
Mason Currey walks us through the four funding models his book explores — family money, day jobs, patronage, and schemes — and what the lives of creatives from Kafka to Murakami can teach us about building a practice that actually lasts.
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Mason Curry
The great artists through history are people who know how to listen to their instincts and trust them, and people who know how to follow their energy, even when it is not at all clear where it might lead or how it might lead to funding or not. And I'm not saying it always works out financially, but I think it does work out in a creative satisfaction way and in a energy creates more energy kind of sense.
Eli Woolery
At several points in my life, I imagined what it would take to become a full time artist, a photographer or illustrator, free from client work. What I didn't realize was that I already had an example of a different path right in front of me. My dad a practicing physician whose published poetry earned recognition from luminaries like John Ashbery. Mason Curry's most recent book explores these alternate paths. He's the author of Daily Rituals, the beloved book that cataloged the working habits of nearly 200 artists, writers and composers. His new book, Making Art and Making a Living, goes deeper into the financial realities, schemes, compromises, and the surprising strategies that creatives have used to keep their work alive across centuries.
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What he found is both humbling and strangely reassuring. Virginia Woolf had inherited investments. Kafka had some insurance, Chantal Ackerman had a cash register that she skimmed from, and John Cage, believe it or not, had Italian game show winnings. And yet, running through all of this is the same question that Mason has been asking about his own life since the day he sat down to write a novel and couldn't how am I
Aaron Walter
going to pay for this?
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In this conversation, Mason walks us through the four funding models. His book explores family, money, day jobs, patronage, and our personal favorites schemes. And with the lives of creatives from Kafka to Murakami, can teach us about building a practice that actually lasts.
Eli Woolery
This is Design Better, where we explore creativity at the intersection of design and technology. I'm Eli Woolery.
Aaron Walter
And I'm Aaron Walter.
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Aaron Walter
And now back to the show. Mason Curry, welcome to Design Better.
Mason Curry
Hi. Thank you for having me and glad to be here.
Aaron Walter
We're very excited about your new book, Making Art and Making a Living and it's something that really resonates with me. I actually studied painting and drawing and I remember in grad school, me and all of my fellow art student grad students were trying to figure out like, how do we build a career out of this? And a few made it and a few didn't. I've certainly seen a lot that didn't work. Maybe we should start with what brought you to this book. It does seem like a very salient topic right now.
Mason Curry
Yeah, I mean, it's been the great question of my writing life is how am I going to pay for this? You know, I mean, I started off after college thinking I wanted to write a novel and I got a day job at a library and then, to be honest, wasn't getting much writing done. I sort of blamed my day job, although I don't think that was the problem really. But ever since then I've always thought, how am I going to pay for this? It takes so much time and experimentation and trial and error to do creative work in any field. And so often it doesn't come with any reliable income attached. And so I think everybody from the get go is trying to think about how to navigate it. And for me, seeing how writers and artists through history have navigated it is a. It's just entertaining. But also I think it gives me a sense of being in a lineage of people who have confronted this problem and also seeing the ways that they dealt with it. Give me some ideas or at least give me some strength as I try to keep doing it myself.
Aaron Walter
Yeah. Dan Pink once told us that all research is me. Search.
Mason Curry
I 100% agree with that. Yeah, My whole writing career, in a funny way, is trying to understand my failure to write that novel. When I was first starting out, you know, I thought, why couldn't I do this thing that I supposedly wanted to do? And can I somehow adopt the habits or the routines that are going to help me find this discipline or this willpower or this ability? So in a funny way, my writing career has been all about understanding that.
Eli Woolery
One of the concepts that you talk about in the book is this idea of double lives that some of these very well known artists had. Like poets like Wallace Stevens, he was actually a lawyer for an insurance company and William Carlos Williams was a physician. This especially resonates with me because my folks are actually both physicians, they're retired. And my dad had a poetry practice that was actually pretty successful for what it was. I mean, he got recognition by the poet laureate John Ashbury at one point. Sadly, he can no longer really write, but for much of his life was writing poetry. But you know, I had three brothers, had to find a way to support a relatively large family. And both he and my mom worked hard as physicians for most of their lives. So yeah, just reading these stories had a kind of a personal connection for me too. And it was interesting to read them.
Mason Curry
Oh yeah, I'm so glad. That's incredible. I love John Ashbery. So I'm really impressed. Yeah, I think it's one of the big questions. Starting out. It's like, should I get sort of a crummy day job that's not going to suck up too much of my brainpower and do my creative thing on the side and work as a bartender or at a cafe or on a construction site, or should you try to secure a comfortable middle class lifestyle as a professional in some fields? That's what William Carlos Williams did as a family physician or Wallace Stevens working in insurance. Or do you try to like mix the two and do something that is creative or close to what you're trying to do creatively and I tried to sort of make a chapter for each of those strategies to see the ways that it played out for different people.
Aaron Walter
Let's jump into those four models in the book. I thought it was an interesting way to organize the research of these are business models that people have approached their work with. Could you walk us through the four and maybe share a little bit of what you learned from each one of those?
Mason Curry
Yeah, well, the book is in four sections. The first section is Family Money. Because I kind of thought, well, the absolute best case scenario for an aspiring artist would be to have access to some sort of family money, either an inheritance or some kind of parental allowance or sort of mooching off your family borrowing money. So I gave a chapter to each of those possibilities and just tried to explore the ways in which it enabled different careers. I mean, Virginia Woolf is an example of someone who never would have been able to have a serious creative practice without that family money that she inherited. And she had to work incredibly hard to build a successful writing practice and a publishing enterprise. But she also always had this steady income, the interest off of her inherited investments which allowed her to get started on all that. So you know, it's like a little depressing maybe if you don't have that money. But it's also in a way sort of a relief to know that yeah, some people did have a leg up. And it's definitely an underlying factor in a lot of famous artists lives is access to some kind of money that we don't all have. The second section of the book is jobs because that is the obvious thing that so many of us have to do. If you don't have family money, you know, you need to get a job. And so that's where I looked at, well, there's the kind of odd jobs approach, like don't give your brain power or your creativity to the job. Just do something to make the rent and then save as much of yourself as you can for your creative practice. So you people temping, you have just a great variety of jobs, a lot of which don't work out that well for people. And then you have like we were talking about the more sort of parallel careers idea. My favorite in that section is Kafka, Franz Kafka, the writer who also went into insurance and was deeply unhappy working at this insurance office. And his letters and diaries chart his overdramatic, over the top misery, even though he was actually getting writing done and actually had a pretty forgiving schedule by today's standards. It was just fun for me to unpack that after the job section. I have a patron section, because that, of course, is the other big way that artists have funded their work through the ages, either through individual patrons or through government patronage. I kind of lump those together. And then the last section is my favorite, which is schemes. And that's kind of a grab bag for all the other ways that people cobble together income through shoplifting, working as a stripper, trying to implement some sort of get rich quick scheme, going on a television game show. In one case. That stuff I love sort of read and write about.
Aaron Walter
Can you share like one or two stories from that? Because that's fascinating that people would go to those lengths.
Mason Curry
The first chapter of that section is about people who stole as part of their early way that they funded their work. We have the Belgian filmmaker Chantal Akerman, whose work I love. One of her early jobs living in New York in the 70s was working at like a seedy Times Square porno theater. And every ticket she sold, she would pocket half the money. And she saved up enough money to make some of her early short films. And she also stole film, film, like 35 millimeter film from a photo lab that she worked at and hid it under her bed and later also used it in her filmmaking. And then her great inspiration was Jean Luc Godard, the French filmmaker, the French New Wave filmmaker. And he also stole, in his early filmmaking days, I think it was his grandfather had a collection of valuable first edition books, and Godard would steal them from his grandfather's apartment and resell them at Paris book stalls. And he used that money. And then another French, it's interesting, the French connection, another French writer, in this case Jean Genet. His whole entry point to writing was as a thief. He was this sort of prolific shoplifter. And he even had a trick briefcase he would use to steal again books from right out from under the nose of booksellers. He would keep the briefcase under his arm and stick books in there as he would be distracting the bookseller. And he got caught over and over again and was sent to prison for short stints. And it was actually in prison that he discovered his calling as a writer. I love the story about John Cage, the American avant garde composer. He was always broke. He never made much money from his composition work or his musical work. But he did have this hobby of mushroom collecting. He was like an amateur mycologist and over the years became quite serious about it and had this huge collection of books. And he ended up on a tour in Europe in the late 50s, ended up getting on this television game show in Italy, where they would have normal people appear and test their knowledge of a particular subject. And for John Cage, it was mushrooms. And so he appeared on this show in five episodes and they asked him increasingly difficult questions about mushrooms. And he kept getting them right and at the end walked away with the equivalent of like 90 grand in today's dollars. And he said that was the first significant money he ever made. He was 46 or 47. I don't know if that provides a model for the contemporary person, but it does give you a sense of the nerve and tenacity and creative thinking that you can bring to the problem.
Eli Woolery
One of the other sections, and sorry to jump around a bit, but there's interesting stories all over the place. This idea of the bridge that you have, I think in the job section of your book, which is this idea that, okay, if I can't directly make a living from my art, maybe I do something that's kind of adjacent or related to it. So you talk about the story of Remar Bearden, who tried to kind of make a living as cartoonist and he eventually kind of gave up because he felt he was maybe not succeeding in either. The quote from him was, there's unfortunately no bridge between the fine arts and the arts of commerce. And I kind of felt this in another personal connection myself because there was a period of time where I got really into photography and I thought, oh, this is great, I want to make this into a career. And I did some commercial photography. I was working on a cookbook for a pretty well known chef. And it got to the point where that work was like killing all interest I had in photography because I was doing it essentially survive and try to raise a family. And those pressures and stresses, I wasn't doing any shooting outside of that. So it feels like there is a danger. I think some people are able to do it successfully, but there's a danger that it might kill the passion that you originally had for your art form.
Mason Curry
Yeah, I feel that dilemma quite powerfully too. I mean, I really loved reading about Bearden. He was a Harlem based painter in the 1950s and 60s and going forward, and like you said, he got his start in cartooning as a college student and he had the opportunity to have a professional career as a cartoonist publishing in magazines. But then he fell in love with painting and he thought, oh, can I do both? Or can I somehow meld the two? And he decided, no, there is no bridge between fine art and commercial Art. I feel like sometimes I'm trying to stand on that bridge in the writing world, and it's not always there. I'm trying to write about things that are interesting to me, that fascinate me, and also produce relatively commercial books that are going to appeal to a wide audience. And I think that's really the fundamental dilemma for a lot of people. How do you do the work that you want to do and not compromise it, but also find some way to get income? And he decided there was no bridge. I'm hoping there can be, and I think a lot of people are.
Aaron Walter
I wonder if people like Romare Bearden, Robert Mapplethorpe, who famously was a prostitute in New York to make ends meet, if artists of their time, if they live now and had access to, like, Patreon, Substack, YouTube. In the case of Robert Mapplethorpe, maybe OnlyFans, I don't know, like, different ways that you can make money. Find a patronage, build a patronage on your own. Instead of the Medici model where you have to go find these wealthy people, get in access, and you're the Leonardo da Vinci, Michelangelo, whoever, that gets the connection to these wealthy people. How do you think that these sorts of platforms change the possibilities for creative work today?
Mason Curry
I think it's still the fundamental same mission for the creative person. I mean, I write in the book about Alexander Pope, the English poet who lived in the 1700s, and he wasn't the first person to do a subscription scheme for his writing, but he was one of the early pioneers, and he basically did a lot of what we're doing on Substack today. He attracted a subscription base for this big work that he wanted to put out there over the course of a few years and managed to fund the work and actually make a lot of money by the end of the day. And the way he went about it was he was just a very gifted person at making friends, powerful friends, influential friends, moneyed friends. He has sort of a gift for cozying up to those circles and making himself seem indispensable, making them want to be in his good graces. It's the sort of gift that you see throughout this book. People who seem to be able to ingratiate themselves or charm people with power and influence and money. So that's one method. I think Substack is interesting because it democratizes patronage, but also it's so democratized that it can feel like it's just people seeking income and not enough people providing that income. I feel like this is the great dilemma for our creative Economy at the moment is it's like if everyone wants to write a newsletter or fund a creative project through Patreon or Substack, who is left to be the funder? The patron is a disappearing person. It feels like everyone's an artist and no one's a patron anymore. Sometimes I don't know if you'd share that feeling.
Aaron Walter
I do think that there's something going on where people feel oversubscribed. There are people with great intentions and I really like what Patreon is doing. Their founder, who's also a musician, Pomplamoose, Scary Pockets, he has these bands and they have YouTube channels that are very successful and they're always like collaborating with different people. And he wants to make sure that creative people have an income, that the arts are supported. I think that's amazing. But platforms like Substack, we're on Substack, of course, we love Substack. It helps us reach a lot of people. But it is hard because people, they're subscribed to a lot of things and so they have to make hard decisions of what are the things that are most valuable. So for us, I'm always thinking, is this worth your time, your money, your life's energy, which money represents? So as someone who's writing and producing things a lot, I guess it sort of maybe pushes us to think more about how we could create value for people.
Mason Curry
Yeah, I like that way of thinking about it. I've been thinking about that a lot, like, what do people actually want or need in their creative lives? It's not more emails. And I've been doing a zoom accountability group where we meet in the mornings and everyone tries to carve out a two hour block where we can work together with our cameras off and then have a little check in at the end. That's been, for me, not hugely monetarily successful, but it has a really nice energy. That's one theme that really comes through the book, is the artists in this book and the great artists through history are people who know how to listen to their instincts and trust them and people who know how to follow their energy, even when it comes, is not at all clear where it might lead or how it might lead to funding or not. And I'm not saying it always works out financially, but I think it does work out in a creative satisfaction way and in a energy creates more energy kind of sense. I think there's a real lesson to be learned from these people about figuring out what that voice is and trusting it, even if it doesn't seem like it's going to work out. You see the ways that it works out in sneaky, unexpected fashion throughout these stories.
Eli Woolery
Thinking about technology and we have these semi established technologies like we're just talking about with Substack and Patreon. And then there's these kind of emerging things you can think of like NFTs and beeple, which is that a scheme or is that a real thing? I don't know where it falls, honestly.
Mason Curry
Definitely a scheme.
Eli Woolery
Technologies like OpenClaw, formerly Claudebot, where there's examples of somebody and this person's not an artist, but I can imagine an artist doing this, setting up an instance of claudebot or openclaw to go out and like make money for itself, essentially. Like, I'm going to give you these parameters, these constraints go out and it's made, I think over $100,000 at this point. And so that could open up a whole new funding model for folks where they can set up these little robots to go and do work for them and they can focus on their art in a hopeful scenario.
Mason Curry
Anyway, it's interesting to be having this conversation at this moment in AI because I think everyone is sort of like, wait, is my job, my field going to exist going forward? And what we have in this book are people who. Their starting point was, I want to do this work that is meaningful to me, that I feel really powerfully drawn to do. And I don't think there's necessarily any money attached to it or I don't know how the money is going to be attached to it. And so I think in a funny way that's a dilemma that a lot of us are starting to face. Even if we thought we were heading into a field where there was money attached, we might be finding it's not as attached as it once was. So, you know, I think that's why these stories, I hope, resonate with people. Because you see people figuring it out on the fly, trusting their instincts, building networks of collaborators and supporters and potential funders. I think a huge theme in the book is having a scene or a group or friends. So much of the work that gets realized happens in some way through collaboration, through being in like an energetic scene, seeing what other people are doing, responding to it, helping each other realize. So there's a sort of DIY ethos. I think in these stories you often can't expect your work to get paid for, but you can often find ways of making it happen with the resources you do have.
Aaron Walter
Your books, not only your latest, Making Art and making a living. But your prior books require a great deal of research. And I'm really curious how you approach this, because there is a broad landscape here. There's a lot of literature out there on this topic, and then there's stuff where you have to go learn about these people. They may have not written explicitly about how they run their business, like David Byrne has in his book How Music Works. Like, he just lays it out like, this is how much I make. This is how I do it. He does not make that much money as you would think. That founder of Talking Heads would make a bunch of money. He does okay, but it's still tight. Take us into the research process. When you start a new project like this, where do you start? How do you break it down?
Mason Curry
I have a very inefficient research process, which I love, even though people might be horrified. I request books from the public library to be delivered to my local branch. They'll let you have 30 holds out at a time. And I continually have 30 books circulating. So I just go into the online search bar and I type in the name of who I'm interested in, and I order every book in English that looks interesting, and they get delivered to my local library. I go pick them up, and I just constantly have these books circulating, and I don't necessarily read them all, but I read the ones that interest me and I skim the rest. And as I go, I flag pages. If there's something interesting, I put a sticky note on it. Then I scan every page I flag, then I print every page I scan, and then I put them in folders for the name of that person. So for John Cage, I end up with scans from his writing, from biographies of him, from even, like, mentions of him in other books, other people's biographies. And you end up with this sort of critical mass of material. And then I go back through and read it all and I underline things and I make notes in the sides, in the margins. And hopefully out of that process, I start to feel a story forming. I start to feel like, ooh, this is the interesting thing about this person and their relationship to money or how they finance their work. And very often I go try to write that, and it doesn't quite come together, or it doesn't feel that compelling, or it doesn't quite fit in the book, or I don't have enough information and I have to go back and research more. I really like doing that. It takes so long. I have so many folders for people that didn't make it into the book, but hopefully it all ends up in my substack newsletter or in future books. Very often one figure will lead me to another. So it's not particularly strategic, it's very intuitive and I go after people I'm interested in and I kind of see where they lead.
Aaron Walter
We have a hunch here at Design Better that what you've just described is a generalist approach to research and AI is so good at specializing about going deep on a particular task or skill or something like that. It can do stuff like what you've just described, but it doesn't do it very well and it's often not very trustworthy. So this thesis that we have is that this type of thinking, this generalist broad exploration, connecting the disconnected, is an increasingly valuable and important way of thinking and operating. And in my experience, you know, as a former painter, a former artist, art school taught me how to do that. That's just the way that my brain works now is very broad picture research and looking at all these different disconnected things. Curious your thoughts on that thesis and what you see coming next.
Mason Curry
I agree with that thesis. I mean, I think for me the wonderful thing about writing is
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Episode Date: May 6, 2026
Hosts: Eli Woolery & Aarron Walter
Guest: Mason Currey
Theme: Navigating the intersection of creative practice and financial reality—exploring how artists, writers, designers, and other creatives historically and currently support themselves, gleaned from Mason Currey’s research and new book, Making Art and Making a Living.
This episode dives deep into one of the most perennial questions for creative practitioners: “How do I pay for this?” Mason Currey, author of Daily Rituals and Making Art and Making a Living, joins hosts Eli Woolery and Aarron Walter to discuss the many methods, compromises, and sometimes surprising schemes artists have used throughout history to support their creative work. The episode is candid, witty, and packed with historical anecdotes and personal reflections.
Mason Currey on the central challenge:
“How am I going to pay for this? It takes so much time and experimentation and trial and error to do creative work in any field. And so often it doesn't come with any reliable income attached.” (04:54)
Currey explains that his own journey—from aspiring novelist with a day job to chronicler of artist work habits—began with this very question.
A lineage of financial struggle:
Currey’s fascination lies in learning how creatives across centuries have tackled the balancing act between art and sustenance, acquiring both solidarity and practical ideas from their stories.
The Double Life:
Many renowned artists maintained “double lives,” balancing professional careers and creative practices.
Key Dilemma:
Should artists pursue low-effort jobs for financial survival, take up well-paying professional roles, or try to mix commerce with art?
Currey’s book is structured around four main funding approaches found historically among creatives:
Family Money
Jobs
Patronage
Schemes
New Patronage Platforms:
Patreon, Substack, YouTube, even OnlyFans, allow direct audience-driven support, but present the paradox of “everyone’s an artist, no one’s a patron.”
Value and Subscription Fatigue:
Both hosts and Currey discuss the challenge of delivering value amid the glut of subscription-based creative work.
Alternative Community Models:
Currey’s own Zoom accountability group as a source of creative energy, even if not lucrative.
Guiding Principle:
“The great artists through history are people who know how to listen to their instincts and trust them, and people who know how to follow their energy, even when it is not at all clear where it might lead or how it might lead to funding or not.” (18:17)
Emerging Funding Models:
Example of AI (OpenClaw / ClaudeBot) autonomously generating revenue, hinting at a future where technology can subsidize creative work in new ways.
Job Uncertainty in the Age of AI:
“I think in a funny way that's a dilemma that a lot of us are starting to face—even if we thought we were heading into a field where there was money attached, we might be finding it's not as attached as it once was.” (20:13)
The Importance of Scenes and Collaboration:
“So much of the work that gets realized happens...through being in like an energetic scene, seeing what other people are doing, responding to it, helping each other realize...” (21:32)
Mason Currey:
“The great artists through history are people who know how to listen to their instincts and trust them, and people who know how to follow their energy, even when it is not at all clear where it might lead or how it might lead to funding or not.” (00:01 & 18:17)
Aarron Walter:
“Dan Pink once told us that all research is me-search.” (05:46)
Mason Currey (on new funding platforms):
“If everyone wants to write a newsletter or fund a creative project...who is left to be the funder?...It feels like everyone's an artist and no one's a patron anymore.” (15:41)
John Cage anecdote:
“He ended up on a television game show in Italy...and at the end walked away with the equivalent of like 90 grand in today's dollars. And he said that was the first significant money he ever made.” (12:49)
Candid, insightful, and laced with humor and empathy for the creative struggle. Both hosts and guest balance historical anecdotes, research, and personal stories, making this episode both practical and inspiring for creators at any stage.
Summary Prepared For:
Anyone interested in the overlapping worlds of art, design, technology, and making a living as a creative—regardless of background or experience level.