Episode 7: When Success Becomes a Birdcage

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

What is The Knowing Moments?

The Knowing Moments is a podcast about the quiet turning points that shape our lives and careers. Hosted by Joy Chik, a senior Microsoft technology executive who spent nearly three decades building products used by billions of people worldwide. Through real life stories, the show explores moments of clarity that don’t arrive with certainty or fireworks — but once felt, can’t be ignored.