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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

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 feedback@theknowingmoments.com

Logo and other art courtesy of Andy Reddout