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The Challenges of Writing a Series


The Challenges of Writing a Series, guest post by Ian Thomas Malone


The concept of a series should at least in theory, be the dream of every writer. If you love the characters and world you’ve created, why give them up? When one story ends, why not begin another using what’s worked before? Obviously if this consistently produced positive results, we’d see a lot more series than we already do. The truth is, writing a series presents a unique set of challenges.

The first that came to mind actually isn’t much of an issue in the year 2016. The most apparent problem with writing a series is the risk that readers who pick up later installments may not have necessarily read the previous entries. The rise of Amazon, particularly Kindle, has largely done away with this worry as readers are less likely to accidentally purchase a novel that’s in the middle of a series than they might be at a bookstore. Even then, it isn’t particularly difficult to acquire earlier books. This does not necessarily free the author from the associated concerns of having to deal with readers who aren’t familiar with the plot or the characters.

Sitting down to write the second book in a series is a weird experience. You don’t feel the need to re-explain everything, but the feeling that you should can certainly present itself. The desire to endear your characters to your readers is a natural part of writing. A sequel changes that whole dynamic because the audience already has opinions of the characters.

This creates a few interesting possibilities for character arcs. Books don’t have fewer pages because the groundwork for their characters has already been laid out in the previous book. What to do with them? Do you let the plot take charge or do you give your characters new personal challenges to push them further than you ever could in a single book?

The answer is actually quite simple. Do whatever feels natural. That may seem like a big copout, but it’s important advice. As an author, you spend more time with your characters than anyone else, but your readers will notice if characters who were once calm and collected suddenly start behaving rash and arrogant. Character traits need to be consistent.  

I’ve found this to be the case in my “Dialogues” series. Written entirely in Socratic Dialogue, The Dialogues present many challenges for building a relationship between the characters and the readers. Each Dialogue focuses on a theme of college or high school life and few characters make multiple appearances. The series does have one main character, George, who appears in every Dialogue, giving the reader a consistent voice to identify with.

I wrote the series with hopes that a reader could read any Dialogue and still enjoy it even if they hadn’t read any of the others. The third book, Five High School Dialogues, presented a unique challenge as it is the first in the series to not be set in college. Essentially, FHSD is a bit of a reboot in the sense that I hope to attract readers of a slightly younger demographic than those of Five College Dialogues and Five More College Dialogues.

It’s important to not toss continuity out the window, even in a series like The Dialogues. I’ve always been a big fan of Easter eggs in my work and newer Dialogues occasionally mention the events of previous Dialogues. Longtime readers can enjoy the references in a way that doesn’t necessarily affect new readers.

Ultimately, there’s only one consistent rule to keep in mind when writing a series. Make sure there’s a story that needs to be told. Sequels can be fun or they can ruin the original material.

How do you know when to turn a book into a series? You just sort of do, which makes the concept seem simpler than it actually is. I’ve been on both sides of the equation. My “Dialogues” series only became a series when I started coming up with material for a second book. Readers have asked about a sequel to my novel Courting Mrs. McCarthy for almost a year now. I’ve thought about ideas and wouldn’t rule it out, but I’m not going to force it even if it’s something that people want.

Obviously that isn’t a problem if you’ve planned a series, or trilogy, all along but you’ll still want to watch out for many of the same things. Respect your readers and the time they’ve invested in your work. Give them what they need to enjoy the world you’ve created without bogging them down with facts you’ve already said. Most importantly, have fun. That’s why we’re in this business. 


The Challenges of Writing a Series, guest post by Ian Thomas Malone
Ian Thomas Malone is an author and a yogi from Greenwich, CT. He is a graduate of Boston College, where he founded The Rock at Boston College. He is the grandson of noted Sherlockian scholar Colonel John Linsenmeyer. Ian has published thousands of articles on diverse subjects such as popular culture, baseball, and social commentary. His favorite things to post on social media are pictures of his golden retriever Georgie and his collection of stuffed animals.

Ian believes firmly that "there's more to life than books you know, but not much more," a quote from his hero Morrissey. When he's not reading, writing, or teaching yoga, he can probably be found in a pool playing water polo. He aspires to move to the Hundred Acre Wood someday, though he hopes it has wi-fi by then.

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