What’s the metaphorical hill you’d die on — and is it helping or hurting your relationships?

Kate Mason reunites with Enneagram expert Jackie Contessa to unpack the “nine Enneagram hills” we fiercely defend in life, love, and parenting.

They explore how understanding these deep-seated motivations can help us break patterns, improve communication, and parent more consciously.

Whether you’re a perfectionist, a helper, a challenger, or somewhere in between, you’ll find insights that spark both laughter and reflection.

Listen For

4:06 Eat the Fish, Spit Out the Bones: Take What Resonates

6:29 Type 1 (Perfectionist): Managing Impossible Standards

15:39 Type 3 (Achiever): Believing Your Own Press Release

26:24 Type 6 (Loyalist): The Doubt Cycle and Trust Issues

36:36 Type 9 (Peacemaker): Losing Self to Keep the Peace

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Connect with guest: Jackie Contessa, Personality-Based Life Coach, Enneagram Coach.

Contact Kate:

What's Your TRUE Enneagram Type?