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How the Enneagram can help you personally and in your business with Ashton Whitmoyer-Ober

I am so excited to dive into today's conversation with Ashton Whitmoyer-Ober, also known as Enneagram Ashton. I've been an avid follower of Ashton’s Instagram since 2019 and have loved her insightful posts and ability to decode the complexities of the Enneagram. So today, we are diving in deeper to talk about how understanding your Enneagram profile can help you both personally and in your business.

Ashton is an Enneagram expert who is dedicated to helping people better understand themselves and others by educating them on the Enneagram. From personal experience, understanding your Enneagram type is a profoundly uplifting journey. It offers a unique lens through which we can view ourselves, our motivations, and the beautiful tapestry of human behaviour.

In this conversation, we talk about why the Enneagram isn't just another personality test. It's an ancient system that categorises individuals into nine distinct personality types. What sets it apart is its focus on motivations and underlying fears, not just observable behaviours. Ashton takes us through each type, shedding light on their desires, fears, and typical traits.

Ashton highlights how the Enneagram goes beyond surface traits and delves into the "why" behind our actions. It's an incredible tool that helps us explore our deepest motivations, paving the way for genuine self-awareness. The Enneagram isn't about confining us to a box; it's about understanding our tendencies and working towards becoming the best version of ourselves.

We also talk about how the Enneagram can support entrepreneurs and Ashton beautifully explains that by understanding our type, we can make informed decisions about areas we excel at and where we might need assistance.

For me, the most powerful aspect of the Enneagram is the awareness of yourself and others. It's a tool that empowers us to embrace our strengths, work on our growth areas, and foster more meaningful connections, both personally and in our businesses. I can’t recommend this episode highly enough and I know you’re going to get so much out of this conversation.

Topics We Covered:

[00:00:00] Kristy: Hello boss and welcome back to the Run Your Business Like a Boss podcast. To say I am excited about this conversation is an absolute understatement. My guest today is Ashton Whit Moyer Ober, who you may know as Enneagram Ashton. I've been following Ashton on Instagram since 2019, and absolutely love her posts and everything she puts out about the Enneagram.

[00:00:27] Now you may have heard me speaking about the Enneagram here on the podcast. I've also mentioned it on Instagram. And I really wanted to make sure that I brought in an expert that could help you better understand not only the different types of the Enneagram, but also how it can support you and your business.

[00:00:45] a little bit about my guest today, Ashton helps people strengthen their relationships and become better versions of themselves through the framework of the Enneagram. We talk all things Enneagram today, as well as how it can support you to grow personally, as well as support you in your business. It's an action packed conversation, so you're gonna wanna stay tuned right to the very end. So are you ready? Let's go.

[00:01:12] Ashton, hello and welcome to the Run Your Business like A Boss podcast.

[00:01:51] Ashton: I am so excited to be here. Thank you for having me.

[00:01:54] Kristy: Oh my goodness. I cannot tell you how excited I am to have you here. We were just sharing before before we got started today. I've been following Ashton since 2019 on her Instagram page, and I know by the end of this episode, if you're not following Ashton, you're going to want to. But I've learned so much from you, Ashton, and I love your bite-sized information around the Enneagram. So having you here on the show today is just like such an exciting moment for me.

[00:02:20] Ashton: Thank you. Thanks for having me. I'm also excited and thank you for waking up early to chat with me.

[00:02:26] Kristy: Yes. Just so you know, boss, like, it's six o'clock here in Australia. Obviously Ashton is on Eastern US time, so we had to make it work and I will do anything to make this episode a work.

[00:02:38] So Ashton, let's start with what is the Enneagram? I've spoken about the Enneagram before here on the podcast but I'd love to hear your overview of what the Enneagram actually is.

[00:02:47] Ashton: Yeah, so the Enneagram is an ancient typing system, meaning it's a personality type that separates people into nine different types. And I say ancient because it literally was developed like between two to 4,000 years ago, so it's so old that like we can't exactly pinpoint the date, that's why there's such a large range.

[00:03:08] And it's universal. So it started in the Middle East and then it kind of transported to south America and then made it over to the United States in like the sixties. So then it, you know, it hasn't really gained as much popularity until lately because of the internet and, you know, having that information at our fingertips, books being written, social media, you know, all of those different things.

[00:03:35] But it is a personality system that separates people into nine different types. The biggest difference between the Enneagram and other personality tests like DISC assessment or Myers-Briggs, is that those tests are really great at telling us like who we are, some of our behaviors, you know, maybe we're extroverted or introverted. But the Enneagram instead talks about our motivations, the why, the how, the reason behind why we behave the way that we do.

[00:04:07] Kristy: And it's so good that you mentioned that Ashton, because I'm not a big fan of the Myers-Briggs. I have done the assessment, but I do like disc because I think it is a great way to be able to identify the needs of the other person.

[00:04:21] But for me, the Enneagram really told me a story about myself that I just had a lot of questions around and I couldn't understand why and when I realized what I was, I'm a type three. Everything made so much sense, and it, I think that's the power in the Enneagram is that the, the self understanding for me, and, and we're gonna talk about team and so forth later, but I, I, I definitely felt really connected to the Enneagram much more so than a, than the DISC profile for myself.

[00:04:52] Ashton: Mm-hmm. Yeah. And they can be used together, right? Like, you can certainly, you know, think about like, I, I love any and all personality types. It just so happens that the one that I love the most is the Enneagram because. I've seen the most impact with it, but you know, you can look at the Enneagram to explain why you might have some of the, the traits from your disc assessment.

[00:05:14] Kristy: Yeah, that's interesting actually using them in combination. I never really thought about that. So you said there's nine types. Would you mind please stepping us through each of the nine types? 

[00:05:26] Ashton: Yes, of course. So the one, the Enneagram one is the reformer and the titles that I use for the types come from the Enneagram Institute. And there are multiple like titles that are out there. These are just the ones that I was trained in and and speak on. But the other titles that are out there aren't incorrect or wrong.

[00:05:46] These are just the ones that I'm going to use today. So the one is the reformer. Their biggest desire is to be seen as a good person, to be moral, ethical, right, to do the right thing. And then their biggest fear is being seen as a bad person or being unethical or, or doing the wrong thing. And so from those motivations, they're kind of known to be these like justice fighters. Right versus wrong mentality. They're rule followers. If the rules make sense to them, they're orderly and organized and fair, things like that. The Enneagram two is the helper. So their biggest desire is to feel loved, wanted, needed, appreciated, and then their biggest fear is the opposite of that.

[00:06:33] So being unloved, unwanted, not needed by people, not appreciated for the things that they're doing. And so those motivations lead to traits like being super helpful, caring, compassionate. They are known to be sensitive to others' needs and kind of just naturally know what other people need.

[00:06:52] Where they can get in trouble sometimes is they can Kind of like make themselves feel needed or make themselves be needed in order to feel needed so they can be a little needy or have a hard time saying no because they're associating their love and their worth with like what they're doing for other people.

[00:07:11] The three is the achiever. So their biggest desire is to succeed and also to be seen as capable and competent and respected. And then their biggest fear is failure. So they do fear failure the most, but then they also fear being seen as incapable or inefficient or just incompetent. And so this leads to behaviors of, you know, being driven, motivated this need to succeed.

[00:07:40] So like this drive that they have. They're goal oriented, task oriented, but sometimes they can like only focus on their own achievements. So be a little bit self-focused like a little braggy about their accomplishments and also like overly competitive. The four is the individualist. So their biggest desire is to be unique, special, significant, to like create meaning from experiences.

[00:08:07] And then their biggest fear is that something is wrong with them, that they're defective, that there's something missing in them. And so this leads to traits of, you know, wanting to be unique and original. They are highly in tune with their emotions and other people's emotions. They're pretty much the most emotional on the Enneagram.

[00:08:28] They're sensitive. Where they can get in trouble sometimes is when they are like overly emotional or they can become like moody, depressed, like getting stuck in that cycle of sadness. The five is the investigator. So their biggest desire is to gain knowledge and then they also, you know, want people to know that they know the knowledge.

[00:08:51] So they want to like be seen for the things that they know. And then their biggest fear is really like having their Energy or personal space or time depleted. So they are kind of known to be the most introverted on the Enneagram, and so they kind of keep to themselves. You might find them more like a observing in the background of things, and that's to really protect that energy level.

[00:09:18] But they are super knowledgeable. They have like a specific area of expertise typically. They know the things and if they, I call 'em like a walk-in Google search engine. Like you typically can go to them to find answers for things. The six is the loyalist. Their biggest desire is to seek security and guidance from people, and then their biggest fear is typically fear itself.

[00:09:45] So they have the strongest relationship to fear. But then they also fear like being without support, security, guidance, things like that, like their name suggests, they are extremely loyal, they're responsible, they're highly prepared for all things to happen or all things to go wrong, and that's because of that fear that they have, that things will just spiral and they won't be able to kind of get them back under control.

[00:10:10] So, They're known to have like plan A, plan B, plan C to anticipate things that could go wrong. And they're often stereotypically known for like their anxiety, but it's not your typical like generalized anxiety disorder. It's mostly like what could go wrong or like experiencing self-doubt or worry. The seven is the enthusiast.

[00:10:35] So their biggest desire is they ultimately, like, they want to be happy, but most of the time they're seeking contentment. So they're known to kind of, you know, want to experience new things, go on adventures, like they're the most extroverted of the Enneagram, and that's because they're seeking contentment.

[00:10:55] And then their biggest fear, they do have fomo, so they do have that fear of missing out, but ultimately they're trying to avoid any sort of emotional pain or negativity. So they don't like any feelings of sadness or discomfort or boredom, and so then they want to experience things to kind of avoid that.

[00:11:16] So they are known to be spontaneous, impulsive, adventurous, kind of just lovers of life and joyful and optimistic. Sometimes they struggle to focus, though. Sometimes they are just so scattered and, and thinking about the next thing that they struggle to focus on the present moment.

[00:11:33] The eight is the Challenger. So their biggest desire is to protect themselves and other people, specifically people that they feel need protected, like vulnerable populations. People who, you know, just appear to be like weaker than them, for lack of better words. And then their biggest fear is being seen as weak, powerless, or controlled in some way.

[00:11:59] And so they don't want to appear as weak. And so then this leads to them having this strong exterior that is typically hiding like a highly vulnerable interior, but they associate vulnerability with weakness. So they don't like to show that they're vulnerable. But eights are very honest, direct, decisive, assertive.

[00:12:23] They know what they want and they know how to get what they want. They are great in leadership positions and they excel in you know, just leading in that sort of way. Where they can get in trouble is where their assertiveness turns to aggressiveness. And then they can sometimes be perceived as a bully in that sort of way.

[00:12:41] And then the Enneagram nine is the peacemaker. Their biggest desire is to maintain a peaceful environment for themselves, for the people around them, and then their biggest fear is conflict, so they fear conflict the most. That doesn't mean that other types don't fear conflict, it's just for nines that makes up their biggest motivation.

[00:13:03] So they fear conflict and being separated or removed from the people that they love. this leads to, you know, nines are peacemakers at, at the heart of it, so they are extremely peaceful. They're mediators. They go with the flow. They're known to be approachable and nonjudgmental and just really easy to get along with them.

[00:13:26] But where they can get in trouble is because they're trying to like please others, they sometimes silence their own voice or they, you know, don't make their opinions known because they just want to please others, so they merge into others' expectations of them.

[00:13:41] Kristy: That was so helpful. I think even just having that little overview of each and every type has. You know, I like, I've, I know a lot about my own type, but even just hearing about the other types, I know a little bit about the nine. 'cause my husband's a nine. So obviously, the closest person to me, I wanted to understand a little bit more, but I think what's really interesting about the Enneagram or what I've personally found really helpful is the spectrum that is the healthy to the, you know, not so healthy, let's say. And I think that that's what's really important about I mean, you touched on that for each and every type just then around, you know, what are the things that can cause a negative impact for them as well as a positive impact.

[00:14:28] Do you think that by knowing your Enneagram and knowing that spectrum, do you think that that's a a helpful way to help you as an individual to be aware of your own motivations and behaviors and be able to make a shift? Like what are your thoughts on that?

[00:14:46] Ashton: Yeah. I think a huge piece of the Enneagram is the self-awareness piece, right? Of if we know these things about ourselves and if we're honest with ourselves about where we fall on that like continuum, then we can change our behaviors and move into a more healthier version of ourselves.

[00:15:05] Kristy: Yeah, definitely. And it can be quite confronting I think when you look at like, like when you look down the scale, like at the top of the scale, it's great for I think every single type.

[00:15:16] Ashton: Mm-hmm.

[00:15:16] Kristy: But you know, I mean this is the thing when it's a blind spot, it's the same in business. When it's a blind spot, you can't do anything to fix that problem. But when it's something that you are, as you said, aware of, it's something that you can work on and move through and then move up the scale and then be able to live your happy and best life.

[00:15:35] Ashton: Yep. Absolutely. Yeah. And that's really the point is, you know, and that's what I love about the Enneagram and, and like I said, I love all personality tests and so I'm not like bashing one or anything, but I think about the Enneagram. It's not just like, oh, this is who you are now go on with this information. It's like, this is who you are, this is where you want to be, and how can we like use this information to become a better version of ourselves.

[00:16:01] Kristy: absolutely, and I think that anyone who's listening to this podcast has a desire for growth, has a desire for growth in business, and a desire for personal growth. And so knowing that this isn't a something that's fixed and it's nothing that you can change and knowing that you can actually do something to improve yourself is such a positive thing. So speaking about from, from an entrepreneur perspective, how could the Enneagram support entrepreneurs?

[00:16:27] Ashton: In so many different ways because you know, there are strengths and what I like to call, like areas for growth for each of the types. And if we, again, know what our areas of growth are, then we can focus in on that. But for entrepreneurs specifically, you know, it's being able to pull from what are our natural strengths as an Enneagram three, as an Enneagram two to be able to be an entrepreneur or to thrive in this area of business?

[00:16:56] And what do I need to, you know, get help for what do I need to delegate specific tasks that might not come as naturally for me and get other people, maybe on my team or on board to help me that can pick up the slack in some of the other areas.

[00:17:12] Kristy: Yeah. I love that so much because I think that, many of us are very capable of all things, but why wouldn't you want to, especially in the messy middle stage. I get it in the startup stage where you do actually need to do all the things because you've got more time, then less money. But at this stage of business, why wouldn't you wanna bolster your team with the areas that maybe you are not as strong in?

[00:17:35] Ashton: Right, totally. So like for example, I'll use myself, so I'm an Enneagram two, and so I'm really good at like serving my clients, like serving my clients and showing up for them is like, as a two, like that's what I live to do. It's why I got into the Enneagram as a whole, but the organization piece, not my forte, right?

[00:17:56] Not the area in which I thrive. And so instead I found an assistant who can help me with that organizational piece. I have a bookkeeper who can keep my books organized, you know, and I know that this is a privilege to have in your business, right? And we're not talking about like those startup stages where you're like, I need to do everything my own because I don't have any money to outsource for that. But it's being able to really highlight like, what am I good at naturally because of my Enneagram type and who I am and where do I need to fill in those gaps with other people?

[00:18:30] Kristy: Yeah, that's awesome. 'cause I think sometimes we think about it and we're gonna talk about that next. We think about it as in, the leadership of other Enneagram types, but it's actually about plugging in maybe some of those gaps is what you are talking about here.

[00:18:44] Let's talk about team. So, business owners at this stage of business are starting to bring in team members, and I'm curious to know from you how, because I've used the disc as in a leadership capacity, but I've never really used Enneagram in a leadership capacity because I don't have team members inside of my business, I outsource. But I'm curious to know how could the Enneagram support leaders to better support their team?

[00:19:10] Ashton: Yeah, so similarly, like there are going to be Enneagram types that are more naturally good at leading than other types. Like I said, when I was talking about the different types, like eights will lead all day every day, like they're great at it. Whereas somebody who might be, you know, a four. Like they can be great leaders.

[00:19:31] They just might need to work at it a little bit more than eights do. Which is fine, but it's knowing that, right? It's knowing that, and knowing not just, you know, how to lead people based on your Enneagram type, but then knowing the types of the team to know how they need to be led. So for example, if you have a two that's on your team, you know, like knowing that their motivation is to feel loved and wanted and needed, you know, how do you lead that person knowing that, you know, they might consistently sign up for new tasks or continuously want to like, do things for you in order to feel needed. How do you help them kind of form those boundaries and set those lines of knowing how to balance those tasks.

[00:20:20] Kristy: Yeah. How would you suggest that business owners would learn what type their team members are? What's the best approach there?

[00:20:30] Ashton: I am a huge believer in just like utilizing the Enneagram from the start. So whether that be, you know, having a meeting or a conversation of like, Hey, we use this system in my business, like let's sit down and, and see if we can figure out what type you are. Like there are many tests that are out there, and tests are like a great place to start, but ultimately it's up to people to figure out why it is that they do the things that they do.

[00:20:58] And sometimes tests just can't pick up on that, right? Like they're focusing in on Behaviors versus motivations. And so, you know, encouraging them, like presenting them with information, take a test. But then how do you dive deeper into those core fears, like I talked about, are those core motivations?

[00:21:18] And so just setting the scene early on that this is something that we do and we focus on to better understand each other. Like not just for me to understand you, but I want you to understand me as a leader and so on and so forth.

[00:21:33] Kristy: I love that because I think that often you know, it sets the stage for a really positive relationship because if, say for example, you as a leader do or say something that maybe doesn't feel congruent with the other team member that's a totally different type, then at least there's an awareness that the motivation or the behavior wasn't a reflection of the way that they would behave or that it's coming from that same place of intention, I suppose, is more so what I'm saying here.

[00:22:04] Ashton: Yeah. Yeah, absolutely. And it kind of just gets everybody on the same page and understanding like the intentions of each other.

[00:22:12] Kristy: Which is so big, like I think there's this quote, I think it's a Dave Covey quote where he says, We judge ourselves by our intentions and we judge others by their actions, and this is just such a great way to maybe get underneath that rather than just thinking everything through our lens, which is very specific.

[00:22:33] Ashton: And that's sometimes why I refer to the Enneagram as like nine lenses because it is like nine different ways that we view the world, that we view projects, you know, and understanding you know, people's motivations does kind of, put words to intentions, right? That I might not do something or work on a project the same way that somebody else does. We're watching their actions and getting frustrated by their actions or annoyed by their actions and not understanding like the motivations behind those actions. And that's really what like the knowledge of the Enneagram can do.

[00:23:10] Kristy: Yeah, The Enneagram has obviously exploded in recent years, but this is, as you said, this is an ancient type of profiling. This is an ancient type of understanding, people's motivation. So this is not something that's just come along in the modern era and I think that in of itself is so powerful and something that you can know that there's so much strength and data and history behind.

[00:23:37] Ashton: Yeah, absolutely. And you know, like one person, so one time asked me like if I created the Enneagram, and I was like that, like absolutely not. Like, that's so funny. But you know, it kind of solidifies the system as a whole because you're able to, you know, trust that this has been around for such a long time and it's not something that just was like created 50 years ago and then we're like bringing it into the modern day. It's something that has been around for literally since the Stone Angels.

[00:24:07] Kristy: Yeah absolutely. And I think I, I don't know, I'm really interested in this is, this is probably not something that you cover, but I'm really interested in the crossover between neuro type as well as personality type. So, you know, neurodiversity in conjunction with personality type as well. I mean, that's like a whole other episode, I mean it's just so interesting. I think the biggest piece in all of this is awareness of others and self-awareness. If you've got that, change can actually occur. It's the same in business. Change can occur from that place, but without that, you're kind of running blind.

[00:24:42] Ashton: Yep. Absolutely. It's just really important I think in business to like know who you are and know what you have to offer. And like I said, to know those strengths and the things that you're naturally good at, and to be honest about the things that you're not as good at. And, and I think sometimes, like in society, we just think we need to be the best at every single piece of life. And it's the same in business. We feel like we need to be the best and I think it's because of those startup days where you're like, I have to do it all. Like I don't want to, but I have to. And so then we just continue to go through thinking like, I need to be the best at things, but it can be really freeing to own up to the things that you're not as good at, you know, and the things you need to work on.

[00:25:24] Kristy: Yeah. Absolutely. So for my listener today who might like to learn more about the Enneagram, where would you suggest they go Ashton?

[00:25:34] Ashton: Some of my favorite resources, like I mentioned before, the Enneagram Institute is a great resource. Truity is a great resource, but obviously check out my Instagram page, which is Enneagram Ashton to follow along and to learn more about your type and just see you know, the different ways that you show up in the world and the different ways that other people do as well.

[00:25:56] Kristy: And do you support people like one-on-one as well? If they're wanting to learn a deeper dive into the Enneagram?

[00:26:03] Ashton: Yeah, so I help people figure out their type and then if they want to, you know, really see like true change using the Enneagram and maybe they're wanting to just see all that the Enneagram has to offer them in, in pulling out those strengths and areas for growth. Then I do some one-on-one coaching as well, and then I also have a course and some digital products. So definitely the place to go if you wanna learn all things Enneagram.

[00:26:29] Kristy: Yeah, so if you wanna know more, head over to Ashton's Instagram page. As I said, I've been on that page since 2019. I absolutely love it. I love the way that you package up just the different types in different contexts as well. It's just such a consumable way to learn about the Enneagram. Great place to start. And then as Ashton said, if you wanna go deeper and have that more tailored support in how the Enneagram could work for you as a business owner, or if you're building a team, head over to Ashton's website to learn more. All of that's on the Instagram bio page, but I will also tag the details down in the show notes, but Ashton, do you wanna just quickly share your handles and where we can find you?

[00:27:11] Ashton: Yeah, you can find me @enneagramashton. It's E N N E A G R A M A S H T O N. That's enneagram and Enneagram ashton on Instagram and all other social platforms.

[00:27:26] Kristy: Oh, I love it. Well, thank you Ashton, so much for joining me today. I just am so excited to bring more of the Enneagram to our bosses here so that they can learn more about themselves and it can have the same impact on them as it has on me. I have to say, I've never felt more seen and understood when I learned about my Enneagram. So I really hope that you get on board and you can, you can learn from Ashton also, and you can really start to have that self improvement and self growth.

[00:27:56] Ashton: Thank you. Thanks so much for having me, and I'm excited to meet all of your listeners.

[00:28:01] Kristy: And to you boss, thank you so much for joining us for today's conversation. I hope you loved it as much as I did, and that it gave you a little bit of insight into the power and the value of the Enneagram. I love that Ashton uses the Enneagram in conjunction with other personality profiling tools, but as I mentioned in this conversation, Honestly, learning more about myself through the Enneagram has been deeply transformative.

[00:28:30] Enneagram is an excellent tool for better understanding your motivations, and that, as Ashton described in this conversation, is the fundamental difference between the Enneagram and any other personality style. So if you want to learn more, do head over to Ashton's Instagram page over to her website, to learn more about how she can support you and your business. Now if you'd loved this conversation, please go ahead and take a screenshot of wherever you are listening to it and tag both Ashton and I. Because we would love to hear your takeaways from this episode.

[00:29:05] Boss. As always, I appreciate you joining us for this conversation. I look forward to chatting with you next week.

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About your host, Kristy

Hi, I'm Kristy, thank you for tuning in to the Run Your Business Like a Boss Podcast. My purpose for the podcast is to help Business Owner’s in the growth stage of business (messy middle) have a sustainable business, they love.


I’m an online business coach, based in Brisbane, Australia. I provide 1:1 business coaching, to Service Based Online Business Owner's and a group coaching program commencing in 2022. I believe whole heartedly that having a Business Coach is what gives you the competitive edge. As your coach I support you to overcome challenges quickly, uncover blindspots and make business decisions with confidence and clarity. All of which keeps you moving forward and maintaining momentum. 

As your Business Coach, my role is to help you organise and formulate your ideas, turn them into a goal and then into an actionable plan! All while meeting you where you're at and providing you relevant tools and support along the way.


Thank you for tuning in to the Run Your Business Like A Boss podcast!

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