How to Write Extraordinary Characters

I am going to give you a primer on How to Write Extraordinary Characters. This is a window into my philosophy, a good starting place for new writers, and hopefully will offer a few new ideas for the more experienced pensmiths as well.

I absolutely, to the depths of my soul, love characters. And talking about characters. Don’t get me wrong– I’m also passionate about beautiful lines, fantastic plots, and great structure. But ever since the beginning, since Star Wars and The Music Man, since The Last Unicorn and The Sound of Music — I have always been attracted to great heroes and arresting villains.

I especially blame Star Wars. How can such lines as ‘Do or do not. There is no try,’ not ruin you for other stories?

The Empire Strikes Back

Fast forward to today: Besides experiencing media as a fan, I’ve also been studying and writing seriously for over twenty years now, starting with screenplays and then moving into novels and now returning to film and TV. I’ve also started a successful local writing organization and taught classes on everything from writing love story that don’t suck (Twilight reference?) to ‘The Villain’s Viewpoint’.

And the heart of everything I’ve done is characters (some of those writing organization people were definitely characters!). So here’s the breakdown of my five steps for writing extraordinary characters.

Step 1: Find out who lives here

Usually, when I conceive of a story — an idea — it begins with a world. ‘What was it like in the 1950s when someone sneaking out their bedroom window and climbing down a rose trellis could still destroy their whole world?’ Or I’d see a mad scientist working on a cyborg in their laboratory in 1800s London. Or a captain facing a storm of wind and rain, but they are on solid land and they’ll never leave this place. Once these images and ideas entered my head, the next question is — Who lives here?

For me, the answer was: the girl climbing down the trellis was Claire Hanson, a fourteen year old who had always been ‘good’, smart, and quiet — but has now become involved (though not in the way you think) with the coolest boy in school, Tommy Delano (never gonna get tired of saying that name).

And the mad scientist was Tesla Jenkins, gifted with a genetic ability to manipulate metal and an utter lack of respect for the rules, and as uncouth as her twin brother is couth.

And the captain is Capt. Stairington, the leader of a way-station in the middle of a swift and endless current, an ocean that allows only one way travel. If you abandon this place, you can never come back.

Aivazovsky Ivan Konstantinovich (1817-1900) A Storm at the Nothern Sea from

Your stories may be more plot-driven. You may know you want a spy thriller set in the 1970s in Madagascar (!). Someone else’s idea could be more nebulous: A world where there is now only one government. Wherever you start, a first question is — ‘Who do you see?’ In my cases, I saw the (eventual) hero in the first image that appeared in my head.

But other ideas haven’t been that straight forward. I knew I wanted a Jane Austen-type story about a young heiress raised in the countryside that comes to London for the first time and finds both love and a lineage she never expected. But I didn’t know her and it took me a while to learn who she was.

Other good questions to ask are: Who is most interesting in this world? Who has the most power? The least? Who is in the most unusual position? Who has the opposite beliefs from your hero (they might be a good enemy, love interest, or even ally [or all three!])?

Sometimes you can also take an interesting world — I have an idea I call a ‘Star Wars’ killer — and blend it with a setup you’ve always wanted to do. I’ve always wanted to do a story where an average guy accidentally ends up with the chosen one’s object — thus throwing the world higgly-piggily. So I put those two ideas together and both got more exciting for me.

Whatever you’re doing, pick characters that are exciting to you. It could be a street sweeper or a god, but you should choose someone you’re excited to know more about, will have an active role to play in this world, and be a little bit weird to be the main character (I’ll explain more about that soon).

Step 2: If you believe there must be more, there is more.

Once you start to get a cast of characters, I suggest that you really slow down and get to know them. The point here is to move beyond the role (a teen girl, a sea captain) and start to see the person – the human — at the center of the story.

I choose to believe the character is out there — whole, perfect, and believable. You just have to dig deep enough to unearth them in all their brilliance. With my first great character, Maurice the joyful follower of the god of Darkness, I came to a time when I felt like he could do anything, and it could fit into his character.

I’m not positive what I mean by this but I think it is that — with living people — we can imagine a situation where they might do something out of character. Your mom might stab someone with a knife — to protect her children. You might break someone’s heart — because your heart was already breaking. A great father might up and leave his family — if he believed his destiny lay in a new path.

In life, we believe in actions outside the margins because they exist. Sometimes the long-shot wins the race. When you get your hands on a great character (because it can feel like they just appear from elsewhere), they can surprise you, sometimes often. They will make choices you didn’t plan on, that you don’t want, but you should follow them and follow their story — because where they lead is magic.

But how do you move your character from a role to a living, breathing human? I used to fill out those sheets about eye color, height etc. Now, that doesn’t hurt anything but… Knowing someone has Hazel-Green eyes doesn’t tell you that they stopped crying forever the day their father died and they don’t know why. And Mister 6’2″ is not a interesting character, whereas Mister Lost-My-Wife-and-My Shrimpboat-in-the-Same-Hurricane could be.

Instead, I like to think about these people over weeks or months, hearing conversations between them in my head. Other things I’ve found useful are making a playlist of songs that speak to the characters or the mood (even the lyrics don’t always matter if the feeling is right); finding an object or piece of jewelry they would carry with them; or just going for long walks in the woods, listening to the playlist and thinking about the story, the possibilities.

My newest idea is to type up a Q & A interview-format conversation between two of the characters in your story. I’ve discovered some amazing revelations and great dialogue doing that. I wouldn’t use this technique all the time, or for every character, but it is very powerful.

Also, remember every character — and every person in our world — is a mixture of experiences, beliefs, goals, and challenges. There aren’t any bad guys and good guys, no black hats and white hats. Even if they fill that role in your story, try to understand the humanity of even your worst villains and see the flawed cracks in even your best heroes.

‘John Wick’. Photo from

Step 3: Trust your character.

On my wall, for twenty years now, there has been an increasingly faded index card that reads, ‘Trust the story.’ To me, it means that you have to follow your heart and your interests and believe in the weird and wonderful, the unforeseen and the unforgettable. To let a strange and most forbidden story lead you over the locked gate and down the wayward path.

In the same way, trusting your character is an act of faith. Your plan involves a plot, conflicts, love stories, certain intense showdowns as the story wraps up. In screenwriting especially, many gurus and books can get you to ‘pretty good’. They’ll teach you what viewers expect to happen twelve minutes in, how to have rising tension, and in what act your characters should have a ‘reversal of fortune’ (probably all of them).

And while that’s specific to writing for film, we all do something similar when plotting out our stories — we make the best tales we can imagine based on what we’ve seen, and experienced, and learned about.

But here’s the thing — there’s someone ‘other’ in writing. You can call it God or The Universe or The Muse, or your unconscious self, but something happens when you write a lot and trust in what you’re writing. One day you’ll wake up, sit down with your coffee and laptop — and the wrong thing will happen. Your characters will rebel; your careful plots will go out the window, your plans will get jostled, and you’ll hate/love it.

In that moment, stop. Take a breath. And be grateful. This is the beginning of everything you want in writing. Because that other, that unexplored part of yourself, is wilder and more beautiful than all the standard plots devices and well-placed climactic arches in the world. It doesn’t care that you’ve never heard of a salamander-raising, shotgun-totting ‘Wendy’s’-employed spy before — it wants you to write the first one. That voice will write that your hero’s suitor doesn’t ask her to marry him, but instead flees for Tibet. What’s your romantic comedy to do now? That otherness in your writing will one day tell you to turn an enemy into a friend or vice versa, or kill off half of your cute couple, or reveal that the kindest man in your story murdered his whole family when he was young.

Now you don’t have to listen. You can write what you want. But I think a lot (maybe most) of my greatest writing comes from this wilderness. Sometimes it’s small — the odd phrasing in a single line that somehow sums up a character. And sometimes it’s a titanic shift that changes the entire ending of a book (which became my best novel so far).

And you get to this place by writing a lot, by reading, by watching great movies and plays to learn how many weird and wonderful ways there are to succeed in storytelling, by learning the rules of writing so you can break them, and most of all by trusting yourself and what stirs your soul.

So when your character speaks, listen. Let’em be weird. Let them be as refreshing and bold as when Katharine Hepburn’s character in ‘Bringing Up Baby’ says, ‘I was born on the side of a hill…’

And allow for the ‘wobble’. Wobble is when something doesn’t quite fit in you story, isn’t quite supposed to be there, a line that heads off the margins of the page… If your story is strong, we’ll love that the hero has a great fear of returning to Bangkok and we never learn why. The wobble haunts, suggesting that you are seeing only part of a larger world.

Step 4: Push your character… off a cliff.

Once you have a world you’re interested in and characters that are starting to break the mold of ‘cop’, ‘hero’, or whatever else, and are interesting to you, then it’s time start fuckin’em up — uh, I mean, challenging them.

When your characters enter any situation, you want to be in that place. Really see it. Slow down. Look around. Listen hard to the words people are speaking there. For Claire, my rebellious 1950s teen, what people said sometimes set her off or made her life harder. Not just disagreements with her parents, but certain phrases made her challenge friends or even the boy she liked. He might say something thoughtless, and I, the author, would murmur, ‘No, no, let that pass. You like him. This is the ‘Sweet, getting to know each other scene.’ And instead, Claire would challenge the boy on what he said, turn it into this whole debate, go home, and then the boy would catch up to her later and they’d have this amazing talk. All because I heard his words clearly and wrote her response honestly.

In the same way, try not to ‘ex machina’ your way out of problems for the hero. If they have no money for a plane ticket to Buenos Aires, let that be the truth. Sit with that problem. Think about it. Let your hero stew. The resulting solution may be more funny or dramatic than you planned — and it will certainly be more satisfying than suddenly having their great aunt bump into them at the terminal and offhand have an extra ticket (please, please…for me… never do this).

Never. 😉

Great characters are forged out of great conflict. This doesn’t mean fighting people and things all the time; it means placing them in situations that challenge their fortitude, integrity, ingenuity, humanity, humor, and humbleness. Put them between the rock and the hard place. But that ‘hard place’ may be finding a kind word to say to their stepfather, or stopping in the middle of a chase to help an old lady cross the street, or staying quiet about their big accomplishment when they realize their friend has had a hard day.

If we don’t push our characters into these situations where they will grow, then they become slightly like cattle: you usher them from one pen — or scene — to another, placing them in the right spot for the moment and they do more or less what’s expected of them. ‘Yeah, yeah, I’ll go save my girlfriend from the terrorists.’ Moooo.

But. What. If. He. Doesn’t? WHAT??? Suddenly that’s interesting. Maybe he didn’t love her. Maybe he was afraid. Maybe he was part of the terrorist cell and this was all supposed to be a ruse. The point is, your story isn’t about saving his girlfriend from the terrorists. It’s about him saying no, and the story picks up five years later — the real story — and you find out that these terrorists have now gone too far and our hero finally, finally is going to do something about it. But how much more interesting is that story going to be, because he’s guilty, he’s covering something up, he’s got grief — and beefs — aplenty. I’d watch that story today. And I’m sure some actor would love to play that character.

There’s a quote by Fred DeVito that says, ‘If it doesn’t challenge you, it doesn’t change you.’ Danger isn’t enough. Arguing isn’t enough. If the only challenges your hero is facing are plot-related, you are missing a world of possibilities. We know they’ll ‘hide from orcs’ — everyone would. We know they’ll argue with the know-it-all about the better path for the group — that’s expected. We know they’ll be tired but carry on — that’s what leads do. And it’s not wrong to have them do these things. But…

You want your hero to grow into the person they are meant to become, for good or ill. And we grow outside our comfort zones. When the villain makes a surprisingly good point, when the love interest says something unforgivable, when the evil boss hands out a promotion instead of a pink slip — our heroes have to grow, to change, to soften or stand firm, to reevaluate who they really are and what they really want.

A challenged hero is a fantastic gift to an audience.

Photo from Harper’s Bazaar

Step 5: Your story will only be as good as your characters.

For me, playing with character is one of the most fun parts of the job. And it’s an ongoing task through every part of the writing process. From character creation and trusting yourself and your story in the first draft, through rewrites and beta readers, your characters will continue to learn and grow as long as you write about them.

After your first draft, let the story ‘rest’ for a week or more and then return to it with fresh eyes. Pay special attention to each character and their journey — is there a scene missing in that journey, or does it make sense? Do you need to add something earlier that explains a character’s decisions later?

Most of all, if you’re not happy yet, keep digging and unearthing your characters. Write her ten-page, first person backstory. Write the speech the villain would have written if he had won. Let her niece tag along on the adventure — how does that change things?

To me, characters are the jewels in the crown. No matter how great the metal, the style, the craftsmanship — it’s going to look bad if you have broken stones, or plastic ones, or some important jewels are missing.

In the end, the secret to great characters is just caring a lot about the outcome, examining how other people do great heroes and villains, casting a curious eye on your fellow humans, and — in your writing — be willing to slow down, look deeply, and challenge your first impulse or the status quo.

Orson Scott Card said to take a character and then turn them 180 degrees to see if that worked better. Your character hates his mother? He loves his mother! She’s the hero of the city? She’s the most hated woman in the city! See if the opposite would be more interesting than the planned.

And the more time you spend writing the easier it will become to find those weird, memorable, and challenging characters, and the more you’ll trust yourself to follow them on the storytelling adventure of a lifetime.

And remember, Donald Miller said, ‘Fear tricks us into living a boring life.’

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