Ross Simonini is gracious and generous. He also has relentless curiosity, a virtue proven by his range of work as a musician, painter, writer, editor for The Believer, and literature professor at Columbia University.

Recently, I tagged along with Ross to the grocery store as he retrieved tulips for his wife, Katie. We talked about practicing creativity in all aspects of life – art, music, business, cooking, etc. I explained my motivation behind The Jalepeño, how I hope to learn about the people behind creative work and to ignite an enthusiasm for creative pursuits by sharing those stories. He seemed to agree that everyone has the potential to be an artist.

After our conversation I left with a stack of books and a headful of ideas and recommendations, gratefully reminded of how little I know and how much there is to explore. 

(all photographs used in this post are of original artwork by Ross and are borrowed from

THE JALEPEÑO: Creating seems to require an openness. You have to be willing to fall down, to appreciate the process, to have a welcoming relationship with failure. Then you can start making progress. Do you agree?

ROSS SIMONINI: Completely. If you keep working toward failure, you’re working toward betterment. Forming a relationship with failure has been a large part of my life, especially because failure was not presented in such an open way when I was younger. Failure was simply the opposite of success.

Hard work is the American ethos. Pain leads to gain. Not always true. Pain can lead to pain. In the last few years I’ve become less sure about the hard, painful work.

When I was younger I felt that without suffering or feeling the failure, without experiencing all of that, then I wouldn’t feel the true satisfaction of accomplishing something.

I’d become addicted to the feeling of hard work. I’d play the piano 8 hours a day until I develop wrist problems. Relentless band rehearsals trying to get every note “right.” I’d adhere to rigorous schedules, diets. I’d create strict ideologies and live them out until I exhausted myself.

Since then I’ve started to appreciate the feeling of ease. Like when I walk, I try to feel the ground gliding under my feet. If I stomp, it hurts. Now, I‘m much more interested in the kind of work that can be woven into a day without being in conflict with the rest of my life. Seems more appealing to me.


Health Care Drawing No. 2 (Turmeric, cinnamon, blueberry, raspberries, wine, green tea, olive oil, and pencil on paper)

THE J: What is failure, to you?

RS: The most important failure I’ve experienced so far was a shift in occupation, away from music. After touring and releasing music for a decade in various bands, making my living through it, I didn’t feel like the success was great enough to outweigh the difficulties – not of making music, but of the lifestyle and career surrounding music.

At the time, I viewed that as a failure. It felt like a failure of foresight, or an inability to have seen exactly how my life would play out.

I thought it would go in one direction, and when it did, I realized I wasn’t enjoying myself and I had to rethink it.

The failure felt like I had been preparing for the wrong life, putting in all this time for the wrong reasons. Of course that wasn’t really true, but superficially, it was.

THE J: Failure in the sense that you didn’t realize what you were going after, or why.

RS: Yeah. At a certain age you decide: this is my goal. And you forget to keep questioning that goal.

You get to a certain point and you realize, you’ve been addicted to the goal.

Everything had been hard and I had assumed that because of that, I would receive great benefits at the end. Because, again, that’s the ethos – work hard and eventually receive satisfaction. Delayed satisfaction.

THE J: That’s one of the big themes in Infinite Jest, which is discussed in Although of Course You End Up Becoming Yourself (Now in theatres as End of the Tour). This carrot chasing. This idea that once you achieve this specific thing, you’ll be happy. Then when you achieve it, and you’re still unfulfilled, there’s a personal crisis.

RS: Right. It’s the way we quantify things. This meme of 10,000 hours, quantifying what it means to be a master. I reached my goal – making a living playing music for people, in various ways – and when I started paying attention, I realized I wasn’t very happy with where I was.

I had spent about ten years touring the world, probably half the year, recording albums, receiving press, making a living, at times. All the basic check marks.

THE J: And very difficult things to achieve.

RS: But it also allowed me a window into what the reality of that success is. And the reality of the next level. What were musicians five years ahead of me doing? What was their life really like? Still living on the road, eating road food, not sleeping, doing drugs to stay alert, sitting in cars most of the day, cramming art into an hour a day. Sure, you’re living the artist’s life, but in reality I am far more creative now, at home.

But no one can know this until they themselves get there, to that place of so-called success. In a way, it’s part of the process.

You romanticize everything until you experience it.

Of course, some things are great once you get there, and for me, a lifestyle compatible with my interests – that’s the biggest success – marrying life and work, symbiotically, no difference between the two.

THE J: It seems like you’ve begun to find that.

RS: Just the beginning.


Podiatric Landscape 2 (Acrylic and tea on paper mounted to canvas with yoga mat frame)

THE J: What’s it like working on so many projects at once?

RS: The single-job model doesn’t fit with my brain very well. I tend not to work on one thing for an entire day. I skip around between activities. By doing that, it enlivens each discipline.

Things that are considered work and not considered work, it all becomes one. For instance, as a teacher I read, as an editor I read, as a writer I read, and as a recreational reader, I read but it’s never clear to me when I start a book whether it’ll affect the world of work or non-work.

So it quickly becomes irrelevant trying to break down leisure time from work time. I like that. I like constantly short-circuiting that distinction.

Another example is cooking.

A lot of the art I’m making is made out of food that I’m eating. I’ve ended up using food as dyes for paint, and have been considering food as a medicine, which I’ve also ended up writing about. So the cooking itself is not an act of remunerative work, but I bring the mindset of work, the mental engagement of work, to everything that I do. And it just blossoms.

Bringing a focus and a sensitivity to everything. Because, of course, cooking could be seen as leisure or work. So could drawing, writing, reading.

THE J: There’s a tendency to compartmentalize. This idea that you can only be onething. You’re a businessman or you’re a chef or you’re an artist. But you can broaden that, once you realize you can bring creativity to everything. And that is, maybe, the most valuable skill.

RS: Right. And in the case of reading, how would I know that two years ago, when I picked up a certain book that it would have engendered certain thoughts, which I would write a novel about, which would become something I teach a course in? I couldn’t have known that at the time.

Had I been very strict and not picked up that book because it didn’t have a clear connection to what I was doing at that point for money, then I would have been sabotaging myself. It’s nice because it makes me embrace the chaos. Ride the chaos wave. Keep learning. That’s all I try to do.

THE J: How do you do that?

RS: If I’m interested in a subject, I read a hundred books on it.  After school, people seem to lose that compulsion, that enthusiasm for exploring. Just take a walk and go explore the neighborhood. Go to a place you’ve never been. This fundamental kind of engagement.

Go to the library and wander around and pick three or four books that seem alien to you. I used to do this all the time. It’s not like I loved all these discoveries, but it constantly pushed me outside of the boring routine of basing my life around liking and disliking. It disallowed me to be mentally or physically sedentary.

THE J: And it builds on itself by igniting curiosity.

RS: Curiosity and experimentation. When I was younger I viewed books as an accretion of information and knowledge, building up this invisible library of information and language in my mind.

Over time, I’ve stopped seeing it that way, and now I see each book, each song, each wind quintet, each piece of art I see no longer as information to be stored inside me, but as a little bundle of energy that I’m allowed to access, for a moment, and use like food.

I read a good book and it gives me a little more energy. I listen to a piece of music, it gives me a certain energy. I listen to somebody speaking, it gives me energy. I need that.

THE J: It inspires focus – nudges you to observe.

RS: Conversations are another one of those bundles. A good conversation is certainly as valuable as a good book. Interviews are a way of transforming that energy into another form.


Itinerant Canvas (Fire Island Botanical Elements on Canvas)

THE J: What about teaching?

RS: I’m just learning about that, but I’m finding that to be similar. I feel very energetic coming out of a class

THE J: And because you’re new to it, how do you go into a class? Is there a discomfort in that, at first?

RS: For sure. The holding of that pedagogical space, the ability to maintain attention and magnetism, which is essential for a teacher, requires a certain energy.

I’ve noticed, going into a class, I have to get myself up to a certain ecstatic point, just as I would going on stage for a performance. I’ll jump up and down to get the lymps (lymphatic nodes) moving a little beforehand.

THE J: Students expect that energy.

RS: The onus is on me. It should be.

THE J: Is there anything in particular you’re trying to get them to notice?

RS: Recently I wrote on the board, “Develop a Sensitivity”. I wanted them to think in that mode first, as opposed to developing a skill or a technique or a method. I think those more systematic approaches will come out of sensitivity.

It’s a hard thing to teach but important to learn. A lot of times in school, systems and techniques are placed before awareness, but I really want them to become sensitive to things they’re not already sensitive to.

THE J: Like what?

RS: This class I’m teaching now is about dialogue and interview and oral history and the way spoken language differs from written language.

So, in that case, becoming sensitive to ‘um’ or ‘like’ or ‘you know’ or any other number of modifiers. We think of them as space-fillers but there is meaning behind everything we say or do.

There is resonance, something to be learned from everything. Every ‘um’ has some meaning behind it. Or to look at the word “like,” for instance, you could say, in a reductive way, that it’s common use these days gives an insight into our generation. We tend to be equivocating, indecisive.

There’s an intense desire to be noticed and “like”-able and inoffensive to the point of pleasing everybody. A lot of the language like ‘sort of’ or ‘kind of” or “like” is there to allow people to diffuse anything they’re saying.

THE J: To soften their position.

RS: Pillow words. So that they might not offend anybody. So that they will be liked. So that no statement is too direct.

On the other hand, a word like ‘amazing’, people seem to drop it every other sentence. Why? To amp up the energy of the situation, which is what we all want.

You can look at each of these linguistic artifacts as a window into a single personality or larger ideas about psychology and culture and society and go obnoxiously deep with all this stuff, which I’m trying to do in my classroom.

THE J: What’s on your syllabus?

RS: Since you mentioned him, one of the classes I’m going to teach is an attempt to look at Wallace’s use of voice (David Foster Wallace). We read his fictional interviews, his written ones, his spoken ones, Lipsky’s book on him, and we listen to a few radio interviews with him.

What do all these different forms say about his voice? Was there a real voice? A different voice in each format? And he has a deep conflict with the interview and the ego.

Also Plato and George Berkely, philosophers who worked with dialogue as their primary method to arrive at a thesis and antithesis, and then a synthesis between the two. Also psychoanalytic transcripts, courtroom transcripts, interviews with artists. Zen Koans. We’re looking at any verbal language that ends up as text.

THE J: Conversations?

RS: Of course. This is the beginning of language. Grunting at each other and creating conversation out of that. Why wouldn’t that be taught to people trying to learn language – to writers? The conversation is always an attempt at understanding another person. True communication is an attempt to share a perspective, at least just for a moment. Because it only happens for brief moments and that’s OK, that’s good. It’s not something that will stay. It’s not a static stationary thing. You get the experience in flashes with nice moments of confusion.

THE J: The novel you just finished, it’s an ongoing interview?

RS: It is a series of interviews. As a writer, it’s difficult to hear both sides of a conversation. So that’s one of the great challenges – trying to put your mind into somebody else’s mind. Which is what fiction is, a form of compassion.

THE J: Do you have a specific process, writing or otherwise?

RS: Dozens. I go through different processes. I try not to get stuck in one. For instance, in writing one draft of my book, I woke up and immediately wrote an hour every day for three months, working with those results and seeing what I could do with that. But I didn’t maintain that throughout the book. That was an effort at getting certain access to my unconscious.

I also tried a draft of speaking some of it aloud. In both of those cases, I let the results inform the way I write other passages. I didn’t want to exclusively use a single process.

It’s the same thing with painting. I paint with different limbs. Like my feet or my left hand, using different fingers and interspaces. Sometimes I’ll like the results, sometimes I won’t, but this informs my whole vocabulary of art making.

So that now, when I paint using the traditional handheld approach, I’ll make a mark informed by my foot style. And with writing, I’ll become attracted to a sentence structure I used after having just woken up, which was messy and incoherent, but capture something essential.

THE J: Maintaining openness.

RS: Never allowing a system to dominate. I think systems are beautiful, but systems aren’t life. Nature is not a system. Same with art – I see systems as a way to navigate art.


Antioxidant Drawing (Blueberries, red wine, green tea)

THE J: Are you reading a lot?

RS: Yeah. I tend to read about a dozen books or more at a time. Probably about 200-300 a year. This morning I was reading Yoko Tawada, some students’ papers, which have become mulched into my reading habits, Eric Satie’s journals, Thomas Merton’s writing on Zen, and Ellen Sandbeck’s book on non-toxic cleaning products – which is a glancing, perusing kind of reading, but just as useful – and then I read a wonderful essay about Philip Roth in The Believer.

THE J: Why is reading important?

RS: For me, it’s food for creativity. And it also helps me get out of my own head and into someone else’s stream of internal language, which can be therapeutic. It’s generally my favorite form of communication. It’s suited to my personality.

THE J: What advice do you give to someone interested in creativity?

RS: Try to understand the connection between your life and work. What we talked about at the beginning. I try to do what I want as much as possible.

If you can do that, get that basic enjoyment going, and you can get work and money and satisfaction to flow out of that, then you’ve solved one of the fundamental conflicts of contemporary life.