Dave Gray describes himself as a possibilitarian. He focuses on helping people and teams realize their creative potential. Dave the author of several influential books, including Liminal Thinking and Gamestorming, which he co-authored with Sunni Brown and James Macanufo. He also founded the pioneering visual thinking company XPLANE. In this conversation, we discuss how to move beyond mental models that constrain us to open up new possibilities.

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Jorge: Dave, welcome to the show.

Dave: Thank you, Jorge. It’s good to see you.

Jorge: It’s very good to see you. I feel like this conversation is a long time coming. I have to say right off the bat that you’ve had a big influence on my life, both through your work — you’ve written several books that have been very influential to me, Gamestorming and Liminal Thinking, in particular — but more than that, also because of the way you take on life. I’ll put it like this: it sounds very high-minded or something, but I just love the kind of spirit and energy that you bring to things. And anyway, it’s my privilege to host you in this conversation. As folks might be able to tell from hearing my introduction, you and I have known each other for a while, but folks listening might not know about you. How do you go about introducing yourself?

About Dave

Dave: Oh, wow. I don’t spend a lot of time introducing myself anymore, but you were saying that this conversation has been a long time coming and the first thing that came to mind actually feels like this is a little piece of a much longer, larger conversation that started for you and me in 2006 or 2007 when you reached out to me and invited me to an event. I don’t know if you remember that. It was a very seminal, important moment in my life because you invited me to talk, and I knew there was a group of — the name for this group has been changing over the years.

But I think at the time it was information architects, people who design infrastructure and apps and interactive experiences on the web. And, I remember saying to you, “I don’t have anything to say to these people.” And then you said, “Well, what do you want to talk about? Whatever you want.” And I said, “Okay, I guess I’ll tell them all the things that I think they need to do as users of the web, all the things that I feel like they should be doing and they aren’t.” So I made this talk and it was just actually a little bit, almost like a scolding, but I think in a gentle way, in a friendly way.

But it was very well received and it ended up being a wonderful introduction to an amazing community of really interesting, thoughtful, bright, and intellectually curious people who were forging the future. And I feel very privileged to have — and in fact, my first book came directly out of that invitation because people were tweeting about it back when there was Twitter, and I had a publisher contact me and say, “Hey Dave, do you want to do a book?” And they weren’t at the conference. All they saw was the number of people tweeting. And I said, “What should the book be about?” And they didn’t have any idea what my talk was about, so the publisher was like, “I don’t know.” Yeah. But, so you launched a kind of second career for me, so thank you.

Jorge: That’s very gratifying to hear. I have to say, at the time that you spoke at that conference, I was already familiar with your work. I think I first came across your work in the late nineties in a business magazine. I think it was Red Herring. And they published this feature called XPLANATIONS, like the letter X-planations. And they were drawings that were just generally clarifying in some way. And I knew that they were produced by a company called XPLANE, and I had the sense that this company focused on making things clear through visual communication of some sort. That was the impression that I had.

Dave: Yeah. And that was very valid. So, to answer your question about how I introduced myself, I’m always a little bit confused about how to do that because it has to do with the approach to life that you mentioned earlier. Nowadays, I just tell people either I say I’m an artist or I say I’m a possibilitarian if I want to have a deeper conversation about what I mean when I say art.

But yeah, I went to art school, Jorge, and when you get out of art school, the training is very much about training your body and your mind to hone your imagination and creativity and the skills that you need to express novel ideas. And, when you graduate from art school, there’s not a line of recruiters out there; there’s not a bunch of jobs that are obvious for an art school graduate. Nobody’s hiring. BFA — Bachelor of Fine Arts — doesn’t pop up on a lot of job skills requirements or lists.

When you graduate from art school, that’s the thing: figure it out. It’s your time to figure it out. And you trained on these skills, we gave you some space to explore and practice your creativity. Your job is going to somehow involve creating novel, new, and interesting things that we can’t yet imagine. So, go find your way. That’s been my life: a process of finding, figuring it out, finding my way, applying creativity and imagination to getting as close to the life I want to live as I can.

So, that’s why these days I say possibilitarian, because I think that’s as good a description as any to describe this approach to life. And by the way, I can’t take credit for that term. I got it from Greg Petroff, a mutual friend of ours, who uses that to describe himself.

Jorge: I love it. And I feel like I want to spend the bulk of our time together here talking about that word and what it means, and more than the word, the approach to life that it suggests. And I’ll tell you, just hearing you talk about it now and talk about your journey from art school, I think that what’s implicit here is that you forged your own path, right? You said there’s no one hiring for that kind of role fresh out of school. And I know a little bit of your backstory, but long story short, you ended up founding this company, XPLANE, that does that.

And when you were talking about reinvention and possibility as the mindset coming out of that experience, where my mind went was there’s an awful lot of people right now who are being laid off, and this is a very challenging market for people who do this kind of work. And I think that it would be really useful for folks to have a sense of what the possibilities might be.

Dave: Yeah. I’d love to talk about that. Tell me if this scenario sounds familiar. You start out looking for a job and you look at the different kinds of careers that are available and the kinds of jobs that are being listed or the people are hiring for. And, while there are some that you feel like you could do, there are zero of them that you feel are really going to take advantage of all the skills and abilities that you could bring to bear on that job or on a problem or in, you’re not maximizing your potential in any of them.

Like for me, there were jobs where I could use my brain. There were jobs where I could use my drawing skills. There were jobs where I could use my creativity and imagination and apply them to really not interesting problems. There were lots of potential paths that I could take, but if I was designed for a role, none of them were… I wasn’t designed for any of these roles. It was like, there was more to me, I felt, than any of these jobs were able to recognize inherently.

So that was where I ended up backing into starting a company. You may have heard me say this — I’ve been saying this a lot recently when I talk about possibility, how to take advantage of possibilities — but in general, a company has jobs, they have roles: it’s like a desk with cubby holes; they’re looking to fit you into a category. And so, they want to shave off all the carb away, all the roundness, so you can fit into their, so you can be a square peg and fit into their square hole. And that’s what a company will do to you.

But customers are a whole different ball game. A customer wants to know what’s unique about you, what’s different, what stands out. This is a lot of me looking back and retrospectively analyzing what was going on, but when you start thinking about your life, instead of finding a job and fitting in but creating a customer and standing out, you can change your mindset; you can change your world. The conversations

that you have with people are different. They’re not about, what can you prove that you can do, or, what did you do before? Sometimes they’re a little bit about that, but they’re not so much about how do you fit in our system so much as how can you have an impact on our system or my system. “How can you help me create a change that I want to see in the world?” And when you start imagining your work life in terms of what’s unique and what’s different and what stands out about you and what’s special about you, and you start creating customers, then the tone of those conversations becomes much more interesting and you start… I do believe that a lot of opportunities come out of exploratory conversations like the one we’re having right now.

Jorge: I love this image of the company looking to shave off the edges to fit you into the hole that they’ve identified because the hole might be by definition imperfectly defined. You might bring capabilities, mindset, a way of being, to the organization that, if fully deployed, a) would redefine the role, and b) I would expect would make you much more satisfied because you bring more of yourself, right? Like, you’re not shaving off the edges. Do you think that this notion of creating a customer is something that people can do within a job, or does it require doing it independently, like starting a company?

Dave: You can. Absolutely. Here the thing is you. You always have, unless you’re independently wealthy or you live on a farm and grow all your own food — in which case I salute you — but if that’s not the case, then you have customers, you’re going to have at least one customer, your boss, who, wherever your income is coming from, if it’s an exchange for any kind of work that you’re doing, that is a customer. And a lot of times within a company, you’ll have multiple customers. You have your boss, but your boss will have his or her customers within the organization. Maybe if you’re on a design team, you might have a customer and a product team or a sales team or whatever. So, you always got customers.

And, I think the thing that can be the most liberating thing is to find the customer that truly understands you and appreciates you. Especially if you don’t exactly know where you want to go. Some customers can just see you as a lump of clay and go, “Oh, wow, this person has a huge amount of potential.” and they can, in a way, design an experience for you, or they let you roam free.

My first boss — my first ‘office’ boss — was a newspaper guy named George Batistas. He was the head of the art department. He was so excited to have me. He had been kind of stuck with these two very old-school artists who were practically close to retirement. In fact, one of them would actually be snoozing half the day in the office at her drafting table. I’d have to wake her up to ask her a question. It was 1984. The Macintosh had just come out. They had just bought their first Macintosh in the newspaper. He basically said, “Look, your first job is just figure out this machine here. Figure it out. Figure out how we can use it in our work.”

He was probably one of my favorite bosses I’ve ever had. And of course, when it was time to leave, it was almost like saying goodbye, it was almost like leaving a treasure. Any kind of treasured relationship, when your kid goes to college or something. But he’s still around. He’s at the Boston Globe now, still doing great work.

But, yeah, so if you’re not ready to go out on your own, I think sometimes you might want to be in a place where you can learn some really useful skills, both social skills of figuring out the culture of work. But also just tangible skills. Like for me, I was privileged and lucky. I was paid to learn how to use one of the first Macintoshes, and I was paid to figure out how to apply it to a business problem, a media problem. And, yeah, he was a great boss: very tolerant of mistakes, very open-ended in terms of what was possible, very apologetic when he had to do stupid things like tell me I couldn’t wear shorts to the office on summer days. He was the kind of boss who was like almost ashamed to have to ask for something like that, but it was part of the deal.

Anyway, that’s a great boss, right? And the, number one reason people leave their jobs is their immediate supervisor or boss. So I think everyone intuitively understands if you can get a great boss, that’s pretty special. I think a great boss is someone who is probably both to some degree open-ended in terms of letting you explore what your potential value can be, but also has some vision and can point you in a direction that knows this environment well enough that they can point you in good directions. It’s like a guide.

Jorge: That combination sounds especially useful early on in the career, like you were saying, right? Because you need both guidance, but also some leeway to discover what your capabilities are.

Dave: Yeah. And a newspaper — and these days, it’d be more like a content-oriented website; there’s tons of them out there. Maybe even a company like LinkedIn; any place where your job is generating clicks, right? Would be a real equivalent to a newspaper these days. Something where your job is to produce content on a regular basis. Every day, I’d go in and I wouldn’t know what the problem was going to be, but I knew I was going to have to do something visual for the newspaper. It could be charts, could be a map. And it’s a great way to hone your skills and get over the hump of fear of publishing, fear of putting your ideas out there. If you have something that you know is going to push your career forward, but you’re having trouble pushing yourself to do it, get a job that will require you to do it.

Sketching as an Antidote to Fear

Jorge: I’m so glad you brought up the word fear because I wanted to circle back to this. You said in passing if you’re not independently wealthy or live on a farm, and most of us aren’t either of those two things. And especially in a tough market, the idea of being selective about what you’re going to do or who your boss might be, might feel intimidating. There’s also this idea of imposter syndrome, where we might think, “Who am I to do this?” I try to shave off the edges, right? And I suspect that a lot of it is rooted in fear. One of the characteristics that I associate with you is a kind of joyful fearlessness. And I don’t know if that’s an accurate reading, but do you have any suggestions for how folks might overcome apprehensions about bringing their full selves to bear into what they do?

Dave: This is a great segue into… This is where we can talk about sketching because I think of sketching as… When I was an art student, and when I also taught art students, you got your work by showing your work. And this is true in UX, I think as well; you have a portfolio to show what you can do, what you have accomplished. And a big chunk of art school is getting your portfolio ready. It’s different than a resume because it’s showing examples of what you can produce; the kind of thing that you want to do, the kind of thing you’re good at, the kind of thing you can produce, right? And the secret of sketching, or maybe the secret of playful fearlessness, as you put it, is sharing things while they’re still in the creative phase.

It’s much easier to show someone a sketch of an idea than to show them a finished product because when someone is presented with a sketch, you’re inviting them to contribute, to be a part of it, to propose ideas. A sketch is the first stage of improvisation — it could be just between you and the sketch, it could be between you and other people. And by sketch, I don’t necessarily only mean drawing. I mean like improvisational comedy is also a kind of form of sketching.

Jorge: They use the phrase ‘sketch comedy,’ right?

Dave: Yeah. So if you think about your idea, whatever it is, that if you have a thought about something you want to propose, put it out when it’s still a sketch, put out a really rough drawing, or act it out with someone in a very low-risk, playful environment.

For the last year and a half or two years, even longer, I’ve been sketching this idea of a School of the Possible. And I think to some degree the nature of a sketch is that it’s the beginning of a conversation. It’s like when you asked me to come to the IDEA Conference in 2007, that was the beginning of a conversation between you and me and potentially a lot of other people about how could the web be better? How could we be better? How could we be more creative? How could we be more imaginative? What could we look at in the past that might now, in the face of our current world, create different possibilities and ideas? I think that talk was all full of sketches and it was comparing…

I went and researched the history of the book and I compared the book to slow innovations; things we don’t think of very much like page numbers and where they came from and even the idea of being able to fold pages and so forth. And through examining that history, a bunch of different ideas emerged about things that could make browsers more interesting; browsing the web more interesting.

There’s so much literature and knowledge that’s been accumulated over the years and that’s just sitting there in libraries or closed books that can generate tons of ideas for things that could become conversations that could become products and services, or could become jobs. And I think the earlier you enter into that conversation, the more it’s like putting a lump of clay on the table and asking someone to help you shape it. And if you’re the lump of clay and you’re creating a conversation around how we might shape this, what could happen with this, what could we do with this, the best ideas are probably going to come from other people. Even if there are ideas about your future, like you don’t know all the things that they know. You don’t know what you haven’t thought about. There are things you don’t know about the ecology and the environment around you that other people might know a lot more about. And the more you can put something out there that other people can take a hand in helping you shape, the greater the possibilities are going to be, the greater the potential.

Jorge: In making a sketch, you are extending thinking to the world and in so doing, you open the door for others to participate in the thinking so that they can contribute to the thing. And this is something that…

Dave: Everything that’s human-created in the world probably started as a sketch. Every skyscraper, every Starbucks, every coffee shop, every big box retailer. Southwest Airlines started as a sketch on a napkin. Everything that ends up creating our reality starts with a sketch of some kind.

Jorge: One of the keys to me, and this is something that I don’t think I heard for the first time from you, but you have certainly embodied it for me, and you wrote about it in Liminal Thinking, is the role that judgments play in our understanding of what’s going on. And you have this stack model in Liminal Thinking that is rooted in reality. And there are several layers, right? And one of those layers is judgments. And I want to name it because I’m thinking of sketching possibilities. One of the reasons why it is so beneficial to put your sketchy thinking out there — and by ‘sketchy thinking,’ I mean non-finished; you’re not saying, “This is my final thought on the matter” or whatever.

Dave: Yeah.

Taking Judgment Out

Jorge: By opening yourself up to the possibility of sharing half-baked ideas, you are suspending judgment, is the sense that I have. Like you’re saying, “Don’t judge me too harshly because this is not fully thought through, and I’m inviting you, moreover, to be part of the thinking.” Is that a fair read?

Dave: Very fair. In fact, I think when you present something that looks finished, and I’m sure the UX people come across this all the time, you present the finished thing. Like, if you go back to 2000, you presented the Google homepage, it’d be like, “What did you design? It’s so basic. It’s so simple.” What you have to share, the final result, may actually be extremely simple, extremely elegant. That doesn’t mean it’s simple and easy to get there.

And, yeah, so to your thought on suspending judgment, when you present someone with a finished thing, then pretty much people get the impression they’re not being asked to contribute to this. So they’re, you’re putting them in a place of judgment. It’s not even yourself; you put other people… when you show something that’s finished, even if it didn’t take you that long, it looks complete. The perceived finish of something is inhibiting feedback.

So that means I have to, you’re asking me to judge it, right? Yes, no — positive, negative. What I like about it, what I hate about it, not what else could it be? Not what if you added or what if we… when you present a sketch, the perceived finish of it is, yeah, it’s half-baked; it’s loose. No one’s going to judge the quality of your ideas by your handwriting. But if it’s a handwritten note, people are going to experience it very differently than a printed page in a book. And that’s why conversation is as fluid as it is because it’s not written down. So it’s by its very nature, it’s improvisational and half-baked, and it’s less prone to judgment than when you write down and make a formal-looking thing.

So yeah, I think judgment is a byproduct of belief, what you believe about things. You make judgments based on the beliefs that you hold. So if you walk up to somebody and you present them with something that you know is finished, they’re going to make judgments differently than if you present something that’s in process or in progress.

Jorge: Yeah, it sends the signal, “This is closed for feedback.”

Dave: I’m sure you know this, but some of your listeners may not. Douglas Engelbart, when he was talking about the idea of a mouse, he would just carry around a block of wood to show people how this idea could work. I think it may have even been before he had the word ‘mouse’ for it. But he had a block of wood that he would carry around and show people this idea of a computer mouse. And I think the fact that it was a block of wood and not a finished product probably had a lot to do with the kind of conversations that he was able to generate around it.

Making the Value Real

Jorge: I think that we’re obviously aligned here. I agree very strongly with the mindset that you’re espousing here now. There’s a long way to go between the block of wood and a product that is generating revenue for the company and for the designer or what have you. And again, bringing it back to the fact that it is a tough job market and folks gotta bring home the bacon, how does one bridge the sketching of possibilities to the making of real things — making real things — that are generating value, both for yourself and for others?

Dave: Are you asking specifically related to looking for work? Or…

Jorge: Maybe ‘looking for work’ if both of those words are capitalized. Like, looking for your life’s work somehow.

Dave: Yeah.

Jorge: It can’t stay at the sketch stage, right?

Dave: Right. I would just simply say, look, if you don’t have a job, you’re looking for a job. You have a certain level of control of that environment and that situation. There are a lot of things that you don’t control. You don’t control other companies, their hiring policies, whether they need somebody or not. But, we do have this thing these days called the internet, and if you’re in a situation where you don’t have a job, you can always create an offer. And this is definitely a pretty hard leap for a lot of people to say, “Okay, I’m going to run a workshop and I’m going to charge $250 a ticket and I’m just going to put it up on the internet.”

There’s nothing that’s stopping you though from doing that as long as you’re sitting around anyway, waiting to hear back from a potential employer. You might as well. The best way to market yourself to employers is to demonstrate that you have some abilities and some expertise. And one of the best ways to do that is to start teaching people what those things are. There’s nothing stopping you from… I mean, it doesn’t guarantee, of course, that people are going to turn up. But maybe it’s a little bit easier for someone to say, “Yeah, I’ll spend $50 or $100 or $200 to spend a half a day with you and learn what you have to say.

That’s easier than bringing you on board for a full-time job for sure. And it’s even easier than bringing you on as a contractor probably. And by the way, anyone who’s got $200 to spend to learn about what you have to say is someone that you should be paying attention to as well. It helps you separate… All your friends are liking your stuff on LinkedIn or whatever. But the people who are actually going to pay a hundred dollars or a couple of hundred dollars to listen to you are people whose feedback is going to be really valuable to you because those are going to be the people who are really interested in what you’re focused on. It’s a way to separate… We both know this: your friends will lie to you. They will tell you they like things. Customers don’t really lie so much.

Jorge: Yeah, they’re putting their money where their mouth is.

Dave: Yeah. I got an email from a customer this morning or last night. “It’s way too complicated. Why should I have to do this? I don’t want to do…” Your friends aren’t going to say that, but your customers will. And even if you have a goal to have a full-time job or a contract job, putting a price tag on a particular kind of service — a teaching, a workshop, or something — putting that out there and putting a price tag on it is part of discovering what you do that’s interesting and valuable to other people. And I think we can all say, “Oh, the life I want is X or Y.” You have to also find the intersection not only of what you want, but what other people value as well. And that’s inherent in the search for work. Generating some kind of value is how you generate income usually. And what’s the value and who is it for?

The one thing I will say on this topic of customers is if you can get to a point where you have five customers, you can never be laid off, really. You can never be fired because the chances are very much slimmer than if you have a single boss. A single boss, you’re always going to be existing at the whim of the organization, maybe not even the boss but the organization. It’s basic law of diversification: if you buy ten stocks, the likelihood that they’re all going to tank at the same time is much lower. If you have ten customers, the likelihood that they’re all going to abandon you at the same time is very low. If you have one boss, you’re in an extremely vulnerable situation.

Jorge: I’m going to try to summarize what I’m hearing here as a way to start wrapping things up because, unfortunately, we’re running low on time here. But I’m hearing two things. One is, “share early, share often.” There’s also this notion of “working with the garage door open…”

Dave: Yeah. Working out loud.

Jorge: … I think that’s Andy Matuschak’s phrase. So, that’s one thing, right? Don’t wait until things are super polished.

And the other is this notion that even if you are working within the construct of an organization in a traditional job, having an entrepreneurial mindset is really important, right? And that entails thinking of what you’re doing as not so much a job as it is providing a service that you are compensated for by a customer, even if that happens to be your boss. And then, if you see it that way, that’s not such a far leap from, say, diversifying, like you’re saying. You can do work for that one boss, but you can also have other customers and do these other things in parallel.

Dave: Yeah.


Jorge: All right, Dave. Again, this has been such a privilege. And I hope that it’s not the last conversation that we have. Well, I hope it won’t be the last that you and I have, but I hope we’ll have more opportunities to share on podcasts. So, where can folks follow up with you?

Dave: I think the best place right now is my current project, the School of the Possible. For me, that’s by far the most interesting thing. I’m pretty easy to find on LinkedIn and other places. But I would go to schoolofthepossible.com as the first stop.

Jorge: We didn’t talk a lot about the school. Why don’t we do that? Can you give folks a very brief intro as to what that is about?

Dave: Yeah. It’s a sketch, so I’ll say that right out loud. It’s a sketch. It’s a sketch of a school. What is a school? A school is a place of learning and exploration and play. Often, a school is a group of people with a shared idea or a philosophy. It’s another way to think about a school or a school is also community. And the School of the Possible is all of those things. In a way, it’s like an art school, except it’s an art school for the art of the possible. So that’s what I’m sketching right now with a bunch of other people and learning a lot, in the process. And I would invite you and anyone who wants to come participate in the sketching process with us.

Jorge: Fantastic. I’m going to include links to the school and to your personal site as well, and encourage folks to not just check it out, but be a part of it.

Dave: Actually, the easiest way to connect is, every Friday I host this campfire call from 9:00 to 10:30 Pacific Time. And anyone who wants to explore possibilities is welcome. That’s anybody. If you can get on a Zoom call, you can join that and I can give you the link to that.

Jorge: Yeah, absolutely. I will include that in the show notes as well. Thank you, Dave, so much. This has been such a treat.

Dave: Yeah, likewise. My pleasure.