Failing Forward HQ

From Withdrawal to Wisdom: Failing Forward as an Enneagram Type Five


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Enneagram Type Fives are thoughtful, perceptive, and deeply insightful leaders. But when failure, overwhelm, or disappointment hits, their instinct is often to withdraw.

In this episode, we explore how Type Fives respond to setbacks—why retreat can feel safer than engagement, and how awareness transforms isolation into wisdom.

You’ll learn:

• How Type 5 patterns show up under pressure
• When thinking becomes hiding
• The leadership strengths of a healthy Five
• How stillness supports embodied growth
• What it truly means for a Type Five to fail forward

Failing forward isn’t about forcing yourself back into action. For Type Fives, it’s about gently re-engaging life without abandoning your wisdom or overwhelming your nervous system.

Be sure to also listen to the companion stillness practice episode for integration.

And for deeper reflection, visit the blog at www.failingforwardhq.com.

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Failing Forward HQBy Lady Jaye