it's a pretty intense tool. And I think the kids haven't blunted the weapon by politeness or by fear of looking dumb or by the belief that there are certain things we should know. It's still sharp." - Lulu Miller Lulu Miller first found the power of questions on a subway train, listening to an early Radiolab episode about fireflies that blink in unison. That question opened a door she had been looking for since childhood: another world, inside this one. Today she co-hosts Radiolab with Latif Nasser, co-founded Invisibilia, and created Terrestrials, a nature podcast for kids and families. Her international bestseller, Why Fish Don't Exist, begins with a question many of us carry quietly: what is the point? Her answer reminds us that the categories we trust are often questions we stop asking. But the power scared her. She once fled journalism for a fiction MFA, convinced her questions could hurt people. Jad Abumrad's reframe brought her back: those worries are the sound of your moral compass. In this conversation, Lulu shares three ways to move a conversation past the rehearsed version: ask something tactile, ask the elephant-in-the-room question, and interrupt with care. Then the kids on Terrestrials take over, asking NASA scientists and the poet laureate the blunt, open questions adults soften away. Real curiosity, unsoftened, is still sharp. Who blunted ours? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning! Resources Mentioned Radiolab (https://radiolab.org/) Latif Nasser (https://latif-nasser.squarespace.com/about) NPR (https://www.npr.org/) Invisibilia (https://www.npr.org/podcasts/510307/invisibilia) Terrestrials Podcast (https://www.wnycstudios.org/podcasts/radiolab-kids) Why Fish Don't Exist by Lulu Miller (https://www.simonandschuster.com/books/Why-Fish-Dont-Exist/Lulu-Miller/9781501160349) This American Life (https://www.thisamericanlife.org/) Radiolab, Fireflies "Emergence" episode (https://radiolab.org/podcast/91501-there-is-no-lord-of-the-fireflies) Olbers' paradox (https://en.wikipedia.org/wiki/Olbers%27_paradox) Jad Abumrad (https://en.wikipedia.org/wiki/Jad_Abumrad) Robert Krulwich (https://en.wikipedia.org/wiki/Robert_Krulwich) Jocelyn Ford (https://mediaeducationlab.com/about/jocelyn-ford) Nell Greenfieldboyce (https://www.nellgreenfieldboyce.com/) Gregory Warner (https://gregorywarner.substack.com/) Ellen Horne (https://www.linkedin.com/in/ellen-horne-78a45a2) The Addams Family (https://en.wikipedia.org/wiki/The_Addams_Family) Radiolab parasites episode (https://radiolab.org/podcast/darkode) Hanna Rosin (https://en.wikipedia.org/wiki/Hanna_Rosin) Alix Spiegel (https://en.wikipedia.org/wiki/Alix_Spiegel) Zoopharmacognosy (https://en.wikipedia.org/wiki/Zoopharmacognosy) Terrestrials, "An Ocean in Space" episode (https://podcasts.apple.com/au/podcast/an-ocean-in-space/id1504895463?i=1000702888723) Europa Clipper (https://en.wikipedia.org/wiki/Europa_Clipper) Europa (https://en.wikipedia.org/wiki/Europa_(moon)) Ada Limón (https://adalimon.com/) Voyager Golden Record (https://en.wikipedia.org/wiki/Voyager_Golden_Record) Producer Ben Ford (https://www.producerbenford.com/) Beauty Pill (https://www.beautypill.com/)

"What do former members say about the organization?" - Ken Woodward Ten years ago today, I asked a question on my daily practice, IOTD365: what do former members say about an organization? I wrote it after my daughter gave up on an internship. One conversation in a hallway with a senior who'd done it was all it took. In 2016 I read that question as an insider asking leaders to listen. Today I read it as a former member who left federal service after thirty-two years without anyone asking what I knew. I also read it as a founder who can't hear what's said after I leave the room. In this episode, I reread the original post and question the man who wrote it. I look at where reputation really lives and the courage it takes to tell someone the truth. Then I borrow a habit from my years navigating submarines in and out of port. Taking a fix on an old question shows how far I've moved. What question did you answer years ago that deserves a second look? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"Disagreement makes the map visible. Agreement lets it pass for the terrain." - Ken Woodward "Thank you for your service" arrives with a script already written. A World War II veteran taught Ken Woodward a better reply: "You were worth it." That exchange opens a solo episode about the worlds hidden inside the questions we answer. Ken starts with a single verb that put broken glass on a road where there was none, then turns to survey research showing how answer choices define normal, and to philosopher R.G. Collingwood's idea that every question stands on assumptions. From there he returns to the streets of Washington, D.C., sorting the questions strangers asked his "Black and Brown Lives Matter" sign by the maps they carried, including the ones pointing back at the sign itself. The hardest case comes last: a question Ken agreed with, never examined, and what his nod cost the conversation. Disagreement makes the map visible. Agreement lets it pass for the terrain. What world did you agree to before you answered? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"  I ate of that apple. It tasted like safety." - Ken Woodward Once a submarine goes under, nobody aboard knows exactly where they are. The boat runs on an estimate that drifts, and being off course feels exactly like being on course. The only remedy is to come up and take a fix. In this solo episode, Ken asks whether certainty is what keeps us safe, or whether safety comes from our ability to keep checking our position against the world. He draws on his time as a Navy Radioman plotting fixes, Arie Kruglanski's research on the need for closure, a Listerine ad campaign that manufactured a fear to sell a cure, and John Keats's idea of negative capability. He also tells the story of a political and religious certainty that once absolved him of responsibility, and what 2,085 miles of D.C. streets taught him about fear. The episode closes with a question to take with you: Is my need for certainty making me safer? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"The biggest reason somebody will avoid answering a question is because they don't trust you with the answer." - Debbie Millman Debbie Millman has spent 21 years asking questions on Design Matters, the show she started in 2005 before podcasting had rules. In episode 100 of Curated Questions, she takes the receiving chair. Debbie traces her craft from a survey-style list she asked everyone, work she now calls terrible, to a method she describes as storytelling through questions, where each question carries the context a guest needs to respond to a fully realized moment in their life. She explains why she avoids false wisdom language, multiple-choice framing, and interpretation the guest hasn't offered yet, and makes the case that people withhold answers when they don't trust you with them. The conversation ranges across branding, her clients, the questions she brings to any redesign, the rebuild of The Rumpus with Roxane Gay, and what AI costs students who skip the difficulty. She closes with the question consuming her at 65: how to live this last third. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning! Resources Mentioned Debbie Millman (https://www.debbiemillman.com) Design Matters (https://www.designmattersmedia.com) Sterling Brands (https://www.sterlingbrands.com) AIGA (https://www.aiga.org) SVA Masters in Branding (https://branding.sva.edu) Roxane Gay (https://audacity.substack.com) The Rumpus (https://therumpus.net) Lambda Legal (https://lambdalegal.org) NASA (https://www.nasa.gov) U.S. Department of Justice (https://www.justice.gov) Paula Scher (https://www.pentagram.com/about/paula-scher) Dr. Dan Formosa (https://sva.edu/faculty/dan-formosa) Kevin Kelly (https://kk.org) "If You're Over 40, You're Ready to Use A.I." — Debbie Millman, NYT (https://www.nytimes.com/2026/07/27/opinion/teaching-kabbalah-ai.html) The New Yorker (https://www.newyorker.com) Kottke.org (https://kottke.org) Craig Mod (https://craigmod.com) The Marginalian (https://www.themarginalian.org) The New York Times (https://www.nytimes.com) The Washington Post (https://www.washingtonpost.com) Los Angeles Times (https://www.latimes.com) Maria Popova (https://www.themarginalian.org) Jason Kottke (https://kottke.org/about) TED Talks (https://www.ted.com/talks) Tim Ferriss (https://tim.blog) Dax Shepard, Armchair Expert (https://armchairexpertpod.com) Krista Tippett, On Being (https://onbeing.org) NPR (https://www.npr.org) Glennon Doyle (https://glennondoyle.com) Andrew Caulk (https://www.curatedquestions.com/podcast) Barbra Streisand (https://www.barbrastreisand.com) Terry Gross, Fresh Air (https://www.npr.org/programs/fresh-air) Sam Fragoso, Talk Easy (https://talkeasypod.com) Adam Grant (https://www.adamgrant.net) Brené Brown (https://brenebrown.com) Frances Frei and Anne Morriss, Fixable (https://www.ted.com/podcasts/fixable) Figuring, by Maria Popova (https://www.themarginalian.org/figuring) Natascha McElhone (https://www.audible.com/pd/Figuring-Audiobook/198484475X) Traversal, by Maria Popova (https://us.macmillan.com/books/9780374616410/traversal) Arcosanti (https://www.arcosanti.org) Santiago Carrasquilla (http://www.santiagocarrasquilla.com) Art Camp (https://madeatartcamp.com) Ruth Ann Harnisch / The Harnisch Foundation (https://thehf.org) Sukey Novogratz (https://justsit.com) Producer Ben Ford (https://www.producerbenford.com/) Beauty Pill (https://www.beautypill.com/)

" I had to start trying to think beneath the questions: what are they really saying?" - Wanda Herndon Wanda J. Herndon trained as a journalist, then spent forty years on the other side of the notebook. Dow. DuPont. Eleven years as Starbucks SVP of Global Communications while the company grew from 550 stores to more than 11,000. Her curiosity starts with a middle child in Flint, Michigan, who wore out her siblings asking why. She describes learning, after being misquoted, to ask what a reporter is really asking. She calls listening a discipline she never mastered. And the question that carried her through divorce: what is this moment trying to teach me? Crisis work as a puzzle solved with who, what, why, when, where, how. Mentoring as a two-way street. Why she always asked Howard Schultz why. Being the CEO of you. Owning Flint rather than letting others define it. And her right now question: will we survive this chaos, and what can I do to help? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning! Resources Mentioned Orin Smith (https://en.wikipedia.org/wiki/Orin_C._Smith) Nikki Giovanni (https://www.nikki-giovanni.com/) Starbucks (https://www.starbucks.com/) Audre Lorde (https://alp.org/about/audre) Flint Michigan (https://en.wikipedia.org/wiki/Flint,_Michigan) Howard Schultz (https://schultzfamilyfoundation.org/team-member/howard-schultz/) Onward by Howard Schultz (https://a.co/d/0cG7QyPF) Pour Your Heart Into It by Howard Schultz (https://a.co/d/00OhYP7W) Alpha Kappa Alpha Sorority, Inc. (https://aka1908.com/) Greater Seattle Chapter of The Links, Inc. (https://www.greaterseattlelinks.org/) Wanda Herndon website (http://wcommgroup.com/) Wanda Herndon on LinkedIn (https://www.linkedin.com/in/wandajherndon) Wanda Herndon on Facebook (https://facebook.com/wandajherndon) Wanda Herndon on Instagram (https://instagram.com/wandajherndon) Producer Ben Ford (https://www.producerbenford.com/)

" You do not knock on a door that's been painted over. One word scores the paint and reopens it." - Ken Woodward Researchers paid people to admit when they didn't know something. Given access to AI advice, they almost never did. The design made it startling. Participants could decline any question with no penalty. Guessing wrong cost them money. The AI advice they received was usually wrong. Every incentive pointed toward three simple words, and access to a machine nearly eliminated their willingness to say them. What got suppressed wasn't accuracy. It was the willingness to be seen not knowing. In this solo episode, Ken opens with a lie he told a friend in a room where nothing was at stake, then traces the same reflex through a sidewalk in Southeast D.C., five questions he couldn't answer, and a backyard conversation that ran five hours past its twenty-minute plan. "I don't know" isn't a report on empty shelves. It's a doorway, and it's the only one. What question are you avoiding because not knowing would cost you something? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"Every unasked question has an expiration date." - Ken Woodward Ken tries to say goodbye to a shipmate before leaving the submarine. The man goes on emergency leave, and the goodbye has already happened without him noticing it. He had the calendar, the date, the list of names. The last one got past him anyway. That is the shape of this episode. We do not know which time is the last time, and preparation does not change that. Ken walks through Tim Urban's arithmetic on parents, a return to his hometown that was supposed to be final and wasn't, and an upcoming lunch with his ninety-three-year-old aunt, who is the last door into a generation that has already closed. In Ambiguous Loss, Pauline Boss offers a useful frame: closure is largely a myth, and the real skill is holding something open without needing it to shut. The question idea underneath it: every unasked question has an expiration date you cannot see. Some are saving for a better moment. Some you can't ask because you don't yet know you will want the answer. Ken is recording before he flies, without a resolution, because the not knowing is the point. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"There is just a slightly smaller life that you experience as a completely normal one." - Ken Woodward Seven experiments. Ten thousand people. Half learned a topic from an AI summary, half from ordinary web links. Same facts. The AI group came away with shallower knowledge, and when researchers propped the door open, placing live source links right beside the summary, almost nobody walked through. Sixty-eight percent of Google searches now end without a click. With an AI Overview on the page, eighty-three percent. This episode is about what that costs. Not wrong answers, wrong answers get caught. It's the second question that never gets asked, which leaves no error message and no gap in the record. Just a slightly smaller life that you experience as a completely normal one. Then: a man on a corner in Northeast D.C. who gave me a name that wasn't his, and what it took to get the real one. One more thing, I need your help naming something. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

" This aporia, this state of confusion and bafflement, is actually a fantastically exciting, liberating, intellectually stimulating place to be because you're really facing something that you don't know that you thought you did." - Lani Watson Dr. Lani Watson has spent her career on a question most of us never stop to ask. What is a question, and why does it hold such power? Known online as The Questions Doctor, Lani is a philosopher and the author of Q: The Hidden Power of Questions in a World That Wants Answers. In this episode, we sit with the idea that questions are a kind of everyday magic. A power we all carry and rarely notice. They change our brains. They change our relationships. They shape the very answers we receive. We talk about Socrates and the gift of not knowing. We talk about a world racing toward answers, and what we lose when we rush past the question. We talk about who gets to ask, and who does not. Come sit with the questions a while. There is power in the asking, and it belongs to all of us. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"Listening is not real until the listener makes a sound back." - Ken Woodward A sound-powered telephone runs on nothing but the sound of your own voice. No battery. No amplifier. I served on submarines, and I never forgot the joke we played on every new sailor: we sent him hunting the whole ship for batteries that do not exist. The power was in him the entire time. He only had to speak. This is a solo episode about listening. About the repeat-back, the discipline of saying a message back until it lands correctly. About a 2025 study that found the follow-up question is the clearest sign that real listening is happening. About what Dr. Haru Yamada taught me, that to ask and to listen are one motion. And it is about one officer I served with, a question I never asked him, and why I let it go unasked. The circuit is always live. Who is the station you have never called? This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

"Nothing in us reports on an absence. No creature ever needed a sense for the path it did not walk." - Ken Woodward More than sixty percent of Google searches now end without a single click. We type the question, read the summary, and leave. The trip is gone. Neuroscientist Anne-Laure Le Cunff argues that curiosity needs a gap to switch on, and that learning deepens while the question stays open. The answer closes the window. But the reaching is not our failure. Wanting the missing piece is old equipment, and it worked well for a very long time, because you used to have to walk over the ridge to find out. What changed is the hit rate. We catch every time now, in three seconds, and the machinery on the other side never gets to run. This week we look at which gaps are worth keeping open, why resistance is the mechanism rather than the toll, and what ten years of a daily question taught me about the limits of my own idea. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!

" Show what you know by the questions you ask." - Robert Doore Robert Doore carries two names, Robert Doore and Rides at the Door, and a journey most maps don't draw: from Big Red football on the Blackfeet Reservation to becoming the highest-ranking Native American in the NFL since Jim Thorpe. Now the President and CEO of Chief Mountain Sports and Consulting, he tells Ken he didn't learn the power of questions early on. He learned it at 21, in a Washington, D.C. room full of generals and cabinet officials, when he found the courage to ask a mentor, "How did you get to be so smart?" The answer, be well read, ask lots of questions, became his Jedi training. The conversation moves through Maslow's summer with the Blackfeet, teaching "Indian 101" to policymakers, representation as a door-opener, and fear as the cousin of failure. Robert's right now question: What does success look like? His answer isn't money. It's impact. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions (https://substack.com/@curatedquestions?)) Keep questioning!