How to tackle a radical rewrite and restructuring

With gratitude to Hashem, I’ve completed the third draft of The Very Next (new and improved title a secret till its release). Here’s how I turned a 24,000-word hot mess into a bit over 75,000 words of a real story.

1. Chapters were WAY too short, and frequently ended or started in media res. My intention had been to make them vignette-length, just little scenes from the lives of these various characters, and to end each chapter with a line of dialogue. Fair enough, but now that just seems like a bad gimmick, not something which complements the particulars of the story. That also meant a lot of chapters were seriously underdeveloped and rushed along.

2. Many too-short chapters needed combined. This was fairly easy, since a lot of these chapters led right into one another. Seriously, they’d cover the exact same scene or day, just with a different topic of conversation. But hey, I was all of 16 and 17 when I wrote the rough draft. I was that pretentious special snowflake a lot of teenage writers are.

3. Cleaning up stupid slang and ill grammar. This was the first major issue I tackled, since it’s fairly straightforward as compared to the others. In eighth grade, I actually went through a phase where I thought poor grammar was cool, and so my characters devolved from proper English into cringeworthy grammar which made them sound like they were from the Ozarks. Their language just stuck, long after I got over that dumb phase. Now, they only say “ain’t” and use double negatives, and even that’s not 100% of the time.

4. Not enough of a period flavor. Apart from the major world events of 1939, including several chapters set in Poland, there wasn’t enough of a sense this is set in the 1930s.

5. Way too many infodumps. I really blame this one on all the older books I’d read. I was merely copying what I’d seen. There were a number of chapters which were little more than pointless backstory about certain characters, like principal Mr. Robinson and Quintina’s oldest sister Liylah. (Yes, that’s a kreatyv spylyng, but I’m too used to it to suddenly change it to Lila all these years later.) There were also way too many backstory paragraphs about the Smart-Pancake family in the opening pages.

6. Too omniscient. I was still writing in that dated, obnoxious God-mode at that age.

7. No one storyline ever emerged, nor did any sort of focused arc and trajectory. The focus needed to be on the animosity Sam and her mother Urma bear towards everyone, and then the later chapters about the characters Mr. Filliard is trying to get out of Poland and to Atlantic City before time runs out. This remains an episodic story, but now it’s imbued with substance.

8. Many new chapters needed to be written, with others destined for a deleted scenes folder.

9. A lot of it was nothing more than mental masturbation for my teenage self. Never, ever make your characters ciphers and force your own interests and viewpoints into anything you’re writing. It’s not that you can’t, e.g., have a character with similar interests or political affiliations. It’s just that it needs to be a natural, believable part of the overall story.

What’s the most challenging rewrite you’ve ever undertaken? Could you have turned 24,000 words of a hot, unstructured mess into over 75,000 words of an actual, polished story?


3 thoughts on “How to tackle a radical rewrite and restructuring

  1. I have done radical rewrites for one book several times. I also have to combine chapters, fix the point of few, and take out info dumping. It’s a real chore.


  2. I love it when you pull something out of the drawer that’s been sitting for years. My first MAJOR rewrite turned into my first published book. It started as a 100 page novella and the finished book (10 years later) only bears a trace resemblance. I love how stories evolve over time.


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