Review of How to Think Sideways – Month 2

As mentioned previously, I’m taking a 6-month class on writing from Holly Lisle. While I promised a review of each month’s worth of material once a month, I’ve been working through it at a slower pace, hence the long gap between review posts. That’s the beauty of this type of class. The lessons come out once a week, but I can work on them at my own speed, taking as long as needed before moving on to the next.

In the second month of Think Sideways, we’re doing our Project Planning.

Week 5 – Define Your Project’s Needs

Holly teaches the Dot and Line technique in this week’s lesson. The Dot helps you to focus on the most interesting, extraordinary or significant details of your character, setting, conflict, etc. The Line marks off the differences between things.

How do you use them? Well, the Dot helps you focus on the details that are pertinent. For example, your heroine has long, blond hair. Who cares? Lots of people have long, blond hair. That’s an ordinary detail. The Dot helps you make that into an extraordinary detail. Not just long, blond hair, but hair that is twenty feet long (ala Rapunzel) and strong enough to support the weight of an adult. Now that’s an extraordinary detail about your heroine that deserves to get mentioned in your story. You focus on the Dot details to make your characters, settings, and conflicts unique and extraordinary.

The Line helps you figure out potential conflicts for your story. For example, Rapunzel is on one side of the line, the Witch is on the other. Rapunzel is young, beautiful and yearns to get out of the tower. The Witch is old, ugly and thinks Rapunzel should stay in the tower forever. Pitting them against each other via the Line, you have young vs. old, beautiful vs. ugly, and escape dreams vs. long-term imprisonment. Lots to argue about there and plenty of material for sarcastic or angry dialogue, or sneaky acts against each other. In other words, plenty of conflict between those two characters. You can apply the Line to characters, settings, motivations… almost any part of your story.

The Dot and Line technique were a real eye-opener for me in how to enrich my story with extraordinary details and conflicts that I might have overlooked before.

Week 6 – Discover Your Project’s Markets

In this week we learned three things:

  1. How to identify the market that our project fits into.
  2. How to change genres with a technqiue called Book Mapping.
  3. How to create our own genre (if one doesn’t currently exist to fit our work).

This is an extremely useful lesson for writers planning a long career of writing. Genres don’t stay static. They grow, change, wither, sometimes die, and morph into other genres altogether. If you can’t flex with the changing markets, you’ll have a hard time staying successful in the publishing world.

Week 7 – Develop Your Project-Creation System

Holly gives an excellent example of how she spent way too much time world-building on her first few novels, only to find that nobody wanted to publish those stories set in her heavily-detailed, fascinating worlds. Over time she learned to build only enough world to get her story started and then add pertinent details along the way. This saved her a bunch of time by eliminating all the hours she spent building worlds, characters, and plot details for stories that were never used, i.e. published.

She walks you through the eight core planning modules that allow you to build just enough details to get your story started. Five of the modules are mandatory for every story – Character, Conflict, Time & Place, Scenes and Math. Three are optional, based on the type of story you’re writing – Maps & World, Culture, Language.

Week 8 – Plan Your Project

In this week, you’re almost ready to start writing. Holly walks you through creating an effective and efficient outline. No, not the scary roman-numeral outline that you learned in school. This is a fluid, easy-to-use outline that provides a high-level summary of each scene in your story. The techniques she teaches in this week are how to use Plot cards and The Sentence Lite. The combination of the two helps you create active scenes with conflict to keep your story moving.


I’m really enjoying this course. Holly is presenting many techniques that have proven to be super useful already in planning my story. I’m adding interesting nuances to my characters and plot that I doubt I could have come up with on my own. I’m very eager to see how the final story turns out when it is all done. Feels like it could be a breakout novel for me.

If you’re interested in signing up for How to Think Sideways, you can check it out here. And check back here in a month for the next report on Month 3.

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