Steven Pressfield

Steven Pressfield

by

Steven Pressfield’s book The War of Art has been so influential to my life and my pursuit of prolific practice, that I naturally went down a Pressfield rabbit hole, reading nearly everything written by the man himself, a lot written about him, and watched dozens of interviews. The more I learned about him, the more I discovered events in his life, ways of looking at things, that enriched my own view of life, and so eventually I decided: I’ll just write about who Steven Pressfield is, and why anyone should care.

The TLDR of his story is that he’s had a long journey to becoming the accomplished author he is today, despite many seemingly dumb career choices, despite being an author who hops genres in the most erratic way. He still considered himself an abject failure even when he was 50.

Quick bio: He was born on 1 September 1943 in Trinidad, where his father, who worked in the U.S. Navy, was stationed at the time. He graduated from Duke University in 1965, and joined the U.S. Marine Corps the following year, where he served as an infantryman. He spent many years working various jobs, from fruit picker to truck driver, driving cabs, teaching, and many other gigs.

Steven Pressfield’s writing journey

Pressfield got serious about writing when he was 22. Started writing his first novel at age 24, gave up at 26. It would be 12 years before he’d finish his first book at the age of 34. Here’s how he felt at the time:

“[…] that moment when I first hit the keys to type out THE END was epochal. I remember rolling the last page out and adding it to the stack that was the finished manuscript. Nobody knew I was done. Nobody cared. But I knew. I felt like a dragon I’d been battling all my life had just dropped dead at my feet and gasped out its last sulfuric breath. Rest in peace, motherfucker.“

Well, that book never got published, and he admits that there was a reason it didn’t get published: it sucked.

But he kept writing. Wrote another book that never got published. Kept writing.

He made a living as a cab driver in New York, and eventually as a copywriter.

During those days, after many years of “being a writer” he’s often overcome with doubt and asks himself why he’s still trying. The answer?

I’m doing it because I have no Plan B. I’m doing it because I can’t do anything else.

— Steven Pressfield, Govt. Cheese, Chapter 49

Getting into screenwriting

At age 37, he’s written 3 novels, and all of them failed. Not a single one got published. This is how he described his state of mind at the time: “This is my third novel. I have poured my heart into it. It’s as good as I can do, and it’s dead, dead, dead. I don’t have it in me to spend three more years writing number four.”

He decides to give screenwriting a shot. Buys a book for $3.95 titled How to Write a Screenplay. He writes his first screenplay, a prison story, and then 11 other screenplays. None of them sold. But he found a job as a copywriter to stay afloat.

At age 42, he got the third paying writing gig of his entire life: a $500 rewrite on a porn flick. A while later, he works on a low-budget action flick, where he received the best advice he’s ever gotten.

Working under Ronald Shusett

He finds an agent who fails to get his scripts sold, but eventually teams him up with Ronald Shusett (whom Steven refers to in the book as “Stanley Duplass”). Ronald is a screenwriter with many hits to his name, and their collaboration looks as follows: Steven does the writing, Ronald gets the scripts sold. The relationship is on uneven footing right from the getgo. Pressfield puts in a lot more work and effort than Ronald, but Ronald has the brand, the network, and knows how the game is played. He knows the business. And he’s obsessed with producing great movies. Steven learns a lot from Ronald in these years.

But you sense that Pressfield is never fully comfortable in that relationship. At one point he options Delilah by Marcus Goodrich for $2500. He now has the rights to turn that book into a movie, and does so on his own, without even telling Shusett about it.

At age 43, he worked on a movie called King Kong Lives. It’s an embarrassing flop, has a IMDb rating of 3.9.

He keeps writing, picks up little gigs here and there, learns, practices, makes connections.

Eventually, Steven and Shusett clash: Steven wanted full screenwriting credits for a script he wrote that was based on his own idea, a movie called Cryptic. Shusett didn’t accept that, told him he can’t no longer work with Steven, and hung up the phone. The partnership between Shusett and Pressfield has come to a sudden end. Pressfield, now 51 years old, calls this his big All Is Lost moment. Here are the words he used in his memoir:

“I’m nobody. I’m fucked”

His plan now: Spend the next 12 months writing two screenplays and trying to sell them. His daily regimen now? Work out in the gym at 5am. Liver and eggs for breakfast. Writing nonstop from 7am to noon. Then networking and reaching out to producers and studio execs to sell his script. Sleep at 8pm.

And then this happened:

“You speak Italian?” I shake my head. Dino [a successful movie producer] slides a drawer open, takes out a movie script, and passes it to me.

LA CITTA’ ETERNA

The piece is in Italian, with the writer’s name—a male I don’t recognize—beneath it. “I want you translate.” It’s common knowledge that Dino never reads scripts in English. He has people who translate everything, even letters and memos, into his native tongue. “I don’t understand,” I say. “You’ve already got this in Italian.” Dino dismisses this. “I want in English. Ten grand cash. I need in three days. You do?” I’d love to. “But how can I translate it if I don’t read Italian?” Dino glances to the doorway. I turn. Silvia stands there. I’m thrilled to see her. “I thought you were in Italy!” She says nothing, only smiles. “You work with Silvia,” Dino says. “She tell you what script say, you write in English.” “When would you like me to start?” “Tonight.” One thing about Dino: He pays. I do the job in thirty-six hours. The check arrives twenty minutes later by messenger.

—Chapter 78, Govt. Cheese

I don’t know about you, but a $10k check for 3 days of work sounds pretty good to me—especially if you’re a struggling nobody in LA in the 1990’s. And somehow, in mysterious ways, Pressfield now starts to see success. He’s selling scripts, one for Joshua Tree, a movie starring Dolph Lundgren, and Freejack, and even though they he hates how both of them turned out, he’s making some money writing.

You’d think he’s happy with the progress he made, but instead he’s busy pondering whether there can be “a single shittier writer than me in all of Hollywood”.

He keeps doing free rewrites and works on various projects, nothing serious ever materializes though. He still gets schooled on how the business works. But he’s working his way up in Hollywood, his name carries some weight, he’s on a trajectory to success. Until…

A ludicrous idea

Then one day the strangest thing happens. I get an idea. In truth, I’m seized by an idea. I have to do it. I have no choice. There’s only one problem . . . The idea is not for a movie. It’s for a book.

—Chapter 86, Govt. Cheese

And with that, he throws away the Hollywood career he’s built over the past years. He’s just at that point where he’s about to really make it in Tinseltown, and his agent is making a passionate appeal to stop Steven from pursuing that idiotic idea of writing a book about golf. Eventually his agent, who’s been busting his ass to help Steven succeed, sees that he can’t dissuade Steven, and let’s go of him.

If you look at this situation from the outside, Steven’s agent is right. This was an idiotic choice. Steven could make a great living writing for the movies, something he had worked so hard for over so many years. And just when it’s not just within reach, but basically already in the palm of his hands, he abandons it for this ludicrous idea of writing a novel.

And yet, that exactly, despite, or maybe because how unreasonable it is, shows how Steven Pressfield ultimately listens to his inner voice.

Sterling Lord & The Legend of Bagger Vance

That novel about golf is of course The Legend of Bagger Vance, which got published in 1995. Pressfield’s first novel which later gets turned into a movie starring Will Smith, Matt Damon, and Charlize Theron, directed by Robert Redford. A novel about golfing which was based on the narrative structure of the Bhagavad Gita. That ludicrous idea of Steve that should have derailed his career? Yeah, it became a tremendous success.

And that’s due in large part to a guy named Sterling Lord, who put the book in front of so many of the right people that it all, somehow, almost magically, came together. And to him, it seems, finally, he feels satisfied. “It’s been worth it. Everything has been worth it.”

Steven Pressfield’s routines & work habits

Nowadays, he’s at the gym at 5:30 a.m. At 11:30 a.m. he sits down in his office to work. His office is simply a converted bedroom in his house, with a simple desk and an old Mac desktop on which he writes.

There’s nothing special, except a lucky toy cannon that fires inspiration into him, and a lucky horseshoe. Before he actually starts writing, he recites a prayer to the muse. He also has lucky boots, he picks up pennies, and is openly superstitious.

He works for two and a half hours, five or six days a week, and weekends tend to be the most productive days for him. He’s almost 80 years now, so that’s all the productive writing time he gets out of a day, but he makes them count.

Writing advice by Steven Pressfield

Here’s a few random snippets of advice Steven Pressfield has for writers. I’ve got a big notebook full of stuff that I still need to incorporate here, and I will do so in a future update. But for now, I want to get this thing shipped, so here’s a few bullet points for you:

  • If you’re a young writer struggling to find your voice, find some great writing and copy it word by word.
  • “When we sit down day after day and keep grinding, something mysterious starts to happen. A process is set into motion by which, inevitably and infallibly, heaven comes to our aid. Unseen forces enlist in our cause; serendipity reinforces our purpose.”
  • Write about what interests you, what fascinates you, what makes you curious. “I did what I myself thought was interesting, and left its reception to the gods.”

If you’re looking for more writing tips by Steven Pressfield, definitely get his books and check out his blog.

Loving the land

Steven Pressfield loves the American landscape at dawn

Steven Pressfield loves America. Not the politics, not the religion, but the land itself. Here’s how he put it:

One thing about being a trucker and living the trucking life is you see the dawn every morning. You’re on the road when the sun comes up. The high, wide windshield is like a 3-D IMAX screen exploding, if not always with straight-up beauty, then for sure with the horizon-to-horizon energy and horsepower of the United States. I’m with Woody Guthrie. I’m with Walt Whitman. Count me alongside Jack Kerouac, Ken Kesey and Gary Snyder. I love this fucking place. I know it sucks. I see the shit. I read the hatred and the suspicion and the crazy waste of time that is most of our lives. I see the drunks and the wife-beaters and the dirty cops and the criminals at the top of the food chain. I feel the blood that has soaked into the earth from men and women beaten with barbed wire and hung from trees while children looked on and cheered. None of that is lost on me. But this country is still beautiful.

Chapter 87, Govt. Cheese

Steven Pressfield’s best interviews & podcasts

If you just want to binge, here’s a curated playlist of all the best interviews Pressfield did, reaching back 10 years and more. Or pick one of these great interviews here:

Oprah Winfrey (January 2019), audio

Lex Fridman podcast #102 (June 2020), 1 hour 27 minutes, video

Tim Ferriss podcast (December 2022), 1 hour 22 minutes, video

Tim Ferriss podcast (March 2021), 1 hour 53 minutes, video

Rich Roll podcast (January 2023), 1 hour 56 minutes, video

Rich Roll podcast (March 2021), 2 hours 4 minutes, video

Daily Stoic with Ryan Holiday (October 2022), 54 minutes, video

Chase Jarvis (July 2022), 1 hour 6 minutes, video

Aubrey Marcus (October 2020), 1 hour 55 minutes, video

Let me know if you have a favorite Pressfield interview in the comments below.

Book recommendations by Steven Pressfield

Here are books Pressfield has recommended. I’ve tried to add sources to each recommendation.

Movie recommendations by Steven Pressfield:

Steven Pressfield online:

Steven Pressfield’s own website and blog

Steven Pressfield’s YouTube channel (lots of good stuff here)

Instagram (seems to be the social media platform where he’s most active)

Twitter (not very active)

Facebook (not very active)

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