100 Outlines Challenge

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I’m going to do something stupid.

You should do it with me.

Since life has already been crazy with work and personal projects (and I’ve totally neglected things like the Test Cycle), I decided that the best cure is more work with unrealistic deadlines.

100 outlines.

100 days.

Lots of coffee.

It starts Monday, April 3rd, and it will end Wednesday July 12. I’ll be tweeting screenshots and complaints under the #100Outlines hashtag and potentially streaming the milestone days (10, 25, 50, etc). Join me!

  • Any outline counts, as long as it’s an actual outline.
  • You’ll learn as much from failing as you will from succeeding.
  • Everyone who makes it to 100 days will do, like, a Google Hangout or something.
  • goaded me into this. It was a triple dog dare. I had no choice.

But Why?

I learn through repetition. I’m dumb like that. Fiction is awesome but, like most writers, I struggle with the second act. So I’m brute-forcing it. Like a desperately underpaid writer for daytime television, I’m iterating through everything I know with the hope that I’ll eventually figure out how this whole “using words” thing works.

Oh, and I’m a firm believer in idea that any skill can be beaten into shape with the right hammer. This challenge? My hammer.

If you want another way to look at it, think of it like the mirror of NaNoWriMo. Instead of hammering your way through a heavy word count in order to build your “raw volume” muscles, it’s a challenge designed to test your ability to come up with ideas and turn them into functional narrative structures.

Having worked as a managing editor, as a content strategist, and as a senior writer for a variety of startups, I’ve found that topic generation and content planning isn’t a skill that everyone has. Figuring out your audience, your platform, and your distribution channels takes time. Figuring out what you can actually achieve takes time.

And weaponizing that skill can be pretty damn profitable.

So do this challenge with me. Take the “fun part” of writing and wring it dry. Find your limits. Test your ability to make sense. Become a better writer.

And write a metric fuck-ton of outlines.

Share this thing and guilt your friends into doing it. It’ll be awesome! Or something.

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Asher Stephenson
Friends of National Novel Writing Month

Nerd, technical writer, sporadic think-piece producer. Catch up with my latest projects at asherstephenson.com