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.

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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.

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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.

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