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How to Start a Story You’ll Love to Write

The Week in Creativity: Jan 22, 2023

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I wanted to be a screenwriter for a long time. In the late eighties, with no reason to believe I’d succeed, I bought a couple of books on screenwriting and went after it. Within a few months, I’d finished my first script.

It stunk.

But I didn’t know it stunk at the time. I didn’t know anything about screenwriting or the movie business. I thought if I wrote something good enough, I’d be in.

It wasn’t a bad plan…

This was the late ’80s. In fact, my timing was good because starting then and for the next several years, Hollywood was a buying more scripts written on spec, rather than ordering them from pitches. Had I hit upon the right story, and wrote it well enough, it just may have worked.

After five more scripts, hundreds of queries, and no interest, I pivoted to novels.

I just wasn’t the writer I needed to be, yet.

But in 2010, having endured 15 more years of “unsuccessful” writing, I signed on with a coach. It turned out that coach was terrible for me. He was more of a snake oil salesman peddling dreams and access to Hollywood. A year later, I finally snapped out of the spell he’d cast, and found a better coach.

That coach dealt only in tools, techniques, and harsh truth about your abilities. It was humbling, but his lessons changed my writing life. (I also started therapy at that time and that changed the rest of my life.)

What does this have to do with story?

I’ve been pondering the story to write after I complete this novel, and I started a story journal — which is one of the journaling techniques I recommend any writer learn about. I’ve convinced myself that I’m onto a story I want to write, so I began efforts to dig deeper into what I want to write about.

Now I have to take a slight detour to tell you that I use a tool called Obsidian to keep and organize my notes. I have fourteen years worth of notes in that tool, which spans the time I worked with the writing coach who changed my writing life.

One of the features of Obsidian is to display a random note, and I pressed the button yesterday. It showed me the notes from my coach about how to dig deep into a story before writing it as both background for the story and to assure yourself it’s the story you want to tell.

It was a hell of a coincidence to show up — randomly — so soon after deciding to dig deeper into the next story.

How to explore a story idea before writing

My coach recommended three areas to think about:

  • Concept
  • Character
  • Story

Concept exploration

Start with a high-altitude description of your story, and list out some possibilities. You’re not making decisions.

Stay generic, but follow out some of the possibilities to their logical conclusion.

See if it still seems like a fun idea to write.

Character exploration

Think about the main characters in this possible story, and what they may want (as in goals or a quest).

For each main character, describe who they love, where they work, and what’s their family situation.

Most important, what do they fear? What shames them? What motivates them to do things in this story?

Story exploration

Describe some of the scenes that might happen with these characters. If the story is episodic (like a TV show), think up a few episode descriptions (“The one where…”).

What’s interesting about these scenes or episodes? What’s the setting or time frame?

Brainstorm some set pieces or things you’d love to have in your story.

The Story Story

I haven’t done it yet with my new story. I’ve put it on my schedule for next week, as I’m hoping I can wrap up this draft of the novel in the next couple of days.

My growth as a writer has taken me away from the dreams of making a sensational splash in the publishing world or Hollywood (well, it’s taken me mostly away from those dreams). Now, I’m interested in telling a story that matters to me in some way, either because of the characters, or the theme, or I love the story.

You certainly may look at this recommendation for story exploration and think, duh, of course I’ll do that. But I spent over two decades chasing story ideas, sucked into the shiny possibilities of the newness, thinking I really had something.

I might plan the stories, but I didn’t think enough about the characters, themes, and whether I really wanted to spend months on it writing a draft.

What I learned is that a more thoughtful consideration of a story helps me deal with the challenges of writing.

And I hope you’ll consider doing the same the next time you chase a new story idea.

Going Forward

I’m pulling together everything I’ve learned about creativity and storytelling to give it all back to the community.

So If you’re tired of watching others create and you want to finally join in the fun, sign up for my newsletter, Creativity for Fun and Profit and I’ll send you a free course, Awaken Your Creative Abundance.