Reading order
| # | Title | Published | Author | Buy on Amazon |
|---|---|---|---|---|
| 1 | Confessions of a Freelance Penmonkey | 2011 | Chuck Wendig | Buy |
| 2 | 250 Things You Should Know About Writing | 2011 | Chuck Wendig | Buy |
| 3 | Revenge of the Penmonkey | 2011 | Chuck Wendig | Buy |
| 4 | 500 Ways to Be a Better Writer | 2011 | Chuck Wendig | Buy |
| 5 | 500 More Ways To Be A Better Writer | 2012 | Chuck Wendig | Buy |
| 6 | 500 Ways to Tell a Better Story | 2012 | Chuck Wendig | Buy |
| 7 | The Kick-Ass Writer | 2013 | Chuck Wendig | Buy |
| 8 | 30 Days in the Word Mines | 2014 | Chuck Wendig | Buy |
| 9 | You Can Do Anything, Magic Skeleton! | 2023 | Chuck Wendig | Buy |
| 10 | Gentle Writing Advice: How to Be a Writer Without Destroying Yourself | 2023 | Chuck Wendig | Buy |
Chuck Wendig’s non-fiction output is largely built from his terribleminds blog, where he spent years posting daily writing advice with a distinctive voice: sweary, direct, and full of tough love. Many of his advice books started as blog posts that were collected, revised, and expanded into book form.
The early titles, like Confessions of a Freelance Penmonkey (2011), 250 Things You Should Know About Writing (2011), and the 500 Ways series, are short, punchy reads built around numbered lists of advice. They cover everything from sentence-level craft to plotting to the business of freelancing. The Kick-Ass Writer (2013) brought this material to a wider audience through Writer’s Digest Books. 30 Days in the Word Mines (2014) is a month-long writing challenge format.
His later advice books, You Can Do Anything, Magic Skeleton! (2023) and Gentle Writing Advice (2023), show a shift in tone. After years of the tough-love approach, Wendig moved toward more encouraging, emotionally aware guidance for writers. These later books reflect his own experiences with burnout and the changing conversation around creative sustainability.