Sometimes The Outline Happens Last

I have been frustrated that I’m not making as much progress on my book as I wanted to. I finished the first draft in December and my goal was to revise it to the point where I could hand it off to a professional editor by the end of February. But it’s halfway through March and there’s a ton of rework to do before it’s ready for editing.

The biggest challenge I’ve had with the revision process is that the document hasn’t been well-organized. This book was born from a four-page outline that I wrote as a class assignment last July at the Jack Kerouac School. The outline describes what happens when people want to quit their jobs but feel stuck, talks about how to break through those barriers, and goes on to offer a plan for making an exit.

I still like that outline! But when I started writing the actual content I thought I needed to simplify it to three sections about timing, money and how to set yourself up for a positive experience after you’ve left your job. That format was easier for me to describe to people and seemed like a good container to fill.  But I pretty quickly got into a bind when I wanted to write about topics that didn’t fit into either one of the outlines. At that point I was stuck for weeks and the only writing that happened was poetry and journaling.

Finally I gave myself permission to write whatever the hell I wanted to for my book. I had a running list of topics that I logged in a spreadsheet. When I sat down at my PC to write, I would either look at the list or just write whatever I felt like writing. I would open my word document, create a bold header for whatever the topic was about, and get to it.

On December 30th, the day that I finished my rough draft, I had an idea for a third outline based on steps that people could take to quit their jobs comfortably. I was thrilled with this last-minute inspiration because it sounded like something agents and publishers would go for. You know, “the seven steps to quit like a winner”. It has a great ring to it, don’t you think?

However, the more I reflected on it over the following weeks, I wasn’t sure those seven steps were really necessary, and there were topics I cared about that didn’t line up with this version of an outline either.

The problem I created for myself by adding section after section into my word document based on whatever I felt like writing each day was that there was no logical order. My draft was 100 pages of single spaced text and scrolling through page after page to find sections that seemed like they would fit together in chapters wasn’t working very well.

I thought that printing out the manuscript would help. I made a copy and started going through it with a red pen. But I sensed it was a wasted effort because I couldn’t see how the pieces connected to each other or the book as a whole.

I’d heard of authors spreading their manuscript pages on the floor and then walking around, sorting them. Maybe they have bigger living rooms than I do? I got about 50 pages down on the carpet before I ran out of room.

And there wasn’t enough space left for me to walk around and rearrange the papers, so I ended up walking on the paper, which made me feel like I was insulting myself. Milo, my cat, was confused at first and then he started walking on the papers, too. Cats are always happy to insult people.

Then I thought maybe it would be better if I got a pad of Post-its that I could write editing comments on and stick to the papers. Like, “move this section to the introduction.” I made a few notes, stuck them on the papers, and then Milo wanted to go out on the deck and a big gust of wind blew the papers all over. Enough of that.

But the notes gave me an idea. I wrote the different topics of the book on individual Post-its and saw patterns emerge. Before long I grouped each topic that I had written about into chapters, and moved the chapters into a logical order. They are now tidily laid out on my dining room table.

A bunch of pink Post-its might not seem like a big deal, but it is a big step towards making my book a reality. Now I can go back through the printed manuscript and re-order the pages to match the chapters, and then make revisions knowing how each topic flows into the next.

It would have been a much easier process if I could have written the book in order all the way from the introduction to the afterward. I love plans – planning is smart, saves time and helps get results. But that’s not how it went. Sometimes the outline happens last.

Tags: outlines, plans, rework