“There’s bad news, there’s good news, and there’s bad news about the good news,” author, essayist, and educator William Deresiewicz told me over coffee on Portland’s Northeast Alberta Street. Deresiewicz is a winner of the Dallas Institute’s Hiett Prize in the Humanities and author of more than 300 essays and books, including Excellent Sheep, The Death of the Artist, The End of Solitude, and a forthcoming memoir about his Jewish identity. The New Jersey-born author, who has lived in Portland for nearly 20 years, made a name for himself writing poignant prose and piercing works of contemporary relevance on topics including arts education, individuality, the internet, institutional learning, and technology’s impact on culture and the written word. 

Deresiewicz, who has also appeared on shows including The Colbert Report and Eminent Americans, taught at Yale University for 10 years. He took a sabbatical in Portland in 2004, fell in love with the city, and relocated in 2008. His writing considers how things have changed for working artists in a landscape preoccupied with convenience and mass reproduction. We sipped our coffees as he mused on the odd institutional obsession with higher education for artists, as opposed to the tech world, where many are charting a course to career work without going back to school.

“I have a chapter on this in The Death of the Artist,” he said. (Read Brett Campbell’s ArtsWatch review.) “I talked to a lot of people, and we have a terrible situation that schools have created: We’re in this place where credential has become necessary, and it very much didn’t used to be like this. For example, there were no MFAs until around the 1930s. There were very few MFAs until after World War II and the big arts boom, which was also a higher education boom.” As late as the ‘70s,” he continued, “artists not only didn’t need an MFA, but would often scoff at people” who pursued one. Even those teaching at a university generally didn’t need an MFA.

“It’s a catch-22,” he said, “because there’s no problem with getting an MFA, except that the cost is astronomical. It would be nice if it were more accessible to get the higher education degrees as artists, but it feels like a dead end for many who would consider them.”

Deriesewicz took on another difficult topic in The End of Solitude, which reflects on solitude through essays and critiques. In this work, Deresiewicz said he attempted to articulate his experience with the early days of social media on platforms such as Facebook. He joined in 2008, when he was 44, after leaving academia, and quickly began considering what it all meant. To understand the evolving social environment, Deresiewicz distinguished three modes of being alone. 

“There’s being alone, there’s loneliness, and there’s solitude — or the way that I’m defining solitude,” Deresiewicz explained. “Because it could just mean being alone, but being alone is just an objective state. You can look at someone and see whether they’re alone. If loneliness is the negative experience of that state, I’m calling solitude the positive experience of that state. If we want literary antecedents, we can think about Thoreau. We can also think about Whitman. Even in the city, you can experience solitude, but the point is that you experience solitude as a state of fullness, rather than the emptiness which is loneliness. Being alone can mean being in the world … whether you’re in nature like Thoreau, or in New York City like Whitman, or just alone with your thoughts or a book.

“Then there’s the other thing, which is solitude, and sometimes that’s good. Sociability is wonderful, but what the internet and social media have given us is a kind of sociability that’s none of the good parts and all the bad parts. There are some good things about it, but I think we all know by now that it’s not a substitute for real sociability — for sitting in front of someone, talking to them, listening to them, looking at them in real time. Social media also doesn’t let you be alone. It takes away your solitude, and it becomes this compulsive need to constantly get this very attenuated form of feedback. That’s what I saw happening and wanted to make sense of its draw.”

As the world continues its rapid change, Deresiewicz writes to keep up and inform readers of the potential ahead.

 “So back to the bad news: The bad news is — and everybody in the arts knows this — the internet has demonetized creative content, so it’s either free or it’s much cheaper than it used to be across the board,” he said. “That includes how much writers get paid for doing freelance work, indie film budgets, music, photographers, etc. Basically anything that can be digitized. The exception seems to be painting and sculpture, any kind of concrete, physical object. But that’s a small minority. That’s the bad news.”

When it comes to the good news, Deresiewicz’s take is straightforward. He says art is for everyone and that everyone can do it. Using the internet, artists can appeal directly to their audiences.

“That’s what it means not to have gatekeepers,” he continued, “and you can make money directly from your audience. This is the Patreon, Kickstarter, and Substack concept. So there are a certain number of writers who are making a lot of money, and then some who are making a decent amount of money. But now we get to the bad news about the good news, which is that everybody’s heard the good news. Everyone’s trying to succeed in this same way.”

Deresiewicz and I continued to talk about his background and his thoughts on writing. His comments have been edited for length and clarity.

When did you first begin writing, and how did you know that you wanted it to become your profession?

Deresiewicz: When I was around 12 years old, I would compose little speeches in my head. I was completely un-self-conscious about it, and looking back many years later, I realized I was kind of destined to be a writer. I had a knack for it, or a need for it. I didn’t really pursue it in an active way, even in college. At that time, I was mostly writing letters and I would inflict my writing on my friends that way. Some of my friends were probably thinking, “This guy needs an outlet.”

A couple years after college, I went to journalism school, and while that wasn’t a really great fit for me for various reasons — I had been interested in dance — I saw that there was a class in dance criticism being offered at an adjacent school and I took it. And I was really lucky, because it happened to be taught by somebody who was a great teacher and professional dancer, and that kind of opened up the whole world for me. It was the first real mentorship I had in my writing. She helped me get started as a professional writer. She taught this course every couple years at Barnard College, and when she had a writer who she thought could really be a writer, she would urge them to write for Dance Magazine, and she would urge Dance Magazine to let them write. So that’s how I started writing in 1988. I started writing very short reviews of New York dance performances.

So you went from biology and psychology to journalism to English. What was that transition like and how did you decide to study those subjects in school?

I graduated college in ‘85 and at that time, that’s just what you did. If you didn’t know what you wanted to do, you applied to law school, journalism school, or something similar. I kind of knew that journalism school was not the right place for me, but it was a way of not going to law school. I should have been studying English all along, and it took me a long time to get there, possibly because I didn’t have encouragement from my family.

I chose my college major much too quickly, because I think the uncertainty of college caused me a lot of anxiety. It was really just a matter of peeling away the layers until, finally, I realized I should always have done that. I was able to get into at least one graduate program, even though I hadn’t been an English major. I had a lot of grief, actually, in the last couple of years of college, that I had missed my chance to do the thing that I really wanted to do. And I managed to slip through the crack in the door as it was closing.

What genre did you begin writing? You talked a little bit about letters; how did you land on essays?

It’s funny, I never thought about the fact that I started with letters, but I guess that’s true, and then I began writing criticism. I wrote reviews for a long time, and I loved doing it. I still love doing it. I think it’s a real craft, and I think it’s very valuable. I also knew that I wanted to write book criticism. I was studying English, but I didn’t really know how to get into it. I asked a professor of mine at Columbia -– a lot of this is about connections, which is the reality of the arts and writing –- I told him I was interested in doing book reviews. He didn’t really have many connections to make at that time. But a few years later, out of the blue, I was contacted by an editor at The New York Times Book Review. And it turns out that she had asked my professor if she knew any young writers, and he’d mentioned me. I started doing that, and that was great. That was in 1999.

At the same time, I did have the sense that I had arguments to make. I wanted to write essays. I didn’t really know what that meant and had a lot of questions like, “How do you how do you go about doing that? Like, how do you find a topic? How do you develop a topic? Do I really have anything to say? Do I have anything new to say?” The truth is, I’d been really lucky, because I was writing for the Times Book Review, and in retrospect, it was somewhat unsatisfying, because those pieces are so short. So I started to feel like I have more to say. Because the publication was prominent, editors would see my work and occasionally contact me from other publications. One of them was The American Scholar, which is a fairly small quarterly, but it publishes essays, and there was a new editor there that I developed a working relationship with.

A few years later, when even traditional publications started to understand that they needed to engage the internet — and this was also the blog era — he decided that he wanted to start a set of daily blogs. Five days a week, one writer would write a short weekly piece. In fact, the sainted Brian Doyle was one of those writers, and his pieces were wonderful. Everyone had a beat, and since I didn’t really want to have a beat back then, mine sort of became culture, but in the broadest sense, society. I did that for over two years and ended up writing over 100 pieces.

When you wrote longer critique pieces, what was your favorite thing about doing those?

Just sinking in. From the beginning, I think my model was the pieces that The New York Review of Books does. So, you read everything. I would read, sometimes, 3,000 pages to write a proper piece. And it was an opportunity to spend many, many hours thinking about the books, taking notes in the books, developing the ideas for the piece … developing the structure for the piece and crafting the prose. I just loved doing it so much, and I was really happy. I was really proud of the pieces. Because I was writing for the book section of publications that are already considered challenging, I felt that on a literary level of prose, I could write in a way that was a little bit complex. I tried to convey things as concisely as possible but also juxtapose ideas where I’m not holding the reader’s hand, I’m just counting on their understanding of how the second paragraph follows from the previous one.

When you write these days, how much are you writing for yourself, to contemplate or figure something out, and how much are you writing for the audience?

I don’t really consciously think either of those things, and I’m not really the kind of writer who writes to figure out what I think, or to think on the page. I do that, but in my notebooks, and by the time I’m ready to write, I know what I want to say. In some cases, it takes me time to actually figure out what my brain meant, though that’s relatively rare. Generally speaking, it’s both and neither. I would never write if I didn’t have readers, but I also don’t spend too much time thinking about my audience. I assume that my reader is smart and educated, and it’s not so much that I assume they’re interested in what I’m saying, but I feel like it’s my obligation to make them interested.

What can artists do about the societal challenges they face today, due in part to the internet?

I wish I had a better answer, but unfortunately it seems that you have to get in this game, and it’s a really hard game, because now it’s a marketing game, too. You have to be not only an artist, and a successful artist, but you have to be a publicist and you have to do your own marketing. A lot of artists don’t have the means to hire that kind of team. What some people do is just say, “I’m not even going to try to be an artist, to have a day job. I’m going to make my art in my free time.” And that helps them not distort or corrupt their art by having to make it commercial. It doesn’t put this kind of pressure on them — mixing up money with their soul.

What is your experience with that?

As an English professor, I made my passion into my job, which is wonderful. It’s also awful, because that can really limit the amount of time one has to work on their art. And I think, as you get older, your energy wanes.

In your books, Excellent Sheep and The Death of the Artist, you talk about education as well as inequality in education and the arts. Can you talk more about that? What is your current opinion on higher education?

This is a question people are asking about higher education in general, because there’s been this credential creep. The question is, can we unwind that? Can we say, “Look, here are all these jobs that don’t really require these degrees. You don’t need to require one.” But you can’t just say that and expect it’s going to happen, and it’s the same thing in the art world. Obviously, artists don’t need to get an MFA to become artists, because there were lots of artists before they were MFAs.

Another question is, how does it affect their career prospects? It’s not just about being able to teach, right? My suspicion is that galleries care about that, but I think what students care about even more is that it plugs them into a network. Their professor is going to maybe connect them to a gallery or some opportunity. There are people who still want to get their novels published with a big five press — and for good reason. To a really depressing extent, all of that depends on being networked in because you went to a school like Yale. Oftentimes, if you’re just a talented outsider from nowhere, good luck even banging on the door — because you have to find the door, and that is likely not the front door.

My sense from anecdotal stories is that there are a couple of problems. One is just the many people trying to do it. How many people were submitting manuscripts to [eminent New York publisher] Scribner in 1925? Some, but not a million.

In The End of Solitude, the collection and the title essay, you talk about loneliness. Can you talk about the impact of solitude on our society?

In 2006, I was working on an academic project about friendship and the way friendship is represented in literature. I taught a course in the literature of friendship. (Virginia Woolf’s The Waves and Jonathan Lethem’s The Fortress of Solitude were in it.) It was my students who were on Facebook who told me that “friend” was now a verb. One day, we were talking about solitude and the converse of it, and they started to tell me that they were afraid of being alone. That’s when I realized something was going on. When I started to experience social media myself, I remembered that my students had said they had trouble feeling alone, and some even wondered why anyone would ever want to be alone … which really freaked me out. I realized that people were losing not just the opportunity for solitude, but the understanding that it had value. I think things have come back around. A lot of the discourse about social media now, whether they use this language or not, is about that.

I don’t need to tell you or anyone else that we can’t read well. They can’t read for more than, perhaps, two minutes at a time. I do think that it’s part of a larger situation that doesn’t get talked about very much, which is the decline of hand skills. Being able to engage in skillful activity with your hands, whether it’s writing cursive, making art, or building something … it’s an essential element of human cognition. Or even being human. I mean, we’re the tool-using animals. And I say this as someone who does not really have good hand skills … I think in profound ways, it’s disabling. Our brain cannot work fully unless our brain and our hands evolve together. I know people write about this, especially with regard to advances in cognition and advances in manual skill, it is, or was, a type of feedback loop.

What is the key to writing a good essay? How do you decide how to structure your essays? And what’s your advice for someone who wants to write essays?

The first thing I would say is everybody writes differently. Everybody makes whatever they’re creating. There’s no one template, and partly, it’s a matter of figuring out what works for you. Now, having said that, my understanding, based on a lot of information, is that people have been taught to write drafts like college students.… “Just write the draft, it doesn’t matter how terrible.” So people go in and vomit a draft. I don’t do that. I’ve never done it.

The way I do it is that I’m always writing down ideas. They tend to come to me from things that I’m reading or listening to, like conversations, podcasts, or the radio. I usually just jot it down on a little notebook, or send myself an email, and then I will transfer it to my notebooks. I do that in two stages, because I don’t want to take a lot of time when I’m jotting something down. And because that first transfer gives me an opportunity to start to say it better and to expand further. Every once in a while, every year or two, I’ll go back through the notebooks that I’ve kept since the last time and see what I’ve got — what ideas are there that I’ve kept coming back to, that are interesting to me, and that I think have some room to run.

As I’m doing that, I starting to look for how the ideas are clumping together, and which are partial ideas, and which are big ideas that can connect with each other. I ask myself, “What is the larger argument? What’s the point here? How does this all fit together?”

I do, however, write loose outlines. Once I’ve passed the beginning, and I’m really into the structure, every time I get to a new paragraph, I outline it very quickly. I consider, “Where does this piece of evidence go? Where does this point go?”

I try to end the paragraph with a kind of crown … an epigrammatic restatement of the idea. More like a last idea, so that it doesn’t just peter out.

What if you’re in the writing process but either can’t get your idea to culminate or find the point? Does that ever happen, and how do you bring it all back together?

If I can’t find the point, I’m not ready to write the essay. There are people who talk about writing essays as a form of exploration, and there can be some wonderful essays produced that way. But I would never write a piece unless I know what I’m trying to say … unless I have the point. A lot of times, like in my notebooks, I have ideas that I’ve wanted to try but I still don’t know what the point is. I’ve actually tried to start to get a little looser with some of my essays, and to feel as though maybe it’s OK if you don’t have a point if you’ve said things that are valuable. It can sometimes be OK that you don’t exactly gather them all together.