Showing Up: Embodied Inner Work as an Enneagram 5 with Chris Schoolcraft
On this week’s episode of Enneagram IRL, we meet with Chris Schoolcraft. Chris has led and coached individuals, teams, and organizations through adversity for over 25 years. During this time, he has worked in religious, non-profit, and corporate settings, investing in urban, small towns, and suburban communities. He has learned from and supported both the disenfranchised and the ultra-wealthy, personally and professionally, partnering with non-profits and businesses to positively impact communities and lives.
A little over 8 years ago, Chris's life underwent a foundation-shaking shift, prompting him to seek new tools, perspectives, and relationships. He was introduced to the Enneagram, engaged in therapy focusing on inner child work, and enlisted a professional coach. Chris discovered a newfound authenticity and resilience, leading to a richer and deeper life. Out of this life-changing journey, Chris feels a clearer call to lead and coach organizations, teams, groups, and individuals toward greater self-awareness, growth, depth, and transformation.
🔗 Connect with Chris!
💻 https://www.clsleadership.com/
📷 Instagram: @cls.leadership
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📷 Instagram: @ninetypesco
🎥 Youtube: @stephbarronhall
Here are the key takeaways:
Chris talks about his background & how he discovered the Enneagram
Typing as a Five and spending a year exploring his type
Discovering his subtype as an SP Five
“As Fives, we perfected getting our needs met without asking”
Discussing boundaries and privacy
Type Five childhood wound - Either abandoned or too intruded upon
Nervous system overload
The passion of “Avarice” and fixation of “Stinginess”
“Fives want to know the answer before they get to the conversation”
Fives learning to “do”
Origin stories and how they make up who we are
How does Chris see his type in work?
Coming out of the “abstract” and experiencing the present
Connecting to other Intelligence Centers
Chris’ experience in leadership
How can people connect with Fives?
Practical advice for Fives beginning their self-discovery journey
Resources mentioned in this episode:
Enneagram teachers — Russ Hudson, Beatrice Chestnut & Uranio Paes
This Week’s Guest Picks:
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Enneagram Resources for you!
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Listen to the Episode
Read the Transcript
Chris Schoolcraft: Yeah, like now, a part of my work is that every time I walk in, I turn all my lights on because, as a Five, my natural inclination was to have the least amount of visual stimulation possible. So, I would keep the lights down, keep it nuanced, keep the music down, and then be able to handle things.
Operating in that kind of range was really helpful. So now, part of my work is to open up the windows and let the sunshine in. I'm in a bright room now, and I’m wearing a bright-colored shirt. You know, I can't tell you how many black shirts I used to own because I just needed to be smaller, take up a little less space, and blend in.
Stephanie Barron Hall: Hello, and welcome back to another episode of Enneagram in Real Life, a podcast where we explore how to apply our Enneagram knowledge in our daily lives. I'm your host, Stephanie Barron Hall. And on today's episode, we have a truly special gem because we have a Self-Preservation Five.
If you've been listening for a while, you know that I've been asking, “Hey, does anyone know a Five I could ask to be on the podcast?” because it's really challenging. I think Fives are incredible wells of wisdom, but it can also be challenging to find a Five who would really like to come and share about their inner work journey here on the podcast.
So, today I’m meeting with Chris Schoolcraft. Chris has led and coached individuals, teams, and organizations through adversity for over 25 years. During this time, he's worked in religious, nonprofit, and corporate settings, investing in urban, small-town, and suburban communities. He has learned from and supported both the disenfranchised and the ultra-wealthy, personally and professionally. He’s partnered with nonprofits and businesses to positively impact communities and lives. So, he has a vast wealth of knowledge and experience in those areas.
He also has a deep understanding of the Enneagram and has been using it to do inner child work. Through that, he’s discovered newfound authenticity and resilience, leading to a richer and deeper life. He continues to work with organizations, executives, and teams in this capacity. And today, we're going to dive into a lot of these topics—how he got here in his life, a little bit about his background, how he discovered his subtype as a Self-Preservation Five, and the concept he brought forth about how Fives perfect the art of getting their needs met without asking.
He also talks a bit about nervous system overload. We discuss something that I think is really important about the Enneagram because, admittedly, you'll hear me say this later in the podcast, but when I wrote my book that I’m currently working on—and I’m in the final stages of editing now—when I first turned it in over a year ago, I had the passion of avarice and the fixation of stinginess for Type Five a little muddied.
When I revisited it earlier this year, I was like, “Oh, this is wrong.” I was able to rewrite that section a little bit, which was really helpful. Today on the podcast, you'll hear Chris further elaborate on the differences there in his own words. It’s really insightful if you're a Five, but also if you have Fives in your life and you’re like, “Man, I just don’t really understand them.”
This conversation will be perfect for you. So, I really appreciate Chris coming on the podcast and doing this work with me. He mentioned that this is his own inner work, so I truly appreciate his wisdom. You can find him online at CLS Leadership on Instagram and clsleadership.com. So, without further ado, here's my conversation with Chris Schoolcraft.
Stephanie Barron Hall: Well, Chris, welcome to the podcast.
Chris Schoolcraft: It’s great to be here.
Stephanie Barron Hall: Yeah, I’m so excited that you said yes! I’ve been sharing with my podcast audience for a while, saying, “If you have any Fives out there, let me know, I want to interview them,” mostly because I think with an Enneagram podcast, people do want equal coverage of all nine types. Fives are tough!
Chris Schoolcraft: We are.
Stephanie Barron Hall: Yeah, but you’ve been on the growth path a long time, so you're really good at putting yourself out there.
Chris Schoolcraft: It’s part of my growth journey—to put myself out there. So, this is exactly me doing my work.
Stephanie Barron Hall: Yes, I love it! Well, I’d love to hear a little bit about your background and what brought you to this point in your life?
Chris Schoolcraft: So, I’ve always been interested in people, always been interested in working with people and helping people. I grew up in North Carolina, ended up working in the church. That’s what I do on a full-time basis—I’m an ordained pastor. I lived in North Carolina and then moved to Dallas, worked in different settings, and done different things. And then, somewhere along the path, the Enneagram discovered me. It’s been a big part of my life over the last seven years. Now, not only do I lead a church, but I also do executive nonprofit coaching using the Enneagram, and I really enjoy it. As I alluded to, I’m on the path of growth myself, so it’s a big part of my own life journey.
Stephanie Barron Hall: Yeah, what drew you to the Enneagram in particular versus, you know, all of the other tools that we have?
Chris Schoolcraft: Right, it’s interesting. At first, when I was exposed to the Enneagram, I wasn’t really excited about it. And this may be true for other numbers, but especially for me as a Five, there’s something about wanting to be distinctive and unique—probably my Four wing, that kind of individualism that’s creative and interesting. When I first encountered the Enneagram, people were really using it as a weapon. They were talking about people, typing people, and making assumptions about people. I had a visceral reaction to that. So, I really pushed the Enneagram away for a while. But I got to a place in my life where I was really struggling, burning out in my job, and I needed something. A coworker had talked to me about the Enneagram at one time, and I was resistant. But the second time she came back around and talked to me about it, I said, “I need something.” So, I opened myself up to learn, to see what it was, and it was a life-saving experience for me.
Chris Schoolcraft: So, that’s really how the Enneagram found me—in my deepest and darkest moments.
Stephanie Barron Hall: Yeah. How was it to first find your type? Was that immediate, or did it take a while? What did that look like?
Chris Schoolcraft: Right, that's such a… For me, people ask, "How do you find your type?" Well, I found my type by recognizing the worst parts of it. I was burning out, I was really struggling, and so, for a Type Five—paranoia, isolation—all of those things were what I was experiencing at the time. So, it didn’t take me long. I found it almost immediately. I knew what it was and right away began to take some time to dig into it.
Stephanie Barron Hall: Yeah, can I ask what your first Enneagram book was? I'm just curious.
Chris Schoolcraft: Well, I live in Texas, and in the Dallas area, Suzanne Stabile is a really big part of the Enneagram culture here. She was my first access point. I think the book was The Road Back to You, and that was the first Enneagram book that started me on the journey.
Stephanie Barron Hall: Yeah, I find that a lot too. When people encounter the Enneagram through Instagram or something, they'll say, “Oh, I read the yellow one.” They usually mean The Road Back to You, though another yellow one I really love is The Essential Enneagram by Daniels, but—
Chris Schoolcraft: Yes, yes.
Stephanie Barron Hall: —that’s also a good one.
Chris Schoolcraft: Yeah, and with Suzanne, one of the things that she said that resonated with me was: when you learn your type, don’t learn any other type. Spend a whole year just focused on your type because you really can’t do anything about anyone else in terms of your personal growth. So that was something I took her advice on. For that first year, I didn’t read much about other types; I didn’t research the other types. I really dug deep into my type, and that was very beneficial for me.
Stephanie Barron Hall: Yeah. I could also imagine, especially in a season of burnout, how going deeper and sorting through that would be really helpful. I know that sometimes Fives, especially Social Fives, are prone to using the Enneagram for spiritual bypassing—gaining a lot of information and teaching it, but not actually sinking into it. So, it sounds like you were in a place where you had to sink into it more.
Chris Schoolcraft: Yes, and what it really allowed me to do was to identify the lies I would tell myself. It gave me a path forward. For me, in my paranoia and withdrawal: “Okay, I don’t feel like I can trust anybody—well, I need to trust someone. I don’t really want to say this out loud—well, I need to say that out loud. I don’t really want to be around people—well, I need to be around people.” It gave me the opportunity to ask, “What does my personality want me to do, and what do I need to do to get back to a level of health that’s sustainable for me?”
Stephanie Barron Hall: Yeah, yeah. What about subtypes? When did you come across that information?
Chris Schoolcraft: So, once I got past that year and really opened up my view of the Enneagram and what’s out there, I looked into the narrative tradition, looked at materials by Russ Hudson, and read some of those. But the subtype information really came to me as I got involved with Beatrice Chestnut and Uranio Paes. That’s where I’ve done a lot of my work, and I still continue to do a lot of my work with them. [00:10:00] That’s where I really learned about subtypes and started embracing what that meant for me.
Stephanie Barron Hall: Now, I think with Fives, it can be challenging because, unlike some of the other types, the different Five subtypes can be a little more similar. There are similar through-lines that remain consistent. So, the work isn’t always that much different. Sometimes, the cultural overlay can be a bigger impact—at least, that’s what I’ve seen with some of the Fives I’ve worked with. And we both know Uranio, but I’m curious: how were you able to determine your subtype, and what did that look like?
Chris Schoolcraft: Well, I’m Self-Preservation dominant, and that was actually, again, fairly easy for me to recognize. As a Self-Preservation dominant Five—self-isolation, being in my “castle”—I can tell stories about not giving people my address, not answering the door, and not giving people my correct address because I didn’t trust that they wouldn’t just show up. So, there were very clear markers for me about what my dominant subtype was. And as I traced back through that pattern and through some difficult times, I could see where I was trying to use other subtypes but didn’t have the inner structure to balance them.
Stephanie Barron Hall: Okay, so Self-Preservation dominant.
Chris Schoolcraft: Yeah.
Stephanie Barron Hall: It’s kind of interesting what you just mentioned—like not giving people your correct address, for example. That’s something I’ve seen, especially with Self-Preservation Fives, where it feels too contentious to navigate the conversation of, “I don’t want you to know where I live,” or “I want to make sure that if you do know my address, you’re not going to come over.” So, instead of setting that boundary, it’s just easier to make sure they can’t penetrate it by not giving them the information in the first place.
Chris Schoolcraft: Right. One of the things I’ve learned about me—and that I say about most other Fives, and I haven’t heard anyone disagree with me yet—is that Fives have perfected getting their needs met without asking. We didn’t trust that the people neglecting us in our lives would ever answer our call, or that the people who were being intrusive would hold boundaries. So, when that basic sense of trust feels broken, it’s difficult for a Five not to project that distrust onto everyone else. We really feel—or at least I always felt—that it was incumbent upon me, in explicit and implicit ways, to ensure my own safety. It was up to me to make sure I was in a situation where I could take care of myself. That’s something not many Fives say out loud or articulate, but when I do, most Fives—especially Self-Preservation Fives—can resonate at some level with that. Sometimes other subtypes, not as much.
Stephanie Barron Hall: Yeah, yeah, that makes sense. It’s like a way of ensuring self-sufficiency—you don’t even have to ask the question of whether you can trust the other person. I know people sometimes say Ron Swanson from Parks and Rec is a Five. I’m not sure—it’s difficult to type fictional characters because the writers might’ve had different ideas episode to episode. But in that way of redacting personal information or redacting their address, that kind of feels Five-ish to me.
Chris Schoolcraft: Yeah. Fives are always—at least for me—trying not to give so much that it prompts someone to lean in in a way we’re uncomfortable with. Those micro-withdrawals, whether it’s withholding information or showing stinginess, are a way to avoid giving too much that someone might see as an opportunity to lean too far in. Whether it’s through my flat affect or low body language, all of that is designed to keep people from even sensing an entry point into my life, without leaving them much room for that.
Stephanie Barron Hall: My sister is a Six, but for a while, we thought maybe she was a Five. For a long time, we were talking about these things, and I said, “Well, everyone loves to talk about themselves.” And she was like, “No, no, they don’t.” I said, “Yeah, if you ask a lot of questions, people will open up.” And she was like, “No, no, no.” I think it’s so interesting now, through an Enneagram lens, to understand that more. Like, for example, I wrote on Instagram once that I don’t like asking personal questions. Somebody commented and said, “I don’t mind being asked personal questions. But if you ask something too personal, like what books I’m reading, that’s too far.” And I thought, “Wait, that’s a personal question to you? That’s small talk to me!”
Chris Schoolcraft: Well, and for every Five, that’s… You know, Fives are fairly finicky in how we assess what is and isn’t boundary-crossing. And that’s what’s really hard for people. Fives—again, I love being who I am—but we breadcrumb in a lot of ways. We leave subtle hints. We want to be found, but we don’t want to act like it. You’re not going to know what we don’t want to talk about because we’re not going to give you enough information. We just want to see if you’ll be the one or the person who can figure that out, to be in a relationship with a Five. It can be difficult, especially if someone is kind of sitting behind the veil. We’re great poker players, waiting for someone to find their way across it.
Stephanie Barron Hall: Yeah, maybe great poker players, but I’m not sure Fives are always good liars.
Chris Schoolcraft: Well, that’s why we’d much rather not say anything at all.
Stephanie Barron Hall: Yeah, yeah.
Chris Schoolcraft: Our awkwardness can betray us. In my personal belief—and this is again just my own generalization—I think Fives, in their own ways, want to be found. Subconsciously, I think Fives want to give, and to connect, but for the most part, yeah, we’ll stay silent and really stoic. We probably don’t want to lie. Part of the reason for that, I think, is that I don’t want to be caught in a lie and then have to deal with you catching me in it. If I can avoid it altogether, that’s so much better.
Stephanie Barron Hall: Yeah, yeah, for sure.
Chris Schoolcraft: Mm-hmm.
Stephanie Barron Hall: I’m curious because I’ve heard Beatrice Chestnut talk a lot about sensitivity and abandonment for Fives, and I think those are things that aren’t usually in the normal Five descriptions, where they’re like, “Oh, Fives are just robots,” which is not accurate, right? So, I’m curious if you have any insight on that.
Chris Schoolcraft: I’ll speak for myself and give an example. In my experience, the reason we put walls up is that we never developed a baseline of engagement—either because of the extremes in which we grew up, or because of how we felt like we were living through as children. Either it was very invasive or non-existent. For Fives, there isn’t always a real baseline of what intimacy is, what connection is, or what that energetic flow between people is. We don’t know what that is because it was either one way or the other, or that’s the way we experienced the world. So, we’re not robots—the affect and roboticness is partly because we feel awkward in the world, and awkwardness is our superpower. We feel awkward and love to foster awkwardness as a defense mechanism sometimes. But really, we are sensitive—I tell people Fives are one of the most sensitive numbers on the Enneagram, not just emotionally, but even in our nervous system. For example, I was at dinner a few weeks ago with some friends. All of a sudden, the energy in the room picked up. They started making plans, and those plans involved me. I felt this vulnerability wash over me, and I felt my nervous system begin to charge. I almost had a panic attack. It was the first time I realized just how much I am constantly downscaling my nervous system by not allowing access to it. For Fives, if we haven’t done the work, opening up can be a lot.
Stephanie Barron Hall: Yeah, that makes sense. I’ve seen other smaller examples of that, too, where Fives—and sometimes Sixes—have sensitivities to scents or their environment. It’s like—
Chris Schoolcraft: Well, yeah. Like now, a part of my work is every time I walk in, I turn all my lights on because, as a Five, my natural inclination is to have the least amount of visual stimulation possible. Keep the lights down, keep it nuanced, keep the music down. Then, I could handle things. But now, part of my work is that I open up the windows and let the sunshine in. I’m in a bright room now. I’m wearing a bright-colored shirt, right? You know, I can’t tell you how many [00:20:00] black shirts I had because I just needed to be smaller, take up less space, and blend in.
Stephanie Barron Hall: Yeah, yeah. I’m curious if you can share—this is more of a technical Enneagram question—but you mentioned stinginess earlier as the fixation. I’m curious if you can share a little bit about how you distinguish between avarice and stinginess. I think that can be confusing, and it’s funny, I just turned in a book—well, I turned it in for the first time a year ago, and now, as I’m re-editing, I realized, “Wait, that’s not avarice. Why did I say that’s avarice?” So, I rewrote that section, and I think it can be useful to clarify those differences.
Chris Schoolcraft: So now, I may not be the best person to ask this question, but I’ll tell you how I think about it. Avarice, for me, is—at its most basic sense—a withholding of life. For a Five, I wake up every morning, and if I’m not careful or aware, I feel like there’s not enough within me to handle life. The reality is that, just like any other number, a Five has access to energy, relationships, and life. But part of me wants to withhold that connection, withhold the connection with you. I don’t want to say too much, I don’t want to ramble, I don’t want to let my face be too expressive. I don’t want to... “What are these hands doing?” I don’t know. But the whole idea is to withhold that life connection because, if I share it, if I open up, will I have enough? So avarice really is that sense of, “I don’t have enough life within me to share with everyone else and still exist.” So, I need to withhold that.
Now, what that does, in my mind, in terms of stinginess, is that I’m always playing it safe. I’m dividing, measuring, and rationing in my mind: “Do I have enough to be here? I don’t want to give too much to this moment, so I’m going to start doing something over here.” That’s stinginess. I don’t want to give all of my energy to this one thing, so my mind is creating distractions.
Stephanie Barron Hall: Yeah.
Chris Schoolcraft: Fives tend to dabble—we’re dabblers. We’ll dive deep into certain things but dabble in others. Some of that is stinginess because we don’t want to take the risk of really pouring everything we have into something, someone, or a situation, because of how vulnerable that is. I don’t know if that makes sense or if it’s clear, but that’s how I think about it.
Stephanie Barron Hall: I think it does. I was talking with a Five who gave an example that, when they share an idea with someone else, it’s like that idea is no longer part of them. It’s like they no longer own the idea; now someone else does too. And so, I thought that was interesting because I never think of it like that. I think, “Oh, we can both fully possess this thought,” but for a Five, it’s not that way.
Chris Schoolcraft: Well, again, we love our thoughts. If we’re not careful—as a Five, I think all I have to offer is my thoughts. If all I have to offer is my intelligence and competence, then it’s a zero-sum game. I really loved one person who said, “Fives want to know the answer before they get to the conversation.” But sometimes, you’re not going to know the answer until you’re in the conversation. That was helpful for me because it told me, “Chris, you’re not going to have the energy you need until you start the conversation.” You’re not going to have all the ideas you need until you move into that team-based collaboration. That reframed the idea of withholding and helped me trust that sometimes the answer isn’t there until you get there. That opened doors for me.
Stephanie Barron Hall: Yeah, that’s so useful. It made me think of about a year ago, I was working with this group of realtors. Of course, there were tons of Sevens and Threes in the audience, and just a few Fives. The Fours were in their own space, but there was this one Five who said, “What do I do when I need to make a decision, and I come to a conversation with a client? How do I navigate that?” I told him, “You just have to try.” He said, “But how do I know when I’m ready to try?” And I thought, “I don’t know, actually.” What would you say to that type of person?
Chris Schoolcraft: Yeah. So, for doing-repressed numbers—Fives are fluent in thinking; we’ve been doing that all our lives. But we’re not fluent in doing. That’s why, when Fives show up and say, “Look, I did this thing,” a doer might look at it and go, “Okay, you did that. I do that every day before 8:00 AM.” What a Five really wants to know is, “Look, I did something. Can you see that I can do?” It takes a while for Fives to build up the fluency of doing and to feel all the feelings of doing, to maneuver through that in a way they feel comfortable. If not, all a Five will think about are all the ways they don’t do and haven’t done. Instead of seeing all the resources available to them, they’ll focus on the reasons why they can’t do.
Stephanie Barron Hall: Yeah, yeah, that makes sense. I always tell Fives to take the mental model and put it into real life and see what happens. For me, I’ve had my fair share of being stuck in a freeze response, but for me, a lot of things I do, I should have thought about more before doing them. Sometimes, doing the thing is just part of life. But I understand how it can be challenging for some to make that first move.
Chris Schoolcraft: Well, for many Fives, doing wasn’t encouraged. It wasn’t safe to do—either someone didn’t recognize it, or the risk of failing was high. So sometimes, Fives will struggle with, “Is it even worth it? Do I really want to muster up the energy to engage or get excited about this?” Apathy and ambivalence are strong protective measures for Fives because someone in their life didn’t appreciate or encourage their efforts when they started showing up. So, that became the pattern. For Fives, they have to be willing to feel the feelings that come with doing—rejection, criticism, constructive feedback, praise—because a lot of that didn’t filter through for them. Now, I do have to push back on some Fives. Sometimes, people were offering feedback or encouragement, but in our Five-ness, we filtered it out and didn’t hear it. We just heard the same messages we always expected to hear, instead of seeing what might have been there.
Stephanie Barron Hall: How do you think about how our types are formed, especially given the patterns from childhood you mentioned earlier?
Chris Schoolcraft: In general, I believe our types are formed through a combination of our genetic inheritance and environment. Then, there’s the alchemical experience of how that manifests in life. Sometimes, we experience our type as an expression of ourselves, and sometimes, we groom our environment to reinforce those patterns. It’s a really interesting interplay. So, you have to be aware of your story—the story you tell yourself, the filters that shape your environment—and learn about what role other people play in that as well.
Stephanie Barron Hall: Yeah, I think that’s so important. I look a lot at cultural context, especially because I work with many cross-cultural teams. We have to have conversations about how your cultural perspective plays into how things come across. For example, how I grew up as a Three—what I consider to be successful and appropriate—is very different from someone who grew up in Los Angeles. It’s interesting to see how those different things play out. But I agree with you on that idea of the [00:30:00] lens we have. There’s research on the heritability of personality traits, right? But I agree with that perspective too.
Chris Schoolcraft: One of the things I’ve started saying more in my team work is that the Enneagram is not a tool to make better assumptions but to ask better questions. I think your idea about social identifiers and context are part of the better questions that the Enneagram can help us ask, especially around our origin stories and the layers that come with them. I really think that’s a great way to approach it.
Stephanie Barron Hall: I’m curious about your work and how you see your type show up in the work you do. You coach people, and you said you’ve always been interested in people. Some people think Fives don’t like people, but that’s not true.
Chris Schoolcraft: No, for Fives, it’s whatever their interest is. Mine happens to be self-development and personal development, not auto mechanics or computers. In terms of my work, I feel more comfortable in one-on-one interactions. Fives, especially Self-Preservation Fives, prefer one-on-one work. Part of my growth, though, is that I lead a congregation and a staff, so I’ve had to integrate working with teams. Leading a group of people isn’t the first thing that comes to mind when I wake up. But I’ve integrated that into my life to balance my growth as a Five and as someone who is socially repressed.
Stephanie Barron Hall: Yeah, just being really intentional about your own work, which is actually a trend I see among Fives who are into inner work.
Chris Schoolcraft: Yes, once we commit to it, Fives can be pretty courageous in that. It’s one of the cool things about Fives.
Stephanie Barron Hall: I’m curious about your work with individuals, especially what you’ve learned about yourself through coaching others.
Chris Schoolcraft: In terms of being a Five or just in general?
Stephanie Barron Hall: In general.
Chris Schoolcraft: I think, for a long time, I felt like my sensitivity as a Five was a disadvantage. But now, I see it as an asset. When I’m not protecting myself and that sensitivity is available, it allows me to really connect with people on a deeper level, to be more compassionate and empathetic. I can notice things about people that they don’t always see themselves. When I’m guarded and self-protective, though, it’s harder for me to connect. I become more cerebral and thoughtful, but when I’m open and available, I can really connect and reflect back parts of people they may not see. That’s something my work has taught me.
Stephanie Barron Hall: Yeah, that makes sense. This is a bit of a technical Enneagram question, but I feel like I hear a lot of Fives talk about things in an abstract way—
Chris Schoolcraft: Yeah, the moment you said “this is going to be a big question,” my little Fiveness went on alert! But yeah, I think for Fives, we can stay in the abstract. I think for me, my entry point into being more present and embodied came through dealing with loneliness and sadness. I spent a lot of time processing those emotions, and through that, I learned to trust my body to hold them. That work allowed me to access my body center. I’ve always been active and played sports, but emotionally, I had to process my sadness and loneliness before my body could come into play more fully.
Stephanie Barron Hall: That makes a lot of sense. I’ve seen that with clients too—those who can’t feel very easily sometimes reconnect to their emotions through the body.
Chris Schoolcraft: Yes. I was listening to Russ Hudson talk about a Sufi tradition that said the beach is your body and the ocean is your heart. The only way you can get to the ocean is through the beach, meaning your body has to hold your emotions. That was a powerful metaphor for me.
Stephanie Barron Hall: That’s a really great metaphor. It helps show how everything is connected—our bodies, emotions, and minds.
Chris Schoolcraft: Absolutely.
Stephanie Barron Hall: I just lost my train of thought. Sorry. As we’re talking through this, I’m kind of thinking about a conversation I had last week where somebody said—I said, “Would you rather talk about your feelings for three hours or climb up a mountain?” And he was like, “Oh, no, neither.”
Chris Schoolcraft: Like, “No,” he didn’t want to climb up the mountain, or he didn’t want to feel the feelings? Or both?
Stephanie Barron Hall: He was like, “No, thank you to both of those.”
Chris Schoolcraft: I think for me, where I am in my life right now, is that I want to explore those things. I think for so long, I lived my life pulling away from what was possible, not living into my body. So, just interestingly, right now I’m going, “What could my body actually do? Could I climb a mountain? What would that feel like? How would that energy open up? How would I have to train for that?” And then, in terms of my feelings and emotions, I feel a lot more comfortable with those. Again, I think there’s some of that Fourness that plays out. What I find is that I like talking about my emotions and experiencing them with people. I can relish my own emotions, spend time feeling them, and sensing them and tracing them inside myself. But it is in their ability to both connect me to myself and to really be a way of sharing emotional conversations with people that I find that intimate connection. I never would have done that before, but I find it a lot more interesting now.
Stephanie Barron Hall: Yeah. It’s kind of a new way to research and understand and do something different. And even your reaction to the first part—the climbing a mountain—it kind of makes me think of the arrows, your Seven and Eight arrows.
Chris Schoolcraft: Yeah. And leaning into the boundaries, the strength, the energy of that as a way of holding that space, it took me a minute to really understand to go and to lean into that Eight arrow and to really set boundaries, be assertive, ask for what I wanted, and show up with energy. That holds the space to be [00:40:00] playful and have fun, balancing that Seven energy. As a defense, I would usually go to Seven as a way of being playful or passive-aggressive, or doing whatever I needed to do to get where that was. But showing up with good Eight energy and just being solid, trusting the moment and trusting myself, has been a game-changer.
Stephanie Barron Hall: Yeah. What was it like for you to become a leader early on?
Chris Schoolcraft: Well, I think… I’ve always been in leadership roles. I think there’s this idea of trying to manufacture energy. So again, as a Self-Preservation Five, one-on-one is really good. I can deal with people one-on-one. But what does it mean to stand up in front of a church? What does it mean to stand up in front of a thousand people? What does it mean to stand up and lead a group of people and do that? Well, I didn’t have the development to be able to do that because that wasn’t—that was my social subtype that was repressed. So, it took me a long time to work through and grow to where I can really be authentic in front of a group of people. I don’t have to engineer, amp up, or rev up. I can just be, just like I’m being with you now. I’d be the same in front of a group of people or with another individual. It’s being able to balance that. It took me a while to stop, and that’s part of the reason I burned out—I had created this persona of a leader that didn’t have any inner support. Once I burned out, all those coping skills were revealed, and I had to really rebuild from within. Now I would say I’m a more authentic leader in leadership roles.
Stephanie Barron Hall: Yeah. I think that’s a good point too, where I’ve heard Uranio talk about this as well, that Fives can actually do a bit of the chameleon thing that we normally attribute mostly to Threes. How does that play out for you?
Chris Schoolcraft: Oh, well, the distinction I make is that Fives blend; we don’t become. So we can pose as if we’re fitting in, but we don’t integrate and allow that to become a deeper part of ourselves. If I’m in a room, I can stand and act as if I’m somebody that belongs in the room. But it’s a lot harder for me to act as if I belong in the room, or if I do, I can only do it for so long. I don’t get energy from that.
Stephanie Barron Hall: Mm-hmm.
Chris Schoolcraft: Whereas in my experience of Threes, and correct me if I’m wrong, they’re able to generate energy and show up, lean in, and really be more involved in what’s happening in the room. Is that fair?
Stephanie Barron Hall: Yeah. And I think, for me, if I feel like I’m really connected with everyone, it is energizing. You know, I’m not like, “Oh my gosh, my life force is leaving me.” I’m like, “This is amazing! Let’s go!”
Chris Schoolcraft: Yes, yes. I feel my life force leaving me at the moment, yes. That’s… If I was in that situation, I’d be like, “This is draining. I don’t want to be here. I don’t want to do this.” I’m having to resist what feels like things being taken from me in that situation. It can feel like an intrusion. Like, “This is being taken from me.” That’s how I’d experience it. So yeah, that’s a great distinction.
Stephanie Barron Hall: I also think of blending in as being kind of like we were talking about earlier. It almost feels a bit Nine-ish, where it’s like, “I’m just going to blend,” but for a Five, it’s more like, “I don’t want to stick out, so nobody calls me out.” It’s the minimum amount of energy that you need to put out there.
Chris Schoolcraft: Exactly. And Nines… You know, because of Three, Six, and Nine being the attachment types, Nines can blend by really merging with people. They can be energized by that. I haven’t met a Five yet that loses themselves entirely in what they’re doing. Fives are always retaining a sense of separateness. I mean, it can happen to blur a bit, but I haven’t met a Five that doesn’t maintain a real clear sense of, “I don’t want to be here. I don’t like this. This is what I would rather be doing.” Instead of seeing all the resources available to them in the moment, a Five often maintains that internal boundary.
Stephanie Barron Hall: Yeah, well, that’s really interesting. Yeah, I’ve heard sexual Fives talk about merging more, but even then, they say there’s this deep, dark panic that comes up at the thought of being subsumed by somebody else. Like, “Why would I want to blend with somebody else? I would lose myself,” and that feels like an existential threat.
Chris Schoolcraft: Yes. That’s very true. Our sense of existential dread and threat is a big motivator for us.
Stephanie Barron Hall: How do you think people can connect better with Fives?
Chris Schoolcraft: That’s really hard because Fives dictate inside themselves what that connection looks like, and we don’t always give people the information they need to figure it out. So, I’d say whatever expectation you have about connecting with a Five, hold it lightly. I think that creates a different kind of energy with Fives. If you show up and say, “Hey, I’d love to connect, but if you don’t, I’m good,” then that’s good. Talk about things Fives want to talk about, but hold it loosely. Unless the Five chooses you as someone they want to give access to, almost any move toward them can feel intrusive if it’s not held lightly, or if it’s done too insistently. Fives are great at placating people. We can sit in front of you and smile all day long, and you wouldn’t even know that we have no desire to connect with you whatsoever. We’re just counting the seconds until you lose interest and we can move on. It’s really hard to read that in a Five, and maybe no other Fives do that, but I have certainly done that in my life.
Stephanie Barron Hall: Yeah, I’ve certainly heard and experienced that from other Fives too. It’s not something I take personally, though I’m sure it does feel personal for some people and in some relationships. But for me, I don’t have a very close relationship with those Fives, so it doesn’t affect me as much.
Chris Schoolcraft: Yes, and for numbers that really need connection, validation, or some kind of emotional feedback, that can be really challenging for Fives. They’re going to sense that need in the interaction, and if a Five senses that someone needs something from them, and they haven’t been asked directly about it, the Five might perceive that as something they need to manage or handle. That can make a Five pull away even further.
Stephanie Barron Hall: Yeah, that can feel really challenging, you know? I think for both parties, for sure. I have a lot of empathy for Fives when they feel like they can’t escape or that they’re feeling stuck without the ability to set proper boundaries.
Chris Schoolcraft: Mm-hmm, yeah, and that’s really on the Five. I love how Fives sometimes project that onto other people being “needy” or needing things. That’s just another game we play because we’d much rather make it about what you’re needing or your intrusiveness than talk about the needs that we’re not acknowledging. I’d much rather make it about you than deal with my own emotional stuff. That’s part of the dynamic for Fives.
Stephanie Barron Hall: You’re honest.
Chris Schoolcraft: It is honest, and it’s real.
Stephanie Barron Hall: Okay, so I’m curious, kind of wrapping up here—what would you recommend to someone who’s a Five and brand new to their Enneagram work? What are some practical steps they can take?
Chris Schoolcraft: I think for Fives, the biggest thing for me was to find a therapist. I needed somewhere I could trust, where I could be my whole self. I needed to find someone who could play a role in my life that allowed me to model trust, to actually do the work of trusting another person. I also realized I needed to expand my friend group. I needed to find one more person I could talk to, someone to practice with, and to trust in ways that didn’t come naturally to me. What I just said is a lot to ask of a Five. But those two things were really big steps for me, and they led to other opportunities for growth and development. But until I had a therapeutic presence in my life and began to open up my life to relationships, I couldn’t make real progress.
Stephanie Barron Hall: Yeah. Did you find a friend who had a very different personality, or was it more about adding someone into your existing circle?
Chris Schoolcraft: You know what was funny? So I really started practicing this when I was really at my lowest and I [00:50:00] ended up that particular time attracting a lot of body types into my life. So I had a lot of eights and ones, and I still have some good friends who are eights and ones. And they really were. I think intuitively I felt like I wanted protection and so I wanted, I wanted some of that in my life, but I also I needed some people in my life who weren't going to sway, who while I was up and down, they were solid.
And at that time, those body types were the ones that really provided that for me. So yeah.
Stephanie Barron Hall: Yeah, gotta appreciate that.
Chris Schoolcraft: Yeah.
Stephanie Barron Hall: Final two questions. Tell me about a book that has helped you, refreshed you, or shaped you in the last year.
Chris Schoolcraft: Right. In the last year, I read a book… I’ll have to look up the exact title, but it was on shadow work, and that book really helped me. I’ve been doing personal growth work for several years now, and I felt like I had reached a bit of a plateau. Reading about shadow work and showing up to see the parts of myself that I wasn’t seeing, that I wasn’t accessing, and wasn’t working through—was really eye-opening. It was a bit of truth-telling for me. As a Five, I can be dismissive of people, and if I’m not careful, I can fall into arrogance. I realized I needed to take a hard look at the ways in which I dismiss others and protect myself by filtering out people’s feedback. Doing shadow work opened up a lot of doors for me.
Stephanie Barron Hall: Yeah, that sounds really useful. When you let me know the name of the book, I’ll make sure to add it to the show notes. I’ve been using Jerry Wagner’s Nine Lenses on the World a lot recently, and I really like how in that book, there are two columns of adjectives for each type: one for “Me” and one for “Not Me.” One of the exercises is to integrate both and recognize that, as a Three, I’m both efficient and inefficient, and it’s okay to embrace both. It can be a stretch mentally, but it’s so important.
Chris Schoolcraft: Yeah, that’s really helpful. Fives tend to be defiant, at least I experience myself that way, and I haven’t met a Five yet who isn’t a little defiant. Shadow work is essential because it gets us to look at our arrogance, our capacity to dismiss others. There’s great thinking that comes with being a Five, but there’s also thinking that we struggle with, and shadow work really brings that to the forefront.
Stephanie Barron Hall: Yeah, I think that’s so important. Great. So, finally, tell me a piece of advice that has really stuck with you.
Chris Schoolcraft: I think for new Fives, the best advice I can give is to focus on your type. When you first get into the Enneagram, especially because it’s picked up so much energy online, there’s a temptation to focus on other people. My advice is: Don’t worry about anybody else. Don’t worry about your partner, your neighbor, your coworkers—just take a year and focus on yourself. Learn about yourself, do the work for you, and whatever else comes from that will move you forward much faster than trying to figure everyone else out. That’s probably what I would say.
Stephanie Barron Hall: That is really good advice, especially because, even when I bring the Enneagram into teams, I see people getting hung up on different types—like, “Which type can I work with best?” or “Which type should I date?” It’s like, well, that’s not really what we’re doing here. We’re trying to do our own inner work.
Chris Schoolcraft: Right.
Stephanie Barron Hall: Suzanne also said you have to learn about your type for at least two or three years before you can even think about teaching it. As a Three, my tendency would be to start teaching it right away, but I took her advice, and I think it was really useful for me. So, there are definitely some good tidbits from Suzanne there.
Chris Schoolcraft: Yeah, I think that’s helpful. The only other thing I’d say for Fives is that there is so much more available to you than you can even imagine. Continuing to realize that over and over again is the journey of a Five.
Stephanie Barron Hall: Yeah, that’s great. Well, where can everyone find you? Where can they work with you or connect with you?
Chris Schoolcraft: You can find me at my website, clsleadership.com. You can schedule an appointment there, and my email address is on the site as well. I’d love to have a conversation with you, and even if you’re just interested in more of my perspective on Fives, I’d love to talk. So, please reach out—that’s where you can find me.
Stephanie Barron Hall: Thanks so much! I will make sure to link that in the show notes.
Chris Schoolcraft: Thank you for allowing me to be here and for giving me the space to do my work by showing up and sharing. It really means a lot to me, [00:55:00] so thank you.
Stephanie Barron Hall: Of course. I really appreciate you joining me, and I know our listeners will get so much out of this interview and your Five wisdom.
Chris Schoolcraft: Thank you.
Stephanie Barron Hall: Thanks so much for listening to Enneagram IRL. If you loved the show, be sure to subscribe and leave us a rating and review. It’s the easiest way to make sure new people find the show, and it’s so helpful for a new podcast like this one. If you want to stay connected, sign up for my email list in the show notes, or message me on Instagram @Ninetypesco to tell me your one big takeaway from today’s show. I’d love to hear from you.
I know there are a million podcasts you could have been listening to, and I feel so grateful that you chose to spend this time with me. Can’t wait to meet you right back here for another episode of Enneagram IRL very soon.
The Enneagram IRL podcast is a production of Nine Types Co., LLC. It’s created and produced by Stephanie Barron Hall, with editing support from Brandon Hall and additional support from Critz Collaborations. Thanks to Dr. Dreamchip for our amazing theme song, and you can check out all of their music on Spotify.
