#81 Ken Woodward: What the Machine Can't Hold

"Some questions need eye contact. Some questions need silence. Some questions need the telltale crack in our own voice that tells you, you've finally said something true." - Ken Woodward

We live in a moment when almost any question can be answered instantly, eloquently, and for free. That is a remarkable thing. It is also worth examining carefully.

In this episode, Ken Woodward draws a distinction between two kinds of questions: tool questions, which AI handles brilliantly, and threshold questions, which require something the machine cannot provide. Time. Risk. The sound of your own voice saying something true for the first time.

This is not an episode about the dangers of AI. It is an episode about the quiet cost of convenience, what we give up when we trade a live, risky question for a fast, polished answer. And what it looks like to protect the capacity for wonder in an age that makes outsourcing almost everything feel like efficiency.

Three practices. A few guardrails. And one question to carry with you when you close the machine.

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!

#80 Ken Woodward: Still Asking: Ten Lessons From A Decade With Questions

"Claiming your agency to question is a renegade step into your full humanity." - Ken Woodward

April 12, 2016, marked the first public demonstration of Kenneth Woodward's obsession with questions. A decade, 80 episodes, and 140,000 downloads later, he returns to the shoreline to share what a decade of study, conversation, and lived experience has washed up at his feet.

From a daily inquiry blog that cost him sleep, to 1,300 conversations across 2,085 miles of Washington D.C. streets, to podcast conversations with some of the world's deepest thinkers, questions have been the through line.

In this milestone solo episode, Kenneth offers ten honest observations about questions, how they create space, signal desire for change, exercise agency, and reveal what we most need to face. Not conclusions from a master, but mile markers from a fellow pilgrim still very much on the road.

The practice continues. So does the asking.

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!

#64 Ken Woodward: What Questions Are You Carrying Forward? Reflections on 2025

"What are the questions you will be carrying into the year, such that it will be a celebration of your becoming?" - Ken Woodward

This year-end Curated Questions episode is a reflective curation of the questions that shaped several conversations throughout 2025. Rather than offering a rapid recap of every episode, Ken highlights a handful of moments that reveal how intentional questioning can clarify purpose, interrupt unhelpful patterns, and guide meaningful becoming.

Across stories from entrepreneurs, scientists, artists, and personal reflection, the episode explores questions that ask us to define the change we seek to make, consider who we are becoming, and choose where to place our attention. Along the way, listeners are reminded that good questions often emerge only after many imperfect ones, that perspective shapes dignity and connection, and that small mental reframes can act as powerful resets.

As the year closes, the episode becomes an invitation: to name the questions that mattered most in 2025, to carry one forward with intention into 2026, and to trust that a better world is built by those willing to keep questioning.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Ensure to subscribe to the Curated Questions Dispatch weekly newsletter on Substack.

Keep questioning!