Hero’s Journey Trials: How to Fill the Middle of Your Story with Conflict

by David Safford | 0 comments

If you've ever written a book, you know that writing the middle of your story is tough. There's a reason the saying “muddle through the middle” is common language in a writer's conversation. Your protagonist must face the Hero's Journey Trials and make Allies and Enemies in these moments. Let's look at how it's done. 

trials hero's journey

When you master the Hero's Journey's twelve steps, an age-old story structure theorized by Joseph Campbell, constructing the middle of your story—full of tests and trials—gets easier.

In this article, you'll learn writing strategies to help you raise the stakes and successfully develop one of twelve important steps in the Hero's Journey—and the longest one at that.

Here's what to do.

The Hero's Journey: How We Got Here

Professor of mythology Joseph Campbell originally published his “monomyth” about stories in his book The Hero With a Thousand Faces. For those who want the condensed version, they need look no further than the work of Christopher Vogler, who summarized much of Campbell's theory into a twelve-step journey, known commonly as The Hero's Journey.

One of the greatest aspects of this monomyth is that it applies to ancient as well as modern stories. It teaches writers about common archetypes and characters who tend to appear over and over again, representing humanity's changelessness in time. These archetypes are derived from much of Carl Jung's work.

To reach the middle of the story, the hero must take several journey steps. First, they must depart their Ordinary World, after a Call to Adventure, and Initiation stage, wherein the hero will meet a Mentor who prepares the way. Readied by the mentor's teaching, the hero ventures of the ordinary world into the new, special world, often in a scene that pits them against a threshold guardian, like a monster or representative of the story's enemy.

All of these work as a previous step that drives the hero to this next important stage.

Once the hero has succeeded in leaving home, it is time for the next stage in the Hero's Journey: The series of Trials, Allies, and Enemies.

Want more help on The Hero's Journey? Take our three part class here and learn how to use The Hero's Journey to craft stories readers can't put down.


Step 6: Trials, Allies, and Enemies

Let's begin with a simple explanation of this step.

The middle of a heroic journey is filled with Trials, Allies, and Enemies. These are scenes where the hero faces challenges that improve their skills, meets and befriends strangers who join the hero's journey, and encounters characters and creatures who oppose the hero's progress and aim to destroy them. All of these scenes come together to move the hero toward the final confrontation with the Shadow in order to obtain the final goal.

Take a break to think about this for a bit but looking at Harry Potter:

After Harry Potter boards the train to Hogwarts, he immediately meets Ron Weasley, who becomes an ally, and Draco Malfoy, who becomes an enemy. Both characters will be essential for aiding or initiating conflict that Harry must face in the middle of Harry Potter and the Sorcerer's Stone, and much of the series.

And all of this builds Harry's skills and relationships that will be paramount in the climax of the book.

Overall, step six in the Hero's Journey tends to be the longest in the story, often taking up most of act two. However, it isn't formless or without direction. It is the the bulk of your hero's growth, and it must be developed intentionally and carefully.

Let's learn how to make the middle the absolute best part of your writing experience!

Fill the Middle with Tests and Trials

The purpose of a heroic story's Middle is to refine the hero through a series of tests. While they ultimately acquire some skill and knowledge from the mentor, the hero still must be unprepared for the ultimate challenge that lies ahead: Facing the Shadow. That's why your story's Middle should be filled with Trials.

This is all part of a common journey and stages in a classic tale.

A trial is some sort of test that measures the hero's ability, worth, or talent.

These tests can take multiple forms:

Physical Test

The hero must prove their worth through strength, stamina, or skill. We see this when Harry impresses his classmates by skillfully riding a broom in Harry Potter, and Katniss demonstrating her ability with a bow before the gamemakers in The Hunger Games. In classical mythology, Odysseus's escape from the Cyclops's cave is a prime example you may have read in high school.

Mental Test

The hero must demonstrate superior intellect or wisdom. For Woody in Toy Story, this involves figuring out how to outwit the sadistic Sid and escape his house of horrors. In classical mythology, this is easily seen when Oedipus answers the riddles of the sphynx in order to redeem Thebes.

Spiritual Test

The hero must prove their loyalty to God, the gods, or a spiritual power. This is clear when Luke Skywalker uses the Force rather than his targeting computer to destroy the Death Star, a move that sets him on a colision course with Darth Vader for the trilogy's ultimate act of spiritual purity, rejecting the Dark Side.

The tests must strain your hero's strength, mind, and spirit, humble them, and then allow time for triumph/ defeat, recovery, and then reflection.

No matter what, the purpose of the trial is to push your hero past their limits and reveal his or her true nature. Part of what makes a heroic journey so special is that it shows why we need to be forced out of the duldrums of mundane life and forced to do something special. A heroic story is such because it abandons the ordinary world, which is true to its title, and explores the special world that lies beyond: The world of adventure.

That adventure MUST test your hero and force them to adapt and grow, or else it won't be interesting, and it won't be heroic.

To that end, never put your hero into a trial merely to show how “awesome” they are. This may seem cool in your mind, but for a reader it is quite boring. Readers want to see a hero work through a nearly impossible problem and triumph in the end. If you deliver anything but, and your story will be a disappointment.

Fill the Middle with Allies

In the Middle of your heroic story, your hero will also make friends. These are often chance encounters that begin anxiously, only to produce friendships. Consider the Indiana Jones franchise, where Indy travels from continent to continent, meeting people who know something about the MacGuffin he seeks.

In Raiders of the Lost Ark, he first meets Marion Ravenwood, an old flame who hates him. While she seems friendly at first, the audience experiences shock with Marion smashes an empty bottle over Indy's head. Is she a friend? Or an enemy?

Then we meet Sallah, an Egyptian foreman who is helping the Nazis search for the lost ark. From the beginning he strikes us as an ally . . . but will he remain true to Indy?

Great heroic stories are filled with supporting characters like these, most of whom are met somewhere along the journey. This is also a core principle of a hero's journey: Our ordinary lives rarely contain all the characters we need in order to become our best selves. We must travel to a distant land, whether in body or spirit, and reach outside our comfort zone for new, challenging relationships.

Here are some common character types your hero will meet:

Loyal Retainer

Some characters will be what's known as “Loyal Retainers,” Allies who remain true to the hero. In other words, they “retain,” or keep, the hero's values and goals.

They may fall away due to frustration or brief disagreements, but never forever. Ron Weasley is the perfect Loyal Retainer for Harry Potter, as he is the boy-who-lived's best friend. Sure, they engage in difficult spats, but never for good. Ron always comes back because of his incredible loyalty.


These characters are tough to pin down due to the fact that they will be loyal one moment, but traitorous the next. These characters tend to appear in the mysterious adventure where the hero is in an unknown land, unaware of what may be lurking in their blind spot.

The Shapeshifter is frequently a self-serving character whose alliances are fleeting. Captain Jack Sparrow of Pirates of the Caribbean is a classic Shapeshifter, changing sides with the tides.

Damsel in Distress

As long as there have been hero journeys, there have been women in need of rescue. Of course this trope is dated and sexist, but there is truth behind the fact that bad men do bad things to women.

Some authors like to flip the script, making a female the hero and the man the damsel. Other times, like in Pixar's Ratatouille, the damsel will be anything but, often behaving more fiercely than the men around her.

As you write your heroic journey, sketch out some encounters for your hero. Consider how you can make your hero uneasy. Rarely write a scene where an ally is 100% trustworthy, and instead come up with reasons to keep your hero—and therefore your reader—on edge.

Fill the Middle with Enemies

Finally, the middle of a great heroic story features lots and lots of monsters, Enemies, and obstacles. Sometimes the enemy is in hiding, posing as a friend. But more often than not, the enemy is an obstacle blocking the hero's way. Sometimes the enemy is a character or creature in pursuit of the MacGuffin or possessing a crucial tool the hero needs to defeat the Shadow and/or obtain the MacGuffin.

There are several kinds of Enemies you can employ, and each should be somehow related to your story's ultimate bad guy, the Shadow:

Another Threshold Guardian

Your hero must overcome a minion of the Shadow, a devoted servant who believes what the villain believes. Bad guys tend to be the “bosses” in video games and the stars of fight scenes in the middle of action movies.

A great example of a villain in disguise is Bathilda Bagshot in Harry Potter and the Deathly Hallows, a walking corpse who is secretly harboring a deadly serpent that is ready to strike.

A “Monster”

Monsters are evil creatures that the Shadow uses to stall the hero, or natural creatures that live in the unsafe, foreign special world the hero must travel through. These are trolls and orcs in The Lord of the Rings, or tyrannosaurs and velociraptors in Jurassic Park. 

Classic tales like The Odyssey are filled with them: The Cycopes, Scylla, Charbydis, and more. Never skip the opportunity to feature a great monster in your story!

Natural Obstacle

Not all problems are human or animal. Your hero's progress may be guarded by a natural obstacle, like a canyon, bridge, wall, thorn bush, and so on. The special world should be filled with natural barriers that the hero doesn't normally face at home.

These are unique opportunities to show your hero's emotional state during the journey; how do they handle these new challenges that never appeared during the old, mundane life of the ordinary world?

Throughout your story's Middle, there must be Enemies and obstacles that impede your hero's path, filling them with dread, pain, and struggle. And while your hero will always overcome these mid-story Enemies, they must leave wounds, physical and emotional, that your hero can't easily get rid of.

This, too, is an archetype:

The Unhealable Wound

For example, in The Lord of the Rings, the Ringwraiths represent a formidable act one enemy hunting Frodo and the hobbits as they flee the Shire.

In the climactic moment of these journey steps, the Nazgul find the hobbits on Weathertop and one of them stabs Frodo with a cursed blade. What follows is a frantic sprint to Rivendell. While Frodo is healed of the wound's immediate effect, it never truly heals, and on the anniversary of the stabbing each year he falls ill.

This kind of unhealable wound is a powerful way to leave marks on your hero as they strive to achieve their goal. It makes the middle matter. When you put your hero in a literal house of death, fighting to survive, and the story is only midway over, your reader will struggle to put the book down.

Dont' save your hero's struggles for the very end. Fill the middle with one struggle after another, forcing them to face their fears and weaknesses. It's the only way they can grow and become the inspiriational figures readers long for.

Handing Death in the Middle

It's not uncommon to place a major character death in the middle of your story. This could be a mentor or loyal retainer, but it's essential that the character be of great importance to your hero. This has several benefits to your story, as morbid as it may sound.

First, you add the benefit of the “supernatural helper” archetype, or the “voice from the heavenly land.” Consider how Obi-wan Kenobi speaks to Luke during the finale of Star Wars, saying, “Use the Force, Luke!”

While you may not (and probably should not) have a literal voice speaking from the heavens, you do want to force your hero to internalize the lessons learned from the mentor OR the precious memories of the loyal retainer who has been sacrificed.

Faced with the immediate consequences of their journey, the hero is required to reckon with the cost of what is happening. Quests for physical objects almost immediately become supernatural adventures with deep, moral stakes.

You also don't have to pull the trigger. It's entirely possible to sideline a character with a lasting, debilitating injury. This, too, can be physical or emotional. While this won't have the full power of a character death, it might be a better fit if your story doesn't involve life and death stakes, or killing a character off isn't the right choice for your story, book series, or style.

Master the Middle

How does a writer figure out the tricky Middle of a heroic story?

And how can you figure out what to do with all of these Trials, Allies, and Enemies?

Plan, dear reader. Plan. 

I recommend a bubble/mind-map strategy, listing and linking all the possible Trials the hero could endure, all the potential allies they might befriend, and the necessary Enemies stalking the hero and trying to end this journey early. List, link, detail possible scenes, and decide what steps your hero needs to take in order to be ready for the ultimate showdown with the Shadow.

Because it's coming. The Shadow must be confronted.

But not yet. For now, your hero has to struggle, and the Middle is the perfect place to make that happen.

What Trials, Allies, and Enemies can you think of from stories you love? Let us know in the comments.


It's time to starting throwing everything at your hero, including the kitchen sink. Take fifteen minutes to brainstorm a trial your hero might encounter in the middle of their journey.

As you freewrite your Practice, try to throw in each of the follow elements of your story's middle:

  • A character who will be an ally
  • A character who will be an enemy
  • A trial or challenge of some kind

Don't worry about perfect structure. Just try to brainstorm a moment when your hero collides with each of these crucial “middle” elements of your story!

When you're done, share your writing in the Pro Practice Workshop here! Then read other writers' practices and leave them a constructive critique!

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You deserve a great book. That's why David Safford writes adventure stories that you won't be able to put down. Read his latest story at his website. David is a Language Arts teacher, novelist, blogger, hiker, Legend of Zelda fanatic, puzzle-doer, husband, and father of two awesome children.



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