The Enneagram with Ashton Whitmoyer-Ober (ep 130)

boutique business tools growth the inventory genius podcast May 22, 2023

I'm so excited to talk about the Enneagram with expert, Ashton Whitmoyer-Ober. Ashton's sharing about her work with this amazing tool. She's a psychologist by trade and uses the Enneagram to help people better understand themselves and others. Join the conversation as I talk to her about how we can use this tool to become our best business selves.


How can we use the Enneagram in our work as entrepreneurs and business owners?

The Enneagram isn't about your behaviors. It's really about your motivation - it's about your biggest fears and your biggest desires. For entrepreneurs and business owners, it's not about the characteristics you have that make you a good business owner, it's about what motivates you and what holds you back. Through the Enneagram, we can understand that we have these parts of ourselves, and we can learn to rely on the strengths that come naturally to us and change the behaviors we don't like. 

When we know our biggest fears and desires it helps us understand why we're asking certain questions and why we're avoiding certain situations. We can pinpoint where we struggle and where our strengths lie. This helps us change our mindset as necessary in order to grow and achieve goals.


Let's talk through the different Enneagram types:

Type One is the Reformer. Their biggest fear is being seen as a bad person and not doing right thing. Their motivation or biggest desire is to be right, good, moral and ethical. As business owners, type ones thrive on structure, routines, systems and organization. They're going to always make sure they're doing the right thing.

Type Two is the Helper. Their biggest fear is being unloved, unwanted, unappreciated. Their motivation or biggest desire is to feel loved, wanted, appreciated and needed. As business owners, type twos thrive when they're helping other people. They may be passionate about serving a population or helping in some specific way. In their interaction with teams, type twos often play a supportive role. They look to fill in gaps and help as needed.

Type Three is the Achiever. Their biggest fear is failure and being seen as incompetent or incapable of doing something. Their motivation or biggest desire is to succeed and to be seen as capable, confident and successful. Type threes tend to take on more projects and work because they tie their value to what they're doing. They care deeply about respect and status.

Type Four is the Individualist. Their  biggest fear is that something's wrong with them or that there's no space held for them. Their motivation or biggest desire is to be seen as unique, special and significant. As business owners, type fours will only take on work about which they're passionate. They thrive on passion and things that interest them, and they want to be a unique part of a community. Type fours are great at meeting people where they're at and are often in tune with the emotions and feelings of others.

Type Five is the Investigator. They are the most introverted and tend to keep to themselves. Their fear is depletion. They need personal space, resources and energy. Their motivation or biggest desire is to be knowledgable and to be seen as competent. As business owners, type fives tend to be in the background observing rather than participating.

Type Six is the Loyalist. Their biggest fear is fear itself or to be without security and guidance. Their motivation or biggest desire is to feel safe and secure. Business ownership can be really hard for type sixes. They need to be able to plan and prepare before taking risks and moving forward.

Type Seven is the Enthusiast.  Their biggest fear is missing out or being trapped in negativity. Their motivation or biggest desire is to feel contentment. As business owners, type sevens are great at generating ideas and coming up with new things. They are typically well liked and enjoyable to be around.

Type Eight is the Challenger. Their biggest fear is being weak, powerless, or controlled in some way. Their motivation or biggest desire is to protect themselves and others. As business owners, type eights are natural leaders and are known to take the lead when working on teams. They like to get things done yet sometimes have a hard time delegating. Type eights are typically champions of their people.

Type Nine is the Peacemaker. Their biggest fear is conflict or being separated from the people they love. Their motivation or biggest desire it to maintain a peaceful environment. As business owners, type nines are able to see multiple prospectives and sides but can have a hard time making decisions and voicing their opinions.


Ashton's a Type Two and has a huge drive and motivation to help others. She works with individuals and with groups to improve team dynamics. She loves seeing people learn about who they are and how to effectively use their voice.

Coaching sessions with Ashton start at ground zero. Ashton helps people figure out their Enneagram type through testing and conversation. From there, Ashton works with clients to overcome barriers and roadblocks. Knowing your Enneagram type helps with decision making. It helps you realize your natural talents, strengths and passions.

Ashton's written many books and loves the process. As far as one she recommends? The Enneagram Made Simple is a great handbook and starting point. 

And Ashton's parting words? If you're just discovering the Enneagram, be gentle with yourself! Some of the qualities described can be like a punch in the gut. Take in all of the knowledge you can, see what resonates with you, and go from there.


Here's a glance at the episode:

[2:32] Ashton shares about her background and about how she found the Enneagram.

[3:25] Ashton explains how entrepreneurs and business owners can use the Enneagram.

[17:30] How did Ashton decide to become an Enneagram coach? What's a success story?

Click here to listen to the episode.

*Don't forget to leave a review of the episode on your favorite streaming service.


Work with Ciara

Get Going with the Quickstart to Inventory Genius - (save $100 when you use code, "PODCAST")

Book a Consult Call -

Read the First Chapter of my New Book -


Connect with Ashton:

Website -
Instagram - 


Questions? Want to learn more about working with me? Please feel free to get in touch by emailing me at [email protected].

Get tips and trainingsĀ delivered to your inbox.

Weekly bite-sized advice from Ciara Stockeland.