Episode 224

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Published on:

10th Jul 2025

How the Enneagram Can Supercharge Your Self-Awareness with Ashton Whitmoyer-Ober

If you've ever wondered why you do what you do, the Enneagram might just hold the answers. In this episode, Ashton Whitmoyer-Ober of Enneagram Ashton joins us to talk about how this ancient typing system can transform your business, relationships, and self-awareness. Ashton breaks down how to go beyond the test results by understanding motivation, wings, and behavioral patterns, allowing for authentic transformation in business and life.

Explore the Enneagram Types

Type 1: The Reformer - The Rational, Idealistic Type

Type 2: The Helper - The Caring, Interpersonal Type

Type 3: The Achiever - The Success-Oriented, Pragmatic Type

Type 4: The Individualist - The Sensitive, Withdrawn Type

Type 5: The Investigator - The Intense, Cerebral Type

Type 6: The Loyalist - The Committed, Security-Oriented Type

Type 7: The Enthusiast - The Busy, Fun-Loving Type

Type 8: The Challenger - The Powerful, Dominating Type

Type 9: The Peacemaker - The Easygoing, Self-Effacing Type


Find It Quickly

01:29 - Meet Enneagram Ashton

02:10 - Ashton's Background and Transition

04:12 - Understanding the Enneagram

06:30 - Personal Experiences with the Enneagram

11:39 - The Role of Tests in Enneagram Typing

17:20 - Healthy vs. Unhealthy Levels

26:47 - Using the Enneagram in Relationships


Mentioned in this Episode

Ashton’s Instagram: @enneagramashton

Ashton’s Website: enneagramashton.com

RHETI Enneagram Test: enneagraminstitute.com/rheti

Truity Enneagram Test: truity.com/test/enneagram-personality-test

Show artwork for Business-First Creatives

About the Podcast

Business-First Creatives

Every creative deserves to turn their craft into a business that brings them joy and profit. Here you'll find a no-BS approach to what it takes to put the business first, prioritizing the systems and strategies that will actually move the needle and ensure your creative business is profitable rather than an expensive side-hustle. Your host is Colie James, a Disney-loving family photographer, and filmmaker turned Workflow and Automations Guru who helps creative service providers automate their sh*t, reclaim their time and get back to living!