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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Type 4: The Individualist - The Sensitive, Withdrawn Type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

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About the Podcast

Business-First Creatives
A podcast about systems, workflows, and business advice for creative service providers.
Business-First Creatives is a podcast for photographers and creative service providers who want to build a profitable, sustainable business without drowning in admin work, client experience chaos, or systems that let you down.

This show delivers clear, actionable conversations around marketing, CRM workflows, client communication, Dubsado and Honeybook automation, Airtable systems, and workflow strategies, giving photographers and creative entrepreneurs the systems that scale, operational clarity, and strategic, human-first client experiences they need to build streamlined, referral-worthy business operations that don't require working 24/7.
If you're tired of babysitting your inbox, chasing down contracts, or watching your workflows break the moment you look away, this show will help you move beyond "figuring it out as you go" and toward a creative business that brings you joy and a paycheck.

This podcast provides answers to questions like:
How do I automate my client journey without losing the personal touch?
What CRM workflows do photographers and creative businesses need?
How can I use Dubsado or Honeybook to streamline my client experience?
What systems do photographers need to save time and deliver exceptional client experiences?
How do I reduce admin time in my creative service business?
Why do my workflows keep letting me down (and how do I fix them)?
How can I build a profitable creative business that brings me joy and a paycheck?
What's the best way to communicate with clients throughout their journey?
How do I create systems that work even when I'm not babysitting them?
How can I map my client journey to convert more inquiries into bookings?

Hosted by Colie James, a Dubsado Certified Specialist, Honeybook Educator, and Workflow and Automations Guru with 10+ years helping creatives systemize their businesses—this show delivers practical, no-BS guidance for photographers and creative entrepreneurs who are ready to streamline their client journey, automate their operations, and make money from their craft.

If you're done dropping balls and ready to build a business-first creative operation with systems that scale, you're in the right place.

Find out more about Systems in Session ➡️ https://coliejames.com/systems-in-session