"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)

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)

Keep questioning!

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

#100 Debbie Millman: Earning Trust & Storytelling Through Questions