• create the mirror moment in the middle of your story, which you can work forward or back from
  • write or plan your characters darkest moment in the story


I wrote the following in a newsletter recently and thought that it’s a good starting point for Dark Night of the Soul, and that general region of the book.

If we’re talking structure and the Hero’s Journey, this about 2/3 of the way through, at the end of Act 2.

So, let’s discuss the Dark Night of the Soul. Or the Darkest hour, All is Lost, or whatever other story structure phrases apply.

I always think of that moment in the Return of the Jedi, where Luke stands before the Emperor, cuffed, and Palpatine says:

‘Everything that has transpired has done so, according to my design. Your friends, out there on the sanctuary moon, are walking into a trap, as is your Rebel fleet. It was I who allowed the Alliance to know the location of the shield generator. It is quite safe from your pitiful little band. An entire legion of my best troops awaits them. [mockingly] Oh, I’m afraid the deflector shield will be quite operational when your friends arrive.’

For Luke, everything that could go wrong, has. It’s Murphy’s Law, but on the biggest scale possible (for that character and their wants/needs).

Luke enters the Death Star II voluntarily, with the firm objective of turning *SPOILER* his father, Darth Vader, from the Dark Side back to the light. Meanwhile his rebel friends are trying to take out the planet-destroying Death Star’s shield, to allow an attack.

In that moment, Luke is as far away from any of his, or his friend’s, objectives as they can be. We believe all is lost, and it’s at this moment that our hero (our main character) must use all that they have learned in the story leading up to that point to overcome this biggest of obstacles and achieve their goal. 

If the emotional journey of our character were to be plotted as a graph throughout the story, this would be where they graph was lowest, even lower than when they started. Sure, there were some high moments along the way, but whatever small wins they’ve had, we must plummet them down so far, that everything seems impossible. Even our reader should doubt if our main character is going to succeed.

Now, Luke has to fight his father, but then he decides he will fight no more, whatever the consequences. He will not be forced into believing that darkness is inevitable, and he states his belief in Vader’s goodness before throwing away his weapon. Luke, in his most vulnerable moment, has displayed all that he has learned on his journey. That his father is not pure evil, that he was once a Jedi, a good man, and he will happily lay down his own life in exchange for that belief. 

And it’s that sacrifice from Luke, taking the harder path and resisting the Dark Side, that causes the change he desired in his father.

Meanwhile, other events have improved in the fight on the forest moon of Endor, and we see growth in our secondary characters, again, showing the importance of giving each character their own arc, to develop a richer and more rewarding experience for the reader.

Suggested Writing Task

Wherever you are in your novel, think about your main characters darkest hour. What is their Dark Night of the Soul? What is the biggest thing they have to overcome? Ensure as they face that, that all appears to be lost. Keep piling it on. Sometimes we worry about being too tough on our characters, but more likely than not, we are being too kind. And your reader won’t thank you for being kind. The real reading reward comes from seeing our main character have to overcome the very greatest of adversities.

So, let’s get a little more structural about this section of our novel. As I mentioned at the start, we’re looking at about the 2/3 mark or towards the end of Act 2 of a 3 Act structure. And don’t worry if you don’t write like this, with lots of structure, it’s just as a way to gauge where we are in the novel – anywhere from mid-point to before the climax.

This is obviously a key point in any story, where we are about to put our hero up against the worst yet and really test them to their breaking point. We may even break them. So, here’s the general structure (and I’ve borrowed from a hybrid of models here).

  • Antagonist (antagonistic forces) close in

At this point our hero begins to really face their flaws/doubts. We can see them closing in, like birds of prey surrounding a limping animal. This is also a good point to hint at the coming of the antagonist or the antagonistic force in your story. Perhaps your hero and the antagonist are both pursuing the same thing, or have opposite goals, which will result in an inevitable clash. 

  • Encounter with the antagonist

But our protagonist is probably not ready yet…perhaps they are taken by surprise or haven’t learned what they need to or learned how to overcome their fear/flaw. But we should be very worried about our hero. It is likely the antagonist wins this round and thinks our hero is defeated. Our hero believes they are defeated. That all hope is lost.

  • Crisis/All is Lost

This is often an event which is deeply affecting to our hero. Maybe their mentor, or close friend/family die or sacrifice themselves to save our MC. Think Obi-Wan. Or something dear to our hero is lost. It may not be a person but an idea or their goal may now seem impossible.

  • Dark Night of the Soul

This is an emotional rock bottom for our hero. They usually believe at this point that they cannot achieve their goal, they cannot overcome the antagonist, or their own fears or flaws. Our hero may wallow and think about all of their bad choices and why they even came on this journey in the first place. It all seems pointless. Lots of interiority likely here. A good place to link to the hero’s past and why they have their flaws/fears. What caused them to have to overcome them? This may introduce a small spark or motivation to keep going, to give their objective one more shot. It is a do or die moment – go big or go home. Fingers crossed no-one’s hero is going home at this stage!

  • Rock Bottom

Our MC may well be at the very bottom of their emotional ladder…but from there, the only way is up – cue Yazz earworm! Perhaps our MC unlocks that thing from their past which has caused their fears/flaws and now knows what they must do. Perhaps something from earlier in the story, some kind of story-plant or similar, is triggered or remembered or worked out and our hero emerges from the smoking crater (or whatever other metaphor you like) and rises one final time, to take on the forces of antagonism and try to finally overcome them. Weirdly, I always think of the moment in Shrek 2, when he rides into the city on the white horse (donkey) to out Charming and win back Fiona. ‘Holding out for a hero’ is blaring in the background. There is no way we cannot root for Shrek in this moment. He’s gone through hell and now we cheer him and his faithful donkey to the tones of Bonnie Tyler. We feel good. The MC is buoyed for one last shot…

Hope that is all useful and helps you navigate this tricky, but so important, section of the novel. Without it, we don’t appreciate what the hero has gone through – we cheer less when they finally win in the climax and it doesn’t feel as earned.

So be tough on them – really, really make them suffer and you’ll be rewarded with a much more satisfying climax.

Stuart’s evil checklist to ensure it really is the DARKEST night of the soul:

  1. Have we enacted Murphy’s Law to the fullest? Has all that could go wrong, gone wrong? If not, make it happen, Scotty!
  2. Have we dug deep into our main characters flaws and fears? Are they exposed as fully as they can be? This is a must, so our MC can confront them, and overcome them to make that change which is necessary in the story.
  3. If the antagonistic character or force at its most present and dangerous? If not, why not? What are we waiting for, make that MC suffer!
  4. Have we made sure of agency – has our MC really, really tried to make things better, but in doing so, has made them worse? Go on, get your hero to mess up, and mess up bad!
  5. Has our hero suffered? Have they had to fight hard to earn every single thing they’ve won or achieved? Have they lost big when things haven’t gone well? If not, now is that time.

Suggested Writing Task

Work through the checklist and be as unkind as you can. I promise you; it will pay off. Your reader will be far more engaged, the tougher you are to your hero. Nothing in your story world should come easy, and your MC should know it!