The more experience you have, the easier it is to stop asking questions.

So what happens when your expertise starts answering for you?

Joy Chik and Ana Pinczuk explore how experienced leaders can use pattern recognition without becoming trapped by it, why one honest question can reopen learning, empathy, and humility, and what it takes to pause before jumping to advice.

Ana is President and Chief Product and Technology Officer at SentinelOne, and has served on several public-company and nonprofit boards. Joy and Ana got to know each other through their work on the Board of Trustees at AnitaB.org. From a founder's "$40 million in bookings" that meant something different from what she assumed, to a whiteboard session relearning her own field, to starting over at Cisco, Ana has repeatedly had to set down what she knew in order to see again.

Together, Joy and Ana unpack how experience can quietly turn into certainty, and the one habit that keeps it alive: ask one more question.

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Logo and other art courtesy of Andy Reddout.

This podcast was produced by Tom Larson and Sue Corcoran, and edited by Amy Enser.

What does it take to build something when there's no big name behind you?

Joy Chik spent 28 years at Microsoft -- inside one of the biggest brands and teams in the world. Building this podcast has meant something different: no communications team, no built-in audience, no institution opening doors. Just her, a guest, and whoever chooses to press play.

In this episode, Joy talks with Laura Clise, founder and CEO of Intentionalist, who faced her own version of the same question. Laura spent six years between the idea for Intentionalist -- planted by a piece of hand-woven fabric she brought back from Cambodia -- and actually launching the company, all without a big institution behind her either.

Together, Joy and Laura get into what building from scratch actually requires: the point where

complaining about a gap turns into deciding to close it yourself, what it costs to confront your own fears with nowhere to hide, and what building something slowly -- one relationship at a time -- has changed in each of them.

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For video episodes, visit our podcast on Apple, YouTube, or Spotify.

Follow us on LinkedIn, Instagram, and Facebook.

Send your feedback and suggestions for future episodes to feedback@joyofreinvention.com

Logo and other art courtesy of Andy Reddout.

This podcast was produced by Tom Larson and Sue Corcoran, and edited by Amy Enser.

The more successful you become, the harder it is to be bad at something again.

So what happens when reinvention asks you to start from zero?

Joy Chik and Boaz Ashkenazy explore why accomplished people resist becoming beginners, why learning in public can feel so exposing, and why confidence rarely comes before action.

Boaz is an Executive AI Advisor at Redapt and the founder and host of Shift AI. From a teenage bet that got him onto the basketball court, to launching a podcast with no experience, to raising his first round of startup funding, Boaz has repeatedly put himself in situations where he didn't yet know what he was doing.

Together, Joy and Boaz unpack what those experiences taught him about starting before you're ready, learning through imperfect repetition, and finding the courage to keep going before confidence shows up.

For newsletter updates, sign up here.

For video episodes, visit our podcast on Apple, YouTube, or Spotify.

Follow us on LinkedIn, Instagram, and Facebook.

Send your feedback and suggestions for future episodes to feedback@joyofreinvention.com

Logo and other art courtesy of Andy Reddout.

This podcast was produced by Tom Larson and Sue Corcoran, and edited by Amy Enser.