Wild by Design | Gwyneth Hagan

Gwyneth Hagan grew up moving. Air Force family — eight, nine, ten different schools, no one place long enough to put down roots. What she could count on was this: finding some small natural space wherever she landed, some patch of grass or stand of trees, and letting that be enough. Later, she dropped out of college, drove across the country, and spent a year on an organic farm in coastal Maine with no electricity and no running water. It was there — watching a spider cross a field with an egg sack on its back, going somewhere with such care — that she decided to become a teacher.

What came from that decision: a decade at EL Education, where she worked as a school designer, helped build the architecture for professional learning, and watched an organization she loved make the transition every mission-driven organization eventually has to make. From forty people on a shared vision to a system that could be communicated to people who hadn't lived it. From oral tradition to written codification. From wildness to clarity.

*Wild Design for Learning* is her answer to what gets lost in that transition — and what it would look like to get it back. The book, organized around six patterns from the natural world (spirals, waves, fractals, fractures, bubbles, symmetry), publishes in fall 2026. Pre-orders open in June.

In this conversation: what EL was at forty people; what clarity costs; what the forest offers that the factory cannot; why artists have something to teach that educators don't; and what the doubt looks like right now, from the inside, when you've put the most essential part of yourself into a book and are about to let it go.

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NOTES FROM GWYNETH

- Visual Thinking Strategies come from the work of cognitive psychologist Abigail Housen and museum educator Philip Yenawineare

- The full quote about complexity from Charles Mingus (accidentally attributed to Thelonius Monk in the episode): “Making the simple complicated is commonplace. Making the complicated simple—awesomely simple—that's creativity.”

- Along the same lines, from Oliver Wendell Holmes: "For the simplicity on this side of complexity, I wouldn't give you a fig. But for the simplicity on the other side of complexity, for that I would give you anything I have."

- The Substack article related to complexity and root cause analysis Gwenyth referenced.

- Gwyneth's thinking about planning and presence was informed by adrienne maree brown’s book called Holding Change.

...you can learn more about Gwyneth's extraordinary work on her substack & her website.

Transcript

WILD BY DESIGN | GWYNETH HAGAN

The Principal Uncertainty | Episode 8

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GEORGE: I'm dying to ask you — I was so bummed that I couldn't make it to the gathering you had a few weeks ago, the online exploration of the deck. Tell me how that went. What was it like for you?

GWYNETH: Well, first of all, I was so nervous, because it was one of the first gatherings I've hosted for Wild Design. I had invited folks to come and just gather in community to talk about how learning communities could be more abundant and relational, more adaptive. The focus for that particular gathering was: what can we draw from spirals — how they show up in nature — and what might that tell us about our own learning and development? So it was really an open question. I was excited to see what people dug into, whether in their personal lives or their professional lives. It was really fun. I was super nervous.

GEORGE: What did the visual thinking piece look like in practice? Not the dictionary definition — what did you actually do?

GWYNETH: So visual thinking is a great strategy, particularly for those of us who are very verbal in our internal monologue. You can get caught up in perseverative loops — that three-in-the-morning thing where your brain is only half awake and the only part that's running is the verbal rehash. For me, that's something that needs to be disrupted through creativity. Visual thinking is such a powerful way to take something out of your brain, unpack it, analyze it, give yourself a little emotional distance so you can think about it more clearly.

I love using it. And it was really cool to see how it showed up for folks, because when it comes to drawing, people are sometimes more or less comfortable. But I talked about it as doodling, and I think that brings the pressure way down. People came up with some really cool ways of thinking about problems they were grappling with — how they might reconceptualize them, move from a more linear approach to a more spiral one. How does the pattern of a spiral help you think differently about a particular problem?

GEORGE: What was the felt experience of the gathering? This was the first one.

GWYNETH: I think it was one of those spaces where people show up and they're like, what's this going to be? We're so used to Zoom rooms that go one way or the other. I was really intentional about the first moments — Priya Parker's work on the art of gathering is fantastic on this, the idea that how you invite people in matters before they even arrive. So I reached out to folks beforehand with a poem I had written, as a kind of gift. And I also gave them a request: bring paper and pen. And a suggestion: go outside and get your feet on the earth and breathe some fresh air before coming to the screen.

I'm not sure how many people actually did those things, but I do feel like there's something about the virtual space that requires us to be super intentional about how folks get invited in, if we want it to feel like actual community building. And you could see the dynamic of the group shift as we became more relational with one another throughout our time together — people who arrived present and ready were smiling and laughing and wanting to continue their conversation by the end. If you give people a good enough prompt and ask them to spiral through it together a couple of times — instead of just randomly throwing people into a breakout room — something cool happens.

GEORGE: You mean inhabiting the metaphor a little bit?

GWYNETH: Yeah, exactly. I inhabit my own design approach. Otherwise it would be the other version.

GEORGE: Are you envisioning these gatherings as a linked sequence? Is there a commitment from participants?

GWYNETH: I'm going to keep it open rather than a committed space. A lot of my work feels like an experiment — my writing is active experimentation for myself in understanding how people learn well together. This feels like an invitation to gather and experiment together more than anything else. I do hope to have a series of them, with organizing themes and meaningful repetition. But as a facilitator, I always think about how any time you get a group of people together, you can do about fifty percent preparation. And then at that point, the other fifty percent is presence. You have to be present — the work has to emerge through the experience. So I'm curious to see what emerges.

GEORGE: What was behind that question was really about how you think about conjuring community in this context. You're staging a micro-community. That's part of how I think about facilitation — and my experience when it's done well is that you're building the container, making the space safe, and it's a different flavor depending on whether there's a longitudinal dimension or whether it's a single, fleeting thing.

GWYNETH: Yeah. I'm very conflicted about the digital space as a gathering space. So much of our lives is getting pulled in there, and I really miss gathering folks in person. It does afford us the ability to connect with people across the country and the world at any moment, which is genuinely incredible — you can really meet and bump up against people you never would have encountered in your daily life. But the experiment for me is: how much of the aliveness of in-person gathering can I get into the digital space?

I mean, if I could do everything, I would send people a special package wrapped in paper with a little string, and they'd open it — I just want to feel the humanity of the experience as much as possible. It's going to be strange days, I think, but also fascinating ones. The more we put up these digital mirrors for ourselves and think we see ourselves in them, the more we encounter strange and sometimes warped views of what human is. The machines tell us: this is what is human. And then we're like — wait. That's not it. The uncanny valley, right? And for me, the question is how vast is that valley, and how deep can we go into understanding our own animalistic nature by holding up those strange mirrors. I think it's going to be fascinating.

GEORGE: I was thinking about the uncanny in the sense that Freud talked about it — the distorted mirror. But the valley is an interesting metaphor too. There are a lot of different things you can do in a valley. That image immediately made me think of one of my favorite valleys, in the Fishlake National Forest in Utah, where I worked as a wilderness guide in a therapeutic program years ago — and what it was like to arrive in and dwell in that valley. It was like the opposite of uncanny.

GWYNETH: Yeah, just thinking about all the beautiful valleys I've been in — and canyon spaces. I did a river trip with Outward Bound, almost eight or ten years ago. And it was uncanny in a way, actually. Because we're so often in spaces of curated or manicured nature — and it's a bit uncanny to be in a completely wild space. It is, because you have to reorient yourself to your environment. There's a real dissonance. I think that's part of why nature is frightening to us — it should be. Crazy things can happen. And we kind of institutionally know: this is a wild space. I could die here.

GEORGE: The stakes are different.

GWYNETH: They are. We pretend we have everything under control. But it's harder to believe that when you're actually in the valley.

GEORGE: It's a lot harder to sustain that fantasy. That's what I think is one of the most powerful dimensions of the wilderness as a context — that radical reframing that happens there.

So — I love jumping into the middle of things, as you've probably gathered. But for folks who have no idea what we're talking about, I want to pull back for a second. You were kind enough to share with me the early chapters of your book, Wild Design for Learning. I was struck first, I think, by the extraordinary generosity of your presence in the text — clearly very intentional work, placing yourself before moving yourself out of the way so the work could happen. That reflection on nature as the vector of experience that was so powerful for you as you moved around — and the teacher as anchor point, Ladybug City and all of that.

GWYNETH: I have a funny story about Ladybug City being burned down — but I won't.

GEORGE: Go ahead, what happened?

GWYNETH: Okay, one small detour. I did move around a lot as a kid. My dad was in the Air Force and I probably went to eight, nine, ten different schools — we never lived anywhere longer than two or three years. Every time I went somewhere new, things are very hard as a kid when you move. But the thing I could always count on first was finding some kind of peace in some natural aspect of wherever I was — some sense of place beyond the buildings. I didn't have friends and I wasn't going to make them quickly. I had to find some other kind of solace. It's not like we were living in beautiful spaces — crappy apartments, base housing. But as a kid, just finding a little natural space, a little patch of grass with dandelions, really grounded me.

One space behind our apartment complex was a tall patch of grass full of ladybugs. I called it Ladybug City. Come to find out, years later over a Thanksgiving discussion, that it had burned down. And who set the fire that destroyed Ladybug City? My brother. He'd been playing with matches out there. Twenty years later.

GEORGE: You wrote about roaming in your late teens — and landing on a farm that saved you. What was the farm?

GWYNETH: My extended family lives on the coast of Maine, down east — a very rural place. My grandmother was a weaver and fiber artist, and she was part of a group of old hippies who had moved to the area in the seventies during the back-to-the-land movement the Nearings had started in Vermont and then migrated to Maine. The idea was that you could become closer in relationship to the earth by growing your own food and building from local materials.

I was really drawn to that, because I felt very lost. And I think it was the same anchoring impulse I'd had as a young child — finding the space where I could feel home. I had dropped out of school. I'd been living with a boyfriend who was an alcoholic. And I thought: this is a path I could stay on — and I did not want to stay on that path.

So I asked my best friend, hey, do you want to drive me across the country? I'm going to move out there and work on a farm my grandmother knows. And she, being just as crazy as me, said sure. She quit her waitressing job. I packed everything in my van and we drove from Colorado to Maine so I could go work on this farm and ground myself in the natural world and do work with my hands. There was too much emotional stuff going on and I needed a space that felt simpler. I was also very into Walden at the time, which tells you something.

GEORGE: There's a tension there that I want to name, because you're a systems person. Walden is magic — it's this kind of interior travelogue. But the book is abstract in a way that putting your hands in dirt is categorically not. When you started telling the story of the farm, I had this image of you in a deep exhale, shoulders dropping a couple of inches. Was there a moment where it's just: I'm here now?

GWYNETH: I think I probably felt that as soon as I got in the car and started driving. I was just ready to be out of the situation I was in.

I would describe coming to the farm — and any time I drive up to Maine to see my family — as arriving with lots of armor, lots of layers of clothing. And the more I drive up the coast and things become more and more rural, I feel like I'm taking off layers. And then there's a smell that hits me — sweet grasses, conifers, moisture, salt air. As those things hit me, I'm just taking off more and more until I'm just the core of who I am. To place myself in a space like that for months — in a cabin with no electricity, no running water — was a very extreme way to go back to myself. But sometimes that's what you need.

GEORGE: There's a story in the book about a spider — but it cuts off in the sample. I was hoping you could finish it.

GWYNETH: Oh, right. So part of the reason I wanted to find myself again was that I had bought into — and I think this is a story we're constantly sold living in a highly capitalist society — the idea that achievement leads to some place of success. That if you go to college and do the things, life turns out a certain way. I had to work through college because my parents couldn't afford to pay for it. And I knew people who had graduated and were working the same job I was already working, and I thought: what is this? The story about how you get success or happiness just felt like bullshit to me at that moment, among lots of other questions about what life was actually about.

When I was working on the farm, it was about gaining perspective. I was doing a lot of writing, a lot of observing the natural world. And I think when you observe things in the natural world, it allows you to observe yourself differently. As a poet, I'm often thinking about the actions of birds and plants — what do these things outside of myself say about the internal ecosystem operating within me?

In that moment, I had been weeding. All by hand, because it was an organic farm. I would go out and there'd be whole fields of tiny weeds, and I'd pick them one by one. And when I'd close my eyes at night, I would still see weed patterns — you know that afterimage you get from looking at something too long? I was constantly looking at these tiny plants and little bugs, this whole world unfolding in front of me.

One day I saw a spider with an egg sack on its back — the sack was larger than the spider itself. It was crossing through these little divots in the ground, going somewhere. Going there with such care, for its young. And in that moment I thought: what care am I going to be giving? How might that be the place where I find my meaning and my sense of success? That's when I decided to become a teacher.

There's just such wisdom in the natural world, if you're able to slow down and observe it. You make meaning for yourself in ways you can't through conversations or even through reading a book like Walden — as beautiful as it is. Mary Oliver is one of my favorite poets for exactly this reason. The way she takes something in the natural world and reveals its meaning, the depth of it. Actually, I have a line of hers I'm putting in the book. Can I read it?

GEORGE: Please.

GWYNETH: It's from "Green Greens, My Sister's House," in A Thousand Mornings. The line I'm putting on the front page is: "It is impossible not to remember wild and want it back."

That's how I've felt my entire life. That's why I wrote the book — and why I hope people will feel that they want it back too, in their learning spaces.

GEORGE: Education as an act of care. Called to it in a moment.

GWYNETH: Yeah.

GEORGE: What was the transit like? Getting from the farm back into teaching?

GWYNETH: It wasn't automatic, that's for sure. I had to move back in with my parents. I had to go explain why I'd walked away when they were contributing to my tuition. They were gracious about it. And I went back to work — but I went back with a new perspective on what I wanted, and I think that helped.

Over the next year and a half, I got myself back into college and into the program I wanted to be in as an educator. I started doing work at an afterschool daycare program while I transitioned back, because I had to keep working. And just being in a space with young people who hadn't become jaded — there was something healing about it. They haven't forgotten yet. I think that's what I love about working with young children. Even if they're growing up without access to forests or wild spaces, there's just something — they're still in touch with that part of themselves.

That's the hardest part for me as a parent. My kids were in a school where they were outdoors most of the day in their early years. And then everything changes when you enter the public school system after kindergarten. I love educators, and I'm glad I chose to be in the education space. But I don't think you can be in that world for long without realizing that it's part of the problem — that the approach we take to educating young people is part of why our society operates the way it does.

So many educators burn out. Or people supporting any kind of social impact work — the heart of it is to make the world better, and you can see that in glimpses. But the larger systems at play. I was reading an article on Substack about root cause analysis — how it's actually a faulty approach to thinking about complexity. And what is more complex and dynamic than educational systems? The belief that we can pull these little levers and things will improve — I just feel like it's so much bigger than that.

The people who tackle the biggest problems in the most beautiful ways, I think, are the scientists, the naturalists, the conservationists, and the artists. Being able to operate in that space as a practitioner was where I needed to go, to remain hopeful and in good relationship with the work.

GEORGE: So one of the things we first geeked out about together was expeditionary learning — the pedagogical model and framework that came out of the partnership between Outward Bound and the Harvard Graduate School of Education. About ten years ago, I was still trying to figure out whether I wanted to stay in academia and getting increasingly disillusioned with the higher-ed version of what you're describing. And I was captivated by EL. On paper it looked amazing — this hybrid of progressive education's commitment to solitude and reflection as part of a learning space design. And from the outside, what seemed like a genuine ethical commitment to standards in a way that was so different from how standards were being talked about everywhere else.

The factory model — define it for me, not the building. The mental model.

GWYNETH: Something happens when you try to scale things. They become more standardized. As soon as you go from an organic group of humans who can make sense and meaning together through storytelling and direct knowledge sharing — and I think those group sizes have real limits — to something bigger, the ability to share knowledge through watching something unfold starts to break down. So you have to think about: what are the structures that allow this to go further?

For meaning-making, lots of societies have grown up religions and institutions to help people understand the world and pass on their stories. Schools and education systems are similar. But there's something that happens when you scale, and especially when you scale in a way that prioritizes control — a way of thinking where you want to really know you're getting a return on your investment. As soon as you shift into thinking about it as a business, a scarcity mindset grows. Who gets the most? How do you measure it? How do you know it's working?

The mental model I'm describing is really about how capitalist ways of thinking have built themselves into systems that are supposed to be about social good, not profit. Robin Wall Kimmerer talks about this when it comes to knowledge-sharing in scientific communities, particularly in botany. If education is a space where we want to share knowledge in a spirit of contribution and reciprocity, we're going to have to understand that we currently hold a very different mental model — one that's linear, one that holds people accountable through measurement.

I don't think measurement is wrong, necessarily. But we use it for punitive control rather than cultivation — as information we're gaining from a system to better cultivate growth, rather than proof that what we did mattered. The best educators I know are the ones who operate in that cultivation space and can see the areas of gray. But I think it's a bigger problem than any one approach can fix. We need to understand that we hold a mental model that is holding us back.

GEORGE: How I've been interested for a very long time in how that kind of experience — especially shared experience — gets sustained, tended to, cultivated. What we do with it. Whether you think about it as what social scientists call the routinization of charisma. You got to EL when it was forty people on a mission. What was the heart of the work at that size?

GWYNETH: The heart of the work was creating learning experiences that were, I would say, whole child, whole world, whole community. The learning experience wasn't prescriptive — it wasn't if you do X, Y, Z, you get this outcome. It was more about educators being oriented to their sense of place: what does this space afford to the people you're with? What are the real issues and dilemmas that need to be solved in the world? How might we gather as a group of humans and learn more deeply in order to contribute to our communities?

What if schooling was that? Was about caring about your craft so that you did right by your community? Was about creating the communities we want to inhabit in the future — again and again, with that renewal? For me, that felt like the heart of the work. It was most akin, in some ways, to a Reggio Emilia approach — educators as researchers, as learners of their learners and their communities, moving alongside and with the people in their care. That was the heart of it, and why I felt so drawn to it.

GEORGE: The word clarity comes up in interesting ways in the book sample. The line that stood out to me was that clarity is the one thing the factory mental model has going for it. And it seems to me that when organizations grow, they tend to choose clarity over wildness. What was that like in the EL context?

GWYNETH: Concretely, it was like: how do we onboard new employees? Because when you've been a more organic, knowledge-sharing organization, you're moving from oral tradition to written codification. Everyone's been practicing it every day and there's an intuitive sense of alignment because you know each other — you can feel whether you're doing it the same way. But as soon as the group grows, that ability to sense alignment or misalignment becomes much more difficult. So you have to have technology in place — writing, different forms of communication — that allows you to convey things in a more standardized way.

What happens is that most nonprofits stay in oral tradition a little too long until the car is wobbling — there's a wheel in the back that's wobbling and you can't quite tell why, because you're a little too removed from it. And so you have to get the ducks in a row: what's the essence we want to communicate, and what's the best way to communicate it?

Here's where a breakdown often happens: organizations might know what their message is, but how they deliver that knowledge really matters — especially when the organization is focused on a set of values and a mission beyond itself. You had better operate internally in ways that reflect your espoused values. Because when people start to see a little light between those things, things fall apart even more. That's a struggle for most nonprofits, and it can be a very difficult thing to manage for leaders. Culture matters enormously, and culture is a very complex thing to understand when you're inside it.

GEORGE: What's the cost of clarity? What does an institution lose when it gets really good at knowing exactly what it's doing?

GWYNETH: I think when leaders allow for creativity, riffing, improvisation — when there's a culture of that — you can have clarity and still riff on it. But for the most part, organizations want alignment, and that creates a rigidity, a rule-following posture: if you didn't do it this exact way, you're not doing it the right way. There becomes a right way and a wrong way. And there's always the person who rebels against that. Sometimes I'm that person. Sometimes I'm the rule follower. We play different roles depending on the dynamics of the situation.

I think about it this way: if you write a piece of music and ask a musician to play it, you can expect a certain thing. But if you write a piece of music and ask a group of jazz musicians to play it — what would that be like? Thelonious Monk talks about moving through complexity in order to make something simple and beautiful. There's something about being able to work within a structure — you can't just have chaos, organizations need their structures — but they also need to move through that place of rigidity and complexity into a space where improvisation can actually occur, and where there are enough feedback loops to move the group through that improvisation together.

GEORGE: When you look at the forest as a model, what does it offer that could replace clarity as an orienting principle?

GWYNETH: Presence, I think, more than anything. You can have moments of clarity, but when you're in a space that shifts constantly, you need to be present and observant. You need to be able to respond in that presence.

You could be clear that this is what a forest looks like — and then imagine being thrown into a deciduous forest in North America in winter, when it's gray and brown and everything looks dead. How thrown would you be? Clarity in the moment fails us. So I think that the ability to be present, to be willing to renew clarity often, is what matters. That's what nature teaches us — that you never walk into the same river twice. I don't think you walk anywhere twice, really. You don't walk into the same group twice. You don't walk into the same organization twice. That pace of shift and change is always there.

And what does the factory avoid at all costs? Entropy. Because entropy means waste, and waste means losing money. But what happens with waste in the forest? It's not loss — it's transition. It's decomposition. It feeds what grows next.

GEORGE: I'm so fascinated by your project here, both as someone in full solidarity with the mission of moving education in this direction, and as someone interested in how an individual makes the kind of move you're five years into making. You've pivoted out of something that was in many ways beautiful and compelling. One of the blurbs on the back of the book is from Ron Berger — someone I know a little and whose work I deeply admire, and whose blurbing of your book strikes me as something like graceful or elegant. There's something Robin Wall Kimmerer-esque about a pivot that doesn't shoulder past what came before and leave it behind — that engages with it. Something about the grounded transition: I'm moving into a new thing, and that doesn't require a narrative that says everything before was awful and I've now found the truth.

GWYNETH: Right. That would be the factory mental model speaking.

GEORGE: And I use performing in the ritual sense, not the faking-it sense.

You grab onto words like transformational, experiential, holistic — rallying cries in the best of the institutional ed reform movement — and you describe them as inspiring but lacking anything to design from. What makes a framework actionable instead of just inspiring?

GWYNETH: I think a good framework is the one that works for you when you need it. What I need right now — and what I think some other people might need — is a way to come back into relationship with the nature of us. Many frameworks in education and learning are helpful and inspiring in certain moments. And let's take root cause analysis, as we mentioned earlier: that approach can be super helpful in a particular context. But it has limitations. For me, I want people to look at those limitations and understand how to ask better questions — and to seek understanding from the natural world about how to answer them.

The wildness we invite into spaces — the more we can understand that, the better we can operate together. More interdependence. More willingness to accept that there isn't one right way to do things, and to let go of things that no longer work for us. Frameworks are like that too — in five years, I'll probably look at mine and think, man, this needs to change. Because I'll be different. The world might be different. But the invitation is to be okay with renewal. And I think frameworks allow us to take different perspectives, try things out, see what works, and then move into a different space together.

GEORGE: A public school teacher comes across your work and finds it deeply compelling. And then says: I have thirty kids in my classroom. I have a standards-aligned curriculum and a vice principal coming in to do observations. I love this. What do I do on Monday?

GWYNETH: This is actually the last chapter in my book — the one I didn't share in the sample. And instead of it being the "how-to" of Wild Design, I think about it as the "how might." Because if we're thinking about how through a different lens — one that acknowledges there isn't one right answer — I think the invitation of "how might" is really powerful for anyone learning something new. It invites you into experiment. It invites you to think about: what's within my sphere of influence that I can think about differently?

I don't expect that anyone's going to read Wild Design and think, I've solved all my classroom problems, everything is beautiful now. That would be silly. It really is more about inviting people into conversations and reflection. And that's something teachers are not given. Teachers are not given the luxury and gift of reflection and deep introspection. That's not invited in most educational spaces right now. And the cascading consequences of that — when the adults in those places of care are not being cared for in this way — are real and painful.

My hope is that the book is a gift — an invitation to hold space for reflection and inspiration, to think about themselves more gently, and their young people more gently. Something to cultivate, not to get right.

GEORGE: There's a thread in your work that I'll reduce, unfairly briefly, to: artists have something to teach that educators don't. And it seems like that's something of an internal permission structure for you.

GWYNETH: Totally. For me, yes.

I think artists are meaning makers. What I love about the work of artists is that engaging in making and creative practice isn't about the end point — it's about the process. And I think about this through poetry too. I'm giving myself permission, and I want to give other people permission, to play more than just the one role you were told through your schooling and societal enculturation that you had to play. Engaging in creative practice allows us to do that.

So many of us are taught within our roles that we can't develop into a strange space — that the strange is wrong, that deviating is wrong. And I think that holding people in spaces where they're scared, where there's real fear around deviating into something unusual, stifles a lot of growth and learning.

Artists have something to teach us about how to move through fear. And for me, it's a self-permission mechanism. When I went to write this book, I thought: I can't write — not like this. If I'm going to write, it has to be an academic text. Boring and dry. Black and white. A million citations. But what if I was able to be more of an artist with my writing? What if I could include poetry? What if I told people I'm a poet — what does it mean to say that on LinkedIn? Will it be taken seriously?

Allowing yourself to get weird and go into those deviant paths in order to make sense of the world — that's what artists have to teach us. So I'm leaning into it.

GEORGE: When we talked in March, you said something about doubt and faith that I've been thinking about since. The way you put it was: if you don't encounter doubt, it's not faith. And you talked about a script you run when you're tempted back toward the solid ground of employment or traditional structure — you run the worst-case scenario all the way out, and then jump in. That strikes me as a lot more practice than philosophy. What's the doubt right now? What's the living edge of it?

GWYNETH: The doubt is that what I have to say — particularly in this book that's coming out into the world — is going to resonate with anybody. That it's not just some strange thing that gets tossed aside. When you bear part of your soul through art and actually put it into a public space, there's a real fear of rejection — rejection of the value of your work. And how do you pull apart whether or not that's also a rejection of the value of you?

Some people can let go of that more easily. I think as you do it more and more, you're able to. But sometimes the closer you get to the essence of who you are and put that out, the scarier it gets. Because you went out there more than you ever have before.

GEORGE: It seems like the sort of thing that only gets easier in practice if you're doing easier things.

GWYNETH: Yes. I don't think it ever gets easier unless you're playing it safe. Which is fine. But is great art or writing or anything great ever made by playing it safe? I don't think so. I think somebody risks some shit. And a lot of times it probably gets rejected and thrown away, and they give up, and that's the end of their life.

GEORGE: What happens if Wild Design works? If the book lands?

GWYNETH: My dream — and this is not so much for me as for others, though I hope to witness some of it — is that people get to create something magical for themselves with the work. I think great works of art or scholarship inspire incredible iterations. My friend Sam Bennett talks about throwing a rock in a pond and watching the ripples go out. My biggest dream is that Wild Design is that for people — that it's a moment of a rock in the pond, and that they're able to create amazing things with their communities from it.

GEORGE: Design is such an interesting word. The first time I encountered it in something like this context was probably in an EL job description for a school designer role, which I found utterly captivating. And yet — forest, garden, wild.

GWYNETH: I chose that word intentionally, because I felt like design had been co-opted by the factory mental model — especially when you think about design thinking in its worst application. There's such a mechanicality to it, a treatment of people as users in a way I find very allergic. But when you think of design as something artists do, as part of a creative practice — something that isn't going to be optimized, but is part of a process of creation — it feels different. I wanted to reclaim the word design in that context. I wanted people to still be able to say, I want to use a design process to think about how I do this work. But I didn't want design to mean figuring out exactly what users want so you can manipulate them into the outcomes you're after.

GEORGE: What's the question nobody has asked you yet about Wild Design?

GWYNETH: I don't even know. I've been brought it out slowly — it's not fully in the world yet. I'm curious to see what patterns emerge from it being out more, what kinds of questions and inquiries arise. I think I'd have a better sense of what's missing if I had the space to observe that, and I haven't yet.

I've been in the forest and can't see the trees — the book is ready. I'm ready to step back and release it and see what it does in the world. Maybe it's too much of a parenting analogy, but I've instilled the values I can. Now: what will this person go off and do? I can't control that. And that's actually the cool part. It's going to mean something different to different folks. And so I'm most excited about the surprising things I just didn't expect — hearing from people who are using it in ways I never imagined.

GEORGE: Do you know the Khalil Gibran poem about the archer that starts with your children are not your children?

GWYNETH: I feel like I've heard this one before and I have to hear it again.

GEORGE: I'll dig it up and send it to you. The deck is out in the world — when does the book go live?

GWYNETH: I'm finishing editing this week, which is exciting and also tedious, as editing can be. Then it goes off into production and the graphic design stage. I think September or October — but pre-orders should go live early June. I'll have a link to share out.

GEORGE: Fantastic. And we didn't talk much about the deck, which is an incredibly cool object in the world — folks will just have to go to your website and take a look. Gwyneth, thank you so much for your time. It has once again been an absolute pleasure to think with you about all of these questions.

GWYNETH: Thank you.

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End of transcript. Runtime: approximately 93 minutes (pre-cuts).