How Outlining Has Taken Over My Life

For the longest time, I detested outlining. Well, maybe that’s a bit too dramatic. I was largely indifferent to it.

In the first phase of my writing passion (middle school to high school), I thought writing outlines was pointless. I just wrote. Brazenly, passionately, badly. I was discovering a part of myself that I never knew before and things like planning and outlining were foreign hindrances that I didn’t bother indulging in.

Even as I grew more self-conscious about my writing, I still didn’t think outlines would help me. After all, I was more of a free write writer. My first “novel” was me coming up with ideas at the spur of the moment and then carrying onto the next thing. Why spend so much time on something I may not follow through on? What’s the point of planning stuff out when the best strategy would just be to get the idea down and see where it would take me.?

But those years are filled with basic idea sketches, character thoughts, isolated scenes and WIPs that went nowhere. My early writing self couldn’t get my mind out of  (what I pretentiously termed at the time) “novel-length” concepts. Ideas that couldn’t, wouldn’t, will not fit in a short story. They were epics of adventure, love, magic, and chaos!

But I wouldn’t  put the work into those ideas. I obsess over them, write out the basic start, then move on.

In college, I started to reject the notion of “novel-length” concepts in favor of short stories. I didn’t want to start anything that couldn’t be finished in 20 pages. I got caught up in finishing stories. A lot of ideas were allowed to die because I didn’t think I could complete them. On those rare occasions when I tried to go beyond that, I found myself stuck. I write passionately for 20, 40, maybe 60 pages but then I would get stuck somewhere.

I didn’t truly start to embrace outlining until 2017 when I started the Festival of Shadows. I wanted to write a story centered around a group of characters I created. I also wanted to try my hand in a long cohesive narrative. So I tried outlining and I’ve been converted.

Now I live by the outline. Outlines have become my guide and savior. I worship at the bullet point altar and weep at the feets of schedules and planning. Every major project I prelude with an outline. I’ve finished three different outlines for stories at the moment. Two, I’ve officially started acting on.

But of course, outlines aren’t sacred texts. A good 50 percent of the Festival of Shadows outline was changed, rearranged, or ultimately discarded because I wanted to do something else. My outline kept me on track, however. Even if I didn’t like the initial route, writing it down gave me a better sense of what I wanted to do instead. The writing process usually helped me decide (rather than hoping my imagination would drop me a sign, out of the blue to help me fix all those dirty plot holes).

Outlines help me visualize the plot. I’m pretty good at coming up with the beginning and end of a story. The middle tends to be this big gray blob with bits of clear details sprinkled in. When I try to reach for them, they’re lost in the mess of this big unknown.  I tend to get really intimidated which leads to a lack of motivation. I do all I can to make the idea more and more concrete lest I lose interest (which has happened to me with too many other stories).

My outlining process tends to be pretty involved. My most recent one numbers 14 pages, single-spaced, with lots of bullet points (I’m OBSESSED with bullet points). And that was the second draft of it.

I wish I can be a low key outliner who can get their whole novel planned out on a single sheet of paper. That’s the real dream.