Main Points
• Playlists are a helpful list of questions/solutions to overcome specific challenges.
• Keep refining your playlists as you continue to write.
• When you come across a pertinent problem, review your playlist to generate new ideas.

I came across the formalized version of playlists from the book Decisive: How to Make Better Choices in Life and Work by Chip and Dan Heath. While the book is about making better decisions in life (not on writing), the playlist section really stood out as being applicable.

The basic idea of a playlist is you write down a list of premade questions or solutions to go through when confronting specific issues. Going through your list will hopefully generate new ideas to explore. I can’t count the number of times I’ve gotten stuck on a plot, a character, or a magic system, and playlists can be a great way to move forward and think about things differently.

My Playlist
I’ve compiled this from my own experience, from other authors, and analyzing great fiction. The biggest thing here is to create your own playlist, updating it whenever you can. Here’s a list of common issues I’ve faced and some of the playlist questions I have for them.

My beginning is wrong.
-Can you start at a different time?
-Can you start later in your novel (cut the first few chapters) or start further back?
-What are your strengths in your novel? Can you use those in your beginning instead of what you have? (If you’re strong at dialogue, try starting with dialogue. If you’re strong with action, setting, mystery, then try starting with those)
-Can you add a prologue to draw readers in and make promises for the reader to look forward to?
-Can you start with a different point of view character who is watching a related event or is watching your main character?
-Can you start with another problem separate to the main plot that the main character has to overcome?
-What have other authors you enjoy done in their beginnings?

I’m writing my novel and it’s boring. I don’t know where to go with it or how to get to where I want to go.
-What is the worst possible thing that could happen to each character (including the villain)? What if one of those things happened right now?
-What is the best possible thing that could happen to each character?
-What’s the most bizarre thing that could happen right now?
-What if a natural disaster hit? Or a famine? Or a plague?
-What would happen if each character, or someone close to the main characters, died/fell ill/was injured/was maimed?
-What if there was a hidden threat that the main characters (including the villain) didn’t know about? What would it be? How would it change things?
-What would cause the most conflict right now?
-What’s the one thing that’s going right for the characters, that if it changed would most impact them?
-What if you had role reversals? If the warrior suddenly had to become a scholar, or the wizard had to become a fighter, or the thief had to become an accountant? What would happen if your characters were forced to change their natural roles suddenly?
-What do your characters care about most? Kill it or otherwise damage it. See what happens.
-What’s a deeply held belief that your characters have? Find a way to turn it on its head.
-What have other authors you enjoy done to make their books more exciting?

My book feels too serious.
-Can you do role reversals and put your expert character into funny situations where he/she is a neophyte?
-Can you add a jokester character, or make your character have a dark sense of humor?
-Can you add something for the characters to hope for? (a spouse at home, a friend, a pet, an ideal, etc.)
-Can you interject happy memories or happy visions of the future?

My character is flat.
-Can you add some odd personality quirks to your character?
-Can you add a limitation or a special skill? (he/she has panic attacks, suffers from a mental illness, is allergic to a common food, has physical limitations, has a troubled family history; the character can make better waffles than anyone living or dead, character is a singer as well as a warrior, character is great with kids despite expectations)
-Can you add other, more interesting characters to interact with your character?
-Who are some of your favorite characters and why? Can you implement some of their character traits into your own writing?

My romance stinks.
-Can you pretend there isn’t a romance and just have the characters interact on a joint task together?
-Can you make one character have to take care of the other one? (one of them gets injured, sick, etc.)
-Can you have someone else fall in love with the character first?
-Can you add more time together?
-What does the character specifically notice about the romantic interest?
-What romances have worked for you?

My magic system needs work.
-What are the limitations of my magic system?
-Can you write a short story about a scientist who is playing around with your magic system where they push the limits, try interactions, try to break it, etc.? (I got this from my buddy, Dan)
-Where does your magic come from? What’s its history? Who can use it? What are the various belief systems around your magic?

I don’t know much about the culture of my world.
-What’s your language?
-What are some weird cultural distinctions in your own location or in other countries you’ve learned about?
-Can you make one of the following unique to your culture? (parades, sports, religion, holidays, clothing, food, dialects, how they deal with newborns, how they deal with death, rituals to transition to adulthood, music, art, colors, flags, hobbies/pastimes, view of men/women/children, beliefs on sickness, superstitions, dating/relationships, taboos, waste disposal, architecture, unique landmarks, unique buildings, governance, etc.).

You’ll notice I have a lot of “what have other authors you enjoy done?” which can be a great starting point for research. I hope you’ve gotten a flavor for how playlists work. Now, when I’m struggling with my beginning, I can go to this playlist, read through the questions and see if it generates any new ideas. Then I start writing.

I’ll continue to add to my own list and trim it down so I can get the most essential questions without looking so cluttered. I’d recommend doing the same.

What questions have been useful in moving your own writing forward?

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