Interview with Ashton Whitmoyer-Ober (Enneagram 2)

Today I’m going to be talking with Ashton Whitmoyer-Ober! If you don’t know her yet, she is the beautiful soul behind “Enneagram Ashton”, is the author of three books, and is just a fabulous human being! Let’s get into it. Here’s my interview with Ashton!

So just as an introduction for those that haven’t met her, Ashton Whitmoyer-Ober has a Bachelor of Science in psychology. She started her own retail business at the age of 22 and ran it for about five years before deciding to go back to school for a Master’s Degree of Arts in community psychology and social change, and now she is an amazing Enneagram coach, teacher, and author of three books (all of which have come out during the pandemic!) And on a personal note, I consider her one of the people who has cheered me on from the sidelines in my own work with the Enneagram, and has been an inspiration to me as I’ve watched her journey. So, welcome, Ashton, to the Christian Enneagram Podcast!

 I feel like I could cry, listening to you talk about me; but then I’m also an Enneagram Two; so at the same time I’m like, “Tell me more! Tell me more about how I’m a wonderful soul!” I just love being able to watch so many people take on space as their own, so it has been one of my favorite things to cheer people on and watch their growth occur. It’s been an honor to see yours.

I can definitely feel that one of your biggest values is lifting other people up, and I’m sure that anybody who has come in contact with you is as grateful for it as I am. So, what we’re going to talk about today is probably a little bit obvious: We’re going to talk about the Enneagram! First, though, I’d love to know a little more about you, Ashton. How did you find the Enneagram? What did that look like? 

So like you said, I decided to end my retail business in 2017 and went back to get my master’s degree, but was still working full time in the “helping field” as I like to call it, so it took me a little bit longer than the traditional “two-year program.” But it was during that program that I was learning about personality-typing systems, and I was introduced to the Enneagram! What I loved about it was that it could be used as a tool to better understand other people, and that it wasn’t just about who you are, but why you do what you do. It was so impactful for me to witness the changes that I saw in my relationships with other people when I applied the Enneagram; we were able to understand each other more deeply and offer empathy, which are some of my core values.

When I came out of my master’s program, I was still working in the field of sexual and domestic violence prevention, which I had always done, and I tried to do both that work and my new work with the Enneagram by just helping people “on the side.” But after creating Enneagram Ashton and seeing how quickly it grew, I decided I just wanted to focus my efforts on helping people become the best version of themselves and also strengthen their relationships with other people. So that’s what took me down that path and allowed me to be able to meet so many incredible people and develop relationships. I’m so thankful for the journey!

So you found the Enneagram as a part of your own education and your own learning, which is the way I think a lot of people come to it; and then the two other ways I’ve heard people find it are through enthusiastic friends sharing it, or coming to it like I did: in a moment of crisis, needing something to help you where you are at.

And I think that is the truth for a lot of people: we receive the information that we need often. And that is my hope for all of us who are on the platform of sharing about the Enneagram; that we are sharing the things that people need to hear and see.

That is so true! The vessel that it comes in or the package that we find it in isn’t as important as us needing to find it.
I think that people sometimes think that the Enneagram is just for fun, and while there are fun things to it, there is this deeper knowledge, like you said, of why we do what we do. We get to become a part of adjusting or influencing how we see and respond to the world. The behaviors that come out become more under our control if we know why they happen, and we can help our needs be met in healthy ways when we understand that we may not be seeking them in a healthy way (without belittling the need itself!)
So we talked about how the Enneagram shows us a lot about ourselves, and I think that is so true. What is one of the most important or impactful things that you’ve learned about yourself while on your own Enneagram journey?

A lot of people–my family, my husband, my friends– would have sworn up and down that I was a Three, because I look a lot like a Three and I have a lot of behavior characteristics like a Three! But for me, it always came back to those messages of wanting to feel loved, wanted, needed, appreciated… all of those things about a Two. I think people assume that those of us that are on a very public platform talking about the Enneagram and helping other people with it must have our entire journey figured out; that we are the healthiest versions of our type. But it’s a journey that I’m constantly on!

My best friend in the entire world right now has breast cancer, and she just completed her third chemo treatment yesterday. Usually when she has her chemo, I teach in the morning and then I go straight to her treatment center to be with her for the last leg, and then drive her home. This last time, though, she didn’t need me. And I was like, “What do you mean you don’t need me?” I had that moment of, “Oh yeah, this is my Enneagram, a hundred percent.” That’s part of the reason why we learn, is so we can start to recognize those feelings!

So I started to have those feelings, and I asked myself, “Why am I feeling unneeded in this moment?” And I was able to move through that and recover; whereas previously, before having the knowledge of the Enneagram, I would not have been able to move past those feelings. So to answer your question, I think the awareness of some of those moments has been the most impactful thing for me; the awareness of “Why am I doing this for somebody else? Am I doing this because I want to feel needed, and I want the gratification that I’m getting? Or do I actually want to be the helper in this instance?” Also, really just learning how to say no, which I’m not perfect at; I’m getting better! But I think that’s, again, part of the growth. 

Thank you for sharing that, because I think that a lot of times people do think that we have it altogether, as the people who kind of guide or teach or coach around the Enneagram; but I think that self-awareness piece that you talked about is really what it is that gives you the ability to be intentional. Without the awareness, we can’t be intentional; we’re kind of just tied to our motivations “driving the car” while we are just in the passenger seat. 

I think what’s interesting is that I always assume that people won’t tell me what they need, because I am not good at sharing what I need. I was talking to my friend’s sister and told her, “I just need you to tell me it’s okay for me to not go.” And she explained, “She would tell you.” And that was a big realization for me! “She would tell me if she needed me.” I assumed that I needed to go because she wouldn’t tell me if she needed me, because that is a Two’s tendency. So that’s part of what’s been so impactful about the Enneagram, too, is realizing that other people do things differently than me, and learning that my natural reaction is going to be different than somebody else’s.

That is such a big piece, the awareness that our perspective is one valid perspective and how we come up with the expectations of others is really based on what we know about ourselves. We still think that other people will react and behave like we would, or have the same longings and desires that we do, and that becomes the way that we interact with people. Being able to see other people a little more fully and clearly is such a beautiful gift, because not only does it allow us to work through the things that are ours to work through, but it doesn’t put any of that expectation on other people to have the same things they need to work through. They are going to have their own set of things to grow in, and that gives everybody in the the relationship this beautiful freedom to be themselves, as well as allowing others to be themselves and work on their relationship when it needs to be worked on. Knowing that you’re free to be you, and I’m free to be me, has been one of my most freeing things with the Enneagram as well. So, thank you for sharing all of those! I know that is going to speak to a lot of people, no matter where they find themselves on their Enneagram journey.

I’d love to know, how has using the Enneagram in your personal life affected your spiritual journey?

So my spiritual journey has been an interesting one, I will say, and I feel like it’s definitely been impacted over the past several years; and the Enneagram has been a tool to remind me of things, if that makes sense. It reminds me of the way that I was created, of my gifts and what I have to offer people; and really to demonstrate Jesus’s characteristics and ability to understand others and to see the image and the way that they were created to be, and to value and respect that about them. I don’t think that it has been my entire journey with the Enneagram, but I think that it has been a great tool to remind me of who I am. 

Also, the key about needing to be loved and wanted is really how I have always viewed my relationship with God; I didn’t feel worthy of love and acceptance. So being able to tap into that and understand why I felt that way, and then to really embrace His love for all of us, I think has tied together as a whole the truth that He does love me! He sees me for who I am, which gives me the ability to really see all of these other people that He has gifted with different things than I have been gifted.

I totally agree! The Enneagram can show us where we are on some level: believing some lies, telling ourselves some lies, reinforcing those lies about what I need in life to be okay and the “hierarchy” that I’ve made for myself of the things that I need in life. For me as an Enneagram Type One, I need to be right and perfect. If I love some people or feel some love, then that’s alright; but I can put that into balance and recognize that it’s good to need these other things too! The way that I was created was to embrace and embody this balance of needs and meeting other people’s needs, being in community and showing love; not just in the way that I understand it to be (based on my motivations), but in the ways that, Jesus embodied and showed, and that other people can experience.

My biggest goal is to seek to understand others. I say it all the time: I just want to understand other people. And I really feel closer to Jesus when I want to do that, because I feel like that is one of His major goals as well.

Yeah. The way that Jesus showed compassion was through action, but it came from empathy and understanding; He said He would help, but did not judge who the person was, or why they were there; and that does come from a fullness of understanding, so that the people He interacted with felt known, even in ways that confused the people that were witnessing it! They would ask why He was helping a person like that, and He would reply, “No, I love them. I understand them. I know what is going on in their heart.” 

And I love that you have understanding others as an overarching goal of your Enneagram work and how you teach and write about the Enneagram, because as you understand yourself and other people better, intentionality becomes an actual possibility; whereas when you don’t seek to understand, or you just can’t understand, then being intentional is out of our reach because we are just tied to our patterns, living as we have been living, without being able to really understand the inner workings of what’s going on. And the Enneagram can help so much with that. 

So speaking of how you, how you have this goal and this reason for how you approach the Enneagram, you have written three books so far: “The Enneagram and Relationships”, “The Two of Us” which is a three-year guided couples’ journal, and then your latest one, which is “Enneagram Made Simple: A No Nonsense Guide to Using the Enneagram for Growth and Awareness.” I love that “no nonsense guide” part! I’d love to know, why did you write this book? What about it felt important to you?

 I feel like everything that I produce, there has to be a level of importance and passion for me to actually do it. People are constantly coming in to my DMS, sending me emails, asking me questions, and that’s really what this book is about! Let’s answer some of those questions; let’s talk deeply about what the Enneagram is; let’s learn about all of the types. People’s instant reaction is usually to just want to flip to their own Enneagram number in a book, but this one is really an encouragement to read all of the numbers and learn about all of them. My favorite part of the book is that there are actual exercises in there for each of the types, because we aren’t just learning this stuff to know it and then move on with our lives. The Enneagram is a complex tool, a complex system! We have to know how to use it in our life to continue to grow, and our growth levels are fluctuating all the time. One year you might feel like you’re the best version of yourself, and the next year you might be going through a challenging season. Being able to have this book as a reference guide, not just for now, but for the future to refer back to, look at the mantras, go through the exercises, and just have it to share with people who need assistance. 

I highly recommend this book. I love the exercises in it! That is one of the most important things. There are heavy, meaty books about the Enneagram, which I think are very valuable, but it’s hard to know how to apply them! Being able to put the Enneagram into this concise, relatable way of really filtering yourself in the world and others, I think is so important, and so needed in the world. So thank you for this book and “The Enneagram for Relationships.” sorry,”Enneagram for Relationships” That was the first book of yours that I read, and it is so helpful, too; I think it is so, so needed by people who might be overwhelmed by the number of available Enneagram resources and teachers. It can be confusing and overwhelming just to know where to start. So if you’re listening and you haven’t read Ashton’s books, I highly recommend that you start there, because it is such a great place to start. It gives you this way of viewing the Enneagram that’s so accessible and so deep at the same time, which is a difficult balance to achieve!

Ashton, where can our listeners find you? 

You can find me on Instagram at “Enneagram Ashton” and also my website is So it’s super easy to remember! I would love to hear from people. 

If you were encouraged by Ashton and what she shared here, definitely go let her know! As an Enneagram Two, she wants to know if you were positively impacted by what she shared here! I certainly was. I’m always encouraged by what Ashton shares and how she teaches.

Ashton, do you have any final thoughts or an encouragement, kind of breaking down what you shared with us into one thought?

I always just remind people to remove the pressure and really just take the time to sit with the information that you’re learning. You don’t need to figure out your type in 10 minutes and move on with your life; you don’t need to become the healthiest version of yourself in 24 hours; just take the time, be patient with yourself, care for yourself, give yourself grace and recognize that you were created to be this way. And that’s a true gift!

That was beautiful. Ashton, thank you so much for being here and, and we’ll talk soon. 

Enjoy this post? Have a question? I’d love to hear your thoughts in the comments or over on Instagram. If you’re ready for the next step in your Enneagram journey, grab a copy of The Enneagram for Beginner’s book (affiliate link, thank you for your support!) or enroll in Enneagram 101, the on-demand course that will help you no matter where you’re at. If Merch is what you’re looking for, check out the Christian Enneagram Shop. Happy learning and growing! ~ Kim


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