Advertise on podcast: The Knowing Moments

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. 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 [email protected]  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. 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 [email protected]  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 [email protected] 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. 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 [email protected]  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. 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 [email protected]  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. 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 [email protected]  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. 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 [email protected]  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. 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 [email protected]  Logo and other art courtesy of Andy Reddout

When you leave a long chapter of your career, you don’t just leave a job. You leave a tribe. For almost three decades, my community was built into my life automatically — the people I saw every day, solved problems with, learned from. And when that structure changes, you start asking a different question. Not “What do I do next?” but “Where do I belong now?” In this episode, I take you through three recent moments — learning to be present after years of half-listening, missing my team and discovering the belonging was changed but still there, and walking into a room full of strangers and finding a new belonging. This is about a hidden part of reinvention no one warns you about: rebuilding not just a career, but a sense of belonging — one conversation at a time. 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 [email protected]  Logo and other art courtesy of Andy Reddout

There's a question that sounds simple. But for most of us — especially those who've built something real — it's one of the hardest questions to sit with. Who are you outside your job title? In this episode, I take you with me to Antarctica, to the Winter Olympics in Milan, to my farewell gathering on Microsoft's campus, and to the moment I almost didn't share my podcast publicly. Each of those moments taught me something different about identity. About how quietly it becomes wrapped up in a role. And about what it actually takes to start designing it from scratch. This is what it looks like — and feels like — to begin again. 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 [email protected]  Logo and other art courtesy of Andy Reddout

There’s a phase that’s harder to name than failure. It’s when the role that once felt impossible now feels… routine. When the business is growing, the team is strong, and your calendar has never been fuller. And yet. Something starts to feel different. Not wrong. Just different. In this episode, I go back to the years when I had built something real at Microsoft — and began to realize, slowly, that the very things making the work meaningful were also making it impossible to imagine leaving. The platform. The recognition. The rhythm that had quietly become a birdcage. Because success, it turns out, creates its own kind of invisible trap. The question isn’t whether things are working. It’s whether they’re still growing you. 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 [email protected] Logo and other art courtesy of Andy Reddout

There's something nobody talks about — the phase that comes after you feel out of your depth. That messy middle phase. Not the fear itself. Not the doubt. But what happens when those things slowly start to lift. When the role that once felt impossible starts to feel like yours. In this episode, I go back to those early years leading the Identity team — and the moments that quietly shaped me. The first time I stood in front of a thousand people and didn't feel ready. The leadership decision that kept me up the night before I made it. The crisis that lasted through the night, and what I learned about showing up when you can't fix anything directly. And the customer trip overseas where I finally started to find my footing. Because confidence doesn't arrive before the moment. It comes from the moments themselves. That's what it means to learn to swim. For email updates signup 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 [email protected] Logo and other art courtesy of Andy Reddout

As I step into a new chapter, I’ve found myself reflecting on the last time I felt truly stretched—not just challenged, but uncertain. It takes me back nearly a decade, to one of the biggest moments in my career: stepping into the role of leading the Identity team. On paper, it was an incredible opportunity. In reality, it was that - and so much more. The scale was bigger than anything I had done before.  The expectations were higher. And for the first time in a long time… I wasn’t sure if I was ready. In this episode, I go back to that moment—what it felt like to step into a role before you feel fully prepared, to lead without having all the answers, and to navigate the quiet doubt that comes with real growth. Because sometimes, the moments that shape us the most… are the ones where we feel the least certain. For email updates signup 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 [email protected] Logo and other art courtesy of Andy Reddout

What happens when your decision becomes public — and everyone has their own interpretation? In this episode, I share the reactions that followed my announcement to leave Microsoft — from a heartfelt message from a junior engineer to unexpected labels like “retirement,” and the questions that made me pause. This episode explores what it means when a private decision becomes public. And how to stay grounded when your path doesn’t look the way others expect. For email updates signup here. For video episodes, visit our podcast on YouTube or Spotify. Follow us on LinkedIn, Instagram, and Facebook. Send your feedback and suggestions for future episodes to [email protected] Logo and other art courtesy of Andy Reddout

After 28 years at Microsoft, Joy Chik faces a question most leaders eventually encounter: what comes next? In this episode, Joy reflects on the final stage of her sabbatical — exploring the startup and venture ecosystem, rediscovering the energy of experimentation, and confronting the emotional weight of leaving a place that has shaped her identity for decades. It’s a story about risk, belonging, and intentionally designing the next chapter. Because sometimes the hardest decisions aren’t between good and bad — but between what has been home and what is calling you forward. For email updates signup here. For video episodes, visit our podcast on YouTube or Spotify. Follow us on LinkedIn, Instagram, and Facebook. Send your feedback and suggestions for future episodes to [email protected] Logo and other art courtesy of Andy Reddout