Kitces & Carl Ep 23: Following Through On Your Business Creativity By Saying ‘Yes’ And Figuring It Out Later

***Editor's Note: Can't get enough of Kitces & Carl? Neither can we, which is why we've released it as a podcast as well! Check it out on all the usual podcast platforms, including Apple Podcasts (iTunes), Spotify, and Stitcher.

Show Notes

• Dan Roam's Napkin Academy

Kitces & Carl Podcast Transcript

Michael: Welcome, Carl.

Carl: Greetings, Michael. I can't wait to hear where we're going to go today!

Michael: You can't wait to hear where we'll go today. Well, we're continuing the travel journey, right? Last podcast, you were asking me about the world of travel, traveling around the world, and all the speaking travel that I do these days. So I wanted to turn this back to you in the same way.

I know you do a lot of travel as well for conferences, but I actually wanted to dig more directly into what you do, which is this whole world of drawing – of Sharpies – like, you pull out napkins and draw on them with Sharpies, and you've made a business out of this.

How Carl Began Creating Sharpie Art [01:35]

I'd love today to take a few minutes of understanding how that journey came about and what that creative process is for you. How you sit down and just take these ideas and draw them up with a Sharpie. Last week I was at the CFP Board's headquarters for a meeting, and their napkins in the cafeteria had Carl Richard's drawings about financial planning on them! They’re everywhere. So how did the Sharpie thing get started?

Carl: Yeah, that's a fun question. What's really interesting about stories, I think, is that they're all made up, right? So I'll try to actually stick to the fact pattern here and not make up some beautiful narrative, because it was all a giant accident. The truth of it is, I was sitting across the table, and I can remember who it was – I think it was Dave and Diane, two of my favorite people and best clients;  smart, successful people – and we were talking about some concept. I wish I could, but I can't recall what the concept was.

But there was something that they really needed to understand in order to make the decision they were trying to make. And again, they're super-smart and successful. So the fact that I was just getting blank stares was a reflection of me, not them. And I thought I was pretty good at explaining stuff; even though this was still in the early days, I still thought I was pretty good at it, but I was getting nothing.

I hadn't ever done this before, and it should be obvious to everybody that I have no art background. And I wasn't a doodler, right? I didn't do any of those things. But there was a whiteboard, and just out of an act of desperation, I stood up and I said, "No, like this."

And I drew...it was like a circle and a square with some arrows. If I remember right, it was around like the flow of money, like cash flow...I can't remember what it was. But it was a circle, squares, arrows, nothing complex. And I remember distinctly – they were like, "Oh!" Right? I distinctly remember the feeling in the room of...

Michael: Was it that light-bulb-above-the-head-Eureka moment, like, "I've got it?"

Carl: Yeah. It was, to me, that dramatic. Now, I know to them, it was probably just, "Oh, okay, that makes sense." But to me, that feeling – I was like, "Oh, that was cool. Can I do that again?"

Then a couple of weeks later, I was explaining something; I recall it was around asset allocation and I sort of drew it. We all know the printout of the beautiful pie chart; instead, I drew it. And then I drew an arrow: "We're going from this allocation to this allocation." After the person that I was meeting with left, they called me later and said, "Hey, that thing that you drew on that piece of paper, would you mind scanning it to me and emailing it to me so I can show my spouse?"

Michael: Because he didn't take the paper with him, you kept it because it was just scrap paper at the end of the meeting...

Carl: It was just a yellow pad or whatever. It just wasn't anything important. So I scanned it, and sent it to him so he could show his spouse. And I remember when I saw it digitally, I thought, "Oh, I could send it to other people." That was as simple as I thought it was. Like, "Oh, I could send this to other people."

So I kept doing those things. I would notice if anybody asked me the same question, if I answered the same problem, and all the listeners and viewers would relate to this.

Michael: Yeah, we all get certain questions from clients the same way, over and over and over again.

Carl: Yeah, based on the news cycle or whatever. Like if anything was happening, and if I would say, "Oh, that's the third time somebody has asked me today, I bet there are other people who are wondering about this question too. I'll write up what I said, and then I'll try and illustrate it really quickly with one single little drawing."

So I put it up on this website and named the website “Behavior Gap”. My mom and my sister were the only readers (and I found out that my sister was lying). So it was really just my mom. But I kept doing it. And then one day – his name was Keith, I can't remember his last name – another financial planner somewhere sent these to Ron Lieber and said...

Michael: At The New York Times.

Carl: At The New York Times. He said, "Hey, you'd really like these." I still have that email, and I've thanked him like 1 million times because this Keith has changed my life. And then Ron said, "Hey, I love these, would you mind doing sort of a..." I can't remember what he called them, like an experiment or something. "You want to do it for a couple of days with us?" I knew enough to say yes and figure things out later.

So that's how they happen. I struggle to point to something that's repeatable, except for one thing, like playing in traffic. Not being scared to play in traffic is the only repeatable skill out of that, right?

Michael: Meaning that your clients had a question or an issue and you would say, "Well, I'm no artist, but let me just sketch this out and see if I can help connect what's going on for you." And that was the breakthrough moment that kicked it off. Like, "What the hell, I'm not an artist, but I'm just going to try to draw this and see if I can get a better connection to these clients."

Carl: Yeah. In fact, maybe that's a good way to think about it. We can go there if we want to in terms of doing public work and the book and whatever. I just learned this again today, when I hired a designer to do some work for me, and there were no images in the work, none of my images, and I sent it out and said, "This work is amazing. It's so great." But when I sent it out to people they said, "Wait, where did you go?" I was like, "Well, wait, aren't we supposed to grow up at some point and stop playing with crayons?" And they're like, "No, no, no, no, no."

So I think what I keep learning and what I would encourage people to do – do not tell me you're not an artist, neither am I, we're not talking about being an artist. There is just something incredibly approachable, and people are impressed when you have command of the material enough that you can go, "Oh, kind of like this." Right?

I think if you want to learn to do that it's an amazing communication skill. When you look at the data around people...the research around people who understand things visually, right, and it's like 85% or something. Like, visual representation enhances learning for like 85% or 90% of us. And then you look at the inverse of that, how many people are comfortable communicating visually, it's like 5%. I would suggest everybody do it. And if you want, the best way I know to do it is Dan Roam's Napkin Academy, right? He teaches business people how to communicate effectively using hand drawings.

Michael: Using napkins?

Carl: Yeah, essentially. And Dan is the master. I didn't know that I was doing a thing. One time he...

Michael: Because I didn't know this was a thing either. So there's actually an academy for napkin drawing.

Carl: Yeah. It's tongue in cheek, the Napkin Academy, but the drawing, like visual thinking is a thing, right? And Dan Roam teaches people how to do it.

Michael: Yeah, we'll add a link in for the transcript on this or for the show notes if people are listening by podcast. If you want to see the Napkin Academy and learn to be a better visual artist communicator person, maybe we'll just do it with yellow pads and whiteboards because it's our industry, but we can pretend they're on napkins.

Carl: Yeah. And I think it does point to a bigger thing, though, which is visually communicating. I don't think our industry has to be among the worst at design, right? Nobody wants to open anything from our industry.

Michael: So what does the creative process look like as you've produced these over the years? Is there a tortured artist in there? Like for every napkin drawing we see there are 172 crumpled up ones that didn't come out right off in the card. You're like, "Ugh, this one's not good through this side. Ugh, this one didn't come out through this side." Or do you just kind of sit down where there's a thing in your head, you just drop it out, there it is, and boom – it's done?

Carl: No, it's actually closer to the latter. I used to do them all on cardstock and Sharpie. I would buy just reams of cardstock and I would sit down; this was always on...I can't remember what day, it seems like it was on Wednesday or Thursday...because the main forcing function was a deadline for "The New York Times." And it was weekly for 10 years. This month is 10 years.

Michael: Wow.

Carl: Yeah. It's pretty crazy. So that's whatever that number is, 500-plus, every week. So I'd sit down and often I'd have the column written. Sometimes I'd have an image in my head, and I would write the column to match that. But most of the time, what's happening, I think, is applicable whether you want to draw it or use a graphic illustrator.  Most of the time what was happening was there'd be a drawing, or sorry, a column written, and then I'd think, Okay, if I had to sum those 500 words up in a single image and I only got one chance – I wanted people to think about one thing – what would be the logo or the icon of this idea? That's the way I would think about it.

I think of them as shortcuts into an idea. The good ones are shortcuts and souvenirs – there are shortcuts into an idea, and there are souvenirs of the learning experience. And so I just think, "250 – 500 words, what's the one thing?" Then I'd sit down and I would play with things, and I would draw and I would crumple up paper. I wouldn't crumple, I would just throw it and try to make it like a Frisbee.

Michael: Well, because it's heavy cardstock, you can wing that pretty well. It's going to sail like a paper airplane.

Carl: Totally. So in my studio, sometimes you'd come in and there would be stuff everywhere. Now I do it on an iPad with Apple Pencil, so there's not quite the fun of just hocking stuff.

Michael: I didn't realize that. Like, your Sharpies predate tablets, because you've been doing this for 10 years. I think we've only had tablets for like eight.

Carl: Yeah. And really, Apple Pencil changed all of that for me. It was the first time I felt comfortable doing that. Before, I tried every single stylus and just couldn't get anything that I liked. So that's the process – just sit down, work and work, work, work, work. Some of them were like “boom!” like one take Frank Sinatra, right? I just nailed it. Other times it was hundreds of pieces of paper.

Where Carl Finds The Inspiration For His Art [13:44]

Michael: And where does the inspiration come from?

Carl: Well, it comes from the column, the words, because I've done this on other people's work, too. I've illustrated other people's books. There have been lots of projects like that. So those words. Then there are a couple of things going on. One, I've got a set of constraints, and that's called my skill. If I can't do it basically with a Sharpie and cardstock, there are no graphic design tools; I have none of those things.

10 years ago I tried to download Adobe Illustrator and learn how to use it. And the little bar that showed download time said eight hours or something. And I thought, "Any software program that's going to take eight hours, I shouldn't touch." So from then, I've embraced that constraint. A couple of times I felt like, "I'm going to learn to be a graphic designer, and draw." And I've said, "No, no, no, no, if you can't do it with a Sharpie..."

So that's where the inspiration comes from is simple tools...I like Sharpie-level resolution. It's not a fine 0.5 mechanical pencil, it's simple tools, broad strokes, chainsaw, right? That, plus the words on the page that become the inspiration.

Michael: And do you get critical of your own art? Like, "Oh, that circle isn't round enough."

Carl: You have no idea. People who have come in to see the floor with all the paper, they're like, "What was wrong with that one?" I'm like, "Oh, the circle was just a little off." You have no idea. It's ridiculous. Like, nobody else cares. Nobody knows. There are so many of them that I want to fix. Oh, so many.

We've been going through putting them all up on the sketch store because other people want to buy them, and I'm like, "I've got to fix that one." And the team here is like, "No, it's part of what makes them great is they look like crap." And I'm like, "Oh, that's nice."

Michael: They're authentic.

Carl: Somebody sent me a note the other day that said they're...she used the word "immediacy" and "approachable."

Michael: Well, I know there are advisors out there who...well, as I said, like the CFP Board uses these in their offices. I know there are advisors that have some of the popular sketches you've done. “Financial planner is the thing between you and stupid,” some of those fun images, and the value of what we do that hang as art in their offices, that hang as art in their conference rooms. I know, at one point, you got to show this at an art gallery, right? Like, you've done art gallery showings?

How Carl’s Work Led To Art Gallery Shows Around The World [16:44]

Carl: Yeah. Look, you can't bring that up without me telling this story. I moved back to Park City, Utah, and I had taken a pottery class when I was eight years old in the Kimball Art Center. The Kimball Art Center is like, I considered a jewel of Park City. And Park City is like a cute little mountain town, but it punches way above its weight artistically. The home of Sundance Film Festival and the Sundance Institute, all that stuff. They emailed me and they didn't know that I lived there or that I grew up there. They emailed me and said, "Hey, we'd love to invite you to do a solo 50-piece, 8-week show." And I replied and said, “There are three words in this email that I don't understand: solo, piece, and show. Like, I don't know. I don't know. But, yes.”

So I said yes; I knew I’d figure it out later. Say yes. Then I immediately called one of my artist friends and said, "Hey, come over here, Nelson. Nelson, come to my office. I don't know what to do. What does this even mean?" And I was like, "What can I do with 50 pieces?" I was drawing on an old weather chalkboard that I loved in my old studio/office, and I was writing things. He was like, "You know what? Let's do old weather chalkboards." And I was like, "That's the craziest idea I've ever heard. Let's try it." So we used these old weather chalkboards, and then we had to figure out how to price them. I was like, "Well, how do you price things?" And all my artist friends were like, “I dunno…” Then I said, "Well, where's the book? In my world, we know how to price things. Where are the comps? How do you...?" There's no book. So I just decided to do it per square foot because everything else was per square foot.

Michael: You priced your art per square foot.

Carl: We didn't tell anybody that. Nobody will hear it now either. So these chalkboards; I did the calculation on the calculator and it was like, that's $1,500. And I was like, "Oh, that's just...that's fine."

Michael: What the hell.

Carl: I was like, "Whatever." And I didn't expect to sell anything. But it was one of their most successful shows. We basically sold the whole show out. I came in on opening night and there were these little tags next to all of them. It was an eight-week show. You've seen these at art places you've been to. There were black dots on a bunch of them. And I was like, "Oh, that's sad. That must mean something like somebody didn't like them or something." And I went to ask the lady and she was like, "No, those are the ones that have sold already." So I was just like, "What is going on?"

So anyway. That led to a show in California, and then a show in London. I did a show in London, in the old city palace. That was amazing.

Michael: Does that mean all the art critics come out and grade your art? Do you get newspaper reviews on the art show?

Carl: Look, you're just pointing at all these. So the London show, I flew my dad over. We were building these big chalkboards. We had to find a studio space. We build these chalkboards. We do this. This was with Greg Davies. It was a whole big thing. It was really fun. And I thought we would hang these on the wall. But this is...I can't remember what it's called, the lord of the manor's house. It's like the oldest city palace in London. I'm sure I'm getting some of these things wrong. Please don't send me bad emails. But it turns out you don't put nails in the wall. I don't know, in the Egyptian Hall...

Michael: These walls predate nails.

Carl: Yeah. So they built walls. We're putting these things up, and the guys who were there to put them up – there's a chalkboard, and behind it on the actual wall is like a Dutch master, right? So the guys that are putting them up, I saw them laughing as they were putting them up. I went over, I was like, "Hey, boys," they were all men, but I said, "Hey, boys, can you do me a favor? Just hang the art. You don't need any..."

Michael: I'm nervous enough here. You don't actually have to laugh at it while you're hanging it.

Carl: "Just hang the thing." I couldn’t even use the word "art." I was like, "Just hang it, please! I don't need you guys laughing." So anyway, those are...I have probably 50 more of those kind of art-world stories. But that's how it all happened. It's been super fun. Now I'm doing seven big canvases for an Australian firm tomorrow or the next day. So I do a lot of these now. The CFP Board, did you see the canvases too?

Michael: No, just what they had out in their dining area – you're even down to the napkins.

The Benefits (And Adventures) That Can Come From Saying “Yes” [21:31]

Carl: Yeah, that was a fun project. Super fun.

But here's the point. Besides the creativity and the impostor syndrome stuff, which we'll dig into in future podcasts, the point to me is that you can't make this too simple. The ability to communicate effectively can be enhanced, if you have any inclination, to just draw it out. If you don't have that inclination, go through and think, "What's the main point and how am I emphasizing it?" Right?

Michael: Well, to me, the other interesting lesson or reflection from this journey is this effect that, as I think you’ve said more than once, has unfolded for you over the years, which is that sometimes when a weird, cool opportunity comes and you're not really sure if you should do it, just say yes and figure it out later.

Carl: Totally.

Michael: You didn't set out to be an artist that does global art shows with the Sharpie. You drew a thing with the client and some stuff happened and you said yes, then some more stuff happened and you said yes, and you compounded 10 to 15 years later and it's like, "Holy crap, look how far that went."

Carl: Yeah, there's that great "Freakonomics" column that they wrote where they did the little test on people who were looking to make major life decisions, and they created a randomizer. Basically, they said, "This is a coin toss." And it had a picture of a coin. They had people making major life decisions, asking them, “Enter the life decision you're trying to make, then flip a coin."

And people were just looking for permission from a coin toss. The conclusion of the whole study was, basically, if you're thinking of doing something, just do it. Then as tailwind develops, and I'm not very good at knowing where to go, but I'm kind of good at like catching some wind in the sail. Like, "Oh, that's it " And I'm only good at that because people hit me over the head with it. You know what I mean? Like, the universe has a way of saying, "No, this way! You, stupid." So, yeah, that's what's going on.

Michael: So I guess the one other takeaway, as we wrap up, for anyone who's listening to this – if you've got your own weird version of this journey like Carl's been down, and there are some weird leap moments and you're not sure, Carl and I give you permission to say yes...

Carl: Permission granted.

Michael: ...and figure it out later.

Carl: Amen.

Michael: Amen. Well, thank you, Carl.

Carl: Thanks, Michael. That was great.