stephen pressfield & ryan holiday on creative work, writing, and resistance

Ryan Holiday recently published a conversation between him and Stephen Pressfield. Right from the get go, they touch on an interesting subject: Ryan had a day where he wasn’t feeling well, and struggled to get into a writing groove. But he sat down and wrote anyway, and it turned out to be one of the best writing days he’s had in a long time.

It’s the days on which you show up when you don’t want to that make it work.

It’s not fun at first, but you break through that barrier, and once you’ve broken through, that’s when you get into a joyful flow state.

If you could do a good project by only showing up on the days when you feel like it, everyone could do it. The difference maker is whether you showed up on the days when it was hard, when you were tired, when you weren’t feeling it. That’s what separated the wheat from the chaff.

You have to write every day. Not well, but you gotta do it

[around 20 minutes into the video] The difficult thing Pressfield expects of himself is to write every day, to put in his writing time every day. (He also talked about this in his latest book Put Your Ass Where Your Heart Wants to Be.) The easy thing is that he doesn’t hold himself accountable for how well he’s written on any given day, or how many words he wrote. This is also at the core of prolific practice, and why I’m so passionate about building a daily writing habit.

“Most of what we do is not so great”, said Pressfield.

“I don’t torture myself with ‘is this good?’ as I’m writing. The main thing is just keep the ball moving. And at the end of the day, the week, the month, you’re gonna have something. You might have to redo it, but the big danger for me is falling off the wagon, losing the momentum.”

It takes many, many drafts

Steven Pressfield: “I’m a big believer in multiple drafts of things. I will write 15, 16, 17 drafts. So when I’m on draft two or three, I’m not torturing myself about ‘is this great’?’. I’ll get the words right on the 17th crack. My only thing each day is: Am i gonna sit my ass down and put in my time?”

Both Ryan and Steven are believers in the idea of writing a couple of crappy pages every day.

The bad version technique

Another technique that Steven Pressfield recently discovered and found useful was to write: “And the bad version is…” and then write a bad version of what he wants to say, and more often than not, the bad version turns into the good version after about ten times.

Don’t interrupt your writing flow. Write incomplete sentences and fill in the missing parts later.

Ryan shared an example if he were to write:

In the midst of the… ‘wait, was the war in 65, or 66?’. Many writers at this point would research now when the war took place to make sure to use the correct information. Ryan on the other hand would just write: “In INSERT…” and then complete the sentence to get to the point that he wanted to make, rather than get hung up on researching a detail. And then he’d later, after the writing session come back and do the research and fill in the correct information at insert. “The facts can always be corrected, but the gist of the sentence, or the momentum of what you’re trying to put down is more important than getting it perfect.”

Steven Pressfield calls this the magic of TK.

Don’t get hung up on finding the right words

[around 23 minutes into the video] Pressfield says not to noodle too much with “Is this the right word?’“, and instead it’s much better to write some shitty sentence first, but actually be in the scene you’re writing, fully immersed, imaginging. You can always come back to fix the language.

Keep writing ahead, don’t look back

[Around 24:30 into the video] Ryan references a bible quote:

But Jesus said to him, “No one, having put his hand to the plow, and looking back, is fit for the kingdom of God.” – Luke 9:62

They then think about how this applies to writing, and that by trying to finetune your writing while you’re in the midst of writing the story, you’re actually veering off the task in front of you: which is to keep moving the story forward.

Don’t rush. There’s enough time.

Don’t rush the work, don’t try to get things done faster. It’s not a race. Make time for what matters. If what you’re doing is worthwhile, then give it—and yourself—the time it needs. No good work comes out of rushing things.

5 year journal

[around 32:50] Ryan has a one-line a day journal (probably something similar to this). It’s five lines on each page. And each page has 5 slots on it, and you keep this journal for five years. And he can see what he did on the same day a year ago, two years ago, three years ago, and so on.

It’s a fascinating journal idea that I love.

Fascinating fact: Superstitious spartans

[around 49 minutes into the video] Apparently the Spartan army would mobilize to go into war, which of course is a huge undertaking both psychologically (you say farewell to your family and loved ones, knowing that you might die in battle) and logistically. They’d go to the border of Lacedaemon, tale the almonds, and if the almonds were bad, they’d turn back, and if the almonds were good, they’d continue and make war. Apparently they believed that this was the Gods’ way of telling them whether their war was just or not.

I did a quick Google search on this and wasn’t able to find any references to the historical accuracy of this, but I’m still curious.

The big theme of Steven Pressfield’s work

Pressfield answered that what he’s exploring is best encapsulated in a Marcus Aurelius quote: “Life is warfare and a journey far from home.”

What’s the purpose of discipline?

I believe that life operates on 2 levels:

  • the muse level (aka the higher level)
  • the material level (which is where Resistance is, and it stops us from reaching the higher level).

And if we don’t get to the higher level, because we don’t follow our calling, because we don’t do our work, then shit happens: disease, suffering, etc.

Discipline is what takes you to the higher level. You can’t wish, manifest, or chant your way there. The only way to get there is through hard work. Because the beings that inhabit this higher level are looking for that: someone who does the hard work. That’s the only thing they respect. That’s the price of admission.

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