Write Yourself Into a Pit (Then Dig Your Way Out Again)

6 minute read
Author: Jo

No matter how much you plan, outline, and prepare to write, there are gonna be times when your writing ends up going off-piste in a potentially catastrophic direction – one you’re not sure you can recover from.

This is, obviously, a bit of a pain in the arse.

But sometimes writing yourself into a corner can be a good thing. Because when you find yourself in an impossible situation, you’re quite literally forced to come up with a totally original and hitherto un-thought-of solution. And, ultimately, you might find it makes your story even stronger.

It actually takes a lot of guts to allow your story to tangle itself into an absolute mess. It means you’re taking risks. Digging yourself into a pit with the confidence that at some point you’ll have to break through the other side of the world is a ballsy move. And a lot of writers shy away from this kind of experimentation because they don’t believe that you can dig that far. Instead, they focus on the sheer walls rising up around them, and panic that they’ll never be able to climb out again. It’s just too hard. It’s too much effort. It’s not worth it. BUT. The worse a predicament you throw your protag into, the more risks you take, the greater the impact, emotional resonance and redemption when your character (and your story) finally emerges on the other side…

Take, for example, one of my favourite writing stories, by legendary novelist and screenwriter William Goldman (seriously, this guy wrote Marathon ManMiseryThe Princess BrideButch Cassidy and the Sundance KidAll the President’s MenA Bridge Too FarHeatA Few Good Men and The Stepford Wives – he is a LEGEND). In his memoir Which Lie Did I Tell? he talks about writing The Princess Bride: “The only novel of mine I really like. And I don’t know how I did it.”

The first draft started off okay, as they often do, in the early stages of new-idea-excitement…

“But then I went dry.

The nightmare of all of us who put words to paper. I stormed around the city, wild with ineptitude, because, you see, all these moments had already happened in my head – the sword fight on the Cliffs of Insanity, for example; Inigo and his quest for the six-fingered man, for example; Fezzik and his rhymes – but I didn’t know how to get to them, had no way to string them together. And I could feel the window of creativity stating to close. We move on, we move on, it’s okay, we’ll find other stories left to tell…

But I didn’t want to tell other stories, I wanted to tell this one.”

And so, wracked with writing angst, Goldman decided to only write the ‘good parts’, and cleverly structured the book as an abridged re-telling of another, longer book, by S. Morgenstern, which was read to him by his grandfather, who decided to leave out the boring bits. “And then I started to fly,” Goldman says.

If that wasn’t interesting enough, this is exactly when he inadvertently wrote himself into a (literal) pit:

“The most startling creative moment of my life happened here.

Protag has been captured by antagonist (and love rival) and is being tortured mercilessly in the Pit of Death by henchmen, Count Rugen, a masochistic psychopath. Frustrated by Westley’s endurance, Prince Humperdinck turns machine up to its full capacity and Westley’s friends are on the way to the rescue when the Deathscream begins and they track it and…

As I was going to work that morning I kind of wondered how I was going to get Westley out of it. I sat at my desk and had coffee and read the papers and fiddled a while. Then I realised I wasn’t going to get him out of it. And I wrote these words: Westley lay dead by The Machine.

I think I must have looked at them for a long time. Westley lay dead by The Machine. He was perfect and beautiful but it hadn’t made him conceited. He understood suffering and was no stranger to love or pain yet the words were still there. 

Westley lay dead by the Machine…”

[BTW here’s where it appears in the book – at that perfect ‘all is lost’ moment towards the end of the second act:]

Image of two photographs depicting The Princess Bride book by William Goldman. The first picture shows the book open at about three quarters of the way through. The second image shows a close up of a page that says: Westley lay dead by the Machine.

“You killed him, I thought. You killed Westley. How could you do such a thing? I stared at the words, and I stared at the words some more, and then I lost it, began to cry. I was alone, you see, no one could help me get out of where I was and I was helpless. Even now, more than twenty years after, I can still truly feel the shocking heat of my tears. I pushed away from my desk, made it to the bathroom and ran water on my face. I looked up and there in the mirror this red-faced and wracked person was staring back at me, wondering who in the world were we and how were we going to survive?

I tell you this because I guess I want you to know that although I don’t think it is a good life, writing, not insofar as having relationships with other people, having loves, all that emotional stuff we all long for, or say we long for, still, there are worthwhile times. And if you were to ask me the high point of my creative life, I would say it was that day when Westley and I were joined. 

The rest of the book went the way it’s supposed to, but never does.”

If you’ve read/seen The Princess Bride, then you’ll know that what follows is the best resurrection story since Jesus…

Gif of Westley, Inigo and Fezzik from The Princess Bride. Westley asks, "Why won't my arms move?" and Fezzik replies: "You've been mostly dead all day."

So. Here endeth your lesson for today. Don’t be afraid of giving yourself unanswerable questions. Sometimes you just have to dig yourself into a pit.

Share this article:
Bookmark (1)

No account yet? Register


Join our amazing writing community!

  • Get three free writing courses
  • Gain access to online writing retreats and Flash Face Off spoken word nights
  • Meet like-minded writers and get support and resources to keep you writing
  • Oh and it’s free

Want to be a better writer?

Or just to laugh at bum jokes? Either way, you need the famous Writers’ HQ newsletter. You know what to do – put your thing in the thing.