How to Write Engaging Stories

How to Write Engaging Stories

(This post was converted directly from a conversational 2020 Twitter thread.)

Let's talk about how you learn to tell engaging stories today.

This is one of the hardest parts of writing and the one that people struggle with the most without understanding what they're actually struggling with.

Most writing advice on this is bad, because just because you're a writer doesn't mean you're a good teacher. Many authors and writers have no idea how they actually create the stories they come up with. 

You hear a lot of stuff about "the muse flowing through you" and "writing your truth" and you hardly ever see a concrete explanation about how to craft a story that will resonate with your audience. I suspect that many writers don't think about their work mechanically. 

When I say that, I don't mean that they don't think about the craft of writing--obviously writers consider word choices, tone, grammar, style, characterization, plot, all of it... but I believe that most of us don't analyze the cultural osmosis that produces stories. 

I'm not going to go deep on the theory of storytelling here. Go read Campbell et all if you want that. What I'm going to do is explain concretely how to know if your writing will resonate and how to tell better stories.

But first, a story. 

I've wanted to be a writer for most of my life as far back as I can remember. I was an early reader with a love of books imbued in me by my mom, and often I related more to the characters in the books I'd read than the people around me in my day to day life. 

Despite harboring this desire to write for so long, I never actually did much creative writing. I didn't know what to write about. I didn't feel like I had anything interesting to say. I did a lot of op/ed and article writing, but fiction remained elusive and daunting. 

After I got a "real" job and spent a few years getting thrashed by the corporate world, I was pretty miserable and my mind kept flitting back to trying to "make it" as an author. But it seemed terrifying. Authors didn't make money, after all. Everyone knew this. 

Still, I realized I wasn't getting anywhere by letting my fear prevent me from getting started. I made it a personal goal to get better at writing and started making time to regularly try my hand at fiction.

But everything I wrote was boring and terrible. 

I remember this idea for a short story I had early on where I wanted to write about some young boys who meet up at their secret treehouse in the woods and hang out together. When I'd actually written a few hundred words of it, I re-read it. 

It was grammatically correct, had interesting characters with personalities, had a well-described scene, and it was excruciatingly boring. I couldn't figure out what I had done wrong. I was so frustrated. Why wasn't my scene coming together? Why didn't it feel right? 

I was in that weird creative space so many of us are familiar with where you're experienced enough to have good taste, but you don't have enough skill at the craft to see what you did wrong.

I knew my story sucked, but I couldn't explain why. 

Looking back, I can see the problem very clearly: It was just a vignette, like a photograph of a moment I had portrayed. It's not enough to just throw some characters into a scene and have them do things. That's not relatable or interesting. That's not what a story is. 

A story resonates with its reader because it tells us something about life. Interesting stories are interesting because they convey information about someone who did something and we get to find out what happened to them. 

This resonates with our brains on two levels: First, humans are creatures who learn by observation and emulation. We crave information about people who want the same things we want because we want to know what they tried in order to get it (or not). This is instinctive. 

Second, stories satisfy our emotional needs to feel seen and understood. We like characters that we perceive to be like us--characters whose motivations we can understand and whose decisions we can relate to, whether we're cringing at their failures or celebrating their successes. 

When I wrote about how to get paid for your writing, I explained that you're selling an emotional package when you go to sell a piece of creative fiction. The emotions have to appeal to the audience's genre expectations.

It's non-obvious how you make that come together. So many aspiring writers feel like they don't know what to write about, or they try to write something and it falls flat (like my vignette about the boys in the treehouse). 

But literally anything can be a story if you understand the structural mechanics of what makes these stories resonate. I was demonstrating this to some friends by spinning off stories made-up in real time about any character or scenario they'd throw at me. 

The secret is very, very simple:

Your characters have to want something, try to get it, and change in the process. 

If you finish reading a piece of writing and any of these things are missing, it won't be satisfying to you. It's going to feel flat and boring.

Furthermore, every single scene in the book has to relate back to those three elements in some way. 

One of the hardest things to understand when I was first learning how to write good stories was how to tell if a scene or a description or a character was "necessary" to my story.

You hear a lot of advice to only include "necessary" elements of stories and cut the rest, but no one was able to explain how I could tell when something was necessary. I'd spend time looking at my work and wondering if the color of someone's shirt mattered, or if I really needed to describe the interior finish of the building or not. How can you know? 

Once again, the answer is very simple: Does the detail provide information to the reader about your character's motivations, desires, goals? Does it help you understand the context of their decisions, actions, or circumstances that tie back to what they want? 

This is less complicated than it sounds. You understand context instinctively because you're bathed in it. Details like clothing color tell us something about the character who chose it, which in turn gives us clues about how they might act to achieve their goals. 

This is why it might be relevant that a character is wearing jeans (relaxed, utilitarian) but not what the jeans look like down to the stitching level unless it's unusual (boring, probably not something the character even considered). 

I could extend this out with dozens of detail examples, but we'll get lost in the weeds of nuance if I do that. Let's zoom back out and look at some concrete examples of how to form a good story mechanically. 

So often I see people pitch an idea that isn't a story: it's a setting, or a character idea, or a scene, but it lacks one of those key elements. This, by the way, is what you're experiencing when you're trapped by someone telling you a boring story at a party. It's often boring because it doesn't go anywhere. It's just a thing that happened.

You might have struggled with this yourself if you tried to tell a story about something that happened to you once and it felt incomplete. Did you want something? Did you get it? 

A story idea about a woman who lives in an apartment with her cat and goes to her 9-5 job and has some bad dates isn't really a story. Make her want something, make her learn something, and make her change in the process and you suddenly have characterization and plot. 

Your characters can't change without obstacles and struggle. This is where your antagonists come in, whether they're people or situations. Something has to be getting in the way of what your protagonist wants. It might even be your character themselves! 

This "getting in the way of what they want" is where your conflict comes from, because the character suddenly has a problem to solve. Their repeated attempts to solve the problem (as well as new emergent problems) create your escalating drama. 

All of this ultimately results in them getting what they want or not, as a result of the successes or failures of their repeated attempts to try. Brandon Sanderson discusses try-fail cycles in his fantasy writing courses, but they're applicable to any genre. 

Setting up this structure is a skill you can learn, and if you're struggling to know what to write about (or what should come next in your story) it's because you haven't honed this skill yet. 

A good exercise for this is to pick up short stories you really enjoy and analyze them through that lens.

  1. Make a list of characters in the story.
  2. Try to identify what each character wants and needs (maybe different!).
  3. Identify the actions they take in pursuit. 

You can map this out further by listing how each of those actions either moves them toward their goal or doesn't and note what changes in their behavior or personality arise as a result of each attempt. 

Getting stuck on a story or having a boring scene happens because you've written yourself into a place where a character is no longer pursuing a goal or is unable to take another step toward their desire but haven't actually come to a place where they've learned anything. 

You can "unstick" yourself anywhere in your writing by going back to those initial three questions. Usually you just need them to take another step toward the thing they want by trying to do something about it. If they stopped wanting the thing, your story is probably over. 

So if you're struggling with writing that feels like that vignette at the beginning, it's easy enough to turn it into an actual story. Let's revisit that: We have a few young boys in a treehouse in the woods. It's not a story yet. Why are they there? What do they want? 

Well, maybe they're horny, as teenage boys sometimes are. Maybe their parents are very strict and closely monitor all of their internet habits. But one of them found an ancient relic in grandpa's old trunk: a Playboy magazine from 1994. 

So they sneak off into the woods to read the magazine together because it's the only place they can do it without their parents finding out. For two of the boys, it's their first experience seeing a woman naked. They have very different reactions to it. 

They all read the magazine together and chuckle over the pictures and then go home. But one of them is horrified because his strict parents are religious and he feels like it was sinful. This leads him down a conflicted path of trying to struggle with his innate desire. 

Another feels like a whole new world has opened up to him and he starts sneaking more and more porn on the sly which leads into a tangled web of lying to his parents and friends in his community. 

By the end of the story, both of them end up changed by the experience and it leads to them having very different attitudes toward sexuality and themselves, and we see that evolution unfold up until their first real sexual encounter. It plays out differently for each. 

We get to see the impact of divergent choices and how each character's individual personality and actions shaped their changes that brought them to where they ultimately ended up. They got exactly what they wanted in the end (sex), and their experiences tell us something. 

What that something is depends on the message you want to convey in your story, and this will depend on you. This is where you inject your own experiences and observations about the world into the tale. Your truth. How does it end up? 

But all along the way, at each step, you'd be pushing them further toward that goal in the context of each thing that had happened already. It's a chain of actions and reactions. You can always ask yourself, "What would this character do next?" when you know what they want. 

If you don't know what your character wants and what's stopping them from getting it, you can't tell the story yet because you don't know how they need to change or what they need to learn. 

If you want to tell a fun story but don't know where to start, it's as easy as picking a character and giving them something they want. It can be literally anything. But you have to start there. Cool set pieces and powerful metaphors just act in the service of that. 

Once you understand and start applying this framework, you'll find that many of your issues related to getting started, moving a story along, or making your story compelling will simply vanish.