The world has enough bad stories—and bad sequels. We want to read and see new, better, and more fascinating stories. Why shouldn’t every book be a great book, and every movie be a great movie? I happen to know why, because it took me ten years to learn the nebulous art of storytelling. It turns out, writing good stories is one of the hardest skills to master. It was harder than getting my doctorate. In fact, it was like getting a Ph.D. in humility.
I intend to share everything I learned in twelve years of storytelling, writing four novels (two of which I tossed because the story was broken), and a memoir for a Wall Street investor.
I was already a polished nonfiction writer before I decided to become a storyteller. But writing well and good storytelling are very different creatures.
Why is learning story such a tough journey? Because in storytelling, there are very few useful textbooks, and successful authors are unwilling (or unable) to share what they know about story. Unlike many professions, there is very little mentorship in fiction writing. It’s the Wild West, and everybody is competing with each other for reasons that I still don’t understand since readers buy more than one book and read more than one genre. I want to bring the tradition of mentorship to the world of storytelling. By sharing with you everything I have learned, I’ll hopefully spare you a few mistakes—or even a decade of learning.
One problem with storytelling is that readers know better than writers. How is that so? Because readers have been consuming stories from when they were babies—in the form of bedtime picture books and fairytales. Writers, on the other hand, start decades later. As drivers, we know from a single test drive whether a car is a smooth drive or not—even if we will never know how to build an engine. As readers, we can distinguish a good story from a bad story—even if we can’t write one. Once writers start creating a story, however, they lose all objectivity, and can no longer judge their own work. With one exception. If you don’t peek at your story for six months, you will be your best editor—because you will see it as a reader. I learned that by writing two books simultaneously and avoiding looking at one for six months while working on the other.
What is a story anyway?
Very few people can tell you the definition of story in one sentence—or even three. The best explanations of story come from the movie industry. In Hollywood, everybody knows that story is money. No story, no nada. They also strip it down to its essentials, because screenwriters can’t hide behind la-di-dah prose, and they can’t make four-hour movies either.
Bill Idelson, a successful screenwriter, had the best definition I have found. It’s not even a sentence, but a diagram. A human stick figure on the left, a star on the far upper right—and a mountain in between. That is the simplest definition of story. Protagonist(s) has a dream or lofty goal (star), but to reach it, they must climb the mighty obstacle course that is the mountain. That’s it, folks. Try it on for size with any of the stories you love, and you’ll see how it fits. It may seem oversimplified, but Idelson’s diagram of story is in many ways an allegory of the human condition. We all have idealistic goals, but realizing them is grueling, because of the obstacles posed by the world, other people, and our own shortcomings. If your mountain contains all of those obstacles, it will have external, interpersonal, and internal conflict.
Most problems with story can be attributed to the three essential elements depicted in Idelson’s diagram. Sometimes your character is unlikable, and readers don’t really want to follow him on any adventure. At other times, the mountain—a series of obstacles—is not steep enough. Remember, the villain needs to be for real—and not just laughing his head off. Often, the dream or goal is too sappy or too self-focused. The goal can’t just be wanting to make more money or gain more power or privilege. Preferably, it either has some societal value—or it somehow recalibrates a sense of justice. In Good Will Hunting, the young man doesn’t just go from janitor to middle class professional, but he also solves a longstanding mathematical problem.
Once you have the skeleton of the story—who’s the stick figure, what’s the dream, and what are the antagonists that make up the mountain—then you have to decide what type of story you have on your hands.
This is important because readers have blueprints of different types of stories in their collective unconscious. This is what I learned from the best book on storytelling that ever existed in the English language. Christopher Booker should get the Nobel in Literature because he applied analytical skills of Einsteinian levels to study the stories of the world. It is one of the best applications of Jung’s collective unconscious that I have ever seen. What Booker came up with in his opus, The Seven Basic Plots, is that there are seven types of archetypal stories, and readers not only know them and can recognize them unconsciously, but they know when the writer is not meeting age-old expectations. A tragedy must end tragically, whereas a comedy must end happily. A voyage and return must end in return. A quest must end with the protagonists finding the prize they were seeking—or something of equal or greater value, even if it is intangible. A tragic hero is more deserving of his sad ending if he has selfish goals, such as power or riches. I can’t possibly summarize this extraordinary 700-page treatise on storytelling. You will just have to buy it. The first half is the meatiest part. Use it to plan your story—or to correct any story that is ailing. It has helped me problem-solve not just what had been out of place in my own stories—but all other stories I consume or attempt to repair.
If this sounds all too formulaic, don’t be fooled. Formulas are meant to be memorized—then transcended. Know what the reader expects—then give them something they have never seen before. This step is often what disappoints in sequels. In the Star Wars franchise, the destruction of the Death Star was great the first time, but not when the same plot was repeated in the sequels. In a good story, the audience should not know what’s coming exactly, even if they know roughly that the ending will bring relief. Otherwise, the story will not feel like a new and exciting adventure—but a walk down memory lane. A novel must feel new. The James Bond series has a light formula, centered mostly on character, but everything else changes from one movie to another. Bond, M, and Q—and the Martini—remain the same, as well as the mood of the ending. But the villain, the mind-blowing settings, the femme fatale, the love interest, and the obstacle course are wildly unexpected.
That brings me to why we consume stories. Some have speculated that stories are a way for us to learn vicariously the various mistakes made by humanity. Yes, there is some truth to that, though it hasn’t been terribly effective as a learning vehicle. Stories of hubris; tales of smarts and cunning in the face of a mightier opponent; and plots of an impossible challenge defeated all fall into this category. My personal opinion for why we enjoy story is this. Our brain evolved to solve very complex problems, which are extremely taxing and often high-stakes. Yet our very routine lives don’t require solving complex problems on a daily basis. So our brain is underutilized most of the time. After all, even a quantum engineer has to do the mundane tasks of emptying the dishwasher, cooking scrambled eggs, and driving to work. In my mind, stories offer a puzzle for the brain that it is emotionally invested in solving—for fun and make-believe. A story is a kind of low-risk, low-effort teaser for the idle brain. The best stories create some new sparks at the neuronal level. The car must be a smooth drive, sure, but in new terrain, with twists and turns and cliffs and storms—and a worthy destination at the end.
Some storytellers are naturals and have figured out all these things intuitively. They are lucky and few. But what’s funny about them is that they can’t always replicate their magic, because they simply don’t have the recipe. That is why their second novel or second movie is sometimes disappointing. So it is better to make the unconscious conscious, as Freud liked to say.
One of the hallmarks of a great story is a likeable protagonist. There are some master storytellers who manage to create amazing tales with unlikeable protagonists. Take John Kennedy Toole’s unsavory hero. He’s downright gross—but he does make you laugh. And in story, humor is like silver, precious but totally undervalued.
What is a likeable protagonist? A flawed one, who nevertheless displays greatness. Perfection is not endearing to readers. They need to identify with a human, and humans, alas, are simply never perfect. The character of Superman would be annoyingly perfect were it not for the fact that when he’s at work as the awkward Clark, Superman can’t even get a date. Just in case that’s not enough, kryptonite keeps him in check while he is in character. Similarly, Harry Potter is not the best wizardry student—Hermione is. What makes Harry Potter a great wizard ironically resides more in his humanity than in his magic wand. It’s his courage and loyalty that makes him stand up to Voldemort.
Many authors don’t know how to endear a protagonist to readers, so they take the overutilized shortcut: they kill his parents. Enough orphans already. You’d think orphans are having all the fun in the world. Just follow the simple rule: flawed but striving for greatness, and you can give the poor kid some parents. But the parents must stay away and not come to his aid.
Also, protagonists are only as good as their antagonists. The best mountain climber in the world can’t possibly display greatness when you ask her to climb a hill. Put your heroine under extreme pressure. The more grueling the trials, the more we feel for her, the more we admire her, and the more invested we are in her success. Only then will she come out cut like a diamond.
Greatness is defined differently depending on your story. It can be courage. It can be the perseverance to track down the truth. It can just be the smarts to survive a shipwreck or evade a monster. Or to learn how to die gracefully. It need not be saving the world, a cliché that probably comes from the sad fact that the world can now be destroyed by one temper tantrum. Remember the internal antagonists (e.g., insecurity) are just as important—and a way to show the hero’s inner growth.
Before you even write chapter one, start with the one-sentence logline, which Hollywood is really good at creating. It should identify the stick figure/protagonist, and either delineate or imply the mountain/obstacle course and the star/dream. For example, it’s about a composer who lost his hearing—and his struggle to write one last great symphony. If you can’t fit your story into a logline that mentions all three elements, then something is wrong. But you now have the first toolbox to fix it.