Imagined Conversations, One Year Later

By: Jay Duret

A year ago I initiated a project called Imagined Conversations. Every day I would post a drawing of a face along with a snatch of related text or dialogue. Sometimes my drawings were cartoons or caricatures; other times I did my best to capture a likeness. In every case I created the face before thinking and inking the words that, at least in my imagination, went with the face. My conceit was that every face is different and therefore if I drew a new face, it would have something different to say than all the other faces I had drawn before.

ProposalThe Proposal

In my mind an Imagined Conversation was not limited to what passes between two or more speakers, but could include soliloquies or what might be found in a net dipped into the mental meta stream of internal monologue. Sometimes an Imagined Conversation was a sliver of words overheard in the gym or on the street or at a Starbucks. Other times, the words were nothing other than the words that were bouncing around inside the pinball arcade that is my head.


I undertook the project as a sort of cross training from writing stories. I was tying to teach myself to draw and I knew the demands of a daily drawing would be a powerful incentive to learn. I liked the idea of a fixed daily regimen; a concrete and completable creative task that I would need to stick with regardless of the other claims on my time. Most of all, I wanted to explore this concept, though I wondered how far I could go before I ran out of ideas, of energy, of enjoyment. Could I do it for a year and if I did, at the end of the year would I be a runner at the end of the race, desperate to break the tape and collapse?

A year has now come and I can report that I posted a drawing every day, 366 in all, even though this was not a leap year. I snuck in an extra one on February 28th:

Leap Year IGLeap Year

Over the year I travelled to Iceland, to Belize, to Burning Man and still I never missed a day. I learned all about the tools available to time and schedule one’s posts, but by large measure I did not need to use them. With drawing materials, an iPhone to use as a scanner, a laptop, and an Internet connection, I could post a drawing every day no matter how distant I was from the studio/office where I work.

Some conclusions and observations about the series. First, I didn’t run out of ideas, either for the drawings or the text. In fact, I don’t feel as if I come close to finishing the exploration I started. On good days I think I have discovered a rich area between writing and drawing that is not quite the same as cartooning or illustrating. I hoped that my best pieces combined the sharp, quick insight found in six word stories (Hemingway’s classic: “Baby shoes for sale. Never worn.”) with the thousand words that a picture, well drawn, is worth. My worst pieces were as trite and unambitious as the tee shirt you might buy at a click clack souvenir shop on a beach town boardwalk in August (“I AM the man from Nantucket.”)

And while triteness was an enemy, the biggest risk was the problem of context. Because I rarely use props or locational references, sometimes the text is just the words that rattle inside my head, inaccessible to anyone who hasn’t been there. Like the bad writer who assumes the reader knows as much about a character as the writer does, I sometimes left words on the page, but did not tell a story. When that happened – and sadly it happened far too frequently – I would tell myself that the reader who worked would figure it out. But if there is one thing I have learned over the last year, it is that with this form of art, you do not get more than a millisecond to get your reader’s attention. My work is scrolled by, swiped past, clicked through in less than the time it takes you to read this sentence. If there isn’t something that instantaneously connects to the reader, the raging river of meta-consciousness will flow on.

And though that is undoubtedly true, midway through the year I began to create wordier pieces. I realized I was not limited to sloganeering and jingling. I could write whatever was on my mind. And so I didn’t pass over matters of religion and philosophy and politics:

Guns Guns copyGuns, Guns, Guns

 I could dispense my own brand of homespun wisdom, the kind you don’t get on a greeting card from Hallmark:


I could cover metaphysics:

Assembly LineAssembly Line

I could create puzzles. This one, for National Poetry Month, required some knowledge of T.S. Eliot:

Poetry MonthNational Poetry Month

And of course I could not skip over my lifelong painful attachment to The Philadelphia Eagles:

EaglesThe Eagles 

The DefenseThe Defense

In my writing, I often try to tell a story exclusively or almost exclusively through dialogue. During the year I realized that those stories, in their own way, were also Imagined Conversations and so on Sundays I began to post drawings that linked to short stories on my website. I wasn’t able to produce a short story quite every week but over the course of the year I linked more than twenty stories to Sunday drawings:


I don’t have a single favorite post, but I liked these a lot:

HatAll Hat

But the one that most syncs with the reflective mood I have at the end of this year:


Thanks to the many old and new friends who have encouraged the Imagined Conversations project this year. Wishing you and yours a brilliant year in 2016. And for those who might enjoy it, you can get a daily post in the New Year on Instagram @joefaces or on my website.

Jay Duret


Jay is a San Francisco based writer and illustrator. His first novel, Nine Digits, is available from Indigo Sea Press. Jay blogs at


Filed under writing

4 responses to “Imagined Conversations, One Year Later

  1. Wonderful, imaginative post, Jay! I have a feeling the drawings clarified your thoughts. Great exercise!

  2. Great job, man! Congratulations on producing a year’s worth of entertaining, innovative posts. Have a fantastic new year!

  3. Wrote. I missed following these but I remember the start and I love catching up. Thank you for every word and 1000 words.

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