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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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.

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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.

Joy Chik and Sarah Bond explore the quiet signals that a meaningful chapter is complete, why responsibility can keep us there, and how choosing an ending can become an act of gratitude and agency.

Sarah recently completed an extraordinary chapter at Microsoft, where she most recently served as President of Xbox. In this conversation, Joy and Sarah examine the difference between exhaustion and completion, the loyalty that keeps capable people in roles they've outgrown, and the subtle signals that responsibility has replaced aliveness.

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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.

6 months ago, Joy thought she was starting a podcast. What she was really starting was her own reinvention.

In this solo episode, Joy looks back on Season 1 — leaving Microsoft after 28 years, choosing to bet on herself instead of another corporate role, and what it took to become a beginner again. Then she looks ahead: what Season 2 is about, who's joining her, and the new name this show is stepping into.

The Knowing Moments is becoming Joy of Reinvention: Knowing Moments, Bold Choices, Lived Wisdom. Same show, same feed, same host — new name, new chapter.

If you already follow or subscribe, you don't need to do anything. This same show will simply appear with a new name and cover.

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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 makes some journeys become Knowing Moments — while others are simply vacations?

For years, travel was about getting somewhere for me — customer meetings, keynotes, leadership offsites, tight schedules. I'd come home with more airline miles than memories.

These days I travel differently. In this episode, I sit down with Nancy Mounir, my former Chief of Staff at Microsoft and one of my closest friends, to talk about a work trip to Saudi Arabia that changed how we both see the world — and why the moments that stay with us are so rarely the ones we planned.

We talk about assumptions that fell apart on contact, the unplanned detours that outlast the itinerary, and why the greatest souvenir might not be a thing at all.

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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.

For years, I thought I was good at recharging. I worked out almost every day. I took vacations. It seemed like I checked all the boxes. But looking back, I don’t think I really knew how to rest.

This episode kicks off our summer stretch — shorter, more reflective, and for the first time, with a guest. I sat down with Trevor Opalewski, my trainer since 2021, who’s had a front-row seat to the busiest years of my career at Microsoft, my transition out, and whatever this next chapter is becoming.

We talk about why real recharge is so hard to find, the difference between escaping and actually resting, why changing location isn’t the same as recovering, and why rest might be the most underrated source of creativity.

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Logo and other art courtesy of Andy Reddout.

When I started this podcast, I thought I was documenting a sabbatical — a pause between chapters.

What I was really learning was how to redesign a life.

In the Season 1 finale of The Knowing Moments, I share three experiences that taught me what redesigning a career actually looks like: running three ventures and discovering each one required a different version of me; building this podcast from zero and realizing a tribe was quietly forming around it; and sitting at my kitchen table on a Sunday, scanning a calendar that was busy as ever — but that, for the first time in decades, no one had designed but me.

This episode is about the part of reinvention no one warns you about: your title is not your identity, success can become a birdcage, and a meaningful career — like success, belonging, and fulfillment — can't be inherited.

It has to be intentionally built.

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Logo and other art courtesy of Andy Reddout