What Made Raymond Chandler Great – My Most Personal Article

This was an email to my list. To my surprise, it flooded my inbox with responses. I almost didn’t send it. I’m glad I did.

I couldn’t look at myself in the mirror.

I had moved into a freshly built apartment complex in the Golden Triangle area of Denver. A penthouse unit. A Miami-based company designed the building. Nothing exemplified the Miami influence more than the bathroom. The designer flooded the bathroom with white marble and mirrors and a massive glass-doored shower. A beautiful bathroom I refused to appreciate. The mirror had a habit of reflecting back to me.

No self-despising.

No self-loathing.

No self-flagellating.

Rather, I felt in limbo; I felt off.

I should have been thrilled.

My copy career earned serious income. I had reached and started to climb past what I previously earned during my car business days. My salary and commission structure put me well on track for a healthy seven-figure income that year. And more money sat on the table.

The Online Marketing beast I worked with had placed a few appetizing partnership opportunities in front of me. He had pulled me into his minuscule inner circle. I had my own bedroom at his house in St. Petersburg, Florida. And I slept in it more than in my bedroom in Denver. I dined and hung out with his family often. Beyond the generous pay, he offered a generous and gracious package hoping to entice me to move to St. Petersburg. Most copywriters in online marketing would cream themselves at this opportunity.

But I refused to look at myself in the mirror.

I kept asking myself, “In another few years, is this what I want to be doing? Writing or managing scammy affiliate marketing offers or supplement offers?”

On the rare Sunday I was home in Denver, I’d amble around the city, wondering where my life was headed. I was in my second career after the car business and I began feeling like I had made a huge mistake. I felt like I was selling out my soul and integrity. I knew I was writing bullshit offers.

And working at that high a level, higher up in that Online Marketing and famous guru world, more and more dishonesty surfaced. I kept using the guru mindset tricks to try to hide these feelings. I tried telling myself that I needed to clear the toxic obstacles I had around money.

But I knew that was bullshit.

I grew up wealthy.

I loved making money.

But I continued to pacify myself in more routines, Dan Kennedy books, and paying for another event to “level up.”

But I couldn’t shake how shit I felt.

On one of those ambles, I did a normal thing, I found myself in Denver’s Tattered Cover. I did the usual. Order a coffee. Sit down. Ruminate. Get up, peruse the shelves, grab a basket, and stuff it full of books to buy. And one such time, I bought Raymond Chandler’s The Big Sleep. I had heard of Chandler. I remembered Stephen King, Lee Child, and John Carlton mentioning him. I grabbed it. I read it a few weeks later.

When I read The Big Sleep, the main character, Marlowe, answered a lot of the questions I was asking.

What struck me, Marlowe waded into grey areas, but he never compromised his principles; he never compromised his personal code; he never compromised his personal values.

That inspired me.

The Big Sleep is one book among a few other key factors that influenced me to change course. Marlowe influenced me to look not only at my professional purpose but my personal values. I walked away from a seven-figure income that year. I made the right choice. I released the straight jacket holding me back both personally and professionally.

Naturally, Raymond Chandler holds a special place for me. I’ve reread The Big Sleep four or five times. If you’re a longtime reader of mine, you know I love Chandler. I’m honored I turned a few readers onto him and his famed character Philip Marlowe. Chandler arguably stands as the greatest mystery writer of all time. And he arguably stands among the greatest fiction writers. I lack a perfect bridge into the next section, other than I’m excited to talk Raymond Chandler. I read Tom Hiney’s great biography on Chandler. After I finished the biography I read The Long Goodbye. And, as the kids say, it surfaced “all the feels.”

My opening here was deeply personal.

And I’m sharing more in this piece.

I wrangled with how much to share.

I redacted a lot, over five thousand words.

But I hope to inspire you to get closer to an author or figure that means a lot to you. Getting closer to an author you like adds another dimension to their works. As I’ve said elsewhere, reading is a personal conversation. I’m going to share my intimate conversation with two Chandler books here. Then, I’ll share a Raymond Chandler writing exercise. You writers won’t want to miss that.

Enough rambling, let’s dig into it.

Raymond Chandler, Tom Hiney

A fast summary, Hiney wrote a great biography of Chandler. He melded the background of Chandler and he showed the forces creating Chandler the writer. We get a good look at Chandler the man, a good look at how he created Marlowe, and a good look at Chandler creating some of the greatest screenwriting that ever came to Hollywood.

Let’s look at a quick background of Chandler.


In the summer of 1938, in a small Santa Monica apartment, a sober, forty-nine-year-old Raymond Chandler wrote The Big Sleep. And that summer, he created a man needed in his life — his famed character, Philip Marlowe.

Forces and vices led to that creation.

As a young boy, after his alcoholic father vanished one day, his Irish immigrant mother moved herself and her young Raymond from Plattsmouth, Nebraska to south London, England. Chandler’s mother came from a wealthy Irish family. She emigrated, got married, and moved to the small town of Plattsmouth, Nebraska. But her husband, a complete drunk, abandoned her and Raymond. She then went back to London. Due to her previous emigration and being divorced and with a child, she was seen as a philistine back in London. But her brother took her and Raymond in, begrudgingly. And her brother paid, begrudgingly, for Raymond’s classical education. After graduating high school, Raymond worked as a freelance journalist. Bored, he went to America. At the outbreak of World War I, Chandler enlisted in the Canadian Army. He fought trench warfare, got wounded, and then began training as a pilot for the Royal Air Force. During this time, Chandler, at age twenty-seven, discovered his unfortunate appetite for alcohol. Post-war, Chandler met and fell in love with the knockout beauty, former model, Cissy. Chandler thought Cissy was only ten years older than he, but it turns out she was twenty-plus years older, almost closer to thirty. He found work as an oil executive. He made great money, in today’s dollar, nearly $44,000 a month. But booze, sleeping with his secretaries, and absenteeism got Chandler fired. The booze ruined his life. He would go on benders for weeks; never showing up at work or at home. Chandler had the fortunate or unfortunate gene — depending on how you look at it — where he never got hangovers. He found himself out of work, aimless, and his money drying up. He felt he failed Cissy and himself. He knew he needed to sober up. He began reading pulp novels to pass time. He found them authentic compared to haughty literature favored by critics. He found them closer to Shakespeare and the classics he grew up reading. He decided to try his hand at writing pulp short stories. After a few years, and making little money, he gained a reputation. And in 1938, he wrote The Big Sleep.

And the rest is history!

Not quite.

The Big Sleep flopped.

The publisher saw the talent, but despite the best marketing efforts, couldn’t get it to sell. Marlowe gained an early cult following, but never early mainstream success. Yet he refused to sell out and kept chipping away at it. And he made a pittance, barely enough to cover rent and buy groceries.

Cult fan, Hollywood producer and screenwriter, Billy Wilder loved a line from Chandler’s third novel, The High Window, “Out of his ears grew hair long enough to catch a moth.”

From that line, the rest is history, somewhat.

That line got Chandler noticed and hired by Hollywood.

Chandler turned out to be one of Hollywood’s top screenwriters. He earned an Oscar nod and was sought after to fix bad scripts. And right around this time, his books, finally, started taking off in sales.

A happy ending, right?


While working in Hollywood, Chandler started drinking again. At first, all seemed ok. He could keep it somewhat under control. But soon the rails came off. Hollywood could get Chandler to work sober if they kowtowed to his demands. But booze and Chandler’s disgust at Hollywood and its people made Chandler leave.

His book sales at that point were cranking. Yet the tumultuous relationship with booze strangled Chandler. He would go back and forth between sober for a while, and then drunk for months on end. When his wife’s health began deteriorating, he worked on The Long Goodbye. It was the last Marlowe novel he wrote sober, and the most bittersweet, intimate, and sentimental Marlowe novel. After Cissy died, Chandler became a drunken child. He wrote one more Marlowe novel, Playback. He wrote it while completely shitfaced. And during this period, he lived between London, England, and La Jolla, California, and drank 24/7. He proposed to a few women to replace Cissy. He proposed to Helga Greene, a Guinness family heiress. Her father adamantly rejected Chandler’s proposal. Dejected, Chandler flew home to La Jolla, holed himself up in his house for a week, and drank himself to death.

My Idealizations of Chandler Got Destroyed — A Good Thing

When you learn a lot about someone you admire, they rarely hold up to idealized expectations. A well-written biography shows all sides of a person. You see the human side. You respect why you admire them and their gifts. But to balance those gifts, you learn of their weaknesses. A good thing.

I somewhat expected Chandler to be a wry writer with a pipe. A wry, has it together writer. Not the Jack Kerouac degenerate; not the J.D. Salinger drink your urine; not the Steven Pressfield writing melodramatic bromides on writing; not the Ernest Hemingway emo drunk. I was off the mark on Chandler.

Chandler was two men.

Sober Chandler. Drunk Chandler.

Drunk Chandler was a child. An absolute child. An impish, needy, six-year-old child. Sober Chandler proved a driven, creative, and sharp man. He owned the ability to go sober not for a week or a month, but for a few years on end.

During those sober periods, he poured out his best work. During these periods, each day he wrote for four hours, read for four hours, and thought about writing for six hours.

Unlike the romantic notion that artists are tortured and need substances to create, Chandler did his best while sober. He did little while drunk.

It’s easy to play armchair psychologist and claim Chandler was tortured, hence his boozing. Hiney claims this through a popular 1990s psychoanalytic lens (Hiney’s book was published in 1997). Hiney mentions that Chandler’s absent, alcoholic father tortured Chandler’s soul. I’m hesitant to agree or disagree with Hiney.

I’ll unpack why I’m unsure.

One, Chandler was a constant letter writer. He even corresponded with fans regularly. Some letters share intimate details. Yet Chandler’s father is rarely, if ever, mentioned. Also, in most of Chandler’s stories, which as I found out are extremely personal at times, we don’t find much battling with father figures. Not clear evidence of anything, rather, something I noticed.

Two, Hiney poses that perhaps Chandler suffered from depression. This could be true. Chandler made repeated suicide attempts. Albeit, they were peculiar. They were melodramatic and rather laborious in their drama. He’d call the police and say he was going to kill himself and they needed to come to the house to stop him. Then he’d tell Cissy to call the police with the same message. Then he’d call his friends to call the police with the same message. So a big crowd would show up, and often Chandler was found in his office, drunk and acting a like child or passed out. In short, he caused quite a stir during a suicide attempt. That’s not to marginalize depression in any way. But the melodramatic flair deserves a deeper look. We are unable to get that look. It’s left up to question and conjecture. And he only did these attempts while drinking heavily. And generally during a break or a lull in his work.

Three, it’s possible Chandler suffered from Post-traumatic stress syndrome. This is more my theory. But Chandler fought trench warfare in World War I. He was wounded and suffered a severe concussion that knocked him out for several days. All Marlowe stories have blackout themes. Marlowe gets knocked out or injected with drugs, or someone lives so far drunk that they are blacked out from reality. And Chandler didn’t start drinking until he was training to be a fighter pilot, after his trench warfare wounds, at the age of twenty-seven. I wonder, with the brutalities he saw in trench warfare, getting wounded, and also getting a concussion that lasted a few days, perhaps that had something to do with his drinking and eccentricities under the influence.

In the end, it’s impossible to say outside of guesswork. Chandler owned the ability to drink moderately, maybe one or two a week. But at other times, he lost all control. And in his final years, he drowned himself in booze.

Learning about who Chandler was, and the two different men he lived as, drunk/sober, pulled me closer to Chandler. Maybe it’s sympathy. Maybe it’s knowing more. But as I say, reading is a personal conversation. And finding out about drunk Chandler added that dimension. And I believe, when the idealizations get blown to bits, like some of mine, it’s a good thing. You respect the otherworldly gifts, talents, or what made the person a near sage, but you also see how the person was human. You can learn from their foibles, blind spots, shortcomings, failures, and insecurities. That pulls you closer to that writer.

The Big Sleep is important to me.

When I read it, I had no idea that it would inspire me to leave the shady things I was doing. I had no idea that it would inspire me to look into my values, principles, and worldview. That unapologetic self Marlowe owned and oozed, I wanted some of that. And I knew I had to change course.

This biography added more personal thanks and respect to Chandler and The Big Sleep. And as I said, it added another dimension to Chandler’s work.

The next section, it’s going to be personal again. I hope to show how a good biography of someone you admire adds a dimension to their work.

I’m going to cover The Long Goodbye. I’m going to share my intimate conversation with the book and what surfaced for me. I’m not entirely sure if there is a point, other than I hope to inspire you to get closer to figures you admire.

The Long Goodbye, Raymond Chandler

As mentioned, Chandler wrote The Long Goodbye while his wife Cissy perished slowly. The book took a few years. Between Hollywood wanting him back, drinking and not drinking, and Cissy’s failing health, the book took time.

The Long Goodbye reads far more psychological than the previous Marlowe stories. It starts with an act of compassion from Marlowe, from there it takes all types of turns. Chandler immersed himself into this story with Marlowe. Fascinating, since Chandler hated authors that put themselves into their stories. He called them pretentious. But how he immersed himself in this story — bittersweet and brilliant. Most readers would remain unaware that it’s Chandler immersing himself in the story. And it’s the character you least expect. And it’s not apparent until the final scene.

Let’s get personal.

In the previous novel, The Little Sister Chandler bared Marlowe’s soul right on Hollywood and Vine.

And The Little Sister, in many ways, was Chandler’s Hollywood is one fucked up place ode. After a successful period of screenwriting, and being the go-to person to fix a bad script, Chandler was exhausted and shocked with Hollywood.

So it’s not surprising that in The Long Goodbye Chandler has moved Marlowe’s residence. While Marlowe still maintains his same office in the heart of Hollywood, Chandler gives Marlowe a rental home in the hills of Laurel Canyon. The new location gives the reader a different feel of Marlowe. And Marlowe feels displaced. At times, in his newly rented abode, he looks down at the lights of L.A. and it’s sentimental.

I sensed a tugging tension in the atmosphere.

Atmosphere is Chandler’s signature. Atmosphere meaning the physical setting or environment of a scene. Chandler focused on atmosphere versus standard narrative arcs, like the hero’s journey. And Chandler owned a gifted and uncanny ability to breathe vivid, palpable life into atmosphere. Each scene feels real. Many readers of Chandler, and those who have heard of Chandler, recognize his memorable similes. But it’s how he worded a small detail — the stitching on a chair, the smell of a certain flower on a humid L.A. morning, the coloring of a jacket button — to root a scene that made Chandler, Chandler. But in The Long Goodbye, he injects sentimental into atmosphere; it feels bittersweet. And this novel, I felt that tugging, sentimental tension.

Here’s my example of me experiencing that dimension.

Right after Christmas 2021, I went to Hollywood. I stayed for a week in the Equitable Building (it’s the building in that picture above). It sits on the famous corner of Hollywood and Vine, and it’s a block and a half from The Cahuenga Building, the home of Philip Marlowe.

I reveled staying in a building that Chandler himself possibly visited to discuss Hollywood deals.

But it was Marlowe that stood out the most to me, he felt palpable. I stayed in a building that Marlowe would walk by often, maybe even visit for some reason. When I walked the streets around that area, I could see the vapor trails of Marlowe. The sidewalks he ambled down. The buildings that once housed delis he patronized. Even with all the modern renovations, chain stores, chain restaurants, and an ungodly amount of tourists, I could still envision Marlowe’s atmosphere. Marlowe felt real.

And, to add to the Hollywood Noire vibe, The Pantages Theatre’s blue lights glowed into the bedroom where I slept.

And from the other window in the bedroom, a palm tree sat outside the window (the Hollywood and Vine picture, the tallest palm tree to the right), and it added an old Hollywood golden era vibe for me. Across the street, stood another Marlowe-era building.

As I slept, the shades were open (the floor with the gothic-looking balcony). That perfect location felt like the kind of nights, nightly glow and all, Marlowe rested his head, just a block and a half away. And it poured rain for most of my trip, perfection. But the rain slapping the old glass windows, I was in Marlowe heaven. I’d look out the windows and think, right now, Marlowe is sitting in his office, drinking whiskey, playing chess solo, a half-eaten BLT sandwich on his desk, passing time.

Even when I went to the Petersen Automotive Museum, I gravitated towards the cars from the late 1930s, the same cars Marlowe would have driven. Normally, you can’t pull me away from the American Muscle Cars, but this time, being in Marlowe’s hood, I kept looking at the cars from the 1930s.

I tried to visit places that existed during Marlowe’s era. But the extreme Covid restrictions L.A. enforced made that almost impossible. Still, I got to meander the streets of Marlowe and rest my head under the glow he rested his head in.

It added another dimension of enjoyment and another dimension to the brilliance that was Chandler.

And as I read the biography, in early May of this year, my memories of that trip surfaced. In particular, the locations — aka the atmosphere of Marlowe. Right after I read the biography, I read The Long Goodbye. And I got sentimental. I’d sit on my balcony, look out, and could see and feel Marlowe’s hood. I could see that light blue glow in that bedroom; the hustle and bustle of the street below, thinking, Marlowe is walking those streets right now. I remembered standing on the corning, looking at the Cahuenga Building, and envisioning Marlowe being a smart-ass to someone in his office.

But the biography detailed the forces behind The Long Goodbye and why that novel vibes bittersweet and sentimental.

I’ll work to do this without any spoilers.

In the final scene of The Long Goodbye, we find Marlowe in his office. Back in his original home. He feels less displaced. As if he’s back where he needs to be, but not quite yet. A man is in his office (being vague to not spoil anything). But that man is not a character, it’s Chandler. When it hit me it was Chandler, I got that choked-up in the chest feeling. And the atmosphere, and having visited Marlowe’s home, the scene felt palpable. I felt like I stood outside Marlowe’s door, eavesdropping, and witnessing the long goodbye.

Marlowe became a real person to Chandler. Naturally, no one is closer to Marlowe than Chandler. But in the final scene, we see how real Marlowe is to Chandler. We see what Marlowe was to Chandler.

Chandler faced scary questions as he wrote The Long Goodbye. Despite cheating on Cissy multiple times, then drinking himself impotent later, he adored and loved Cissy. They shared a special emotional and logical bond. But Chandler knew she was going to pass. He was scared of being alone. He committed to, or at least in his mind, making The Long Goodbye the final Marlowe novel.

Marlowe resembled many things for Chandler. Marlowe is principled, unapologetic, forthright, masculine, and sensitive. Sensitive in the sense of what some would call introversion: he has a complex inner life, is perceptive, is observant, is choosy about who he spends time with, and at times a bit too much in his head. All that makes Marlowe quite the masculine figure. And Marlowe upheld himself to his standards. Despite Chandler creating Marlowe, Marlowe is the figure Chandler admired and at times a figure he wrestled with. Chandler wrestled with Marlowe because Marlowe had personal determination and character to guide him away from his vices. He could get tempted, but he had the wherewithal to move past the temptation. Chandler didn’t. And it made Chandler feel guilty.

In The Long Goodbye’s final scene, the relationship between Marlowe and Chandler plays out. Marlowe comes to a realization — he can’t help Chandler. He tried, but he knows he can’t. Marlowe can’t save Cissy. Marlowe can’t save Chandler from his vices. Chandler needs to want to help himself, and Marlowe can’t make him do that. No one can. We feel in the scene that Marlowe has had enough with Chandler. He feels compassion and empathy for Chandler, but like in real life, at some point, there is only so much one can do if the other refuses to help themselves. And at that point, you need to move on. Marlowe moves on from Chandler. The scene vibes of telling someone “I can’t do this, I’m going on with my life.” It’s like a relationship you can’t believe is ending but you know it needs to end. The two people love each other, value each other, and work well together. But the other person’s vices tear at the fabric of the relationship. And it might not be anything drastic, but they’re there, working their way like paper cuts.

When the last word is said, it’s bittersweet. We hear the footsteps of Chandler leaving. He goes down the hall, and out. Marlowe ruminates, but Marlowe is back home, and back to being Marlowe. He looks out his window, and time passes.

It’s a distinct ending. Chandler eschewed a lot of standard fiction guidelines. And, usually, at the end of a series with a famous character that the author created, it’s the author saying goodbye to the character they created, not the character saying goodbye to the author. But The Long Goodbye it’s Marlowe saying goodbye to Chandler. Marlowe isn’t killed off. He isn’t retired to Palm Springs. He’s back at his home, passing time, seeing what comes his way.

When I finished the story, I thought of Marlowe, wrangling over to have a drink, deciding against it, and then looking out his office window. I thought of the glow of that street, and Marlowe sitting in his office ruminating on his friend, Chandler.

One more novel exists after The Long GoodbyePlayback. Chandler wrote it while drunk and on a whim. I’ve yet to read it. From what I gather it’s rather comedic and absurdist. Chronologically, the story occurs after The Long Goodbye. But in his final days, in the rare moment Chandler was sober, he considered The Long Goodbye the last Marlowe novel.

Regardless, I can’t wait to read Playback.

What Made Chandler Great & His Exercise

This section will be for the writers in my audience. But if you’re curious about what made Chandler tick writer-wise, then read every word. Ok, you don’t have to read every word, but check out this section at your leisure.

Get Hip To The Classics

Phillip Marlowe is Chandler’s famed creation. Hiney’s biography points to the forces that created Marlowe. And I’ll hazard a few opinions of how I believe Chandler created Marlowe. I see some worn paths Chandler took.

Chandler received a classical education. He excelled at it. He loved it. And later in life, he hailed the classics. A classical education is rarely taught these days (the Barney Initiative done through Hillsdale College is one of the few programs running a classical education). In sum, Chandler at an early age was on a Classic Western Civilization curriculum. He was reading Greek mythology, classic literature, and Greek philosophy. He developed a lifelong love for the classics and a deep love for Shakespeare.

Why does this matter?

Chandler said the classics taught him what not to do. And by this, Chandler meant eschewing fads, popular arcs, or pandering to his audience.

Chandler wanted to give Marlowe a backbone, yet make him a real person. The classics, from works like Aristotle to literature like Dostoyevski, detail the nuance and color of life. We get weak people, strong people, and those rare people that stand out to us. In our lives, we come across people that to us leave an impression. I don’t mean an impression like they are famous or insanely good-looking. Rather, it’s something about their character, their presence, their essence, that we find interesting. Chandler was able to capture and create an impression of Marlowe. Marlowe’s masculinity, demeanor, humor, morals, sensitivity, and insecurities make him so real. That reality comes from Chandler’s grasp and love of the classics. While Marlowe isn’t consoling Aristotle on a case, Chandler gave Marlowe an inherent and habituated sense of duty. A theme we find in classic works.

Consider Marlowe’s love life and interests. In most detective novels, a woman throws themselves at the lead male. The lead male acts bashful about his attraction. The lead female also acts bashful. So it starts with ships passing each other at night type scenario — the scenario making the reader hope for the big hookup. After some back and forth, they have a love scene. Fun at times, but cliched and typical.

Marlowe, on the other hand, rejects most women. He’s sensitive, in the manner I mentioned, so Marlowe demands a deeper intimacy. But he’s outright direct in his interests but he holds off on various women. With the reactions he gets from his directness and sensitivity, we find the character and make-up of the woman he’s talking to. Most stories today, the characters will get a background tidbit explaining why the character acts in a certain way. Whereas Chandler shows this via character reactions, male or female.

(A side note, this is one example of why I believe all men should read Chandler. )

For you writers and copywriters, the classics pack manifold insight. Classics offer rich psychological insights, a deep grasp of human nature, and provide color into how you see the world. Most people view the classics as something of intellectuals quoting intellectuals to sound smart. And yes, intellectuals and academics tend to sound snobby. But to cast off classics for that reason, that’s pigheaded. Classics provide rich insight into the world. Advertising greats like David Ogilvy knew and loved the classics. Now, not every great marketer knows Sophocles or Aristotle. I’m not saying that. But the classics have a way of turning on the lightbulb to see human life and the world we live in.

So, read some classics.

Get hip to them.

They aren’t haughty things for the intellects. Most intellects split hairs on the classics with navel-gazing topics. You don’t need to read all of them. But here or there, grab a readable one, like Aristotle’s Ethics and read it.

Another easy way to read classics without feeling intimidated is either swim upstream or go down a rabbit hole. To swim upstream take a writer you like, fiction or non-fiction, and then go upstream; see who influenced them, and read that author. Then go upstream again. A cool thing about this, once you see who influences a writer you love, you can’t unsee the influence. Plus it helps make that Classic work more approachable, as you’ll see touches of your favorite author. Rabbit holes work much the same way. Find a source or quote the author mentions often, or look at an interview where the author name drops some favorites, and go ahead and read those favorites. Or, if you’re looking into ideologies or philosophies, find the leading thinkers in those areas. And then find an approachable and accessible work, start from there.

Chandler Routine

Chandler had a routine to become the Raymond Chandler.

Each day, Chandler aimed for four hours of writing, four hours of reading, and thinking about writing for six hours.

First, the writing.

Chandler liked to start his days with writing.

And it wasn’t always sitting down at his typewriter and tapping away for four hours.

Chandler said some days the four hours comprised a walk. He would chew over in his head a story, or a scene to re-work. Other times, it was four hours of laying on the floor playing with his cat. And as he played with his cat, he was writing in his head. You could call this allowing for serendipity. A common piece of wisdom says good ideas come in the shower. That’s true. But it’s not the only place. Chandler, I’m guessing, while he played with his cats, it was like those “ideas” in the shower. He perhaps chewed over a sentence, a paragraph, or some other aspect both consciously and unconsciously as he rolled around with his cat.

This looks like procrastination.

It isn’t.

Chandler is intentional.

But I bet, though I could be wrong, he knew at times ideas or writing in his head could not be forced. Other times, he could force or exert pressure on an idea for something to come out. The intentional comes from Chandler blocking off time. He worked for a chunk of time, his chunk of time. He knew when he would be at his best. At times he was typing furiously, sometimes editing, and sometimes chewing over in his head a sentence.

In short, in these four hours, Chandler made it his own. He knew what he had to do, but he allowed for what he needed to create, versus forcing himself to a different writing routine — like writing one thousand words a day.

The lesson to walk away with: make your block of time for writing your own. Find a block of time that works best for you, and devote it to writing. And know, to you, that might be four hours of typing, or it might be a walk. But in that time, in some manner mentally, spiritually, or physically, you are intentionally writing.

Now reading.

Good writers are exhaustive readers. Chandler inhaled books. He mainly read detective novels. Late in life, he loved James Bond novels. He read classics, but he loved reading mysteries. No matter, he read a lot, and he engaged with what he read.

I get asked often how is it I read so many books. I don’t try to read fast. I’m working on slowing it down as of this writing. But the key is that I work to block time off for my reading. If you’re a writer in any capacity, especially a professional writer, block time off to read.

I aim for four hours each day. I know I may not get it. But I work towards that. If I only get a half-hour in due to a bunch of things coming up, I feel mentally off. I notice that blocking off time helps. I also notice if something pulls me away from writing — as of this writing I’m dealing with the IRS — that makes me feel in limbo. When this happens, I double down on the reading. Why? I feel like it keeps my writing sharp, and also it gives me a breather from the task displacing my writing routine.

I’m unsure if Chandler sat down and read for four hours straight. After he finished his writing block, he ate lunch. After lunch, he perhaps read for an hour or two. He also liked walks. So he may have broken it up. Either way, he aimed for four hours.

Four hours may seem like a big chunk if you’ve never done it. It takes work. So if that’s daunting, aim for fifteen minutes, undisturbed. Silence your phone, put it in another room, take your Kindle or physical book, and sit and read for fifteen minutes. Then see if you can increase that time.

If you’re a writer, make time for reading. This is imperative. In time, it becomes a routine. Or, if you’re trying to make time to read, dabble with a routine. It could be anything, a change of clothes, making tea, whatever. Anything that can help prompt you to get into your block of reading. My cat, Halbert (named after the Gary Halbert), is so aware of my routine, that if I’m caught up in something, he will start meowing or even going so far as to knock books off of a bookshelf. He does this until I sit down to read. He likes to sit on my lap if I read inside, or if I read on my balcony outside, he likes to lay against the screen as I lean back in my chair.

Find a reading routine that works for you. I notice in time that once you get it, you aren’t as distracted during it. You aren’t worried about the phone or your tweets or some other aspect. Also, another idea, bring a book with you on your errands. If you’re heading to the dentist, and know your dentist often runs behind, bring your book with you. You can steal a few sips of reading if a delay pops up.

Now let’s look at, thinking about writing for six hours.

Chandler didn’t wake up and make the thinking categorical. He didn’t say, “ok, my reading time is done, now it’s time for me to light my pipe, sit in this chair, and think about writing for six hours.” Chandler ruminated, he went on walks, and he observed people. And he thought a lot about how to use his observations in his writing. Also, he thought a lot about sentence structure, he was obsessed with little details on people and environments, and he was seemingly obsessed with grammar.

I bet Chandler’s thinking about writing wasn’t necessarily him chewing over his sentences. It could have been, but I’m gathering it was a blend of things. He was a grammar snoot, so perhaps he was thinking about grammar. He may have been thinking about what he read, and comparing it to himself or another author. I bet his thinking about writing combined various elements.

The Raymond Chandler Pastiche Exercise

When Raymond Chandler decided to be a pulp fiction writer he didn’t blindly follow his passion. He wanted to be great. He knew, despite being financially cramped, he had to put in the work. He went about it three ways.

First, he enrolled himself in basic writing courses. Some were menial grammar courses where he wanted to polish his old skills. The others were fiction workshops. He saw them as a means to shake off the rust. He aced both classes by the way.

Second, he began submitting stories. He didn’t wait around. He knew what he first wrote was going to be terrible to the professional publishers. But he wanted to learn.

Third, he underwent a writing exercise for a few years.

Let’s lay that out.

As I said, Chandler wanted to be great. He also wanted to master the detective novel. So he did two things. He read — inhaled, more like it — best-selling pulp fiction. And he continued to read authors he admired outside of the mystery niche: Hemingway, Shakespeare, and so on.

Then, he’d pick a story, let’s say a top-selling pulp story, and he’d attempt to recreate the story.

He’d read the story. Then, at some point, he’d sit down at his typewriter, and he’d write that story, start to finish. He’d try to recreate it from memory.

I assume he picked varying lengths, short stories to long stories. But no matter, he’d attempt to recreate the entire thing in full.

Once he finished his version, he’d reread the original.

As he reread he looked for two things. One, he wanted to see where he was structurally weak; what parts did he not get right, where did he lose the narrative, etc. Two, he looked for the hidden effects unknown to the reader but known to the writer; this would be what made the story great, the writing, the prose style, or other elements.

This is a fantastic exercise.

You can use it for sales copy, article writing, or fiction. It works like the Benjamin Franklin exercise. In that exercise you read the story, then write bullet points as hints. Then try to recreate it. Here, you forego the bullet points and attempt to recreate the story from scratch.


And the simple aspect of focusing on structure and then the elements unknown to the reader but known to the writer — a great skill to develop.

Another variation of this exercise that Chandler underwent, he wrote parodies of his favorite writers. He would write a short story attempting to imitate their style. Chandler would make up the story, and write it as one of his favorite authors.

You can do this with copy or any style of writing. And try it in different areas. Say, Hemingway writing a Direct Mail piece. Or maybe Raymond Chandler writing a blog post for NetiPots.

These exercises allow you to steal your favorite writer’s methods, and imprint them in your style, but also deepens your creativity.

This is a fast way to become good. And it’s a common method for many writers. If you’re a new writer, try Chandler’s exercise. And keep in mind that he did this exercise often for around five years. Keep working on exercises, writing as often as you can, and do the creative exercises.

And if you’re trying to get paid as a writer, as Chandler did, do what Chandler did: dissect and imitate the best-sellers. You can hate them. But knowing why they work and how to write in that style helps. So if you’re writing copy, find the best sellers in your field and do this exercise. Read them a ton. Chandler inhaled the best-sellers in his niche.

And brush up on basic writing skills. Chandler didn’t want to be a hack or get sudden success, he wanted to be great. He held himself to a high standard. And his command of prose made Chandler, Chandler.

Short Goodbye

I hope you enjoyed this email. I debated how much to put in. I redacted five thousand words. It got too personal in spots. Maybe in the future I’ll feel comfortable sharing the things I cut out. An extended directors cut perhaps.

But I hope this piece inspires you to deepen your conversations with the authors you like. Doing so adds another dimension to what you read and a whole lot of enjoyment.

Till next time,


P.S. This postscript was not in the email. Sometimes I pick a theme song for a piece. My pick for this piece, and it took on a whole new dimension after writing this piece – Hollywood Nights, by Bob Seger.

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