Why Success Is More Disorienting Than Failure. Roots, Fruits, and the REAL Cost of Winning

2025-11-13

Most leaders expect failure to be hard — but no one warns us how disorienting success can be. In today’s episode, Alan Briggs takes us inside a live leadership session and unpacks the real, often hidden challenges that come with growth: fulfillment gaps, maturity barriers, identity drift, disorientation, burnout, and the pressure of everyone wanting a piece of your time. But this conversation isn’t about fear. It’s about forming the kind of roots that can sustain real fruit. Alan shares practical insights on: Why success often feels emptier than we expect

Most leaders expect failure to be hard — but no one warns us how disorienting success can be. In today’s episode, Alan Briggs takes us inside a live leadership session and unpacks the real, often hidden challenges that come with growth: fulfillment gaps, maturity barriers, identity drift, disorientation, burnout, and the pressure of everyone wanting a piece of your time.

But this conversation isn’t about fear. It’s about forming the kind of roots that can sustain real fruit.

Alan shares practical insights on:

Why success often feels emptier than we expect
The surprising truth that what got you here won’t get you there
How success multiplies options, noise, and expectations
Why leaders lose honest feedback when they gain influence
The difference between external fruit and internal roots
The identity dreams every healthy leader should define
How to build a life that matches the person you’re becoming
What it takes to grow without losing yourself, your family, or your soul

If you’re leading a team, building a company, or navigating a season of rapid growth, this episode gives you a framework to name what’s happening beneath the surface — and an invitation to design a healthier, more intentional way to live and lead.

Key Takeaways