On the challenge of completing a project

How did this book come to exist in this form?

It was a lot of trial and error, mostly error. It was a lot of failure and it was a lot of trauma. I think that it’s one of those books that, not to sound precious about it, but it had to be written if I were going to write a book. Every time I sat down at the keyboard, there was this stuff that presented itself that was unmovable. It became a problem for me. I frankly would’ve loved to have written about other happier things but what I went through was just always front of mind.

I had to write my way out of it. I couldn’t ignore it; I’m not capable of doing that. I couldn’t distract myself with other flights of the imagination. I had to look at what was bothering me closely. And that’s one part of the challenge, the challenge of placing attention on things that are not so fun to place your attention on. Then the second part of the challenge was rendering a narrative that could be palatable to a reader. Who knows if I succeeded, but that was the objective. Together, it was a pretty tall order. I joke about this a lot but I feel an authentic sense of relief to have it done. Not only because it was so arduous, but also because it’s the only way that I could see being able to work on other things creatively. I had to reckon with this.

How did you think about that second challenge, of rendering it in a way that the reader would find compelling?

Well, for one thing it had to be fiction. It’s a work of autofiction and I don’t put on any airs that it’s about anyone other than myself. I mean, it’s me but it’s also fiction. And I had to give myself the freedom to fictionalize for a couple of reasons. The first being that I have a geriatric-level memory at the age of 46 apparently, and I am not a diary keeper. So, I’ve always struggled a little bit with memoir for that reason. These distinctions feel very blurry to me in either direction, fiction or nonfiction.

But for me, calling it a novel, working in an autofiction mode, allowing myself to create when I wanted to or to shuffle timeline when I wanted to or to amalgamate characters when I wanted to, that helped. Otherwise, I was just relaying the facts of the case in some chronological order and I couldn’t figure out a way to do that, a way that was workable at the level of literature. And maybe I couldn’t enjoy it myself, the process of creation, without a little bit of freedom.

The second factor that became apparent to me was that it would have to be a shorter novel. I had to be brief. I tend to like the 200-page novel as ideal; that’s just a personal taste. This isn’t to say that I can’t enjoy a 500-page saga if it’s really done well, but I tend to think that most stories can be told in 200 pages and if you’re going beyond that, you better have good reason. What I really like is a book that feels like there’s no wasted motion.

And I think with a story like this, that deals with such difficult stuff, you don’t want to bludgeon the reader for too long. You don’t want to bludgeon the reader at all, but I think brevity is a virtue when you’re telling stories like this. Those two things were my guiding principles and I was able to make my way through.

Were there other versions that were a lot longer?

There have been so many versions. It’s honestly hard for me to even delineate at a certain point. I think this is a common situation for writers in the modern era, where you have all of this digital detritus. By the time you get to the end of a book project, if you’re anything like me, you’ve got a folder filled with failed attempts and documents and notes and scraps and it becomes hard to even remember what you did.

I wrote entire books that didn’t work—I know that for a fact. I tried to work in different modes and would write 15 or 20,000 words and then abandon the project when it became apparent that it wasn’t going to work.

I relate a lot to that. I keep thinking—what if I had to write my whole book with a pen and ink, editing and rewriting it by hand, until I sent it off to the printer or whatever? Would I still be the way that I am, going through 70 drafts of this work? Like, is my computer doing this to me?

I think that’s a very valid question. It’s one of the ironies of technological advances. They bring to us all of these conveniences but what are the downsides? Like a phone, you now have a super computer in your pocket that gives you access to the equivalent of the world’s greatest library and a GPS system and video conferencing and all of this stuff, but it’s also obliterated your ability to sustain attention and it’s made you basically a screen addict and who knows what these waves are doing to our brains when we sleep with the phone under our pillow and on and on and on.

With regard to the way that we compose books using computers, it’s wonderful to be able to word process and save documents and use Scrivener. But what happens to the length of the composition process when you can constantly delete and second guess so easily every single thing you’ve written? I can sometimes find myself getting totally neurotic and rereading the same page 16 times and I end up deleting the whole thing.

You wonder how many good books have been ruined that way. Because, it’s one thing for a book to go out into the world and not be edited properly. It’s harder to maybe calculate this, but it’s also a thing, I think, for a book to be overwrought.

Totally.

You can edit a book to death, you can even kill a book that should live. So, who knows, maybe we should both stop this and just go start writing in notebooks with pens.

I’ll give you a concrete creative example of my learning curve when it came to the composition of this book. There was a previous iteration, which I finished entirely and tried to sell years ago, which featured a protagonist who had been through five miscarriages with his wife. And in that failed the iteration of the book, all five miscarriages were detailed in various chapters. In the book that’s actually being published, there’s only one. That was the right choice in retrospect, but it took me a lot of failure to figure it out. Nobody needs to read all five. Or at least not read all five as written by me. One is plenty.

That makes sense. So, where and how did you actually write this version of the book?

I wrote the book that’s being published in my garage. It’s built of parts that were produced over the years, largely. Though, there is some new stuff in there as well. There was a fevered five or six month period in 2020, right when the pandemic hit, that was very good for my writing. It focused and concentrated me and eliminated distractions in a way that I found really lovely. All social pressure and sense of social obligation went out the window with the pandemic in a way that was obviously not great for a lot of us but was—as I have heard repeatedly in conversations with authors on my show—a boon to many writers who need solitude and quiet and home time to be able to get the work done. So, that’s when it really happened. This book finally clicked into place and I got a version on paper that, whether it would be published or not, I knew I was done with it.

I’d never felt that way before. It was probably the best writing experience or maybe even the best professional experience of my life. It was a huge relief. I cannot emphasize that enough. It was a decade-long process of trying to get this thing into a form that I felt satisfied with. To know that I was finally at a point where I could live with what was on the page, however the cards fell in the publication process, that was fun.

Do you have a sense of what it was that got you unblocked?

I think a big part of it was the pandemic and just being locked in the house. Not having as much to do and not feeling any sense of guilt for not wanting to do anything socially. The kids were not in school and everybody was just at home. I should also say as a practical matter, my son has some disabilities and when he goes to school, he has an aid who has to be with him so that he can stay upright. And when the pandemic hit, we were suddenly in this weird situation where we didn’t know what was going to happen and our aid wanted to keep her job. It was a very abrupt shift as you’ll recall, where one day life was this way and the next day life was this way.

We basically sat down with his aid and said, you’re going to have to move in if we’re going to keep you on, because you can’t be going back to your house and out to the store and all this stuff. We had to consolidate. So, we had live-in help for the first six months of the pandemic. Then she burnt out and moved to a ski town, but that was a rare, unexpected circumstance. I think that was a big practical factor. I knew that bases were covered inside the house with school and I could have some time to write in the garage. It’s a very lucky thing.

I don’t remember feeling a ton of fear about the pandemic, I’m not a hypochondriac or anything like that. But I think that the pandemic did give me a nudge in the direction of thinking about mortality and focusing me. Who knows how long we’ve got? The world is obviously a fucking shit show. I think I said to myself, if I’m remembering correctly, let me just write this book as if I were going to die in six months. What would I write if I knew I had a death sentence? Again, this is possibly going to sound precious and I don’t mean for it to, but there is a part of me that thinks all books should be written that way. Otherwise what?

That’s where I was anyway. What would I say if I knew I were going to die? And if I were willing to be maximally vulnerable.

That makes sense. It applies a pressure that we don’t often get otherwise. You can circle around the thing for years without actually saying the thing that you’re trying to say.

Yeah. Also, I was reading about things that were bothering me or confusing to me and trying to get clarity in that way. I think issues in writing and in creating are often tied to input problems. Your thoughts are built of other thoughts. If you’re having trouble coming up with what to say and you just feel empty or blank, you need to read or go to the museum or to a concert. You need to take things in.

So, it was all of that. It was the pandemic, it was maybe feeling a little bit more acutely the reality of the end, and then it was reading. That was the perfect storm to get this particular book out.

For people who listen to your podcast, we’ve gotten to hear you struggle with your relationship to the podcast and then your relationship to writing. Like, “Why am I spending so much time on this podcast thing? I should be writing my book,” is something we’ve heard you say for a long time. I’m curious how you’re thinking about that tension now that you’ve finished the book.

I think in theory, I could write more books if I didn’t do the podcast, but that’s only in theory. I tend to think of it as a necessary tension at this point. It’s what I like and what I need. I can’t just be all about me and my project, that’s not necessarily healthy for me. I just like to be of service to my community, which is the writing community. I stumbled into the podcast in a way, it was luck in the beginning. Then I found that I liked it and people listening for the most part liked it and it grew.

And then it becomes this thing that’s just a part of the rhythm of my life. It’s a continuing education. I get to spend time talking with super smart artists and to have uninterrupted, no phones conversations about the thing that I’m most interested in. I get to help move the needle ever so slightly on behalf of book culture, because whether we like it or not, I think we need to create book culture. Not just the books themselves, but the culture that surrounds it, if we want people to be interested. We need people, I would argue, to be interested in books more than ever. And so, a show like mine, I’m under no illusions that it’s making some massive difference, but every once in a while it does bring somebody new into the fold or it does move books into the hands of readers who otherwise would not have gotten them. Cumulatively that can become powerful.

I just enjoy it too much. I can’t say that I’ll be able to do it forever, there are financial realities and the practical stuff of life that may get in the way. It’s hard; it’s a lot of work to do that show week in and week out and to prepare and everything, but it’s part of my little creative ecosystem and I think it feeds the writing as much as it takes away the time I would otherwise have to write.

Definitely. I’m very struck by the fact that you were struggling to write this book over a decade, while also having these conversations with people who have, for the most part, just written and completed their books, and you’re talking to them about their processes with that.

I can say that the show has kept me going as a writer and provided me with countless insights and affirmations and anecdotes that have illuminated why it’s important to make art and how to do it and what to do when it’s not working. In the aggregate, it’s been a masterclass. How could it not be? I’ve had almost 800 conversations with a huge swath of contemporary American—for the most part—authors, including some luminaries.

Sometimes it’s useful at the level of practical concern, practical creative concern and other times it’s useful in the sense that it’s inspiring either because it lights the way and unpacks something that previously seemed complicated and makes it accessible and simpler. And other times it’s because there’s a shared sense of struggle. You’ll be talking to somebody super accomplished and here they are telling you about a time recently when they thought all was lost, or about being in some creative cul-de-sac that they’ve felt like they might not ever escape.

You start to realize that it’s the same for everybody. That alone can be a great lesson that can carry you a long way.

I know that a meditation practice is important to you. I’m curious if you thought much about a Buddhist perspective on writing, especially writing characters that are based on real people in your life.

That’s part of how I think about everything, but I don’t always succeed, especially in conversation. I’ll say or do something stupid, that’s just part of life. But as a guiding principle, Right Speech is definitely useful and it’s something that I try to incorporate into my writing. It’s a little bit tricky because you can’t be too scared to offend the reader when you’re writing something or you’ll never take any risks.

I tried to do the best I could to render a truth as I saw and felt it, and to do it with love. There was obviously no ill intent. I didn’t air every last thing; there are some things I kept private. Ultimately I feel like a book of this nature needs to be vulnerable. The hope is that there will be readers out there who will enjoy it. But in particular, I hope there will be readers who will feel a sense of the book really seeing them, or recognizing certain intimate aspects of their experience that they hadn’t seen articulated in a narrative. I wanted there to be a feeling of intimacy and honesty. That’s what I was going for.

How did psychedelics factor into the writing of the novel, if at all?

They factored in significantly. Going into the psychedelic experience that I had, that informed the book, I was thinking a little bit about the possibility that it could factor in. I can’t recall how explicit it was. In my head it was more like, well, I’m going to do this as an experiment, I’ve been reading a lot about this, which is how most of my misbegotten experiments begin. I was genuinely curious. And much like the narrator in my book, I was wanting to correct the ways in which I had used psychedelics in my wayward youth.

I think it was the reading that made me realize how crazy we had all been, my friends and I, when we were in college. Just not having any clue what these things really were, what their true purpose in human life is. So, I wanted to try to do it the “right way” and I wanted to see what happened. And maybe as a secondary thing, I was thinking that it might yield me something for the book or be a big experience that I could write about. I was going to take a very high dose, which I hadn’t done before either, I don’t think. In my wayward youth we weren’t measuring our doses with a digital scale.

Well, it’s hard to nibble on three or four grams casually, you generally have to keep going beyond the point that you want to.

Yeah. So, it was a curiosity, it was a spiritual exploration, it was, I don’t know, a midlife inventory. It was a corrective. It was all of these things. The psychedelic experience delivered a genuine emotional catharsis that I never could’ve mustered on my own.

And a book like mine, or maybe any book, needs to deliver some emotional catharsis so, it makes sense that it would’ve ended up in there. But the experience for me was deeply strange and spiritual and therapeutic. I feel good about the way that I did it; I was pretty responsible. It was orderly, so far as such things can be orderly. I wanted to take it seriously and be respectful. I know there’s always some degree of danger but I wanted to mitigate against that as well. I had enough experience with them in my youth that I felt a sense of familiarity. It was a wild experience, that’s all I can say. I don’t remember it all that well, these things slip away from you, but man, it was beyond words and profound at times and it gave me what I needed.