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.

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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.

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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.

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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.

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Logo and other art courtesy of Andy Reddout

After slowing down, a new question appears: What do I want to grow into next?

In this episode, Joy Chik reflects on the space between mastery and expansion. After nearly three decades operating at global scale in the tech industry, she begins experimenting with something completely new — launching a podcast from scratch during her sabbatical.

What follows is a humbling shift from enterprise leader to beginner again.

Through this experience, Joy explores a question many professionals eventually face: when you’ve become very good at something, is continuing to optimize it the same thing as growing?

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Logo and other art courtesy of Andy Reddout

After nearly three decades at Microsoft, Joy Chik finally pauses.

In this first episode of The Knowing Moments, Joy Chik shares the story behind her decision to take a 12-week career sabbatical — not from burnout, but from a quieter realization that something needed to change.

Leading a large team and responsible for mission-critical systems, stepping away wasn’t an easy or obvious choice. Joy reflects on the resistance, the responsibility, and the internal courage it took to pause — and what the first few weeks of slowing down revealed.

From the mental “withdrawal” of constant stimulation to rediscovering curiosity and redefining productivity without constant output, this episode explores what happens when we finally slow down.

Because sometimes the first step toward clarity isn’t action.

It’s creating the space to listen.

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Logo and other art courtesy of Andy Reddout

The Knowing Moments is a podcast about the quiet realizations that change how we see ourselves, our work, and our lives. Hosted by Joy Chik, a longtime tech leader, the show explores moments of clarity that don’t arrive with certainty or fireworks — but once felt, can’t be ignored.

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