Fiction Writer’s Toolshed | Practical Tools for Authors
You’ve got a premise. You’ve written scenes, developed characters and put real time into the story. Then you start getting close to the end and realize you don’t know where you’re going.
Or maybe you do have an ending. It’s surprising. It’s clever. But the story leading up to it doesn’t make that ending feel like it belongs.
In this episode, I talk with screenwriter and author Doug Hall about writing the ending first. For Doug, choosing the destination helps him build the characters, conflict, dialogue and middle that make the payoff work.
Doug wrote and sold the original screenplay for Leprechaun in the Hood to Trimark Pictures. We talk about how he wrote that draft in five days, why he started from the end, and why an ending can be useful even when it later changes.
As always, this is a current best approach: something to understand, try and adapt to the work in front of you.
Listen to the episode
Fiction Writer’s Toolshed
Writing the Ending First: How to Build a Satisfying Story (with Doug Hall) | ep 031
Follow the podcast (opens in new tab)
Getting to page 80 without knowing the ending
Doug’s reason for starting with the end came from getting stuck.
His first serious attempt at a screenplay eventually ran about 100 pages. Around page 80, he realized he didn’t know what he wanted to say or how to end it.
He had to go back through what he’d written and get to know the character more clearly in his own head. What did this person really want? What had the journey been for from the beginning?
Once he understood that, he found an ending that worked. But it took time, and he didn’t think it was the best way for him to work.
He started thinking about a story as a journey. When we get in a car or on a plane, we generally know where we’re headed. We may run into problems along the way, but we have a destination to help us decide where to go.
For Doug, choosing an ending earlier gives the story that direction.
A destination can give you room to work
I’m a deep outliner, so this makes sense to me. It’s easier for me to sit down and write something meaningful when I have a bounding box. I don’t have to be locked into every choice to know the kind of thing I’m trying to make.
Think of cooking. I like to have a stocked pantry and know I’m making Italian food. I can still switch a protein or change something along the way. I just don’t have to decide what kind of meal I’m making in the middle of cooking it.
That’s how I hear Doug’s approach: choosing a destination that helps you work, with room for the work to change.
He had already decided to start from the end when he wrote Leprechaun in the Hood. The ending he wrote wasn’t the one used in the final draft. Having that first ending still helped him get through the script.
We don’t get into the plot details of the two versions in this conversation. What matters here is that the first ending did its job as a destination, even though it wasn’t the final one.
Writing the ending first is also different from showing the ending to your reader first. This is a way to build the story. It doesn’t require you to tell it backward or open with a flash-forward.
What makes the ending a payoff?
Doug usually starts with a premise that catches his attention. Then he asks where that journey should end. He doesn’t say the answer arrives immediately. Finding the destination is part of the work.
He likes twist endings. In the kind of payoff he describes, the protagonist gets what they wanted, but in a way they weren’t expecting.
That gives him something to build toward. The ending helps him make decisions about the characters, their dialogue, the theme and tone, and any subplots. Those parts need to work together so they support where the story is going.
I’ve heard an ending described as “surprising yet inevitable,” and I think that gets at what makes this useful.
You can come up with a clever twist or an interesting destination. But if the character development, theme, tone and events don’t support it, the ending can arrive without much meaning. You’ve reached a place, but the journey hasn’t made that place matter.
Choosing the destination is the start. Then you build the story that earns it. The reader may not predict exactly what happens, but they can look back and understand how the story got there.
Doug’s preference for twists doesn’t mean every story needs one. It gives us a useful way to think about his particular approach: the surprise grows from the story, rather than appearing at the last moment to replace it.
Build characters who pull against each other
One of Doug’s starting points is creating characters who will have conflicts with each other.
People might want the same broad thing, such as happiness, but have very different ideas about what happiness means or how to get it. Those differences can put them in each other’s way.
Doug works back from the ending, theme and tone to the characters who can express them. How do these people approach others? How do they talk? What choices do they make? What happens when their ways of pursuing a goal collide?
Their dialogue and actions grow from those differences. He wants their behavior to fit who they are, while leaving room for events to force them into choices they wouldn’t normally make.
That’s a connection I like. If you decide you want chicken Parmesan, you still need ingredients that can become that meal. In a story, knowing the result gives you a way to ask which characters belong in the mix and how their interactions could get you there.
Doug isn’t giving us a rule that every character must be the opposite of every other character. He’s showing how he uses differences to generate conflict that fits the story he wants to tell.
Give the middle a turn that belongs to the story
The destination also helps Doug think about his midpoint.
The character has made some progress in the quest. Then they learn something or encounter a development they weren’t expecting. What they thought they understood about the journey needs to change.
Doug is careful about the kind of surprise he means. It shouldn’t be something arbitrary, pulled out of nowhere. It might be something the character could have seen but hadn’t been thinking about.
For a 100-page screenplay, he mentions roughly pages 50 to 60 as a place he might put that turn. That’s his screenplay example, rather than a fixed page requirement for every story.
To me, a useful midpoint can help with the middle drag. It gives you something interesting to work out as the writer, and it gives the reader or viewer a reason to stay with the story. Progress has happened, something has changed, and there’s still a payoff ahead.
You’re building a route to the ending, with developments that make the trip worth taking.
An unexpected sister
Doug gives an example from another action screenplay: two women who are cops, teamed up despite being very different from each other.
The main character wants to find and save her sister. She has lost track of her, knows she may be in danger, and feels the weight of having left her behind when she got away from their difficult father.
The woman she’s partnered with clashes with her over how to handle things. They don’t approach the journey in the same way.
Over that journey, they build an unlikely friendship. Doug describes the emotional payoff as finding a sister in someone the protagonist didn’t expect. The two women become like sisters to each other. Her partner has also lost a sister.
Doug would need to pitch the whole story to explain every part of that plot. The example he gives us is the relationship: something that begins in conflict becomes a sister-like bond.
The ending connects with what the character wanted, but gives it a form she wasn’t looking for. The time the characters spend together and the choices they make can give that surprise meaning.
That’s more interesting than dropping a new answer into the final scene. The relationship built during the story becomes part of its payoff.
How a bet led to a five-day draft
Doug’s path into screenwriting is a good story of its own.
He met a neighbor in Los Angeles who was trying to sell a screenplay. After reading it, Doug asked how selling scripts worked. The possible prices sounded astonishing to him.
He jokes that he’d seen some movies that weren’t very good, so perhaps he could write something that wasn’t very good and sell it too.
Then the neighbor told him he was too old for Hollywood. Doug responded with a bet: he would write and sell something within a year. He says he won.
His background in financial sales influenced how he approached the goal. He set a timeframe and thought about the methods and options that might help him reach it.
He also made mistakes. He walked into production offices with scripts and got sent away. Agents asked what he’d already sold, while he was trying to find an agent who could help him sell something in the first place.
Eventually, a script he left with a contact led to an opportunity. At the end of 1998, that contact had been to a Christmas party at Trimark, where they were looking for someone to write the next Leprechaun movie.
Doug hadn’t heard of the franchise. He went to Blockbuster, watched the first film and part of the second, and decided to take a shot.
Then came the deadline: a completed script in a week. The production was behind schedule, and they were going to move ahead with the best script they already had if something else didn’t arrive in time.
Doug wrote his draft in five days and delivered it on the sixth. He says the producer called later that day, liked it and asked him to come in the next day.
At the start of our conversation, I also introduced Doug as having had four other scripts optioned across four genres. An option and a produced film are different things, but his experience gives us a writer’s view of taking an idea into the work and seeing what happens.
The five-day draft was a particular script under a particular deadline. It followed earlier writing, mistakes and attempts to make connections. It isn’t a schedule you need to copy or a promise about how quickly you can write and sell a screenplay.
Unexpected, but earned
I’d recently read The Science of Storytelling by Will Storr, and Doug’s example reminded me of the discussion of unexpected change. What stayed with me in our conversation was the combination: something changes, it surprises us, and we can understand it.
Doug connects that with the way goals sometimes work in life. We make plans based on what we know. Events happen that we didn’t expect, and we may feel we’re getting farther from the goal. Later, we can look back and see that some of those events helped us reach the destination.
That’s the kind of relationship between journey and ending he tries to create in his stories.
If you want to try thinking this way about a premise or draft, these are useful questions to take from the conversation:
- What does the protagonist want, and where could the journey end?
- Could that outcome arrive in a form the protagonist doesn’t expect?
- Which characters’ goals or ways of pursuing them could create conflict that builds toward it?
- What might the character learn in the middle that changes how they understand the quest?
- What needs to happen earlier for the ending to feel earned?
Those questions give you a way to work on the connections. You can change the destination as you learn more about the story.
If you’d like to explore the related question of which scenes to draft first, What Conan the Barbarian Teaches Us About Writing Stories Out of Order (with Matt Click) approaches writing order from another angle. Here, Doug’s emphasis is on how knowing the ending helps you build what comes before it.
Choose a destination, then give the journey enough care to make arriving there matter.
The Make Existian Toast
Doug joined me in raising a glass at the end of the conversation. Whatever beverage you have nearby, join us in the Make Existian Toast.
May you slay false perfection, the old foe of done.
May you make all you dream of, and let making be fun.
And may you count who can make what you make -- only one.
Sláinte.
Fiction Writer’s Toolshed: Practical Tools for Authors is a Make Exist podcast hosted by Tim Kearney. It offers hands-on training for fiction writers to diagnose writing problems, build their skills, and finish more work.
Doug returns in The Business of Screenwriting: Pitching Scripts and Building Relationships to discuss researching buyers, staying flexible in a pitch and building professional relationships.