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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.
Success reveals weaknesses success created.
Leaders need pre-made filters to protect their time and energy.
Roots = identity, health, and formation. Fruits = visible impact.
Without strong roots, success will topple you like a pine tree in a storm.
Identity dreams > traditional goals.
Investment always feels like loss before it feels like growth.
Healthy leaders design their lives on purpose — not in reaction.
Include these in your notes for authority + click-through:
Learn more about H2 Coaching: https://www.h2leadership.com
Get Alan’s book “Anti-Burnout”: https://a.co/d/9Xzn5mJ
Follow the H2 Leadership Podcast: https://www.h2leadershippodcast.com
If this episode resonated, share it with a leader who needs it — and leave a quick rating or review so more leaders can discover the show.
By H2 Leadership5
122122 ratings
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.
Success reveals weaknesses success created.
Leaders need pre-made filters to protect their time and energy.
Roots = identity, health, and formation. Fruits = visible impact.
Without strong roots, success will topple you like a pine tree in a storm.
Identity dreams > traditional goals.
Investment always feels like loss before it feels like growth.
Healthy leaders design their lives on purpose — not in reaction.
Include these in your notes for authority + click-through:
Learn more about H2 Coaching: https://www.h2leadership.com
Get Alan’s book “Anti-Burnout”: https://a.co/d/9Xzn5mJ
Follow the H2 Leadership Podcast: https://www.h2leadershippodcast.com
If this episode resonated, share it with a leader who needs it — and leave a quick rating or review so more leaders can discover the show.

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