Finding Our Way

Show Notes

Dave Gray, author of Liminal Thinking and founder of School of the Possible, joins Peter and Jesse to examine what’s actually getting in leaders’ way right now: not the disruption itself, but the expertise that blinds them to it. The conversation moves from beginner’s mind to the compression of corporate work, landing on a provocative question — what does your value look like when you define it yourself?

Dave Gray’s School of the Possible: https://schoolofthepossible.com/
Dave Gray on The Practice Economy: https://schoolofthepossible.substack.com/p/the-practice-economy
More on Peter Merholz, his consulting, coaching, and training offerings: https://petermerholz.com/
More on Jesse James Garrett, his AI Transformation Consulting and Leadership Coaching practices: https://jessejamesgarrett.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal. On today’s show, Peter and I welcome Dave Gray, veteran design consultant and author of the book Liminal Thinking. We’ll get his perspective on the mindset and skill set that can help leaders navigate this liminal moment. We’ll also examine the blind spots that result from too much expertise, the future of corporate politics in agentic companies, and defining your own value outside the terms of the corporation.

Peter: Dave, welcome to the show. Thank you for joining us.

Dave: Thank you for having me. I’m thrilled to hang out with you both. It’s been a long time, and we’ve had many experiences together. I’m happy to see you again.

Peter: We have. I remember events going back almost 20 years now where we’ve talked together. But the reason we asked you to join our show is, we’ve been doing this series of sessions on this concept of liminal, liminality, the liminal moment we’re in. We remembered early on in that, that you wrote a book… called Liminal Thinking: Create the Change You Want by Changing the Way You Think.

And so we know that you’ve been thinking hard about liminality and the role that it plays. And so, yeah, we wanted to get your thoughts on this matter. But maybe even before we dive into that, what have you been up to? I know what I last recall is you were a consultant at Xplane, and then you’ve been on your own, and you host communities. What do you do?

The story behind Liminal Thinking

Dave: Yeah, so before we leave the topic of the book, I don’t know if I ever told either of you the story of the book.

I didn’t start out with some idea that I wanted to write about liminality. It started out as something totally different, and it evolved into that. So maybe we can get into that.

But yeah for 30 years I was a design consultant, an innovation consultant. I did a lot of drawings and mappings for large organizations, helping them think through change programs and complex technologies and making them accessible, to sell them usually.

And I exited that business, and I was faced with the question, what are you gonna do now? I sold my company and I just started thinking “Well, what is Dave as a service? What would that look like? What is it that people come to me for when I’m not selling anything? What is it that I like to do? What is it that people come asking me for?”

The School of the Possible

Dave: And yeah, so that’s what I’m doing right now. You could call it Dave as a Service. My name for it is The School of the Possible. It’s a company of one. Me doing the stuff that I enjoy doing in service to a community of creative people.

It’s kinda like a Zoom version of a bar.

Peter: Okay.

Dave: I’m like the, you know, the bartender…

Jesse: everybody knows your name.

Dave: Yeah, everybody knows each other’s name. Make sure that everybody has a comfortable seat and it’s like a bar meets an art studio.

Jesse: You know, one of the reasons that we wanted to talk with you is because liminality has been such a focus of our conversations lately, and you literally wrote a whole book about it. It’s not a new book. I was astonished to discover that this book is almost 10 years old now.

But it is a book that has had some resonance over this last decade. It is a book that I continue to see people reference and call back to. And for people who aren’t familiar with the book, I wonder if you can encapsulate a little bit about the origins and the ideas that came out of that, and what were the big themes that you were trying to drive with writing a book on liminal thinking?

Dave: Yeah. The story of the book, it’s not one that I tell very often, but I think it’s a really interesting one, because it started out with mutual friend of ours, Lou Rosenfeld, he’s, very good about remaining connected with his authors and prospective authors.

And I just had been his friend. And he sent out a little note to his email list asking if anybody knew anybody who wanted to write a book about Agile, Agile software development. And I was like, ” I think that’s really interesting.”

I had just finished a book called The Connected Company. A lot of it had to do with Agile kinds of approaches and techniques to organizing business. And I said, “I don’t really know much about it, but I would love to write a book in the kind of journalistic style. I’d love to go out and interview people and learn about it and write a book that way.”

And he said, “Great.” So I started out to write a book about Agile and

Peter: This is, like, 15 years ago or something now?

Dave: Something like that. And so I started interviewing these people. Agile software development, coaches, professionals, experts, and I’d ask them about agile, and they would say “We know what agile is, but we can’t do it.”

And I’m like, “Okay well tell me about that.” And I kept hearing from these people, who all seem to look like me. They’re, like, very homogenous from a diversity perspective. And I kept hearing the companies are structured in such a way that “We can’t do it. We can’t be agile.”

And I thought, “Okay, that’s not agility then,” to me, because agility, to me, is you’re able to do things in spite of the environment, or you’re able to navigate within an environment that you don’t control in such a way that you can maintain some kind of balance or equilibrium.

So I went back to Lou and said, ” I think we gotta think about this book differently.” And I expanded the group of people that I was talking to.

It got much more diverse, much more interesting. Talking to people, soldiers, people who are in environments that they can’t control, literally, someone’s opposing their efforts. Humanitarian aid workers, firefighters.

And I started learning about real, I guess, what I would call real agility. People who are able to operate these very complex, super volatile, rapidly changing environments. They’re able to achieve some kind of results without having control.

And I think that’s very connected to what you guys have been talking about, this idea of, feeling like there’s rapid change going on. You don’t control it. You’re not in control of the situation, and yet you have you have things that you wanna try and achieve.

And that’s where the book ended up going. And what was really interesting to me is a lot of it ended up being about mindset, and a lot of it ended up being about a lot of the stuff that gets in your way in operating in these kind of volatile complex environments is your own way of thinking about them.

A lot of the barriers are inside your own brain, so to speak.

The Agile Moment vs The AI Moment

Peter: Before we got on mic, we were talking a little bit about the tenor of the discussion right now in places like LinkedIn. Where there’s a lot of people having a lot of feelings. They might be anxious feelings, they might be positive feelings, excited feelings. We’re in a heightened moment. Feeling like they’re out of control.

And it’s interesting to me that those initial folks that you spoke with for the Agile book felt like they lacked control, because agile was seen as a net good, right? Companies were becoming agile, and, like we’re hearing about AI, there was, like, almost this mandate: We’re going to adopt Agile.

And then people like, I’m assuming the ones that you were interviewing, are brought in to help us become agile. So these folks should have tailwinds, right? They’re the ones who are being seen as the ones who are gonna lead us to the promised land.

But even those folks were feeling stymied, right? They got frustrated. They kind of threw their hands up. Which is a little different than what’s happening right now in a lot of organizations where we’re getting this top-down executive mandate about AI, but no one knows how to do it.

Like, at least there was a group of people who could claim some expertise or some understanding of how to drive agility with some evidence in it. Right now, with rare exceptions, it just feels like we’re all making it up as we go.

In the Agile moment there were these organizational or corporate constructions or strictures that prevented agility from arising.

I’m curious, as I’m sharing, a little compare and contrast, what you make of these different moments. When agile was imposed on us, and we had the right people to help get us there, and we couldn’t figure it out, what hope do we have in this moment?

Dave: Oh, wow. We’re all probably roughly somewhat near the same age, and we’ve probably all lived through a lot of different disruptions over the course of our lifetimes.

I remember before the internet, at least before it was a thing that people used all the time.

And I feel like I have a little bit of an advantage because I have been through so many of these that I’ve start to see a lot of common themes.

And when you think about AI, the one that feels the closest to me as a designer was more like in the ’80s, when PowerPoint and graphical user interface, and suddenly everybody was able to make presentations and, PageMaker and, suddenly, you know, a lot of people who were in the design field were really freaked out because now my boss can make the whole magazine, like whatever.

That was at least what we were afraid of at the time, and it’s like, there’re still designers, but there have been so many times when there’s been a prevailing idea that design is going away or that technology’s gonna take over that job.

I forget who the painter was who’s, when photography came around, said, “This is great ’cause now we know what painting is not.”

And I think it’s like, as we look at AI, one way to look at it is to see all the things that it’s gonna take away from us.

But another way to look at it is to say, think of that as an editing out of the stuff that maybe we didn’t need to be doing anyway.

Jesse: So you talk about identity. You also talk about skills, skills and tools, and the way in which we get attached to those things as a part of who we are. And we’ve talked on the show in the past about this same moment that you’re talking about here, where digitization starts to supplant really well-established practices that have been in place for a really long time.

The example that comes to mind for me is in the field of accounting. Let’s go outside of design altogether. Accounting practices stayed more or less the same for hundreds of years until computerization started to change what your role was, and suddenly your penmanship didn’t matter as much.

Whereas previously, like, this was part of how you got the job in an accounting office, was you could write clear numbers that other people could read, and these kinds of granular skills that then become much more fungible as the tooling evolves.

But I wanna come back to the notion of the liminal mindset and what came up for you in your explorations of how people address these moments of change and what it takes for them to not get left behind, to not get left in that place where they’ve got the paste pot and the X-Acto knife instead of the mouse and the keyboard to be able to do their jobs back in the ’80s and ’90s.

What You Know That Just Ain’t So

Dave: I have a quote that I love. It’s from Mark Twain. It’s an old one, but he said, “it’s not what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.” And for me, that’s such a great quote and so relevant today.

Another way of saying the same thing is, Shunryu Suzuki who said, “In the beginner’s mind, there are many possibilities. In the expert’s mind, there are only a few.”

And I think this is the thing. Over many years, you build up expertise, and the expertise enables you to be very effective and efficient, like ability to use certain tools, your penmanship, to your example, other things. Those skills, you start to think of them as part of your identity, of who you are.

But all that focus, it’s kinda like horse blinders. It eliminates your peripheral vision, and it actually gets in the way of you seeing what’s actually going on if things are changing in a very fundamental way.

And I think that’s what’s happening now. Things are changing in a massively fundamental way. To a beginner, someone new to the workforce coming in, they’re not gonna have all the knowledge that gets in the way of them seeing what’s actually going on. They’re gonna be like, “Oh, I can just get on AI and I can do this, and look at that, I made an app. Whoa.”

And I think this is a common theme of a lot of these tools that come along. They create a new level of abstraction that wasn’t available before to the work. For example, when I started, before the Macintosh, before PageMaker and all this stuff, it was really important that you had to be able to use a ruling pen. Okay, a ruling pen is, you dip it in ink and it would make a very straight black line. With Adobe Illustrator or even MacDraw, that’s not a skill that I need to have with my hands anymore. And the people who are attached to the old craft are like “Yeah, but you don’t know how to draw a straight line. You’re letting the computer do that for you.”

The Abstraction Ladder

Dave: A good analogy for me is you go from walking, to getting on a skateboard, to riding a bike, to driving a car, to getting on an airplane. At each stage you’re losing some level of contact with the ground and the detail and the granularity. You’re not gonna see the landscape in as rich and detailed a way from a car as you are from a bicycle or from walking. But, you’re increasing your capability.

So, what happens with the tool is they abstract you away from the ground. So now I don’t have to know how to write Python to code an app anymore. So there’s things that are happening that I don’t understand. Like, let’s say riding a bike. If you ride a bike a lot you have the ability to fix it yourself probably. You really understand how the whole machine works. You can look at it and understand it.

When you’re in a car it’s a little more complicated, but actually, a car is probably easier than riding a bike, as you gain more power and control at a more abstracted level, you’re losing power and control at the more detailed level. You’re losing your attachment and your groundedness to the work, but you’re also increasing the scope and scale of what you can accomplish.

And I think AI is just doing this at such a dramatic level. I’m not sure what corporations are gonna look like after AI’s finished, you know, burning its way through all the, all the- the shit, honestly, that we’ve been doing that is not gonna really matter that much when the AI can do it.

It’s like the version of the ruling pen in a corporate world, a lot of it is, oh, just the politics. Think of all the political back rubbing or whatever you wanna call it that goes on in a large organization and the jobs that are honestly, not that hard.

As a consultant going into large organizations, I felt, wow, there’s so much about just people’s egos and just making them feel important and so much political stuff about, oh, I don’t wanna piss anybody off and all this. When all that work is being done by agents, they’re not gonna need to, kiss each other’s asses.

Jesse: So, are you suggesting the rise of ass-kissing robots?

Dave: I’m actually saying I don’t think they’re gonna need it as much. A lot of that effort and energy and cognitive overhead that’s going into just managing the human aspect of bureaucracy is, I just think it’s gonna be dramatically changed, at the very least.

And I think, I have a picture of what work’s gonna look like on the other side of it. I think a rough sketch kind of picture of it. But I think it is gonna be much less of the fake relationship stuff and much more of the real relationship stuff that you don’t see a lot of in the large organizations.

The Practice Economy

Peter: Before we talked, you shared something you had recently written that I think you’re maybe starting to allude to, that you call the practice economy, and you talk about these waves of work and, agriculture being an early wave, and then you had industry and factory work being this subsequent wave as agriculture declines. And then industry declines as you have essentially corporate work becoming the latest wave.

We’ll link to the article in the show notes. There’s some charts and graphs that are a part of this. And you show the corporate wave actually peaking around 2000. And it’s actually been in decline for a while in terms of, this is the percentage of people doing this type of work.

And you can probably tie it to broad adoption of computers and the internet in the workplace, that initial decline of just what percentage of people are doing corporate work.

‘Cause you can imagine in a pre-internet life, you needed all these manual laborers who were, like, secretaries and assistants and all this kind of moving of information around. But once you had computers and networks, the mail room evaporates, and those types of roles go away.

Dave: Yeah, we used to have typists. That used to be a job,

Jesse: Couriers?

Peter: You think about “Mad Men.” Everybody had a secretary.

So that stuff’s already been going away, and I think what you’re suggesting is that it will go away maybe even more rapidly with some of this new tooling.

And what you have replacing it is the practice economy, and I thought that was interesting.

I’m gonna ask you to define it in a moment. But in our last episode, Jesse and I were talking about, maybe I had some mindset constraints because so much of my thinking as we’ve been talking about liminality is trying to help people survive in their current state, right?Wherever they are at, how can they navigate this uncertain moment and recognize that uncertainty as opportunity and come out the other side with some victory?

But I had, I think, implicitly been imagining people staying at their jobs and trying to make it work. And it was in our last conversation where I’m like, why am I assuming that? Why wouldn’t… if there’s a group of people in a company who recognize an opportunity, a new way of working, instead of trying to win over a bunch of executives or something as to do it, why not the four, five, six of them just leave and do the thing? Especially with the tooling we have now. You can get much closer to the work and just be gone.

I had to free myself of this assumption of working at a co-, context, and that’s the sense I have from what you’ve been writing with Practice Economy. So consider this a little tee up. I’m curious how it aligns with what you’re thinking or where your thinking is going here.

Dave: Oh, yeah. If you think about you think about the tech giants today, right? Mark Zuckerberg, college dropout, started Facebook. Apple, started by, in a garage, pretty much every single one. You know, EBay, a guy programmed it on a weekend.

Peter: Google in a garage by two guys who maybe didn’t finish their PhD. Yeah.

Dave: Yeah, right. And I have friends, and I’m sure you do too, that it is like even with a large organization with tons of money, so Xerox basically created Apple. They built the research center out of which Apple came.

They invested, they put the money in, they had all the creativity. They weren’t able to turn that into a company, turn it into an organization because, again, of that, I don’t have a name for it, but the expert blind spot, whatever you wanna call it.

Peter: They already knew, and they knew that would never work.

Dave: Right. You have an infrastructure in your mind, just like any company has infrastructure, and you have a blind spot that’s associated with what you can’t see because of what you know that just ain’t so, to go back to Mark Twain again.

In a big company, with all the tons of money and resources and capacity that a big organization has, it’s still easier to quit and start it in your garage than it is to innovate within that structure.

It’s mind-boggling ’cause companies pour tons of money into this. And they also buy companies and then destroy them. Like, they buy them without understanding their value.

I saw it at Business 2.0. It was a magazine. It was a very successful magazine in Silicon Valley. You guys might remember it.

It was bought by Time Inc. And they fired the sales force, and the sales force was the engine that ran that whole media business. The salespeople were basically selling into Silicon Valley, into the technology companies, and Time was like, “Oh well, we already have our sales force.”

They had a sales force of people that would go into Ford Motor Company and just basically take orders. They didn’t understand the industry. And so I watched, I had been working for the company as a consultant, like an illustrator, saw the company get bought.

You know, it’s like you buy a car and you take the engine out, and it was like watching it get thinner, and the bureaucracy blaming everything but themselves for the problem that they created.

And I think this happens a lot in business. But again, it’s that expert blind spot that gets in the way of seeing… And I think we each have it ourselves, too. It gets in the way of seeing what’s possible.

Jesse: Yeah. We’ve talked in the past about the work of the philosopher Thomas Kuhn. “The Structure of Scientific Revolutions” is this book where he introduced the concept of the paradigm shift to the popular discourse.

And when I think about what you’re talking about, when I think about these blind spots, I think about the risk of being trapped in an old paradigm, in an outdated paradigm that no longer applies.

And, for our audience, design leaders, I feel like this is a place where they just dwell in this absolute terror field of the Rumsfeldian unknown unknowns, the blind spot that by definition you don’t know is there. You can’t tell that something is being hidden from you by your own perspective because that’s what your perspective does. It filters your reality.

And I wonder what leaders need to do as they are simultaneously dealing with the pressures from executives in their organization, as well as the expectations of the people within their teams to escape that trap of the genuinely invisible blind spot.

How do you see those unknown unknowns?

The Corporate Drug

Dave: I think one of the big unknown unknowns is just assuming that I’m gonna be in a corporation. I’m gonna be in a corporate job. Whether or not it’s the one that you’re in now, I think that those are the things that are most likely to be getting in your way.

Okay, so a design leader in a Fortune 500 company. That’s what I know how to do. Whatever I do, I’m gonna be a design leader in a Fortune 500 company, ’cause that’s how I understand the world. That’s what I know how to do.

What happens if there is not that role, there is no design leader in a Fortune 500 company in your future?

What happens if that role requires a whole different kind of person than you are? In some ways, a corporate job can be like a drug, like an addiction, and if you think about it, okay, addicts are usually not gonna give up voluntarily a drug until they hit some kind of a flat wall that they can’t continue to keep using it.

Jesse: Right. They’ve gotta hit bottom.

Dave: Yeah, so what is that for a lot of corporate leaders? It’s you get laid off at an age where you don’t have a lot of prospects.

And I think one thing, you know, it’s like death. You don’t wanna think about it, but it’s probably good to think about it. Do you have a do not resuscitate order? Have you got your will? You have life insurance? It’s not fun to think about your own death, and I think the same applies to your corporate death. Maybe it’s not fun to think about it but it’s wise to consider what your alternatives might be and to think about that realistically and say, Okay, let’s just say you’re not worried about your job today. That’s great. Maybe if you think about five years from now or 10 years from now, maybe there is something to worry about. What can you do? You could start saving money, number one, right? You could be more thoughtful about your expenses. You can be actually actively cultivating your social network outside of just your immediate colleagues and the people who can do something for you today.

You can start to actually think about your social safety net differently than just thinking about what is available to you inside your company.

Like one of the things I realized after selling my company was that I had a social network that I had invested a lot of time and energy in over many years. Many of those people became my customers when I decided to do Dave as a Service. There was a lot of people out there who had read my books or had been interested in something I had done and, when I was a corporate consultant, If you didn’t have at least $25,000, there was no point in us having a conversation ’cause there was nothing I could sell you, but there’s a lot of people who don’t have $25,000 to spend on a project who maybe I could provide some value to.

The corporate world is all about division of labor. And so we’ve become divided in some ways. The value proposition has gotten so splintered and divided that our value proposition is this tiny little role in this big machine. And, think about the user experience designer, the information architect trying to explain to the taxi driver what you do, right?

“Well, I design experience.” What does that mean? You know, and I think this is the case of a lot of corporate jobs. You can’t explain it to an average person in a restaurant or on the street. And the thing is, if you can’t explain it, that should be a big warning sign in the world that we’re in today.

Because what the jobs, I believe, of the future are gonna be, you have a role in a community, and you know your role.

It’s almost like going back to hunter-gatherer times. Everybody knew their role in their community. Everybody knew why they were useful, how they were useful or not. Everybody understood. If someone runs a Thai restaurant in your neighborhood, you don’t have to ask them to explain what they do. You know exactly what they do, and what they provide. It’s not something that is hard to understand or hard to explain, and I think a big part of what’s happening is all this kind of divided labor is stuff that can be more easily done by agents.

It’s the stuff that’s more tightly bundled, where the value proposition is not so easily automated, that is, about a role that you’re serving in a community, a usefulness.

In the article, I mentioned this friend of mine who runs a newspaper here. It’s a one-man newspaper. He’s been doing it for 40 years. AI’s not gonna take his job away. No way. He shows up at the community meetings. He knows people. They come to him with stories. He’s got advertisers. People write stories for him. He’s deeply interconnected with the community. Everybody understands the role that he plays in the community, and he understands the community.

So I feel like part of what’s gonna happen is, as we get more abstracted and we have more capabilities and powers, you’ll be able to do a lot of things without having to hire employees. And if you are in that corporate job, one thing I’d be thinking about is how do I think about this job not as something that I need to hang onto like a life raft, but something that can actually help be a vehicle for whatever I might wanna do next? And then take a more expansive perspective on what’s out there.

Dave as a Service

Dave: Like when I sat down to say, “What is Dave as a service?” There are a lot of things that did come up. People come to me when they lose their job. They come to me for advice on their career. People come to me asking for advice about writing books and publishing books and doing creative.

So there’s a lot of things that were happening that were not part of my corporate career, but they were in my life. They were in the background, and foregrounding those created a whole different kind of way of thinking about what I actually look like.

This is a question I think any corporate employee should be thinking about. If I were to be a service, you as a service, Peter as a service, Jesse as a service, and I had to do it all by myself without a team, what would that look like? What might that look like? What could I do that I could show up with, joyfully every day, even if it’s something simple as making sandwiches? What could I do that I could really enjoy that would connect me with a community?

Like my newspaper friend, it’s a local thing, but I don’t think a community has to be local in this day and age. And I think that’s what practice work, the shape of practice work is, and it’s older than history.

But whether you run a restaurant or whether you’re a tailor, you know your customers personally. And I think, how many people in a design leadership job in a Fortune 500 company can say they know their customers personally? It just would not be possible.

But I think we’re moving towards a future where you are gonna be required to articulate your value to the people who are actually paying your bills, the people who pay you. And they might not be your boss.

So I feel like the big skill that is gonna be required of all of us is learning how to create a customer. Both of you, I think, are very aware of that is a skill. That is a skill you can develop and that requires a way of thinking about how you show up in the world that’s very different from pleasing a boss to get a paycheck.

Jesse: It’s interesting to think about the implications of this for leaders of design teams inside organizations. So let’s say I don’t want to quit my job. Let’s say I love the leverage that comes with being able to make design decisions that touch literally millions of people every time we deploy.

If that is what’s exciting to me as a leader, then I am there to advocate for something else, which has to do with what design as a function contributes toward the value that we collectively create. And I’m there to stand for that contribution on my part and on the part of my team.

And, as you were talking, I find myself wondering about, how we define community, how we define the value that we create within community, and the shape of these evolving organizations, if it really does become, almost this gravitational pull away from hyper-specialization back toward a little bit more of a generalist kind of a value prop for people in these organizations.

But that generalist value prop is then built upon, as I hear you describe it, personal trust and a certain track record of value delivery. And that’s the means by which you get things done rather than rigidly defined areas of authority and hierarchical structures and things like that.

So then the challenge for the leader is not just to advocate for themselves, but also to advocate for the thing that they are there to spearhead and champion. Which, for us, for many years, it was human-centered design. All of us came into this work during a time when there was no voice of design anywhere in any kind of software development, and the software that we had was painful and difficult for people.

Dave: Yeah.

Jesse: And that gap presented a market opportunity, basically, that created this field.

And now I think there’s a new potential value proposition that design leaders have to advocate for, that doesn’t look like that anymore because it’s no longer about those things. And in fact, as you describe it, the organizational context itself is potentially shifting. Where your title on your business card doesn’t mean you get to make or influence certain decisions, right?

Dave: Yeah. So I was just reading about the guy who made the movie “El Mariachi,”

Jesse: Hmm. The great Robert Rodriguez.

Dave: Is that his name? Okay.

He went to Mexico and made a whole movie for $7,000, like a feature length film.

So this is the kind of thing that people in the film industry are like you can’t even make a trailer for less than $20,000.

And he had a film teacher who said, “No, you’re gonna need a, you need a…” He said, “I’m just gonna hold the camera myself,” you know? “And well, you need a director of photography. You need a…” And you learn the film industry by going and working on a film, and you see all different jobs, and you learn one or two jobs, and you grow in the industry that way.

Whereas he just said, “I’m gonna take a camera. I’m gonna tell a story. I’m gonna go take a camera to Mexico, and I’m gonna do this.” That was a successful movie, and he’s gone on to make other movies.

So that kind of mindset is, I think, what we’re gonna need more of in this AI age. Like, my brother worked at the FDA, and they’re a bottleneck because the people coming to propose different kinds of medical equipment and drugs and different things, they have such a long wait time because of the way they do it.

And I suggested like platform-type things like Kickstarter and other, kinda crowdsourcing, some of that. Because he worked for the government, he was so embedded in a way of thinking. The only way that he could think of to scale the pipeline was hire a lot more people, like triple in size.

Whereas now if you’re making movies the traditional way, you’re never gonna try and do something for $7,000. You wouldn’t even think to try that.

Whereas the potential of AI is that there are things that we just can’t even imagine are possible because of the way that we’ve done them before that are going to be possible. So the way you describe that design leader, “I’m someone who… I care about, I make the decisions, and we push a button and it impacts millions of people.”

Are you gonna need the corporation for that? Or could you do that? Jesse, you’ll be happy to know that the working title for that whole practice economy thing was “The Structure of Economic Revolutions,” which, ’cause it is kinda based on that whole Kuhn thing.

And we’ve had three of them in, the course of human history. One was agriculture, the second was manufacturing, and the one that’s happening now, that’s compressing now, is corporate work. When things get compressed, they don’t go away. We still have farming. We still have manufacturing. And we’re still gonna have corporations.

But the number of people required to run a farm, like one farmer, one person used to generate about five people’s food, like a family. Now one farmer generates about 100, 200 people’s worth of food. So it’s one person. They’re just like 50 times more effective.

And I think the same’s gonna be the case with a corporation. To be making the design decisions that you push the button and you affect the lives of thousands or millions of people, you may not need that corporate infrastructure to do that anymore.

You might be better off thinking like the El Mariachi guy. I’m sure there’s a lot he didn’t know that worked in his benefit, work to his favor. And so that’s where the beginner’s mind comes in, I think, is, what you don’t know that you don’t know, that can actually be your best friend, ’cause you don’t know that it’s not possible. You don’t know that it can’t be done. And so you have the temerity to go out and say maybe I can just do this.

Peter: I’m curious, as you were, years ago, researching liminal thinking, if the beginner’s mind thing came up then and what you saw. ‘ Cause, as you explained it earlier, the people you interviewed were under even greater constraint than anything we’re talking about here, right?

And so you were trying to figure out how do people who are under great constraint still do good work, work they’re proud of, make their way there? Was beginner’s mind part of it? And how do you tap into beginner’s mind when you’re already an expert, right?

Is there a way, like, my desire is, I want both. I want to be able to leverage my expertise, right? 30 years of hard-earned awareness. It’s not for nothin’. So, I, also am a service. I sometimes refer to myself as Peter as a service. And people come to Peter as a service for 30 years of expertise. That’s what they’re buying.

But in moments this, where assumptions probably are worth at least calling into question, I wouldn’t say dismiss them all, they’re all useless. In fact, I think some of that thinking is problematic. There’s plenty that we can take from prior experience into today that, if applied well, I think would make things easier.

But that aside, like, how to balance beginner’s mind, expert mind, and succeeding or, getting traction when you’re not in control of the situation, and it feels like you’re operating within someone else’s imposed structures?

Dave: It is a great question, and I believe I have a great answer. We’ll see what you think.

So when you hear new ideas, right? And you hear them all the time, right? Crazy ideas.

Generally speaking, the first evaluation criteria you have for a new idea is does it fit within what I already know? Does it make sense with what I already know? If it doesn’t make sense within what you already know, the tendency is to reject it and say, ” Okay that’s just an anomaly. That person was just lucky that happened.” And just basically find ways to reject it.

But the thing is, the new ideas that fit within what you already know, you’re not actually gonna learn anything dramatically new by accepting the stuff you already know. It’s the stuff that looks really strange, doesn’t make sense, I think you have to open up your aperture to be able to become aware of those.

So you’re gonna hear things that, you wanna reject it, because it actually challenges something you already know. That’s the stuff where you actually have the greatest potential to learn something new.

There was one that I just saw where it was like some guy started a whole AI company, I forget the name of the company, but he started it all by himself. He’s already making multiple, I think, millions of dollars on this company. He’s only one running it, and what it will do is you go there and it’ll make an AI company for you.

It’s like an AI company that makes AI companies.

That to me is mind-bogglingly weird. I think part of it is just learning to cultivate your curiosity about things that just either grate on you or just things that create that disconnect in your brain, that’s the stuff that’s actually most likely to generate some kind of new insight or learning, the stuff that you most automatically reject.

The story from “The Connected Company” book is the story of the American auto industry. They were like, “The Japanese are making these cars, and they’re so cheap.” And the first thing was the cars aren’t that great. And then they look at the cars. It takes them 10 years to figure out, oh, the cars are actually pretty good.

Then they go to Japan and they actually see the way that they’re making the cars, and people come back and they’re like, “Maybe that works in Japan, but it’ll never work here.”

And there’s all this stuff that they already knew about how to make cars that they couldn’t learn because they already knew.

And so even though they were getting all these signals for 20, 30, 40 years, it took them that long to actually recognize that there’s something happening there that, somehow people in Japan are able to make factories that make cars better and at half the price that we pay to do it, and it’s about the method and, like, lean manufacturing we call it now.

It’s like those expert blind spots. One way to start to mitigate for your expert blind spots is to start paying attention to stuff that you think that can’t be true. That’s the stuff that is most likely to generate some new insight for you, right? Because what if it is true?

Acting As If

Dave: There’s a thing that I talk about in my book called “acting as if,” which is, you don’t actually have to believe something, an idea is true or valid in order to test it. All you have to do is act as if it were true.

Let’s just say, take the example, Jesse, that you gave of the design leader who assumes that they have to be in the company to do the work that they wanna do.

You could also ask the question: What if I didn’t have the company behind me, and I wanted to do the same thing? What would that look like?

And you can act as if it were true, so act as if you didn’t even have the company or act as if you could do it for pennies on the dollar and see what happens.

The nice thing about acting as if is you can suspend your own disbelief about your own behavior. You can suspend your disbelief about anything long enough to try the experiment. You don’t even have to believe that it’s gonna work.

Jesse: Yeah.

Dave: You can act as if it were true. What if I only had $7,000 and had to make a movie and I wanted to do it, and I basically said, “It’s going to be a feature length film”?

Jesse: So I think part of what I hear you suggesting within all of this, and you’ve maybe touched on this a couple of times in this conversation, is the idea that really the whole software industry might look really different a few years from now than what we’ve become accustomed to up to this point.

Dave: I think it’s not just the software industry. The only thing in our world that doesn’t have a lot of competitive pressure on it is government, maybe healthcare, certain industries that are highly regulated, so they literally can’t innovate because there’s laws that keep them from innovating.

But everything else, AI is a really interesting to me technology.

I work with people on it, there’s people in my school who are working with AI, and I am too, and one thing that I’m noticing is that it’s the first tool that I’m aware of that actually can teach you how to use it.

And that’s incredibly interesting. And I’ve seen people go in a week or a month to where they’re talking about concepts that would not even have been intelligible to them a week ago.

The learning curve is rapid. People are making such rapid progress that I can’t even get them in a room to be able to even communicate with each other. They’re so widely distributed on this learning slope that once you get start on that journey, to find someone else who’s at your level is not that easy because people are progressing so rapidly.

I don’t think we can even try to make predictions, but I think what we can predict is it’s just not gonna look like what it looks like today. When the smartphone came along, I don’t think any of us really predicted the way that it was gonna change society.

Peter: Well,yeah, especially if you look at movies from pre-smartphone that, were trying to be future forward, they didn’t take it into account at all.

Dave: Yeah. We thought we were getting connected and we’re really getting more isolated. It’s almost like the opposite of what we thought.

Peter: But on that point actually, ’cause you were talking about Dave as a service. I’m Peter as a service. Jesse’s kind of Jesse as a service.

Jesse: I’m serviceable.

Peter: And while I appreciate the freedom that my independence affords me I have to admit that, I am seduced by the stability of that drug of corporatism that you were referring to before, right? To be independent, to be on your own, is a lot of hustle, a lot of uncertainty, a lot of trying to figure out what the market wants from you and when you do, the market changes and now you’re having to change, right? It’s not easy.

And we touched on this, Jesse and I did, in our last Liminal conversation, which is around kind of collective action, ’cause you’ve also talked about community. And I’m trying to understand how we operate as individuals, but not to be alone, right? ‘Cause I can feel quite lonely in my work, writing or whatever I’m doing.

And it’s nice I have clients, but I meet with them an hour here, an hour there. I don’t have a team that I’m doing stuff with, right? We’ve all been in environments where there was a team and we did stuff with the team and that was powerful, and we’ve all lost that.

I guess I’m just curious, Dave, how you’re dialing that size of productive unit. It doesn’t have to be a massive 300,000 person scaled organization, but is it really just gonna be a bunch of individuals, or, what are you foreseeing there?

Projects, Not Companies

Dave: This is just all speculation and intuition, but I find a lot of interest in the film and music industries. The music industry is a great one because you got a lot of solo artists who are also in bands or you got The Beatles, they started as a band and then they became independent artists.

You’ve got people like Willie Nelson, spent a lot of time with other bands, And I think there’s something about maybe thinking in terms of projects like that.

I’d like to believe that we’re moving towards a society where you could think of things in terms of projects and collaborations and have some kind of fluid movement between, being a solo artist and in a band.

What is a great band? They get together. They know each other. They have that chemistry. They can perform really. They know each other’s strengths and weaknesses. They balance each other really well. There’s something great about that.

And then there’s, we’ve all been in the team that’s dysfunctional, right? That’s like, “This is not a band that I wanna be in again.” So the project to me is a nice way to say, “Okay, if we really do a great album, and we really enjoyed the whole process, then we’ll stay together. We’ll do another one. We’ll do another one.” But for me if I start to think about looking towards the future, what does that look like, I think maybe projects, as opposed to companies.

And even if you look at the way that most companies operate they are projects even for serial entrepreneurs. There’s people who they’ll start a company. They grow it. They sell it. Maybe it was a company for the investors, but for them it was a project.

Jesse: So with all of this change and all of this transition and potential, what are you most looking forward to seeing unfold in the days to come?

Dave: We’re learning what the robots can do and what the computers can do, the computer can now kinda turn itself on, it can run itself, it can operate itself, we don’t have to be computer operators anymore.

And I think there’s something really liberating about that. I don’t think it’s gonna happen without pain and distress.

Not that we shouldn’t have been thinking about this for a long time, but we really ought to be thinking about universal healthcare. Because a lot of people are trapped in these organizations because our healthcare system is forcing that on them. And a lot of people, that’s a big barrier to them going off on their own, and that’s just a failure of our system. So there are some things that we can do to kinda ease the suffering, I think.

But what’s happening in the corporate world today is very similar to what happened in the factory and steel working and the mills and so forth. It’s undergoing a compression, I believe, and there’s gonna be displacement.

And I think as a society, we need to be thinking about how we make that transition easier for people. I think universal healthcare is kind of like a no-brainer. So many other countries have actually done it. But I look forward to what happens when people get on the other side of it.

The Storm, and What’s On the Other Side

Dave: We’re in this turbulence mode. It’s like we’re in the middle of a storm, and the storm’s gonna pass, and the waters are gonna get calm again, and we’re gonna see what’s on the other side of it.

Doesn’t mean there won’t be a lot of destruction, like Katrina kinda level destruction of our economy. I think that’s likely. And we’re in the middle of that storm right now, trying to cling to the rafters or, bailing water or just trying to do what we can do. We have this sense of this storm raging around us. We don’t know what is actually gonna be left or what’s gonna be destroyed or what buildings are gonna still be standing.

It makes sense to be in that mode, but I feel like there is gonna be another side, a calm after the storm, and I think it’s gonna be beautiful.

Peter: Wow.

Jesse: Dave Gray, thank you so much for being with us.

Dave: Thank you. Thanks for having me.

Peter: Yes. Thank you so much.

Jesse: Dave, if people wanna find you and your work on the internet, where can they do that?

Dave: schoolofthepossible.com.

Jesse: All right. Thanks again.

For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

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