#106 Ken Woodward: What Would You Do If You Were Me?

"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.

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Keep questioning!

#105 Ken Woodward: The Question After the Aha!

"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.

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Keep questioning!

#104 Still Sharp: Lulu Miller on the Questions We Stop Asking

" 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.

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#103 Ken Woodward: The People Who Leave Get the Last Word: Revisiting a Question Ten Years Later

"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.

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Keep questioning!

#102 Ken Woodward: The Questions That Make You Nod: How Agreement Hides Assumptions

"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.

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Keep questioning!

#101 Ken Woodward: When Certainty Drifts

" 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)

Keep questioning!