On how not knowing what you’re doing is a good sign

I would describe you as a writer who has made a career out of exploring the creative lives of others. How have your questions about what enables a creative life changed since you started?

I hope that my questions have gotten a bit deeper over time. I think starting with a look at writers’ and artists’ routines and working habits is a fairly surface level interest. It was an interesting window into other things as well. It proved to be a really flexible vehicle. As a writer, you could sort of use someone’s typical workday as an excuse to write about their struggles with procrastination, or how they dealt with having a day job, or how they thought about inspiration, things like that. But I think particularly writing this newsletter, for getting close to 200 issues over the last six years, I’ve just tried to think more about how it is that some people are sometimes able to get to the place where they can do work that’s almost, like, beyond themselves. Like at some point it just seems like things line up in a way, you know? Your talent and your temperament and the opportunity that comes your way, and maybe also the other things happening in your life, and everything sort of lines up in a way where you can do this thing at a level you couldn’t before, and maybe you can’t even again. I think I’m kind of trying to look at that more and more.

If the questions have shifted, has that changed the way that you read about artists or research their lives?

I think I’m more and more interested in the attitudes that people have adopted toward their work, and I’m finding that more interesting than just their habits. So I think it’s just really, for me, useful and interesting to see how people thought about their work and thought about the crises or dilemmas they were finding in their work. It makes me want to read their work or experience their work and it’s always good ballast for my own writing life.

I’m curious about this mode of seeking inspiration through the past. Tell me a bit about how you think about that power of the archive as a source of artistic inspiration or engine.

Sometimes I think it’s something funny about the way my brain works, like when I have a dilemma, I don’t want to know what my contemporaries do. I want to know what, like, Kafka did, in a sense, in similar circumstances. I think it universalizes it somewhat, and it makes you feel like you’re part of this lineage of people trying to figure out how to move forward. And for me, it helps. It adds a wider perspective or a wider context that helps me think through it in a better way. I feel filled with doubt and confusion and then locked in the struggle of my work, and then I read Kafka’s diaries, and I think, “Oh, that’s exactly what I’m going through.” [laughs] Or Virginia Woolf’s diaries, or something James Boswell wrote. And I think, you know, 400 years ago here was someone literally having the same feeling, and it helps me move forward.

What habits or attitudes have stayed with you? What do you do when you’re creatively stuck to move forward?

I read when I’m stuck. I think that’s my go-to. It’s this constant interplay between what I’m trying to do, and then going back to these people I’m interested in and often I feel like it builds me back up again. It kind of restores my faith in myself, or my faith in this project. I think everyone is just kind of trying to find the strength to take the next action or take the next step.

Are there any attitudes that you have found particularly freeing?

The big one for me recently, when I was finishing this book [Making Art and Making a Living], I was reading about John Cage, the composer. The thing that really hit me so hard, that’s not actually in the book, but which I wrote about in my newsletter, is this quote I found in a biography where he was talking about the idea of discipline. And he pointed out that the word discipline comes from the same root as the word for “disciple,” and he said that discipline is giving yourself to something instead of expecting to get something from it. And it just hit me so hard, because I’ve always thought, “Oh, I don’t have enough discipline to do this work,” or, “I need more discipline.” As if equating it with willpower, like it’s this muscle or this thing I have to work to summon. And the idea that discipline is actually like giving yourself over to a project just felt so liberating to me. And it also says that, in a funny way, that like, what you’re making isn’t about you, which also feels very liberating. Like, I think there’s this way in which we think that, you know, making art or being a writer is about self expression and certainly that’s part of it. But I love the idea that that’s actually maybe a small part of it, and that really it’s about having this idea and then sort of doing justice to it. You’re sort of trying to do what the project wants, rather than trying to drive it, using your ego to get something out of it. And I think when I’ve run into problems as a writer, looking back, I think it has been around that mistake about thinking, “Oh, I want to use this project to, like, grow my audience, or get to the next phase of my career, or, like, get a review in a fancy publication.” You know, like, “This is me moving up some kind of ladder as a writer.” And it’s like, more and more, I don’t want to think that way. I want to think, “What does this project seem to want for me? How can I be in service to this idea?”

Would you say that has redefined your idea of success? How do you measure whether a project is a success or a failure, or does that just not matter anymore?

I think when you’re making something, you can hit these moments where you sort of get this wonderful high. A moment of like, genuinely feeling like you’re experiencing the creative process. You’ve really articulated an idea, or you’ve really put two things together in a way that has surprised yourself or delighted yourself. And I think the success of the project is just having those moments. And it’s not about what happens to it after you’re done. I mean, once it’s done, it’s out of your hands to a large extent. And I mean, I know, personally, I often feel bad about things when they’re done in the immediate aftermath, and then later, like, I’ll look back on something and be like, “Oh, that was great,” or, “Oh, that was fine.” Or maybe I think it wasn’t my best, but it doesn’t really matter what I think about it once it’s done. I think it’s all about just trying to hit those patches where you feel like it’s coming together, and it’s alive, that feels great. I want to be always trying to find those spaces.

Is there any element of an artistic practice that you keep just to yourself? Is that important to you?

I mean, my very first wish as a writer was to write fiction, and I never quite got that off the ground. And then I have a few times over the years, returned to trying to write fiction, and really kept that for myself and never, I haven’t felt so far like I’ve been able to do something that I feel good enough about to keep doing it. And I don’t know if that’s just not sticking with it long enough, or maybe my strengths as a writer are just not in that direction. Or maybe I’m almost, like, still building up to it. I wonder if maybe all this reading and thinking about this stuff is my way of finally getting to the point where I can do that work. I would love it if that’s the case.

Have you found any inspiration in other writers, where they’re like, “Yeah, I didn’t start a book until X age,” or whatever. Has anything given you solace in that pursuit?

All the time I’m getting comfort and inspiration from these stories. I mean, I was recently watching some video with Karl Ove Knausgaard and he was talking about how, you know, when he starts a book, his thing is he just doesn’t let himself stop, and then it’s just horrible for the first 100 pages or so, but that if he just keeps going, it’s not so horrible. And then he puts it out, and then he does the next one. I think that really is the way to do it. I think I’ve too often let myself stop when I got to that point where it felt like, “This is horrible.” And a lot of any kind of creative activity is just not stopping at that point.

Your upcoming book is about how artists have made a living throughout time. Is there any guidance that you would give to an artist embarking on their path, or something you wish you’d known when you started out that you feel like you have a better idea of now?

I just feel like, if you feel like you don’t know what you’re doing, that’s not a sign that you’re doing it wrong, and it might even be a sign that you’re doing it right. Like, to me, that means you’re really in it. Like, this is a real dilemma, and it really takes your full creativity and resourcefulness and tenacity and and the experience of bringing all that to bear on this can be hard, and I think feeling that it’s hard is evidence that you’re doing it right.

The other thing is that, I feel like the people who are suffering in the book are the ones who are compromising in some way. Later in the book, [there’s a chapter on] Louisa May Alcott. She never wanted to write Little Women, like it was kind of forced on her by her publisher and her father. And it became this huge success. And she always kind of felt like, “I didn’t want to get stuck writing like children’s literature. I wanted to be like a serious novelist.” But she never could walk away from it, because it was such a machine, and she couldn’t resist the opportunity to keep making money in that way and writing new volumes in that same vein. I feel like there’s not really anyone in the book who sticks with their thing and regrets it. It’s only the people who compromise their thing that seem to feel bitter about it. So I do think there’s a way in which you’re gonna have to make compromises in your life to do the work, but, like, as long as you’re not compromising the work, you won’t regret what you’re doing.