When Doing the Right Thing Still Feels Wrong: Building Moral Dilemmas into Your Stories

Part of the series Writing a Book from Start to Finish

By J.E. Nickerson | Wise Thinkers Help Desk 

Not every story gives its characters a clear line between right and wrong. Sometimes, doing what feels “right” comes at a devastating cost. And sometimes, the only choices available are all wrong—but your character has to choose anyway.

These are the stories that stay with us. They unsettle us. They force us to ask questions we’d rather avoid: What would I do? How far would I go? They remind us that morality isn’t always black and white—it’s gray, messy, and often stained with guilt.

Films like A Walk Among the Tombstones, John Wick, and the series Defending Jacob deliver this kind of tension brilliantly. And as writers, we can learn a lot from how these stories put characters in impossible situations—and then make them live with the fallout.

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A Walk Among the Tombstones – Justice at a Cost

Matt Scudder isn’t a superhero. He’s a former NYPD detective trying to stay sober, trying to live quietly. But when he’s asked to find the men who brutally murdered a drug dealer’s wife, his code of ethics starts to blur.

To catch killers who live beyond the law, Scudder has to work outside it as well. He partners with criminals, makes compromises, and accepts that the justice he delivers will be anything but clean. By the end, he hasn’t just faced evil—he’s let some of it seep into his own hands. As the expression goes, “If you gaze long into an abyss, the abyss also gazes into you.” When you spend too much time confronting darkness and evil, it can become a part of you. 

Lesson for Writers:

Push your characters to a point where their values are on the line. Then make them choose between keeping those values intact or saving someone who can’t save themselves. The cost of “doing good” should leave a scar.

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John Wick – The High Price of Vengeance

On paper, John Wick is a revenge story. A man loses his wife, then his dog, and the last threads holding his humanity together snap. What begins as a personal vendetta spirals into a full-scale war. But here’s what makes it powerful: John doesn’t get to be a righteous hero. Every choice drags him deeper into a world he tried to leave behind. Every body he drops costs him a piece of peace he’ll never get back. He has friends and allies, but even these individuals have motives of their own that conflict with John’s safety. Instead of being able to leave the life he had and grieve in peace, he is forced to “be of service” to the very people who caused the tragedy he is trying to recover from. 

Lesson for Writers:

Revenge stories aren’t about “cool kills.” They’re about the emotional toll of violence. As John Wick progresses through each story, the effects of survival in a world with grey morals wears on him. It grinds him down. Killing isn’t a sport as much as it is a way of surviving. When you write this kind of story, show the weight of choices. Show the wear and tear on the individuals. Make readers feel that with every action your character takes, they’re trading something they can’t get back. This kind of transformation isn’t clean and pretty. The character arch isn’t about the character becoming better or whole by the end. It’s a deconstruction of a life. It shows the effects of the choices the character is forced to make. 

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Defending Jacob – What Would You Do for Your Child?

Few moral dilemmas hit harder than this: Would you protect your child, no matter what?

In Defending Jacob, Andy Barber, a respected assistant district attorney, faces every parent’s nightmare—his son is accused of murder. Suddenly, Andy is torn between two worlds: the law he’s sworn to uphold and the family he’d die to protect. Every decision fractures something: his career, his marriage, his sense of right and wrong. His wife loses her job, questions her son’s innocence and ultimately has a mental breakdown because of the pressure being put on the family. 

The brilliance of this story is its intimacy. It forces viewers to ask, What would I do? Lie? Hide evidence? Destroy my own life to save theirs? The answer is never simple—and that’s the point.

Lesson for Writers:

Anchor moral dilemmas in universal fears. Protecting a child. Saving a loved one. The closer it hits to home, the harder it is to look away.

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How to Weave Moral Gray Zones into Your Writing

If you want to write stories that resonate, don’t give your characters easy answers. Give them impossible questions.

Here’s how:

• Make it personal. Forget saving the world—make it about saving someone they can’t bear to lose.

• Raise the cost. Every choice should take something from them: their peace, their values, their relationships.

• Remove the easy out. If your character can escape without loss, your readers won’t feel the stakes.

• Make readers complicit. Force them to ask: Would I do the same? Could I live with it?

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Why These Stories Matter

In life, we like to believe that doing the right thing always feels good. These stories remind us that sometimes, doing the right thing feels terrible. Sometimes, it leaves you broken. But it’s real. It’s honest. And it’s unforgettable.

When your characters face choices that leave no one innocent—when winning feels like losing—that’s when your story will haunt your readers long after the last page.

Looking for more articles that help you to make your story more gripping and connect your readers to your characters? Read the following articles to create characters that live beyond your stories and make your readers see the world in a different way. 

➡️ Writing Characters Who Grieve: How Loss Changes Them 

➡️When Good People Collide: Writing Conflicting Desires Between Likable Characters

Enjoying the content on this website? Pick up one of my books and discover more inspiration for the journey of life that’s rooted in faith, love and practical life lessons to carry you throughout your day and comfort your spirit. 

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✍️ Worksheet: Writing Characters in Moral Gray Zones

Part 1: Reflection Questions

1. Think about a character in your current story (or one you’d like to create).
   
   • What is their strongest value or principle?
   • What situation could force them to compromise that value?
2. Which kind of moral dilemma do you find most powerful as a reader or viewer?
   
   • Justice at a cost (like A Walk Among the Tombstones)
   • Revenge with consequences (like John Wick)
   • Protecting a loved one at all costs (like Defending Jacob)
     Why does this type of dilemma resonate with you?
3. Imagine your character makes the “right” choice, but it costs them something precious.
   
   • What do they lose?
   • How will that loss shape them moving forward?

Part 2: Writing Exercises

1. The Impossible Question
   Write a short scene where your character has only two options—and both are terrible. Make sure there is no easy way out.
2. The Scar
   Describe how your character carries the emotional or physical scars of their choice. (It could be guilt, a broken relationship, or a literal wound.)
3. Reader’s Dilemma
   Rewrite the same scene from above but in a way that makes your reader wonder: What would I do in this situation?

Part 3: Checklist for Moral Gray Zones

✔️ Is the dilemma personal (not abstract)?

✔️ Does each choice have a high cost?

✔️ Is there truly no “right” answer?

✔️ Will the fallout of this decision echo through the rest of the story?