Episode 39 – Ian Cron, Entrepreneur and Enneagram Coach

To start a new project, a new season, or even a new business – we have to know ourselves. We have to know what drives us and what hinders us. And one of the best resources for discovering our core motivations is the Enneagram. This week, Jessica goes on an emotional journey with Enneagram master, Ian Cron. Jessica and Ian chat about what the Enneagram means for the “starter,” and how we can all lean in and start going scared!

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Jessica: Hey there. It’s Jessica Honegger, founder of the socially conscious fashion brand, Noonday Collection, and this is the "Going Scared" podcast," where we cover all things impact, entrepreneurship, and courage. This week, we are continuing our series of shows that dig into what it looks like to start, to begin, to take the proverbial plunge.

As the founder of Noonday Collection, a huge part of my role is sharing the Noonday Collection Ambassador opportunity. Becoming a social entrepreneur with Noonday involves answering that crucial question, "Where do I even begin?" And so, I’m constantly helping women take those first steps into the unknown. This whole topic is what catalyzed the idea behind this podcast series, what we’re calling our Starter Series.

So, I wanted to have Ian Cron, an enneagram guru, on the show so that he could talk to us how the enneagram specifically can help us become aware of who we are and what may be standing in our way of starting. Ian is the best-selling author of multiple books, most recently and notably, "The Road Back to You: An Enneagram Journey to Self-Discovery." It was co-authored with Suzanne Stabile, who was also a recent guest on "Going Scared." So, if you need more of a primer on the enneagram, go check out that episode with Suzanne Stabile on "Going Scared" and you can check out Ian’s podcast called, "Typology." It’s a wildly popular podcast that explores the mystery of the human personality and how we can use the enneagram typing system as a tool to become our most authentic selves.

So, if you really wanna do some enneagram deep dives, that is where to go. We do a deep dive on this episode. So, if you’re completely lost on enneagram, you really may wanna go listen in on a primer first. Ian is a four on the enneagram, which is usually called the individualist, and I am a seven, usually called the enthusiast. And sevens often live in our heads while fours live in their hearts. So, we ended up doing a deep dive into how to take the journey from our head to our hearts.

We’ll also be talking about what holds us back from doing the thing, getting going, getting moving. And this episode, Ian helps us to become self-aware starters. We all want to be self-aware. Awareness is really the beginning of becoming aware of what is holding you back. So, I really enjoyed this conversation. Give it a listen.

Okay. So, Ian, I don’t know if you remember this, but I actually met you at Telemachus, and we spent a day together with about 10 of us, and you did a deep dive on the enneagram. So, I was with my husband and it was my first time to kinda really do a deep dive on the enneagram. And the weekend ended up being such a gift to me for two reasons. One, Dr. Curt Thompson was in that little group with us and he’s become a dear friend. I’ve flown him down to Texas. He’s led a retreat with me and Jen Hatmaker, and a couple other women. And I meet up with him now whenever I’m in DC. And he’s become a mentor of mine. So, I have you to thank for that because, really, that was…happened at Telemachus.

And then, the other thing that really inspired me is that entire weekend, I just kept hearing about people’s lives that you had changed, people from Greenwich, Connecticut. It was like, "Ian’s changed my life. Ian’s changed my life." And I just felt like I was standing in the wake of your legacy. And it really just inspired me to really go…want to go home and really invest locally. My business has this huge global investment. But anyway, that was really inspiring. So, thanks for creating that space.

Ian: Well, listen, thank you for your kind and encouraging words. They’re always needed.

Jessica: Yeah. Okay. So, I came back from Telemachus and then bought all the books, all the Ian Cron books, and absolutely fell in love with "Jesus, My Father, the CIA, and Me: A Memoir… of Sorts" Okay that…oh, my gosh. What an incredible book. You wrote it in 2011. But you’re such a good storyteller and so much of your work now, I know, have to do with enneagram. And you have a whole podcast, "Typology," that really, you know, does a deep dive around the enneagram. But I really wanted to hear the story behind the story and how this…you know, that was really your memoir that you wrote. And I wanted you kinda to give us that story behind the story of your background, and then kind of how that has led you to possibly have really honed in on the enneagram.

Ian: Yeah. Well, I mean, you know, running a memoir is a remarkable experience. And, you know, the story behind the story there was I wanted to simply write about the complicated relationship between fathers and sons, and between…which is the focus of that memoir, is really my relationship with my very troubled dad. And it was a beautiful telling for me, you know. I think it was Maya Angelou who said something to the effect of "There’s no greater agony than to bear an untold story." And so, that was the great purge of the story and it was really great.

You know, I became a therapist, you know, a long time ago, and an Episcopal priest, and a spiritual director. I was sort of trained in those three fields. And so, it was a natural precursor into working with the enneagram, and because so much of my life has been dedicated to helping people enter into deeper conversation with the mystery of who they are.

Jessica: And what’s been one of your biggest ahas now that you have become such an expert in this area and now, even reflecting back? Because in 2011, when you wrote that, had you really discovered the enneagram yet?

Ian: Well, I certainly knew about it. I first was introduced to enneagram in 1992. I was in grad school. And so, I definitely…and I’ve been to some workshops over the year, Riso and Hudson and others, Richard Rohr. And, you know, so I was familiar with it but I wasn’t as schooled in it, for sure, when I wrote the memoir. And so, you know, I would say that sort of the big aha for me is there’ve been so many. It’s kinda hard for me to say.

You know, I’ll tell you this. It has given me a wider emotional vocabulary and awareness, and empathy, and compassion for difference in human beings. And so, I really do…you know, I’m not a person who sees the whole world through the lens of the enneagram. I don’t…every person I meet, I swear to you, I don’t think, "Well, what’s their type?" I mean, I’m not so, you know, focused in that direction that I…you know, it’s my whole life. But, in general, the result has been that the circle of concern in my life, the people I allow into it, is, you know, deeper and richer, and wider.

Jessica: So cool. So, we actually just introduced my listeners to the enneagram in the last couple of months. So, I kinda kept it quiet because I know there’s like three types of people in the world, you know, those who, like, hate the enneagram. They think it’s a cult, and they’re like, "Quit talking about it," those who love it because it’s absolutely transformed their lives, and those who like it but don’t want us to talk about it anymore.

So, I finally introduced our listeners to it. And so now, I talk about it a lot more freely. And so, Suzanne was actually the first person on the show that we had on the show to kind of introduce us to the enneagram. And we really honed in on this idea of courage because it was during my "Imperfect Courage" series around my book, and we really talked about each type in relationship to courage and vulnerability. And I’m a seven. So, it probably comes as no surprise to you that this series is all about being a starter, which sevens are natural starters. We’re really good at starting, not always good at finishing. And as I’ve been out on tour and in speaking during the fall, I just…so many of the questions that I get are around, "How do I just start?" And I feel like so many people are held back by starting either because they’re paralyzed by perfectionism or analysis paralysis, or they feel like they need to wait till the right time or the right attitude, or the right resources.

So, I’m curious because I really see…I see so many people as entrepreneurs. I see you as an entrepreneur. I mean, you’re a writer, speaker. You’re a podcaster. You’re a songwriter. And I wanted to hear about…you know, I know that you’re a four. And so, can we start with you and let’s talk about the relationship of starting. What does it mean? What does it take to be a starter? And what are the blocks to maybe starting in relationship to the different personality types using the enneagrams, the framework?

Ian: Yeah. So, I do think that there are some people who, just by virtue of temperament and disposition, have a starter’s mind, you know. It just tends to come more naturally. That doesn’t mean that every type can’t be a starter. It just means, I think, there are some for whom it just comes more innately, right? So, threes, sevens, and eights, right, the achievers, the enthusiasts, and the challengers, they are the most assertive, we would say aggressive numbers on the enneagram. That’s not in a negative sense. So, just people who just move right towards other people. So, for those three numbers, I’d say, "Gosh, they’re kinda naturals at it."

Now, other numbers can certainly be, you know, great starters. You know, for example, I guess Mary Kay was a two. We don’t oftentimes think of twos, you know, but they’re…you know, she started a very big corporation, right? You know, Herman Miller Chairs is a number four. Bill Gates, a five. Steve Jobs, you know, there’s kinda little bit of an argument whether he’s a seven or a one, or he was a seven who just lived in one all the time, you know. But you know, I can go on and on…

Jessica: It sounds so terrible as a seven. I’m like, "Uh, when I’m in my basement, it’s no fun."

Ian: Yeah. So, I think everybody, you know, brings a gift to the table. Each of this is sort of, I believe, a divine given gift. We contain all nine types. So, we’re just leaning and defaulting to one all of the time. But we have access to all these other gifts, maybe not in the same abundance as people who hold that type. So, anyway, like I said, I think there are certain people who are just more innately drawn to being starters. They tend to be…oftentimes, I think people who have what’s called openness to experience, which sevens do, openness to experiences, meaning that people who see overlaying patterns really well. They see things, connections to ideas that other people don’t see. So, they’re not very dualistic thinkers. They tend to be people who can think in "both end" categories, not just "either/or" categories.

Jessica: I have a whole section in my book that’s about choosing "and," and embrace paradox.

Ian: Yeah. Well, that’s called openness to experience. And actually, if you wanna know, this is on a…so this…now, I’m just speaking out of general psychology, right? So, openness to experience, what that means is you can hold things intention. You have openness to alternative ideas. You’re not a black and white thinker. And so, all of this presents you a cool opportunity vibe, you know. It’s like, "Whoa, weekend…" Plus you bring all of this energy as a seven, an enthusiast, you bring all of this energy of optimism and forward-thinking and, you know, we can do anything.

Now, of course, the problem for starter sevens is, is that if they don’t do some work, they’re only good for the start. When everything turns toward management, they just start to tune out. And so, that’s what…

Jessica: I’m 8 years in with 60 employees. Thankfully, I’ve got a lot of people that are helping me to manage things now.

Ian: Well, yeah, that’s good. But if you don’t have that, you know, people to fill in your…

Jessica: It’s tough.

Ian: Yeah. Oh, boy. Oh, boy.

Jessica: It’s real tough, yeah.

Ian: It sure is. So, I am…I think people who are starters are people who see holes in the line like in football. You know, you see opportunity that other people don’t see. And you feel this compelling desire to run through and create something new. And for each type, what that new might be could differ. But there’s just that feeling of the creation of the new that might serve in some way that people hadn’t yet considered.

Jessica: Because in a sense, we’re all called to create, right? I mean, I think we could say that we have that innate, you know, made-in-the-image-of-God call to create. And in so many ways, that is starting.

Ian: Yeah. I mean, I think everybody’s creative. I don’t think everybody’s an artist. But I think everyone has some, yeah, natural creative ability. You know, I think that’s the God-given thing. I mean, we have a creator. So, if we’re designed in that image, you know, we all have that capacity. And I think sometimes people who are not artists tend to downplay their creative abilities, which always sort of saddens me.

Jessica: When you think about your journey as a starter, like, what’s the last thing you started? And then, as a four, what would sort of be your obstacle to taking those first steps?

Ian: Yeah. Well, I started a church once and…as a four. And it was the cool…

Jessica: And was that…that was all the people that I met?

Ian: Yes.

Jessica: The Greenwich people?

Ian: Yeah, yeah.

Jessica: Okay.

Ian: I started it from pretty much scratch and I cured about 800 people, which in New England, by the way…you know, in Nashville, I…

Jessica: Like a mega church.

Ian: It is a megachurch in New England. People in Nashville… So I had 800 people in my church. And they yawn, like their small group is 800 people.

Jessica: Oh, my God.

Ian: Do you know what I’m saying? And I’m like, you know, "You have no idea."

Jessica: I think that’s why I was so inspired because I’m meeting these people that, like, work on Wall Street and commute into New York, and they’re, like, it was so life-giving to kind of see people’s perspective of the God that you gave them. It was really cool.

Ian: Well, I mean, I think part of the reason that church worked was… So, I’m a four with the three wings. That three-wing makes me ambitious, and I am. I mean, you know, people tend to think of fours as like wandering around, you know, wearing all black, smoking cigarettes, and you know, the black beret on, reading poetry all day. And that’s a stereotype. You know what I mean? Like, that’s not a type. And so, I’m…actually, I love starting things. I’ve started a bunch of things. And now, that experience was such a learning experience. And I didn’t really know…I wish I had known the enneagram so much deeper and was applying it back then because it would have saved me a lot of pain.

Jessica: But how would it have saved you?

Ian: Well, because of my self-knowledge…I mean, I would’ve known why at year five I was ready to leave. I would’ve known why it took me to year 10 to get out. Yeah, I would’ve known how to avoid… I mean, just knowing people, you would just have so much less conflict, you know, and self-compassion, and just the awareness from moment to moment to monitor and regulate the way that you think, act, and feel. These are things that every leader, but you know, particularly in pastoral leadership, you better get a handle on. You know what I’m saying?

Jessica: Right, right.

Ian: And it just would’ve helped me understand why am I struggling with… You know, for example, there are virtually no fours in Greenwich, Connecticut. Everybody is a three, a seven, or an eight working at financial services on Wall Street, everybody. Everybody’s a banker. You know what I’m saying? And here I am…

Jessica: Yeah. There are a lot of bankers and that call was, like, I don’t know if I’ve been surrounded by these many bankers.

Ian: Oh, my gosh. They’re ultra-successful and they’re very well educated, all of which I loved. And yet, here I am. I’m a songwriter. I’m an artist. I thought in different categories. I felt and saw the world differently. And in the beginning years, that was awesome because that’s what attracted those people. In other words, you know, if they were drawn to an artist’s view of the world and faith, and it was a whole new vocabulary for them, and they were just drawn to it in a way that if I had just been a person who saw the world like they did, they might have yawned. You know what I’m saying? And we were [crosstalk 00:17:40]…you know, we were artists who started it, right? So, it had all of that kind of flavor.

Well, you know, around year five, there was a transition. If I had known myself as a four better, I would’ve made less decisions out of emotions, you know. I wouldn’t have gotten so stuck in my feelings like fours do. I would’ve seen how much dizziness there was between the people I served and who I was, and probably said, "You know what? You know, it’s probably time for me to leave now because I probably exhausted my repertoire," you know what I mean, "of stuff," and it requires a different kind of leader than a starter and, you know…so I’ll just say, man, if I just had that self-knowledge, it would’ve have been so helpful, you know.

But when I moved to Nashville, so this is telling, when I moved to Nashville, it was like I found the Promised Land. You know what I’m saying? I’m like, "Oh, these are my people." You know, there are all these artists and creatives around, and they weren’t in, you know, financial services. They were just, you know, out there hustling to do their work. And oh, gosh, it was like coming home to a place I’d never lived, it was so wonderful.

Jessica: It’s interesting. And one of my best friends in the world is a four. And I’ve always been attracted to fours and really feel like I kind of understand the four because I don’t know what the relationship is between sevens and fours. But I definitely identify with, first of all, the NVPs. That’s something…like always wanting what someone else has or feeling like there’s something missing. I know for a seven it comes more from this just like always, like insatiable desire for more. But I did listen. I don’t know if you hear "The Sleeping at Last Podcast." Of course, I listened to it for the first time this week because it was about a seven. And we’re pretty self-absorbed, so…

Ian: Right, yeah.

Jessica: Okay. I’m gonna listen now that it’s about me. And so, I heard the song and the whole podcast. And one of the new layers, which I actually have just come off of six months of executive coaching with an executive coach with my business partner, and it ends up our executive coach, she’s not faith-oriented, but she is like an enneagram expert. I mean, she’s, like, done the work. And so, we ended up applying a lot of the enneagram to our business and to my business partnership. So, I’ve actually feel like I’ve gone, you know, somewhat deep into the enneagram.

But my new takeaway, which I had never thought about, was it said that, you know, the seven, that’s the only number on the whole circle that doesn’t have a natural connection to the heart. And it said…so, sevens were drawn to people in that heart area. And when we see someone who’s really living out of their heart, it’s like we’re drawn to them like a camp fire, like it warms us, you know. And I just thought, "Man, that’s so my best friend who’s this four, who’s like, she’s actually becoming a therapist right now. Yeah. So, I’m loving her even more because she’s just using all the good language and all the good questions.

And I’m actually going through…I wasn’t even gonna get into this at all, but my dad has cancer. He was diagnosed a few months ago. And he’s a seven, and he’s been flying high. He actually hasn’t felt any sort of, like, bad effects from his immunotherapy. And then, two weeks ago, he had a horrible side effect from the immunotherapy, ended up in the ICU of the neurology unit of the ICU, with encephalitis, which is swelling of the brain. He almost died, it went undiagnosed. So, I had to kinda…you know, of course, I dropped everything and I’m spending the night in a recliner in a hospital chair, which is like my worst nightmare, right, to be holed up in a hospital around suffering, you know, with my dad. And I went into problem-solving mode and it actually went undiagnosed. And so I’m, like, on the phone with all these oncologist friends that I’m connecting with.

And, you know, I’m left now. He’s better. Thank God he’s home. But now, he and I both are dealing with this reality of, like, my dad has cancer. And now, he took this drug that actually he can’t take anymore. And we don’t know what the future is gonna hold. Then, that whole enneagram seven thing came out about, you know…which is, I mean, what I heard was…it’s not what was said, but what I heard was basically we’re heartless, you know. And so, I’ve been really practicing this week, plus, I’m kinda home from travel and, like, I had a hard workout this morning, and then I went to my car. And workouts often help me get in touch with my body and my soul, and I sat in my car and cried. I was like, "I’m gonna be sad right now. I’m just gonna be sad." And then I texted my friend, my four friend later. I was, like, "You would be so proud. I cried in my car alone this morning."

But now, I have this opportunity where I’m on a podcast with you. And I might depart a little bit from the starter questions that I have lined up and kind of ask you, like, in particular, you know, someone who does live in that heart place, what are some tips for those of us that naturally are in the mind place to kind of get in touch like that journey from the head to the heart? And that it’s so interesting because everyone sees me as this, like, probably very emotional, enthusiastic, you know, person. I’ve started a business. It’s like, you know, changing the world and getting people out of poverty. So, it looks very heart-oriented, but actually, my experience in myself is I’m mainly up in my head. So, how do we take that journey from the head to the heart?

Ian: So, by the way, let me just go back and correct you. You are not heartless. If someone told you that, like, you know, run away. That is just not true.

Jessica: That was my story. That was the story I told myself.

Ian: Look, you know, if I were you, you know, I’d cut that movie if I were you, just like turn that movie off in your head.

Jessica: Okay. Thank you. Thank you.

Ian: So, you know, because you’re not in that heart space, it’s not your go-to thing. You know what I mean? That’s just not the way that you meet the world first. You meet the world first with your mind, not your heart. It doesn’t mean you don’t have a heart. It just means… You know, when I walk into a room, I begin to feel what’s happening, right? I mean, that’s the first thing that activates in me. It doesn’t mean I don’t have a brain or a gut, you know, or a body. It just means that’s not what I process or meet the world with all the time, right?

So, you know, what I would say is, you know, for all the numbers, you wanna bring all these centers into balance, all right? And so if you have, for example, a repressed thinking center like I do, or do it…actually, I don’t have a repressed doing center, and thinking when it comes to…I wanna bring…I don’t wanna bring down, for example, my situation, my feeling. I just wanna bring the other two up to the same level.

Jessica: I like that. That’s a really great reframe and you know I love a good reframe. I love that.

Ian: Oh, yeah. So…

Jessica: I love that.

Ian: Yeah. So, my son is a seven, okay? And I mean, he’s a seven with a seven-wing. He makes Rob Bell look depressed. And, I mean, he is really something and we’re very close. And it was fun to raise a seven. They’re so fantastic. And you’re right about this. When you…people think that sevens on first glance, they’re like, "Oh, they live so much from the heart. There’s so much energy and fun."

Jessica: Yeah. That’s what people think. And I’m like, "That’s not what I feel."

Ian: Well, exactly. My son was like 14 before I…you know, I was learning the enneagram when I was like, "Oh, my gosh. See, this kid is a thinker first. He’s not a feeler first." And even though he’s incredibly affectionate, incredibly curious, you know, it’s…you know, now when I’m with him, I can hear the chest pieces moving in his head during conversations. You know what I mean? He’s thinking all the time now.

So, not long ago, we went through a family crisis and it was very hard on my son. And it took months for him to get in touch with what he was feeling, you know. And for me, it took minutes to go the same journey, right? What took him months took me minutes, right? Now, here’s how I help him. When he begins to exhibit behaviors like reframing, like turning every negative into a positive, or becoming kinda manic when things are getting tough, or yeah, whatever, all these different sort of red flags, I look at him and I go, "Stay, stay," you know. He’s like a puppy. I’m always going, "Stay," and I’m telling him to stay with the feeling and let it have its way with him, and it will pass.

Most sevens don’t believe it’s gonna pass. It’s like, "I gotta get out of this feeling because what if I get stuck here, and I’m not supported here in this experience? You know, what if it’s forever?" And so, I always…I tell him and force the safe thing, you know, which is this great quote from Rilke, which is, "No emotion is final." So, don’t get this thing in your mind that, you know, "Whatever I’m feeling in this moment is gonna be forever, and I don’t wanna have negative feelings forever."

And so, what you did was correct, which is you just got in the car and you stayed with it. And that’s so important to learn, how to stay with what is in the moment and not leap into the future as most sevens would do, but just to stay right here with this feeling right now, and trust that, you know, it’s like a weather pattern. It’s gonna come in and it’s gonna blow out. It’s not forever. Feelings are like clouds. They’re not like rocks, you know. So…

Jessica: Well, it’s interesting because after my good cry this morning alone in my car, I didn’t die. And I actually feel like I’ve had a better day today because I am not, you know, trying to just avoid the pain that I feel. But, of course, yeah, I mean this. I’ve never wanted to be at this place where a parent has cancer. I mean, it just sucks. You know what I mean? Sorry, now I’m gonna start crying. But I’ve been…yeah. So, grief is my most feared emotion. And then, I’ve got my seven dad. He’s also, like, in denial. You know what I mean? And we both are, like, take the bull by the horns. We have a bias towards action. We just want…you know, get up and go. And, yeah, it’s just I’m very thankful for my friends and it’s interesting when I look at some of my close, close circle. It is like twos… I mean, you know, I’ve got some twos, threes, fours in there. And I think, "Gosh, I realize now I’m really drawn to those people that, you know, feel and that call me to feel, you know." So, it’s a beautiful thing as a four, you know. So, you…well, how did you phrase it earlier that we just…you just have to get more content…

Ian: Equanimity?

Jessica: Equanimity. So, what do you do to get equanimity and either a thinker, and you’re in your gut?

Ian: Yeah. So, the one thing I do, and you mentioned Martin Laird earlier, I mean, I just tell every type that if you wanna do deep inner work, there’s just no way around the necessity of a regular meditation practice.

Jessica: Yes, absolutely.

Ian: So, that’s the first thing. And I do recommend books like Martin Laird’s book, "Into the Silent Land." And there are some easier ones than that, but that’s first. Because what happens then is you learn to develop an inner observer who can watch from a distance without any judgment, evaluation, or anything else, just what is happening in me at this moment. And you don’t get hooked by what’s happening in the moment. You’re able to sort of step back and observe it, and with compassion and love, respond differently than react. Because I think this is a huge thing in the spiritual life, how do you learn to live in responsiveness to what’s happening versus reactivity, right? And when you don’t know your path…

Jessica: That’s so powerful.

Ian: Yeah. So…

Jessica: I mean, so I think it’s a lifelong journey. But certainly, you have to have at least the moment where you realize, "Oh, my gosh, I’ve been living out of reaction my whole life"

Ian: Yeah. It’s autopilot. And so, you’re in reactivity when you don’t…when your personality has you versus you having a personality, that’s sort of reactivity, you know. I’m off in the loop of my seven or my four, right? And so, that’s one way for me, is just that’s sort of the floor. That’s just a basic practice, right?

And, you know, I’m a four with a five-wing. So, I do have a strong thinking side. So, that’s not so much of a problem. But, you know, I’ve learned over the years that to get stuff done and not be caught up in all these great ideas but lost in feelings that are sidetracking me, you know, I’ve really gotta go, which I do under…you know, when I’m feeling secure, it’s the high-sided one and just sit down and get it done, dude. Like, if you’re gonna write a book, write the book. Stop talking about it, you know. If you’re gonna write a song, stop talking about it. You know, write the dang song. Deliver it."

So, again, it’s just this ability to observe and act with awareness in the world, and to do it with what I call unconditional self-friendship. Meaning, you know, to be your own best supporter and advocate in the process. You know, it’s hard. And I just wanna stop and acknowledge something without just jumping over it. So, a few minutes ago, you became, you know, tearful and were expressing emotion. And I just wanna stop and honor it for a second, and name it. I think grief is maybe the hardest emotion in the world because it’s just this ultimate sense of powerlessness in the face of reality, you know, reality is a tough opponent in the ring. It always wins, you know.

And what I was gonna say to you was that I don’t know you well, but I can always tell when that sort of thing comes up for a seven, people lean in. And the reason is, is it shows a level of depth and courage that, you know, I just wanna name before we just, you know, go zooming by it. And I just wanna encourage you and that, you know, grief is a…you know, it feels like fear a lot of the time. But if you let it have its way with you, there’s nothing quite like it for creating a deep soul. There’s no other emotion that creates more depth than grief. And that’s the first feeling people had, probably grief and shame, walking out of the garden, Adam and Eve, you know. I mean, so it’s a very primal, powerful thing. But if you just sit with it, it’ll pass when it’s ready. And that’s just a…you’ve just gotta trust that.

Jessica: It’s a hard thing to trust. I mean, what Curt would say is when I’ve talked to him about my deep fear of grief, you know…because I think you maybe…I don’t know if you wrote this or if you said this, that what I think is seven’s most feared emotion is grief. Did you write that or is that [inaudible 00:33:53]…

Ian: It sounds like something I have said, for sure.

Jessica: Okay. Okay. And I just sort of remember Curt saying, "You know what? He felt like I think it’s that we all just fear that we’re gonna grieve alone." And so, there’s something, too, about knowing, you know, and that’s where, like, vulnerability, empathy or me even saying like, "You know, one of my best friends is a four," because I think there is something about knowing that whatever does happen with my dad, like, I’m not gonna be alone.

Ian: And that’s a very…

Jessica: You can talk now. So, I just [inaudible 00:34:28], please?

Ian: Well, you know, here’s the problem. As a therapist, I’m always willing to sit in quiet. As a [crosstalk 00:34:34]…

Jessica: I remember, we’re on a podcast.

Ian: I know. But as a four or two, it’s my natural inclination, is just to sit with it. But, okay, so I mean, here’s just a universal idea which is that, you know, really grief is the price we pay for love.

Jessica: I hate that.

Ian: Yeah. It’s true though. That’s just how it is and that’s how reality plays. And, you know, a lot of times, I think sevens are running from…well, every number runs from reality in its own way. But, you know…all right, so this is gonna sound like a bummer, but it’s not, and I’d have to explain. This is it. But, you know, life is suffering. It really is. And I think we spend so much time entertaining ourselves or distracting ourselves because we just don’t wanna face the fact that that’s how it plays here. You know, we…what I mean is suffering…

Jessica: Well, what’s interesting is I mean I work with, like, suffering people, like the most vulnerable communities in the world. And yet, I’ve made it my whole mission, like, though to alleviate their suffering because I think primarily, it really hurts me. I’m like, "You’re in pain. I have to get you out of that as quickly as possible," you know.

Ian: Right. So, you know, and a lot of times, sevens will do that. Sometimes, it’s obviously altruistic. But sevens have to watch this part of it, which is sometimes they wanna alleviate pain because the suffering of the other is causing suffering in them.

Jessica: Yeah, totally. I can see that.

Ian: Yeah. So, it’s like, "Okay, your pain is making me, like, really uncomfortable. So, in order to get rid of my discomfort, I gotta problem-solve," which is where a seven would go first. You know what I’m saying? In the face of [inaudible 00:36:15], they’re gonna problem-solve versus, you know, default to, let’s say, empathy, right? So, your thing is, "Okay. We gotta fix this problem." And so, there’s a little self-interest in it, right, which is "Because I don’t wanna feel this way. I don’t wanna feel this pain. I wanna…" Now, you know, I can’t determine percentages of, you know, self-interest versus altruism in somebody. But I’m always reminding my son. My son is always, like, people come to him for like counseling persons all the time. He’s in college, right? And I’m always like, "Well, you know, Aidan, I think sometimes you just love to solve other people’s problems because their problems are like, you know, kind of like dimming your shine, you know." And he’s like, "Yeah. Sometimes that’s true." I said, "Yeah. So, you know, you gotta figure out, you know, what the source or what’s motivating you and try and get your motivations right for helping other people because you’ll be more powerful at it if you do."

And I love Sevens, and I…here’s what sevens give me. Sevens remind me that life is joyful and beautiful, and just brimming with joy and possibility. What I bring to fours, to sevens in relationship is this reminder that we can survive the narrow straights and be okay. And I can help them kinda navigate it those times in a way that’s helpful. And so, my son used to come to my office. And, you know, I would be in sort of my foury way and he would be like, "Dad, we got to go to the Museum of Modern Art. There’s like this cubist art thing going on and we gotta go see it." And I’d be like, "You know what? He’s totally right." That’s how life should be approached, is with that kind of joy and wonder. And right now, he’s serving as the proper corrective to my default of kind of being melancholy. So, what a gift. Well, it’s great.

Jessica: Yeah. Teddy, my four friend, it’s like, you know, "I will never take a movie recommendation from her."

Ian: Oh, my gosh. Hey, you wanna… I don’t know if you’ve ever heard the story, but I…on New Year’s two years ago, we were in Connecticut. Aidan and I were there by ourselves. Everybody else was traveling. And it was New Year’s Eve, right? And we didn’t have any plans. We had nowhere to go. And so I said, "Well, let’s go to the movies." And he’s like, "Yeah. I love the movies, right?" And so, I took him to see "Manchester by the Sea."

Jessica: Oh, my God. Oh, my God. I watched that on an international flight and I was like, "What are you doing?" I felt that is the most depressing. It was horrible. It was horrible.

Ian: Okay. All right. So, this just goes to show you how every type sees the world differently. I left the theater feeling like, "Oh, man, what a great film, the acting, how honest the script was, how it ended so honestly." And I just left. My son looked at me like, "If you ever do that to me again, I will kill you." He said, "We have got to go find streamers and noisemakers, and hats right now." And I’m like, "Yeah, okay." So, there, you know, I guess I should’ve thought a little bit more about my poor seven on New Year’s Eve.

Jessica: Oh, my gosh. Give me a happy ending any day of the week. Okay. I wanted to reflect on something you said earlier, which is that, you know, as a creator, you know, sometimes you’ll talk about an idea a lot. And then, it just takes you a little bit to actually start it. So, what do you feel like are, like, the blocks in your…what do they call it, not the triad, but like the nines? Are you with the…you’re in your heart, so you’re with the twos and the threes.

Ian: In the heart triad, twos, threes, and fours, right.

Jessica: Okay, so two, threes, and fours. What do you think are those blocks when someone is feeling stuck? Or first of all, why would people in the heart feel a little bit stuck? And then, what does kinda get you to just do the thing?

Ian: Yeah. Well, twos, for example, would get stuck up, you know, because they’re so attuned to other people’s feelings. And so, that’s where they could get stuck, is sort of like all their attention, their habit of attention running toward other people’s feelings. And then, of course, when that happens, they’re very out of touch with what their own feelings are. You know, they don’t…they’re so attuned to what your needs are but out of tune completely with their own because they never really actually paid attention to those in life, you know. So, they can get stuck in other people’s feelings. Threes, you know, threes are kind of…they’re confused about their feelings. You know what I mean? They’re not very good at recognizing them or always being able to name them. And so, they get stuck and they get very stuck in doing, you know, and being so driven for purposes of, you know, wanting to avoid failure and achieve success. But specifically for fours, is we get rather than a two who looks out on people’s feelings, other people’s feelings, I tend to look inward at my own feelings. So, I can get caught. We have very rich imaginations, we fours, and we get lots of ideas. They’re incredibly creative. They’re rich. They’re colorful. They would really help the world if they were put out there. But we get so locked up into our own feeling states that we never get started and execute on all these great ideas.

So, you’ll hear of fours all the time at a party, this is what you’ll hear, "I have the best idea for a novel or a screenplay, or I imagine a store that…" And it’s like, "Okay. Well, what are you gonna do?" You know, it was like, "Well, I don’t know. I’ve got to deal with, you know, this relationship." So, fours just get lost up in the swirl of their emotional space, and so they don’t actually begin to move and do stuff. And so, that’s where, you know, people get blocked and they get stuck when they are too caught up in kind of the weaknesses or the…you know, those aspects of their personalities that are self-defeating and self-limiting. And if you don’t know what they are, I mean, how can you deal with them? I mean, you know, that’s why the enneagram is what it is. I mean, if you don’t have self-knowledge, you don’t know what you’re up against.

Jessica: So, you feel like the enneagram in itself could be this tool to help unstick you from starting?

Ian: Oh, my gosh, not just from starting but from doing and completing. I mean, your life… It’s not like a magic tool, but what it does is it…You know, here’s the deal. Anything that teaches well, it…to me, a good teacher or an instrument that teaches me, it just is all about saving me time. You know what I’m saying? The enneagram can save you time and…from making mistakes that are costly in terms of time, and just help you to either skip over them or identify what’s happening when you fall into that pattern faster. You know what I’m saying? Like I mentioned earlier, if I’d known the enneagram, I probably would have saved five years…

Jessica: Less.

Ian: …less in that startup I was in Connecticut then, you know, if I’d just known, right? It would’ve saved me a lot of time.

Jessica: Okay. What about ones, eights, and nines, what’s their blocks to moving?

Ian: Yeah. Well, you know, for ones, ones can get caught up in procrastination and they kinda freeze because they don’t wanna start anything without it being perfect from the get-go. You know what I’m saying? So, it’s like, "Well, if I can’t do it perfect right away, then I don’t wanna start at all." You know, they’re just, like, when you see a one staring at a computer screen tapping a pencil, you better go over and tell him, "It’s okay. The first draft is supposed to be crap."

Jessica: Yeah, totally.

Ian: Because a one will sit down and they’ll say, "Oh, my gosh. I’ve got to be William Faulkner from the first page." You know, it’s like, "Well, first of all, you’re writing an HR manual, so you could throw Faulkner out of here. And then, secondly…

Jessica: My HR director is a one. That’s hilarious.

Ian: Right, okay. And it’s like, "You know, just get started. That’s okay." So, I think that’s one way that ones can get stuck from, you know, just from going. What was the other one? What are the other two you wanted?

Jessica: The eight and the nine.

Ian: Okay. Eights basically don’t have trouble starting. I mean, they just charge, man. I mean, you know, if anything I’d say about eights is, it’s how they behave when they start, that they gotta watch out for because they can impede progress with their aggression, right? So, for example, how do I say this, they tend to get ahead of everybody else. And like the research, this is just based on pure academic research, right?

So, in business, everyone thinks I’ll get a really aggressive kickass guy or women in there. You know, take the bull by the horns and drive people to the success, it’s like, "Okay." Well, if you have an unself-aware eight who’s just in there, like, throwing elbows around, yeah, you’ll get results in the short term. In the short term, you will get results. In the long term, you will see a negative outcome. Anything you gained from that person being in your organization you will lose, and then some.

Jessica: You’ve created a culture of shame, you know.

Ian: Or fear.

Jessica: Fear, yeah.

Ian: I mean, you know, that’s what happens with the eights, they create cultures of fear. And you know, people are like, "Oh, my gosh," you know, "This person’s like explosive." And I’m talking about a very unhealthy eight here. I’m not talking about one that’s self-aware.

Jessica: Right, right. Oh, no. My business partner is an eight, so…

Ian: Right. So they can be awesome but, you know, they can sort of self-sabotage, you know, pretty quickly. And the other one was nine? Is that what you were saying?

Jessica: Yeah, Nine.

Ian: Okay. Well…

Jessica: They’re in the stop states.

Ian: Yeah. Honestly, I have to stop and think about how many nine starters I know. I don’t know many. I have to stop and think about it. But, you know, it’s not…

Jessica: I do have a nine. My…or we have a social media freelancer. So, he is running his own freelance company. Now, we’ve tried to get him to come on full time. But he really wanted the freedom to…anyway, it was fun. And I was like, "You’re just…" He likes the comfort of, like, the gig that he has. So, he’s not willing to really do the full-time thing that…

Ian: Yeah. I mean, nines, when they’re healthy, I think are sort of like the most spiritually advantaged number on the enneagram. But when they’re not, you know, inertia can set in. They’re easily distracted by inessential tasks. They get off, you know, doing what they’re doing really easy.

Jessica: But there’s a lot of presidents, a lot of presidents have been nines, at some point, that’s what’s interesting when I think about nine presidents because I’m like, "Well, at some point, someone saw them as this leader, but they probably weren’t the one to necessarily say, "I’m gonna go do this." I mean, I don’t know. That’s what interesting to me.

Ian: Right. So, I think part of the reason we have nine presidents is and why they’re so successful… So Reagan would have been a nine. You know, people say Bill Clinton is a three. But I got a strong hunch he is a nine. Nobody can mediate peace deals in Northern Ireland and Bosnia, hundreds of years of enmity, and kind of bring them together and carve a deal. I mean, holy smokes. That’s like a miracle worker.

So, you know, that’s kind of their super power, is seeing things from lots of people’s perspectives, synthesizing what they’re hearing, consensus-building of…you know, they just are so good at this. And so, I think that’s what kinda makes them great presidents. But they usually do have some powerhouse nearby that is…

Jessica: They have to have someone, that kind of that push them, right?

Ian: Yeah. You don’t think Nancy Reagan pushed Ronald Reagan?

Jessica: Right?

Ian: I got a feeling that she did. You know what I mean? But when they’re healthy, you know, they really can take all that stuff and then, you know, take action, right? But when they get lost in indecision and, you know, ambivalence about things, then they derail in terms of leadership. But boy, oh, boy, I’m telling you, you better have nines on your team because they just bring that…an atmosphere of calm and kindness, and space that, I mean, every organization, I think can benefit from in a big way.

Jessica: Yeah. I’ve got some great nines on my creative team.

Ian: I’m married to a nine. I’m a father to a nine. You know, I have two other kids. I have an eight daughter, too. So, it, you know…

Jessica: A very well-rounded enneagram family.

Ian: Well, I’m the only one in the heart center, which is bad for a four because, you know, now I just feel all the more alienated from my family that is not in their heart Center. I’m always down there, you know, bringing the feelings to the game, you know.

Jessica: Okay. Let’s talk five and six in the correlation of starting.

Ian: So, this is a stereotype that people have about fives and they tend to think almost being, you know, nerds with pocket protectors for their pens, you know, and too introverted to be starters or leaders, and it’s so not true. Bill Gates is a five, you know. And I could name a list of others that, you know, they could be powerhouses and they could be very ambitious. So, it’s not like, you know, the stereotypes that people have. Now, where they can get off track is they tend to only share information on need-to-know basis, which really can leave other people who are part of a starting system feeling in the dark about, "Well, I need more information here." You know what I mean? And fives are very generous with information if they’re not very self-aware. They tend to be people who like to work alone, in solitary. That isn’t great with a team that’s in start mode, you know. But when they’re, I mean, well-developed, like every other type, you know, they bring their own kind of leadership style to the table that for starters is…in particular, in certain sectors is really powerful, really powerful. Now, who is your next one, sixes, you said?

Jessica: Six, yep.

Ian: Yeah. So, you know, one of the things that would get in the way for a six is their… If a seven deals with fear with optimism, sixes do with pessimism. You know what I’m saying? If they’re always looking for what’s wrong or what could go wrong in the plan, right? It’s hard for them to get going. They doubt themselves a lot. They self-question a lot. You know, because they deal with…you know, as you know, when you’re a starter, it’s like, "Well, man, you got a lot to do out there and you gotta make faster…and you gotta get…you often have to make fast decisions," you know, that you don’t have the luxury of time, right?

And so, you know, for a six, where anxiety and fear may be, you know, heightened, a lot of times, that leads to the paralysis that you we were talking about earlier. But, again, when they’re healthy, for example, I think sixes sort of hold communities together. So, if you got 60 people working for you, you better have some sixes around because they are loyal. They are funny. They are dependable. They’re earthy. They’re practical. I mean, I love sixes. I mean, there’s nothing I love more than hanging around with a funny six, man. They just have a sense of irony that [crosstalk 00:52:48]…

Jessica: Oh, my gosh, my…our content strategist who helped me write my book, she is a six and she is like one of the most witty people I know.

Ian: Oh, my gosh. Yeah. I mean, you know, think about Woody Allen or George Costanza, you know. They just have a way of talking about life in these…you know, it’s just like they take their anxiety and they just pop it up about 2% greater than most people’s around some idea, and start talking about it and riffing on it. And it just gets so funny, you know. Oh, I love that.

Jessica: It’s so ironic, you know, that like you wouldn’t think six, comedian, but…and yet, yeah, there’s like a witty nature.

Ian: Yeah. I mean, come on. Just think about it, you know, when people are sitting around like thinking, "Oh, my God. What could go wrong? What could go wrong?" And they’re like, "This could go wrong." And that’s kind of six, it’s sort of the quintessential…like, we call them, in New York, we call them Borscht Belt comedians, right? They’re these wonderful Jewish comedians who would take these themes around, you know, "My mother, my mother’s coming," you know. It’s like everything is alarm. Everything is gonna go, you know, crazy, and it’s like it’s hysterically funny. I mean, you know, Woody Allen films are kind of built around that. It’s fantastic.

Jessica: One of my friends, her husband is the head at the state department over all counterterrorism. And guess what number he is.

Ian: Totally a six.

Jessica: Yeah, yes.

Ian: I’m telling you, hey, check this out. Check this out. Because when I go out to speak, like, for a workshop or something, I use panels, right? So, I’ll talk maybe 20 minutes about the type. But I don’t lecture, like, for a whole day. I just bring up people who are of that type and interview them because people learn so much more from that than they do from me. And I had this guy up recently. And I said, "So, what do you do for a living?" He said, "I’m a fire chief and I spend most of my days teaching kids about fire and checking fire extinguishers in elementary schools," you know. And I’m like, "Well, you know, everybody got a place, you know. Everybody got a thing. You got that thing. That’s good. Glad you’re around. We need you."

Jessica: Seriously. I mean, that is what’s so beautiful. And I think what’s been so life-giving for my business partner and I is we’ve embraced enneagram together now. And even within our company, you know, you…it creates such a spirit of empathy, you know. And so, you…it gives you a language…I mean, you can give each other hard times…my husband’s a one and so, we’ll give each other hard times, you know, where I’m like, "Uh, you’re being such a one," and he’s like, "Oh, you’re just being a seven," you know. And there’s a beauty in being able to name certain things that maybe you couldn’t name before.

Ian: Yeah. You can call it, yeah, you can call it saving your marriage sometimes. Do you know what I’m saying?

Jessica: I can name it that.

Ian: Yeah. You can name it that, for sure, like it’s, you know… I have somebody, a one recently said to me, you know, "Well…" because you know how ones have this sort of really a primal need to be right, right? They’ve gotta be right. And she said to me, "You know, Ian, you can be right or you can be married."

Jessica: That’s [crosstalk 00:56:02].

Ian: I thought, "Man, that is wisdom right there, man." She is speaking truth. It’s like, "Yeah. You can be right or you can be married."

Jessica: That’s right.

Ian: And, you know, one’s gonna make that choice sometimes.

Jessica: So, we’d like to wrap up the podcast by asking our guests, how are you going scared right now?

Ian: You’ve gotta elaborate on that. What do you mean how am I going scared?

Jessica: Okay. So, I define courage as being afraid and going anyway. And I realize that, you know, every type interacts with fear differently. So, really, it’s just another way to ask, like, what’s maybe something, a risk your taking or where you’re feeling vulnerable right now, or where are you feeling something that, you know, could keep you seated, could keep you paralyzed, but instead you’re moving forwards?

Ian: You know, I would say that, you know, kind of a issue in my life that has been this way, and boy, read the memoir, it’s not hard to figure out why, that I’ve always wrestled with this shame. And, you know, Curt and I have had this conversation before, and he’s the same. I mean, this has been his lifelong struggle. And, you know, that can be so demoralizing and it can…so, I love it. You know, I can so dim your shine. You get lost in all these feelings of, "I’m not worthy of moving forward, of taking hold of this one wild and precious life of mine," you know, or "I’ll never be enough. I’m just not enough," and, you know, all those storylines. And, you know, I’ve just had to learn how to drop that storyline when it pops up and even be able to, like, identify it when it’s starting to run as, you know, sort of the default story in my head. It’s not a good one.

And so, yeah, I mean, I think…and shame is a kind of fear, right? So, it does tie to your question in a way that’s really important because shame is the fear of exposure that you will be exposed as, you know, unworthy of relationship, unworthy of love, unworthy of…

Jessica: Connection, really.

Ian: Connection. And nobody wants to be seen because, I mean, that’s just, you know, even biologically…

Jessica: It keeps you in hiding, yeah, like, physically.

Ian: Totally, totally. I don’t think that’s uncommon for fours, obviously, that shame part triad. But it has been a lifelong struggle to not buy that storyline. And when it arises, to deal with it compassionately, but proactively, so that I don’t get sort of scared to the point that I don’t write a book, or I don’t carve a friendship because…you know what I’m saying? Starting is like, oh, my gosh, it’s in every area of life. And, you know, you just wanna have courage to start a relationship or start…

Jessica: I mean, like, cook dinner you gotta like…

Ian: Yeah, you know. So, you know, in my early…like in my 20s, for sure. Gosh, I mean, shame ruled through my teens and 20s, and into my early 30s in particular. And it had caused a lot of destruction for me. Addiction and destruction, and you know, distraction and…I don’t know. It sounds like it’s all bummer. But, you know, nothing’s wasted so I don’t worry about it. I don’t look back and regret anything. But, you know, it would have been so much nicer if it had just been a little less, you know.

Jessica: Right. So, low as drugs.

Ian: Just a little less shame, a little bit appreciated. But, you know, that’s all right. I can see the benefits now, too.

Jessica: Well, yeah. And I mean, Curt would say, really, shame is the root of all of our issues, you know. And, you know, the first thing that Adam and Eve did is they went and hid. And, you know, God comes looking for us in our hiding and the first things He asks of us is, "Where are you?" You know, "Where are you," and calling us out of our shame and into being back with Him.

Ian: Well, let me ask you a question though. I mean, I know we’re at the end of the show, but I mean, I’ll drop a bomb on you.

Jessica: Okay, great.

Ian: If you want one. Do you believe in your bones and blood and have you fully embraced, accepted, absorbed the idea that God unconditionally loves you?

Jessica: Heck, no. If I think if I experience that, my gosh, that’s heaven to me. I mean, I’ve had moments. And listen, I’m a seven and I, you know, I can get…well, I don’t know if this has anything to do with being a seven, but I have had moments of revelation of just like being on my knees, on my face, just like letting that love wash over me. But this idea of being…feeling felt by God is the journey that I’m on even this week. I wanna feel soaked by Him.

Ian: Yes. And so, for me, I always think to myself, "If I could get to the end of my life, even, you know, believing it in a way that’s measurably more than I do now, that that would be a success. And, you know, I’m always telling people how beautiful they are, but I’m not very good at doing it with myself. And so, you know, you asked me what fear I have, is probably that at times, a fear might be that I am, in some ways, unworthy or deficient in some way that prevents me from really experiencing my own innate goodness, and therefore, relationship with others, you know. So, there you go. I dropped it. There you go. Well, what is my vulnerability? There it is.

Jessica: As you could hear, this conversation really challenged me, especially when Ian said "Grief is the cost of love." I wanted to sock him in the gut through my computer screen. I mean, Ian, I love you. But I think as someone who doesn’t necessarily want to stop and feel the feels, that was a really good thing for me to chew on. And, you know, sevens, we actually don’t usually have a hard time starting. We have a hard time stopping. And so, I think what I learned from this episode is that it’s important to not only be self-aware but to also go together in this life with people that are different from us, that are different enneagram numbers than us, so that we can all benefit from the beauty of our various approaches to being a beginner.
Make sure you keep up with Ian. Check out his book, "The Road Back To You," his podcast, the "Typology" podcast. Don’t forget to go check out my book, "Imperfect Courage," and give this podcast a review. Guys, I have just loved getting to do this podcast. I love hearing about how these conversations are helping you in your life. So, if they are helping you, then, go leave a review about it.

I love this one review from annakatherine47. She said, "Going scared on my way to 3rd grade every day." She said she listens to the podcast on my commute "…and Jessica you provide my daily pep talk! I’m following my calling to be a teacher and I’m terrified and feel like I don’t know what I’m doing but this podcast is empowering." So, thank you so much for all your reviews. I read all of them. And honestly, it helps us provide direction in how we approach these series.

Our wonderful music for today’s show is by my good friend, Ellie Holcomb. "Going Scared" is produced by Eddie Kaufholz and I am Jessica Honegger. Until next time, let’s take each other by the hand and keep going scared.