20 Questions 8 - What to ask about your story’s ending

The ending of your story is your last chance to make a good impression. It's also the part of the story that can disappoint or alienate readers (or the audience).

Many writers won't even begin a project unless they have a strong ending in mind. And many people who write by the seats of their pants abandon stories – even novels and screenplays – because they can't get the pieces to come together when they come to the big finale.

Every ending is a little different, and one of the most useful exercises I found is simply documenting endings that I'm most passionate about and trying to understand why they succeeded. This isn't so the ending will be copied in any real way. It's more a way to increase my range of options and models for comparison. Whatever ending I draft out gets looked at very closely. This is even more true if I start with an ending because it becomes the foundation on which everything is built.

With this in mind, I'll conclude this 20 question series with questions you might use to explore your own endings.

1. Is the ending clear? Yes, it is fair to have an intentional level of ambiguity. My favorite example of this (spoiler alert) is the spinning top at the end of inception. Does it continue to spin – demonstrating the protagonist has not returned to reality? Or does it fall over? To me, that was fun. To others, it was frustrating. So imagine how frustrating it must be when you're ending has less clarity because it is written sloppily or you yourself don't know what happened. Readers make investments in your work – of time and sometimes of money. Don't annoy them.
2. Is the ending fair? This is easy to answer for most mysteries. If the clues are there when the reader looks back at the work, it feels like a cheat. When lovers are shoved together in a romance without a change in (at least) one of them, there is a falseness about the story that's hard to overcome, no matter how happy the characters are in the final scene. Worst of all, is it a deus ex machina, a tossed in settling of affairs based on the effort of someone other than the main character.
3. Is the ending earned? Does the hero overcome the villain without luck or a change in the rules that were set at the beginning of the story? As the writer justify any surprises near or at the end? Do the obstacles reaching toward the ending get more difficult? Does the power of opposing forces increase rather than diminish? Has the protagonist made a sacrifice that mattered?
4. Is the story at the ending the same story the reader started with? If it began as a comedy, did it end that way? If it began as a romance, did shift into a thriller? Combining genres is fine, as long as you don't pull a switcheroo on the readers. Beyond genre, one teacher of mine made a good suggestion: Expose your (story's) "color palette" in the first chapter or two. And don't deviate from it.
5. Is the story question answered? By the end of the first act, there should be a question that keeps the reader turning the pages until the very end. While smaller questions may occur at the beginning to hook readers, one question (Will Luke destroy the Death Star?) should dominate the story. This actually constitutes a promise to the reader. Breaking that promise will wreck the ending.
6. Does the story end too early? Are there too many loose ends? Does the reader have time to experience the emotion before putting down the book or leaving the movie theater? Is it unintentionally abrupt?
7. Does the story end too late? Can any of the verbiage after the story question is answered be reasonably cut? Does it have a real purpose? (One story I hate to this day spent a dozen pages after it should've stopped tying up loose ends that I couldn't make myself care about. It undercut everything that was positive about the book.)
8. Is the pacing right? Obviously, the pacing of the whole book needs to be right, fit for the genre and designed to keep the reader engaged. Usually this means that scenes and chapters are shorter near the end. But the main elements of the ending should be laid out not just with a sense of increasing tension, but with a real sense that revelations are not too crowded together and there is room for an emotional response. (How this works is often directly related to who the reader is.)
9. Are all the important loose ends tied up? This is especially important if there are engaging supporting characters and subplots. I've seen writers, so happy to have dealt with the meat of their stories effectively, neglects to give appropriate finishes to these "minor" elements.
10. Is the ending sticky? Does it resonate with the reader? You want the ending to be memorable and provocative. Both readers and writers benefit when the ending captures the imagination or leaves the reader just enough work to do so that people can't resist talking about it.
11. Is the ending expected? Obviously, surprises are good. But if nothing of what is expected is delivered, that's perilous. Readers need to have some level of anticipation that's valid. While, for instance, the most obvious suspect in a murder mystery getting arrested at the end can be flat, exposing the real murderer should include an element of "I should have known that" or "that makes sense."
12. Is the ending unexpected? Does it include, without cheating, a twist not anticipated.
13. Is the last sentence as powerful and memorable as it can be? While it is not good idea to have a last sentence that doesn't feel organic, it's a shame to waste the opportunity to give the reader one more gift. Do this even if you have to rewrite the last few pages to set up that one sentence appropriately.
14. Is the ending thematic? This may be a difficult thing for those who begin their work with an ending to answer. Often, the themes the stories emerge with the writing. But the main message or the story proposition needs to fit neatly with whatever ending is in the final draft. So, however you work, save this question for the time when you think you're finished.
15. Is there a roll in the ditch? That is, to the hero and the villain face each other directly in the ending? This can't be done by proxies. It must be personal.
16. Does the entity include a legitimate revelation or surprise? Did you give the reader one more important insight at the end that adds a dimension to the story?
17. To all the important surviving major characters get to play a part in the final few scenes? Comedies almost always do this. In fact, classically, comedies and with a party, wedding, or some sort of celebration that pulls together everyone. It's less important in a drama, but it still can add power to the conclusion of your story.
18. Does the ending include difficult action by the protagonist that makes a difference? The main character needs not only to act in the end, but to personally bring about the ending.
19. When a reader finishes, are there unintentional doubts created that distract from the story’s conclusion? An ending is much less satisfying if the reader can think of one that is equally (or more) satisfying while being equally (or more) logical and likely.
20. Does the ending create a memorable picture? Is it visually striking? Is there an image that sticks in  the reader’s head?

That's it. As usual, some of these may be of more value than others as you explore your story. But I hope you find a few that make the conclusion to your story powerful, satisfying, and resonant.

20 Questions 7 - What to ask about your story’s beginning

Beginnings are the way you and your story are introduced to readers (or the audience). Consider why someone might have come to your story. Perhaps, to be entertained. Maybe to learn something new or to experience a time, culture, or situation about which they know little or nothing. Some people come to stories to be distracted or consoled. Some come for lessons and comfort. And some are attracted just by the beauty of the language as expressed through a fresh voice.

Almost everyone comes to a story for emotion. The promise of a thrill or a laugh or a good cry must be there from the start or another story, which will provide what the reader is looking for, will be selected instead.

It's also the writer's responsibility to keep the reader engaged. New writers especially do not get much leeway on this. The benefit of the doubt – is this worth my time? – may not last any longer than the first few sentences.

To help you bulletproof your beginning, I developed these questions. Not all need to be answered. (You know your story and your audience.) But I hope at least a few will help you to spruce up and make a good first impression.

1. Does the beginning raise questions? It doesn't necessarily have to jump right into the story question, but there should be at least one question that causes a reader to turn pages.
2. Does the story move? Without bullets flying or death-defying leaps, is there sense that you've dropped into something that's already in progress? 
3. Is the reader spared a slog through description and back story many skip past nowadays?
4. Does the story sound promising from the first few sentences? Is there an intriguing hook? Or an arresting opening image? Or a line of dialogue that would make you eavesdrop on the subway?
5. Is it clear? While mystery is okay, readers should believe that everything in the first pages will make sense sooner or later. And they should not need to reread any of the sentences.
6. Does the reader know who the main character is? Do they know who they are supposed to empathize with?
7. Is empathy supported? While characters don't need to be likable, they do need to have human experiences that matter emotionally illustrated within the first few pages.
8. Do readers know the stakes? And are they high enough to worry about? Do they create a sense of foreboding were tension?
9. Is the setting expressed with enough detail to allow the reader to participate? Is there enough description and enough stated so the reader can follow the path to immersion in the story world? Do indicators, early enough so that the reader does not need to revise initial impressions about the setting (unless this is intentional, as is sometimes the case in speculative fiction and comedy)? Note: setting includes era, season, and time of day. Not just place.
10. Is there a perspective, the use of language, or a voice that elicits confidence and may even charm the reader?
11. Are the rules of this world, even if it is mimetic, presented so all that happens can be understood and the reader will not feel anything that occurs is a cheat or unfair?
12. Are there hooks? Does the writer plant intriguing and question-raising information from the very start and throughout the first pages of the story?
13. Is anticipation built? Does the reader quickly have expectations that will be fulfilled, exceeded, and manipulated for surprise and delight?
14. Are clichés avoided? Both in terms of phrases and situations (waking up, arriving, dealing with amnesia).
15. Does the story, even in the first few pages, hint at the overall theme?
16. Are the senses engaged? Is the reader encouraged to experience the story in ways beyond just hearing and seeing and are these in a reasonable and natural balance with the material?
17. Are the scenes in the beginning of the story well-constructed, with clear motives, beginnings, middles, and ends?
18. Within the first few pages, are there any surprises? Does it go beyond the expected in ways that promise entertaining revelations?
19. Is it clear within the first few pages what the genre is? Will the reader know what kind of a book he or she picked up after the first few pages, or, for instance, will they be liable to experience disappointment when they realize that sexy romance is really a horror story?
20. Does the reader have a reason to keep turning the pages after the first scene, the second scene, the third scene, and however many scenes make up the beginning of the story?

It's easy to see that wonderful beginnings are difficult to write. Here's a tip -- don't worry consciously about any of these during the drafting stage. Keep these questions for the rewrite. Also, when drafting the story, be aware that you probably won't know the ideal starting point until you are well into the work. Many writers aren't clear on where the story begins until the first draft is done, and it is very common to end up cutting the first pages, scenes, and even chapters. Does this sound discouraging? There's no reason for lamentations. It's just part of the process that reveals the best beginning to bring to your readers.

20 Questions 6 - Villain vivisection

Not all stories have villains, but all commercial stories have antagonists. Man against man, man against nature, man against himself — you know the drill. And if you've been a storyteller for any time at all you understand the value of having powerful antagonists.

Character change is a big part of why we come to stories, and a good antagonist, opposing the hero or heroine, forces change. So it's worth digging more deeply into your antagonist to be sure you're getting everything you can out of him, her, or it.

I've listed 20 questions that I hope will be helpful. I focused on the idea of a villain, but it shouldn't be too difficult to interpolate these questions to whatever antagonist you have in your story.

1. Is your villain active? Does he or she plan and execute work that impedes, distresses, and discourages your protagonist?
2. Does your villain take advantage of the flaws and weaknesses of your hero/heroine?
3. Does your villain go as far as possible in creating havoc and damage? Is the harm done extreme and is the villain willing to sacrifice to make it as difficult as possible for the hero/heroine?
4. Is the villain vigilant and attentive? Does the villain react to what the protagonist does? 
5. Are his or her responses timely, apt, and punishing?
6. Is the villain humanized? Are there enough dimensions so that readers might suffer the discomfort of identifying with him or her?
7. Does the villain change as the story progresses – not in terms of focus, but in terms of improved ability, knowledge, and judgment?
8. Does the villain surprise? Are some of the choices unexpected while being reasonable?
9. Is the villain in some way a reflection of the protagonist? Would the hero or heroine feel uneasy about some of the things they have in common with the villain?
10. Is the villain powerfully motivated? Are there reasons for his or her goal and do those reasons push him or her hard?
11. Does the villain at some point offer the hero or heroine a choice? (This might include an opportunity for them to join forces.)
12. Is the villain powerful? 
13. Is he or she at least the equal of the protagonist in terms of intelligence, resources, and options?
14. Are the villains plans and goals clear? Where possible, is what the villain wants tangible?
15. Is the villain's potential for causing harm illustrated early enough in the story to make readers dread his or her success?
16. In addition to keeping the protagonist from his or her goal, to the actions of the villain undermine the hero or heroine's sense of identity or self?
17. Is there a time where it's clear that there's more to the villain than meets the eye?  Does a backstory add texture and depth?
18. Are there important scenes where secrets about the villain are revealed?
19. Is the villain fresh? Is there something so distinctive and interesting about him or her that his or her mere presence makes the story special?
20. Do the actions and intentions of the villain support the story's theme? (Often, the villain stands in for the status quo or society's rules or values.)

A great villain can be the spark and the life of your story. He or she will torture your hero or heroine in ways you wouldn't dare. The remarks that come out of the mouths of villains are often so good, writers steal them (with modifications) for their heroes and heroines.

That means you may find this set of questions in this series to be the most fun to work with. And that will increase the delight of your readers.

20 Questions 5 - Make your main character's obstacles more challenging

In stories, characters never change except in the face of adversity. And the conflict they face comes when what they want is blocked in some way. This is where setbacks, sacrifices, and (often) nasty surprises come in.

A sure way to improve your story is to tune up these obstacles so they demand the most of your main characters. Make them fierce. Make things go wrong. Don’t turn away from torturing your characters. To help you in this (sometimes painful) project, I offer 20 more questions for your story, these dealing with the obstacles the heroes and heroines must face.

1. Are all the obstacles expected by the genre and logline included?
2. Can you make the obstacles more challenging for your main character? 
3. Will readers have doubts about whether they can be overcome?
4. Are the consequences for failure or the required sacrifices as extreme as you can make them?
5. Do the obstacles escalate in difficulty each time they crop up in the story? Did you avoid plateauing or deescalation?
6. Is taking on an obstacle irreversible? Is there no way to go back? Must the hero or heroine go through or abandon the quest?
7. Are choices clear and reasonable? Have you avoided advancement of the plot by stupidity?
8. Does the main character have agency? Will it be impossible for the obstacle to be overcome without the choices and actions of the protagonist? Is deus ex machina avoided?
9. Do some of the choices for dealing with an obstacle represent dilemmas, where neither choice is desirable or without important costs?
10. Do all the obstacles upset YOU personally? Do you suffer along with your protagonist?
11. Are all the obstacles related to the goal? Do they make a difference? Are they of the right scale?
12. Does each obstacle advance the protagonist along his or her character arc, forcing change and growth?
13. Are the obstacles visceral? Can they be imagined and related to by readers?
14. Would at least some of the obstacles be insurmountable by the protagonist at the beginning of the story?
15. Do obstacles compromise the fulfillment of as many of the protagonist's needs (as reasonable), up and down Maslow’s hierarchy?
16. At one time or another, is the hero or heroine challenged in a variety of ways (e.g., physically, socially, intellectually, morally, psychologically)?
17. Are some of the solutions surprising while still being fair?
18. Do any obstacles threaten prized relationships?
19. Do obstacles challenge the protagonist’s self-image?
20. Do villains get more savvy and harsh with each obstacle they present? 

Without obstacles, a happy ending isn't earned (and a tragedy can fade to so what?).  By making the obstacles more daunting, the story inevitable becomes stronger, improving both the characters and the plot.