Each Enneagram type brings a distinct flavor to creativity.  Professional illustrator James Yamasaki shares how he came up with the ideas for the number illustrations in the book Teamwork 9.0.  I wanted Jimmy to imbue meaning into the numbers while avoiding any stereotypical associations with human styles often portrayed in Enneagram type illustrations of people.   Jimmy did a masterful job, and his process gives us a sneak peak into the mind of a creative Enneagram Type 5. Learn about his color choice, the types of lines he used, and the inspiration for the distinctive features.

[Video Transcript]

Matt Schlegel:                   I’d like to welcome James Yamasaki, also known as Jimmy. Jimmy’s a professional illustrator. His work appears in Children’s Highlights and National Geographic’s Kids among other publications. Also, he teaches drawing at the Academy of Art University in San Francisco. And you’re my cousin-in-law, and it’s great to have such a talent in the family. And I am delighted that we were able to partner on the book project, and I often find myself admiring what a fantastic job you did imbuing meaning in to the numbers that represent the Enneagram types and the steps in the Enneagram change management problem solving process. So I want to thank you so much for taking the time today to discuss your creative process in coming up with those ideas for the numbers and the illustrations.

Jimmy Yamasaki:              Sure.

Matt Schlegel:                   But before we get started, could you remind me of how you were introduced to the Enneagram, and when was that and what was that like for you?

Jimmy Yamasaki:              I’m pretty sure you introduced me to the Enneagram, and I’m thinking it must have been in the early 2000s, maybe. Or maybe before that, but I guess I was curious about understanding myself and other people a little bit better. And I think as you described it, it kind of opened my eyes to the different sort of mindset or ways to thinking that people have, and I mean, it sounds a little naïve, but I think maybe I didn’t consider that as much before or maybe I sort of projected my own thinking onto other people and then sort of tried to understand things that way. I feel like it helped me understand others, and it helped me understand myself.

Matt Schlegel:                   Yeah, that’s fantastic. That is one of the great ways to use the Enneagram, for sure. Did you find that you were thinking about different Enneagram styles when you were drawing, making illustrations, especially of people?

Jimmy Yamasaki:              Before the project we did together?

Matt Schlegel:                   Yeah, well, just in general because you put so much personality into your drawings. I’m just wondering, do you actually think about, “Oh, this is a type eight or a type seven,” when you’re doing that?

Jimmy Yamasaki:              Yeah, I think. Maybe not all the time, but I definitely… Because I think some of the numbers to me, my understanding of them, at least in my head, is a little more clear, and I think some numbers, they seem more subtle or a little harder to really grasp. So for example, like an eight, I feel like I probably have thought of maybe someone that was expressing some emotion or anger or something and I kind of maybe thought of that number. Yeah, some of the other ones, I think it’s a little harder to… Or it will be more subtle when you show that in a character, maybe like the three or something. I feel like it’s a little difficult.

Matt Schlegel:                   Right, right.

Jimmy Yamasaki:              Yeah. But I have thought of it a little bit, I think.

Matt Schlegel:                   Yeah, yeah. Well, definitely you thought of it when you were making the numbers, that’s for sure. Well, let’s go through the numbers, and I just like to hear your thoughts about how you came up with the ideas for each one and that process. So I’m going to just first of all show the number one, and Jimmy, you can’t see this, but…

Jimmy Yamasaki:              I’m looking at the wheel on my own computer, so I can see.

Matt Schlegel:                   Okay. So why don’t you tell us what your inspiration for the number one was?

Jimmy Yamasaki:              I think, trying to remember back when I did it. I think I was thinking of the perfectionism side to the one, and I think initially, I just made something that was very perfect, and then I think we discussed it, and you said that it would be better if there was a little chip in it or a little imperfection to kind of show that aspect of that Enneagram type. So I thought something that’s perfect to be a diamond or a crystal, and then I guess along those lines, also just in terms of the whole group, I tried to think of different colors for each one. And I thought because I thought of a crystal or a diamond, like a blue-ish color would work well with that. And I can’t remember if I thought about anything else.

Matt Schlegel:                   Right. Yeah. I think one of the things… So you really brought out that perfectionism in the one, and one of the things that we wanted to try to do also with that type one dynamic is to not only focus on the perfectionism but also focus on the fact that they’re usually the first to see something wrong as well. And so then you added that little chink in the one. It’s like, “Oh, hey! This isn’t perfect! It’s not right! We need to fix this!”

Jimmy Yamasaki:              Yeah, yeah.

Matt Schlegel:                   Yeah. I think this is… It’s a great illustration, and one of the other things we were trying to do is to not put any references to necessarily people in the numbers, right? A lot of illustrations, they use people, and that can get complicated because we’re just trying to illustrate a dynamic independent of people themselves, of the individuals.

Jimmy Yamasaki:              Yeah. And I don’t think, maybe it didn’t work for all of them, but just in terms of marks or lines, I think some of them I tried to distinguish straighter edges and sharper corners and things to apply to certain numbers. Some of them, I feel like, doesn’t totally work, but with the one, I think because of the perfectionism, I kind of thought of it as more rigid. And as we go through the other ones, excuse me, I think some, more organic or curving lines worked better with the sort of emotions or feelings that I associated with those or from discussions we’ve had or descriptions that you’ve given me.

Matt Schlegel:                   Right, right. Well, that’s a great lead-in for type two, or step two. So go ahead and describe how you came up with this one. This one just blows my mind how perfect it is.

Jimmy Yamasaki:              Yeah. I kind of don’t remember if we were discussing it, but like I was just saying, the two has a lot of feeling, I think. I think it’s a number that wants acknowledgement for things that they’re doing. So there’s this interconnectedness. So I guess is just associated kind of curving, organic lines with a plant or something or vegetation and then how it kind of branches out to all the other numbers. I think that’s how… My memory’s a little foggy. I can’t remember if we kind of discussed that beforehand, or if I did a few sketches and that was one of the ideas, but yeah. I think the sort of emotional side of that number translated to more organic quality in the shapes.

Matt Schlegel:                   Right, right. Yeah, I don’t remember really having a conversation with you about this one. I think this one really, your inspiration came up with this, and that’s fantastic. It’s like the tangled web we weave, right?

Jimmy Yamasaki:              Yeah.

Matt Schlegel:                   And it’s so funny, too, because twos do feel a connection with every type. A lot of types will kind of prefer some types over others, and twos pretty consistently say that, “No, I have friends will all types. I like everybody.” And that’s the, in step two of problem solving, that is the crucial step. It’s bringing everybody together and including everybody and creating those connections, especially emotional connections with wanting to solve whatever problem was identified in step one. So the two has exactly this dynamic of being connected to everybody and being able to bring them in. So it’s just perfect, Jimmy.

Jimmy Yamasaki:              Oh, thanks.

Matt Schlegel:                   Yeah, yeah. All right. Well, let’s then go on to the three, and this is also fantastic. You want to tell us about this one?

Jimmy Yamasaki:              For the three, I think maybe of the whole Enneagram, the three is one that I have a little trouble with. I feel like I need to read more about it in order to get a good grasp on it, but I think we talked about the three as sort of coming up with ideas or good at coming up with an idea. So that just made me think of a light bulb. This is an example where maybe the way the three sort of presents themselves to others, in my mind, when I’m looking at it, maybe it would be a little more rigid or something or pristine.

Matt Schlegel:                   Pristine, yeah.

Jimmy Yamasaki:              So that’s sort of where the example I was giving earlier where straight edges and curved edges for some of them. Maybe when I’m looking at this one now, I can kind of see how maybe the three could be a little more geometric in terms of the way they present themselves, but I think we were kind of emphasizing the conceptual side of the three, how they can come up with ideas without self-censoring or kind of getting in their own way. They are really good at generating ideas. Yeah, so that’s why I did sort of that light bulb.

Matt Schlegel:                   Yeah. No, it’s perfect. And you do get the straight lines coming out. That’s that projection of the straight line, but also, the three is at the core of the emotion center. So I think you essentially capture both here, right? You captured the straight lines, which is that kind of external façade, but then you also capture the curves of being in that emotion center where the three occupies. So yeah, you may have just inadvertently hit on perfect illustration here. So I guess in the problem solving, we had probably talked about that and how step three in problem solving is the ideation step, the step where you just want to create as many ideas as possible. I think this perfectly captures this idea. So that’s fantastic.

Jimmy Yamasaki:              Thanks.

Matt Schlegel:                   All right. Let’s go on to then the next one, which is the four, another fantastic and definitely no straight liens here.

Jimmy Yamasaki:              Yeah.

Matt Schlegel:                   This is the least linear of all types.

Jimmy Yamasaki:              Yeah. So I think I kind of made the contours of it kind of wavy and jagged. I think this is one where we discussed putting some elements inside of the number. So I tried to keep the overall hue or color sort a purple-ish, just because in my mind, it kind of relates to feelings or something in the color wheel. But then within that, I put a bunch of different things. I think there’s a cloud with lightening, and there’s hearts and there’s a wave. So just trying to show the full range of feelings that the four can have. Yeah. I feel like this one, in the beginning, I feel like I had a pretty good idea of what I wanted for this one just because I think I had an okay sense of what the four is like. So I think the four is associated with artists sometimes. So I was thinking of something that, I don’t know, evokes a painting or art or something.

Matt Schlegel:                   Nice. Nice. Well, yeah, and the type four is the internal feelings type, and they’re essentially feeling all feelings all the time. They’re feeling everything all the time, and I think this really captures that. You’ve put all of these different feelings inside of the number so that the four is feeling all these different things, and all those feelings are always there, and they’re feeling them all the time.

Jimmy Yamasaki:              Yeah.

Matt Schlegel:                   So this is perfect. This is perfect. And then, from the problem solving point of view, when somebody has an idea in step three, then the first thing that happens is that you have some emotional reaction to that. It’s going to be, “Oh, that idea is great,” or, “Oh, that idea is terrible.” And that instantaneous emotional reaction, that is the energy of the four. It’s like, which one of those feeling that’s rolling around is going to pop out when somebody puts an idea out? Yeah, so this is perfect. I love it. I love it.

Jimmy Yamasaki:              Thanks.

Matt Schlegel:                   Yeah. All right. So one other thing is how conscientious you were about the color selection, and I’ve tried to… When I, in subsequent work that I’ve done, I’ve tried to use your color palette when I’m talking about each one of these steps in problem solving or Enneagram types because I think it really helps to bring out and illicit that kind of visceral reaction of what’s going on with the number. Yeah, that’s just another dimension to what you did here.

Jimmy Yamasaki:              Oh, thanks. Yeah, I think not only the shape I wanted each one to be distinct, but each one have a different color so that they’re totally separate.

Matt Schlegel:                   Right. Yeah, yeah, awesome. All right. Now let’s go on to one of our favorites. Now, full disclosure, Jimmy, you’re a type five right?

Jimmy Yamasaki:              I’m pretty sure. I mean, that’s one thing, sometimes Sofia, my wife, and I talk about things, about the Enneagram and about how we are processing something. And there are times when I start to think, “Oh, am I a six, maybe?” But I think overall, I feel like I’m probably a five. It seems like most of the points that are listed under the five apply to me.

Matt Schlegel:                   Yeah, yeah.

Jimmy Yamasaki:              So yeah. So when I was coming up with this one, I guess I was thinking about the kind of research and collecting and, I don’t know, gathering of information that the five does. I kind of looked at myself, I have a lot of books that I’ve just collected. So I thought a book would be a good shape. And then I can’t remember if it says it in the description of the five, but I made the five number kind of like a digital clock type of thing because it seems a little colder, not as warm or emotional contrasted with the four. And then the blue is kind of along those lines, a little bit more cool, detached. Yeah, so that’s how I came up with that.

Matt Schlegel:                   Yeah, I know. That’s brilliant. I love it. And the book is closed, too. It’s not open. It’s closed.

Jimmy Yamasaki:              It should have a clasp on it with a lock.

Matt Schlegel:                   Right! You can’t find out what’s inside my book. Yeah, that’s great. And I think that perfectly captures both the personality dynamic of the five and then also that step in problem solving where it is where you do the research. You get out the books. You make sure that those solutions that pass through the emotional gauntlet of step four, it’s kind of like an emotional filter, you take the positive ideas that pass through step four, and they come into step five, and then you want to do a rigorous analysis of those, and that’s where you pull out the books and you analyze them closely. Yeah, this is fantastic. All right. Now we’re going to get to one of my favorite types, which is the six.

Jimmy Yamasaki:              And this is one that I remember having trouble with. I feel like you came up with the idea of a crystal ball type of thing, kind of I guess showing the six’s ability to foresee problems or look into the future kind of. I think in the beginning, I struggled with it because I know the six deals a lot with fear and whether it’s deliberately facing the fear or avoiding. So I guess some of the green and the kind of swirling shapes are kind of like a spooky kind of imagery, but I think the main shape, the crystal ball is focusing on the thinking of the future and always planning ahead. I guess the number, I take kind of along the lines of the spooky thing. It’s more like a gothic kind of calligraphy. Yeah, I think that’s how I figured that one out.

Matt Schlegel:                   Yeah. No, that’s perfect. And I hadn’t connected the dots on the color, but we’re actually coming into Halloween right now as we talk about this, and I’m thinking about, that’s a scary color that’s often used in spooky stuff is that scary green, right?

Jimmy Yamasaki:              Yeah.

Matt Schlegel:                   Yeah. And the swirling mist and cob-webby type of stuff that’s in there. Yeah, and the gothic number, very spooky stuff. So you capture the fear, but then you also capture that six dynamic of just thinking about the future, just constantly processing, “What if this is going to happen? What if this happens? What if this happens?” It’s like I’m a six, so that’s kind of the way my brain works. It’s constantly simulating future outcomes to see where the danger might be so that we can avoid it. And then in problem solving, step six represents the planning step where you’re thinking about, “Okay, now that we have a validated idea that has gone through step five, now we need to take that idea and get it to the goal and solve the problem.” So what’s the plan? How do you build a plan around getting us from A to B, that gets us from the idea actually to the realization of that idea that solves the problem? And that’s where that six dynamic can really come into play. So I think that’s perfect, Jimmy. I love it.

All right. So now, let’s switch over to the seven. Yeah.

Jimmy Yamasaki:              The seven, I feel like probably of the nine numbers, three, seven and nine were probably the hardest for me… Or I didn’t have a clear idea of what should represent it for those numbers. But with the seven, I guess I thought about they’re the number that wants experiences and… Is that right? They want to kind of go out in the world and take a lot of stuff in. So I just made the number, I think I looked at sort of a circus font type of imagery where it’s very ornate. In this way, I fee like maybe the connection maybe wasn’t totally clear, but in my mind, it seemed like the seven is a little more flamboyant or something, or kind of presents itself more freely. I’m not sure, so kind of contrasted with the five which is very just boring and flat.

And then I kind of added these lines around it indicating maybe movement because I’m thinking the seven is always on the go and trying to do stuff. You can kind of maybe clarify some of those aspects of the seven, I think.

Matt Schlegel:                   Yeah. Yeah. Well, what I saw in this is that it’s exciting. It’s just like, “Oh, that looks like excitement. It looks like I want to engage with you. So those were some of the things that I took away. And I agree with you. When I was thinking about the seven, it is one of the harder ones to put into a picture, and when I saw this, I’m like, “Oh, yeah. This is perfect.”

Jimmy Yamasaki:              Oh, good.

Matt Schlegel:                   Yeah, because it’s really trying to show… If you’re trying to show a number in the best possible light, which is what you’re doing in step seven of problem solving. You now put this plan together, and now you want to take it back to the broader set of stakeholders and show we have a plan now that can get us from A to B that will solve your problem. And you want to get that out and get all the stakeholders excited about moving forward and doing it and solving the problem. So that captures, the lines capture that motion of, “We’re going to move forward, we’re going to do this. Come on. It’s going to be great!” And even the number itself, it’s almost like an arrow. It almost looks like an arrow kind of shooting out and moving forward. Let’s go forward. Yeah. I thought it was great. What was your idea on the color here?

Jimmy Yamasaki:              I think along the lines of sort ornate font, something that was just bright and cheery, I guess in my mind positive feeling. So I wanted to… It looks very similar to the three, but I guess I kind of pushed it to orange a little bit so that… I don’t know if we have a full, I think maybe the rainbow spectrum has fewer colors. So you have add a few in between to kind of fill out or make the spectrum full. Yeah, I think I was just kind of thinking more of positivity or maybe a little bit of [showinenss 00:30:39]. I’m not sure if that’s a word.

Matt Schlegel:                   Yeah. Well, and it’s interesting because both the seven and three can share those qualities. And then you actually captured that in the colors as well because they’re a little bit different, but they can be very similar, too.

Jimmy Yamasaki:              I got lucky.

Matt Schlegel:                   Yeah, no. It was great. That’s why whenever I go back and look at the numbers, I’m like, “It’s just brilliant the way this all came together.” All right. Well, let’s go on to the eight now. This one, probably, this one is outstanding. It’s like, “Oh, yeah. Nailed it.”

Jimmy Yamasaki:              Yeah. I just tried to think of something bold and strong, and I made it larger than the other numbers. Of course, red is a bold color. And just to kind of add to the… I guess I kind of think of the eight as kind of almost like projecting itself out to others. So I kind of made these clouds or maybe steam or something bursting from behind it. Yeah, and again, for this, I tried to use straighter lines to make it real solid. Yeah. I made a little perspective like you’re looking up at it.

Matt Schlegel:                   Yeah. Yeah, yeah. Well, when I saw the clouds, that’s interesting that that’s what you were thinking in the clouds because when I saw the clouds around it, I thought of stamping a foot down.

Jimmy Yamasaki:              Oh, as if it’s coming down.

Matt Schlegel:                   Boom. Yeah. Boom. And there’s just this cloud coming up around it. Yeah, yeah. It totally captures that dynamic. And it’s like on a construction site, a busy construction site where everybody’s working hard and getting stuff done, and there’s going to be just a lot of dust kind of floating around.

Jimmy Yamasaki:              Yeah, yeah.

Matt Schlegel:                   This is the… Step eight is the implementation step. It’s the step where you get stuff done. And of course, there’s going to be a lot of dust raised when you’re working hard. So I thought that was perfect. That was perfect.

Jimmy Yamasaki:              Okay.

Matt Schlegel:                   Yeah. Yeah. And the red, also, just great combination all the way around. Totally captured that. So let’s then go to step nine. And what were thinking when you put this one together?

Jimmy Yamasaki:              Yeah. I think the nine was another one I struggled with a little bit. Kind of like the seven. I know that the nine wants to get along with everyone, I think, is that right? So I was thinking initially something that was maybe kind of softer or rounder in shape, kind of like “I mean you no harm” sort of feeling. But I think we discussed it, and I think maybe you came up with the idea of adding the hands as if it’s going to give a hug. And then also, contrasted with the eight, I made it a little smaller because I think outwardly to the world, maybe the nine doesn’t sort of make its presence felt as much. It’s a little bit quieter. And then the color, kind of along those lines, a little more cool and not as bright, I guess.

Matt Schlegel:                   Yeah, yeah, yeah. I love those words. I don’t mean you any harm. It’s so funny. After step eight, where everybody buckles down and gets stuff done, then inevitably in that transformation, there will be some need to go back in and harmonize the solution with everybody, and there can be some unintended consequences whenever you take an action. And step nine is when you go in and say, “Hey, look it. We did not mean you any harm. It wasn’t our intention. Our intention was to solve the problem.” So if anything bad happened to you, that was not our intent. So let’s look, first of all, is the problem solved for you? Great. And if there’s a new problem that’s come about, then let me know. Tell me because we want you to feel okay, too!

Yeah, and that illustration I think totally captures that dynamic. It’s just perfect the way. It’s very welcoming and kind of draws you in for a conversation. Yeah, that’s fantastic. It’s not so much that they want to be liked. They just want everybody to get along. They just want everybody to get along. They just want to minimize the conflicts. They don’t want anybody to be out of sorts. So that’s kind of what’s driving them, which is a little bit different than the seven who actually does want to be liked more and the twos as well.

Jimmy Yamasaki:              Yeah.

Matt Schlegel:                   Yeah, it’s a little bit different. But I think this totally captures that dynamic.

Jimmy Yamasaki:              And is the nine maybe emotionally, can they be a little distant? Because I think when I’m looking at it now, I made it look a little metallic. So I think that was in reference to maybe emotionally not as organic feeling as the two.

Matt Schlegel:                   Right. Right. No, I think that’s exactly right. I think the nine is not looking out for that emotional connection. They just really want the world to be at peace. So they can appreciate emotions because that’s one of the things that they use, but that’s just one of the tools to get people to be at peace. And that’s why the nine is at the very top of the Enneagram because they can essentially see both sides of everything. They can see the emotional side. They can see the thoughtful side. They’re in the center of the anger. They can understand and appreciate the anger. They have the complete preview of everything. So I think it is… They are well-rounded, and I think by illustrating this with roundedness really captures that, definitely.

Well, that’s awesome, Jimmy. Again, just such a great job with the illustrations.

Jimmy Yamasaki:              Thanks.

Matt Schlegel:                   Do you have any final thoughts on it? What was it like, I guess, for the project? Was it a fun project for you? Was it a hard project for you?

Jimmy Yamasaki:              Yeah. No, thanks again for asking me to help you out with this. Yeah, I really enjoyed it because I think it was a challenge trying to put the Enneagram into kind of a more abstract representation, and it was a fun challenge to kind of think of what would work best for each one and how they would all work together. So yeah, it was great.

Matt Schlegel:                   Awesome. Awesome. Well, thank you again for partnering with me in the project. It was such a delight working with you, and I can’t tell you how much I appreciate just how well everything turned out. So thanks again, Jimmy.

Jimmy Yamasaki:              No, thank you.

Matt Schlegel:                   All right. And I really enjoyed the conversation today and getting your insights. And in the future, I hope you’d consider coming back, and we can have another conversation about some of the different aspects of the Enneagram and how you may be using them in your work.

Jimmy Yamasaki:              Sure. That sounds great.

Matt Schlegel:                   Awesome. All right. Thanks again.

Jimmy Yamasaki:              Okay.

Matt Schlegel:                   Bye.

Jimmy Yamasaki:              Bye.


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