Reconsidered: Jack Kerouac

Left without a new book I had ordered but which had not arrived, I went to our bookshelves, to find something to read in the meantime. I selected On the Road by Jack Kerouac, which I had read and reviewed on this blog in October 2020. I have now read it again, and I think I enjoyed it more this time.

Rather than re-review it, I’m going to share some of the research I have done on the book and its author.

Jack Kerouac

Jean-Louis Lebris de Kerouac was born in 1922 in Lowell, Mass to an immigrant French-Canadian family. His mother tongue was French and it took him some time to become fluent in English. He was brought up in a strict Roman Catholic environment. His father’s business was not successful, he drank heavily, and the family was short of money. However, young Jack was a good student, who excelled at football and he won a scholarship to Columbia University. At Columbia, he met the poet Allan Ginsberg (1926-1997) who would become the character Carlo Marx in On the Road, and the writer William S Burroughs (1914-1997) who would become the character Old Bull Lee. He also met Neal Cassaday, a wildly-driven intellectual who would become the central figure, Dean Moriarity in On the Road. These four men became the founders of the Beat Generation which loved bebop music, alcohol, drugs, sex and wild experiences. Kerouac greatly admired Neal Cassady for his total lack of inhibitions, his enthusiasm, his great spirit of adventure, his love of women, risk and fast cars, idealized him and considered him a hero.

Kerouac dropped out of Columbia when his football career ended. He joined the merchant marine in 1942 and wrote The Sea Is My Brother which was published in 2011, forty years after his death. For a short time he was in the US Navy reserve, but was discharged honorably on psychological grounds (a diagnosis of schizoid personality).

In 1947, Kerouac and Cassady embarked on a cross-country trip, after which the writer completed Town and the City which included the details of his daily life and was published in 1950 having had 400 pages edited out. In 1949 he began work on On the Road. In its original form, Kerouac typed it on a continuous sheet of paper 120 feet long, during 22 days in April 1950, relying on copious notes. Though the book was written quickly, it was not well received by publishers who objected to its sexual content (including homosexuality), drug use and its experimental writing style. According to Kerouac, On the Road “was really a story about two Catholic buddies roaming the country in search of God. And we found him.” According to his biographer, historian Douglas Brinkley, On the Road has been misinterpreted as a tale of companions out looking for kicks, but the most important thing to comprehend is that Kerouac was an American Catholic author – for example, virtually every page of his diary bore a sketch of a crucifix, a prayer, or an appeal to Christ to be forgiven.

For the next several years Kerouac continued writing and traveling, taking long trips through the U.S. and Mexico. He often experienced episodes of heavy drinking and depression. During this period, he finished drafts of what became ten more novels, including The Subterraneans , Doctor Sax, Tristessa and Desolation Angels, which chronicle many of the events of these years.

In 1954 Kerouac discovered The Buddhist Bible in the San Jose library; this was the beginning of his interest in eastern religion and philosophy, of which The Dharma Bums is an example.

Wikipedia says, “Kerouac found enemies on both sides of the political spectrum, the right disdaining his association with drugs and sexual libertinism and the left contemptuous of his anti-communism and Catholicism; characteristically, he watched the 1954 Senate McCarthy smoking marijuana and rooting for the anti-communist crusader, Senator Joseph McCarthy.” and “Kerouac’s novel is often described as the defining work of the post-World War II Beat Generation and Kerouac came to be called “the king of the beat generation,” a term with which he never felt comfortable. He once observed, “I’m not a beatnik. I’m a Catholic”, showing the reporter a painting of Pope Paul VI and saying, “You know who painted that? Me.” (Kerouac was, in fact a portrait painter, having painted Joan Crawford, Truman Capote, Dody Muller and even Cardinal Montini.)

On October 20, 1969, Kerouac vomited blood and was taken to the hospital in St Petersburg, Florida, where he was found to have an esophageal hemorrhage. He was given transfusions and an operation, but cirrhosis of the liver would not allow his blood to clot, and he never regained consciousness. At the time of his death, he was living with his third wife, Stella Sampas Kerouac, and his mother, Gabrielle. Kerouac’s mother inherited most of his estate.

Jack Kerouac was clearly a man in fraught search of himself. There are many conflicts in his character. But even if we set aside the subjects of his novels because we are unsure of the rationale, one has to admit that his characterisations, his descriptions of scenes, and the urgency of his writing are brilliant.

“Write Evert Day” – Bad Advice

On Cal Newport’s blog, he has a post about writing every day. He says,”If you’ve ever considered professional writing, you’ve heard this advice. Stephen King recommends it in his instructional memoir, On Writing (he follows a strict diet of 1,000 words a day, six days a week). Anne Lamott proposes something similar in her guide, Bird by Bird (she recommends sitting down to write at roughly the same time every day).

Having published four books myself here’s my opinion: If you’re not a full time writer (like King and Lamott), this is terrible advice. This strategy will, in fact, reduce the probability that you finish your writing project.”

Cal Newport

Cal launched the “Study Hacks” blog at calnewport.com in 2007, and has been regularly publishing essays here ever since. Over 2,000,000 people a year visit this site to read Cal’s weekly posts about technology, productivity, and the quest to live and work deeply in an increasingly distracted world.

“Here’s what happens when you resolve to write every day: you soon slip up.

If you’re not a full-time writer, this is essentially unavoidable. An early meeting at work, a back-up on the subway, an afternoon meeting that runs long — any number of common events will render writing impractical on some days.

This slip-up, however, has big consequences.

It provides evidence to your brain that your plan to write every day will not succeed. As I’ve argued before, the human brain is driven, in large part, by its need to assess plans: providing motivation to act on good plans, and reducing motivation (which we experience as procrastination) to act on flawed plans.

The problem for the would-be writer is that the brain does not necessarily distinguish between your vague and abstract goal, to write a novel, and the accompanying specific plan, to write every day, which you’re using to accomplish this goal.

When the specific plan fails, the resulting lack of motivation infects the general goal as well, and your writing project flounders.

In my experience as a writer with a day job, I’ve found it’s crucial to avoid rigid writing schedules. I don’t want to provide my brain any examples of a strategy related to my writing that’s failing.

When I’m working on a book, I instead approach each week as its own scheduling challenge. I work with the reality of my life that week to squeeze in as much writing as I can get away with, in the most practical manner. Sometimes, this might lead to stretches where I write every morning. But there are other periods where I might balance a busy start to the work week with half days of writing at the end, and so on.

The point is that I commit to plans that I know can succeed, and by doing so, I keep my brain’s motivation centers on board with the project.

This approach, of course, brings up the question of motivation. Most people who embrace the daily writing strategy do so because they worry their will to do the work will diminish without a fixed system to force progress.

This understanding is flawed.

You can’t force your brain to generate motivation. It will do so only when it believes in both your goal and your plan for accomplishing the goal.

If you find that you’re still failing to get work done, even when you’re more flexible with your scheduling, the problem is not your productivity, it’s instead that your mind is not yet sold that you know how to succeed with your general goal of becoming a writer.

In this case, abandon National Novel Writing Month (which I think trivializes the long process of developing writing craft) and go research how people in your desired genre actually develop successful careers. Your mind requires a reality-based understanding of your goal in addition to achievable short-term plans.

I recalled this lesson recently in an unrelated part of my life. One of my interests over the past few months has been trying to increase the amount of time I spend engaged in deep work related to my academic research.

In December, I tested a rigid strategy that was, in hindsight, just as doomed to failure as attempting to write every day. I had a particular paper that I wanted to complete in time for a winter deadline. I told myself that the key is to start every weekday with deep work. If I commuted on the subway, I would work in a notebook while traveling. If I drove, I would knock off a batch at home while waiting for rush hour to end.

I believed this rigid schedule would help make deep work an ingrained habit, and the paper would get done with time to spare.

It reality, I crashed and burned.

The first week, I successfully followed my plan two days out of five — failing the other days for the types of unavoidable scheduling reasons I mentioned above, as well as the fact that writing in my notebook on the subway turns out to make me nauseous!

After that week, my brain revoked any vestige of motivation for this effort and my total amount of deep work plummeted.

My solution to this freefall was to take a page from my writing life. I went from rigid to flexible planning. I now approach each week with the flexible goal of squeezing in as much deep work toward my goal as is practically possible.

Some weeks I squeeze in more than others. Every week looks different. But what’s consistent is that I’m racking up deep hours and watching my paper starting to come together.

Because I am confident that I know how to accomplish my goal, and my efforts to do so are succeeding each week, my brain remains a supporter.”

To me, Cal’s comments make a lot of sense. As a retiree, I could pretty much expect to write every day, but as Cal says, interruptions invariably occur. So I don’t have a set schedule. Some days I don’t write at all; other days I may write for six or seven hours. And I find that this flexibility keeps me motivated.

What Is a Short Story?

The website Blurb has a post with this title which I found interesting because I am currently writing a collection of short stories set in America. The author of this ‘blurb’ is not identified, and it is not dated.

“Compared to novels, short stories often get overlooked as an art form, but these singular works of fiction deserve a closer look. Short stories give readers all the compelling characters, drama, and descriptive language of great fiction but in a truly compact package.

So what is the secret behind those potent, carefully written gems? Here we tackle the definition of a short story, the key elements, examples, and some of the most common questions about short stories.

What is a short story?

A short story is a work of prose fiction that can be read in one sitting—usually between 20 minutes to an hour. There is no maximum length, but the average short story is 1,000 to 7,500 words, with some outliers reaching 10,000 or 15,000 words. At around 10 to 25 pages, that makes short stories much shorter than novels, with only a few approaching novella length. A piece of fiction shorter than 1,000 words is considered a “short short story” or “flash fiction,” and anything less than 300 words is rightfully called “microfiction.”

What are the key elements of a short story?

The setting of a short story is often simplified (one time and place), and one or two main characters may be introduced without full backstories. In this concise, concentrated format, every word and story detail has to work extra hard!

Short stories typically focus on a single plot instead of multiple subplots, as you might see in novels. Some stories follow a traditional narrative arc, with exposition (description) at the beginning, rising action, a climax (peak moment of conflict or action), and a resolution at the end. However, contemporary short fiction is more likely to begin in the middle of the action (in medias res), drawing readers right into a dramatic scene.

While short stories of the past often revolved around a central theme or moral lesson, today it is common to find stories with ambiguous endings. This type of unresolved story invites open-ended readings and suggests a more complex understanding of reality and human behavior.

The short story genre is well suited to experimentation in prose writing style and form, but most short story authors still work to create a distinct mood using classic literary devices (point of view, imagery, foreshadowing, metaphor, diction/word choice, tone, and sentence structure).

Short stories have one or two main characters

What is the history of the short story?

Short-form storytelling can be traced back to ancient legends, mythology, folklore, and fables found in communities all over the world. Some of these stories existed in written form, but many were passed down through oral traditions. By the 14th century, the most well-known stories included One Thousand and One Nights (Middle Eastern folk tales by multiple authors, later known as Arabian Nights) and Canterbury Tales (by Geoffrey Chaucer).

It wasn’t until the early 19th century that short story collections by individual authors appeared more regularly in print. First, it was the publication of the Brothers Grimm fairy tales, then Edgar Allen Poe’s Gothic fiction, and eventually, stories by Anton Chekhov, who is often credited as a founder of the modern short story.

The popularity of short stories grew along with the surge of print magazines and journals. Newspaper and magazine editors began publishing stories as entertainment, creating a demand for short, plot-driven narratives with mass appeal. By the early 1900s, The Atlantic MonthlyThe New Yorker, and Harper’s Magazine were paying good money for short stories that showed more literary techniques. That golden era of publishing gave rise to the short story as we know it today.

What are the different types of short stories?

Short stories come in all kinds of categories: action, adventure, biography, comedy, crime, detective, drama, dystopia, fable, fantasy, history, horror, mystery, philosophy, politics, romance, satire, science fiction, supernatural, thriller, tragedy, and Western. Here are some popular types of short stories, literary styles, and authors associated with them:  

  • Fable: A tale that provides a moral lesson, often using animals, mythical creatures, forces of nature, or inanimate objects to come to life (Brothers Grimm, Aesop)
  • Flash fiction: A story between 5 to 2,000 words that lacks traditional plot structure or character development and is often characterized by a surprise or twist of fate (Lydia Davis)
  • Mini saga: A type of micro-fiction using exactly 50 words (!) to tell a story
  • Vignette: A descriptive scene or defining moment that does not contain a complete plot or narrative but reveals an important detail about a character or idea (Sandra Cisneros)
  • Modernism: Experimenting with narrative form, style, and chronology (inner monologues, stream of consciousness) to capture the experience of an individual (James Joyce, Virginia Woolf)
  • Postmodernism: Using fragmentation, paradox, or unreliable narrators to explore the relationship between the author, reader, and text (Donald Barthelme, Jorge Luis Borges)
  • Magical realism: Combining realistic narrative or setting with elements of surrealism, dreams, or fantasy (Gabriel García Márquez)
  • Minimalism: Writing characterized by brevity, straightforward language, and a lack of plot resolutions (Raymond Carver, Amy Hempel)”

I don’t agree that the above list represents an inclusive list of ‘popular types of short stories’. The stories I write tend to be either plot or character driven. It is the length of the story (10 to 12 pages) which is challenging; there is only space for essential description, dialogue must be to the point, and action tends to be terse and clear. It is possible to inject tone through the language used by the narrator and the characters.

For me, the most important challenge is inventing new stories. I’ll need at least 25 stories, and at the moment, I’m only half way finished. I do rely on personal experiences, or stories which I’ve heard about which strike my fancy. On several occasions, I’ve started a story, realised that I wasn’t enthusiastic about it, and deleted it. The experience of writing a short story in quite intense compared to writing a novel.

Page One

In yesterday’s email, Harry Bingham , whose company, Jericho Writers, is running a First 500 Novel Competition, provided some feedback from his reading of the submissions. His comments all have to do with Page One, of course, which includes the first 500 words.

“This last week, I’ve spent quite a bit of time looking at your opening chunks. A few things struck me, including how amazingly common it is for people to have multiple time threads on their very first page. Normally, we think a book starts at time T0, then proceeds in a logical sequence to time T100. Contemporary readers are, of course, well used to more complex schemes – multiple time strands, some flashbacks, perhaps a flashforward in a prologue and so on. But the only real purpose of your first page is to get your reader into your story-train. Unless your reader has chosen to embark with you, nothing else can happen. And it’s just astonishing how many impediments we writers put in the way of readers climbing on board. One of the most common issues is that people insert multiple timelines into their first page. So one (otherwise perfectly capable) opening chunk ran like something this: Para 1: Very short para saying what happened at the end of the conference, let’s say Sunday evening. Para 2: Step back to summarise the weekend that had just elapsed. Para 3: Step back to the Friday drinks reception. Para 4: Step back again to what arrival had been like on Friday morning. Written out like that, it’s nuts – but as I say, multiple timelines on the first page are genuinely common. And each time you shift the time, the reader has to mentally relocate. (“Where are we now? We were on Sunday night, I think, but we’re surely now talking about the weekend generally. OK, so yes, we’re in a new place. Righty-ho. Let’s see if I can make sense of what’s happening now.”) Each of those relocations is a small mental challenge to the reader and each of those challenges makes it more likely that the reader’s going to think, “You know, there are other books out there which are going to make me work less for the same rewards.” Perplexing chronology is a common problem. A lot of same-sounding names and relationships all laid out on page 1 is also challenging. Ditto anything without a clear physical setting (such as for example, the reflections of a character about something you don’t properly understand.) Or prologues than run to literally no more than 2-3 paragraphs, before the book starts all over again. The key question to ask yourself is simply this: am I making it easy or hard for a reader to enter my book and get to grips with it? If you are writing high-end literary work (and I mean the sort of stuff that could win the Booker Prize), you have my permission to make things complicated. In all other cases, you have to seduce your reader. Make their life easy and rewarding. And talking of which … If it sounds like writing Elmore Leonard famously said, that ‘if it sounds like writing, I rewrite it.’ I got a deeper appreciation of what he meant when I read your opening chunks last week. Part of the problem, I think, is that we have a “First 500” Novel Competition and those competitions encourage a somewhat flashy response.
For what it’s worth, I doubt if any of my books ever would have been seriously considered for a prize in a “first 500” type competition. My books just don’t choose to reveal much in the first page and a bit. Why would they? But the problem goes deeper. Writers are tempted to write flashily, to show off, to draw praise. And, OK, none of us mind a bit of praise – but, please, not at the expense of clarity. So lots of you wrote something that had this kind of tenor: They were only kids, yes, but kids who could run the universe. Jake could ride the lip of the slide and fly. Crash landings happened sometimes, but even the bruises were proof of something. Jonno had his bruises too, from similar antics. Blood brothers. The universe twins.
Yes, there’s some flashy writing going on there. But what the hell does it mean? How does the reader get on board with a story, when it’s simply unclear what’s happening? Here’s the same kind of thing, delivered in a way that makes sense: It was the hardest trick in the playground, but Jake had mastered it. Ride the skateboard down the raised metal lip that formed the edge of the slide, then fly three or four feet through the air before hitting the scuffed-up dirt at its foot. Jake was confident now, though he’d collected enough bruises over those summer months … [and so on]
You’re more likely to elicit applause with the first of those two chunks, but you’re a damn sight more likely to get readers with the second. So when you’re writing your opening chunk – whether for Feedback Friday, or the First 500 Novel Competition, or just because you want to write a saleable book – please don’t ask, “Does this sound like great writing?”. Ask: Is this clear? Am I obstructing the reader? Can the reader get easily onto my story-train? If it sounds like writing, you really might want to rewrite it.