Chastise and Challenge Your Characters

I just finished a book that drove me BONKERS!! Here’s the premise: a character decides to go on a The Hobbit-like adventure and joins a party to do so.  Despite his complete inexperience with treasure-hunting and monster killing, he is instantly loved by everybody he is traveling with. When trouble would raise its ugly little head, our hero would either accidentally solve the problem, or fall into a trance where something (not fully explained) would fix it for him.

book-textbookThe guy never really had a desire for anything, so he just kind of floated around like a leaf in the wind as nothing but good fortune came his direction. He didn’t complain often, but when he did it usually involved him getting so much treasure he didn’t know what to do with it all.


I’m not going to name the book or the author, but I won’t be picking up another one of this author’s books. In fact, in the end, I was upset because I had actually spent good money on this book!

Let’s talk about another author: Michaelbrent Collings. Now, this guy michaelbrentknows how to torture his characters! In The Colony, his zombie apocalypse series, the main character can tell on page one that something in the world is wrong. Very wrong. I think by page three he was already running for his life. I’m about to start the third book in the series, and it would be very difficult for me to come up with ways Michaelbrent has NOT terrorized his main character, or any character in the book, yet.

I also just finished another of his books, The Loon, which starts off with some guy living the perfect life. By the end of the first chapter, his life is far, far, FAR from perfect. Things got bad, and with every turning page it only got worse. One scene literally made me CRINGE in fear.

I get it, being mean to your characters is hard. It makes me feel like a sadistic jerk. The irony is that writers are the most compassionate people on earth. Nobody likes taking somebody they love and making them go through the ringer.

Regardless, you’ve got to torture your characters and give them seemingly insurmountable problems anyway. When it comes to writing, this is a literal case where nice guys finish last (in book sales).

If Frodo was asked to destroy the One Ring, and all he had to do was hop on the back of an eagle and drop it in a volcano, would anybody read it? Heck no! Well, Tolkein’s Mom might have… out of obligation.

What if Harry Potter was raised by a loving and supportive aunt (or better yet, his own parents) only to trot off to Hogwarts where he was admired by all and a few magic words would finish off Voldemort forever. Would you have read that book?

rudyAnd let me bring up one of my favorite movies, based on a true story: Rudy. Rudy Ruettiger had one goal, to play college football for Notre Dame. He had to overcome obstacle after obstacle to achieve his goal, from getting into the right college in the first place, affording it, making grades, touching the field, dealing with negative influences from his own family, being taken seriously by his teammates, and even being allowed to even dress for one game. Not shown in the movie is the fact that he did all this with dyslexia. SPOILER ALERT!! He played college football for two plays. On defense. He didn’t even end up touching the ball, but he was heralded a hero and he has inspired countless others to reach for their dreams. Decades later, Rudy is still a wonderful story, but if he had the physic to play in the first place and waltzed onto the field with a  full scholarship, nobody would remember him now.

So, challenge your characters. Torture them if you (can) have to. Why?

Make us care about and relate to your characters.

We all have problems, some greater than others. Reading is often a nice escape from our own problems to experience other people’s pains. In a way, it reminds us that ours might not be as bad as it could be. I’ve always said that if everybody threw their problems in a pile to be distributed, you’d probably look at the choices and want your problems back. So when your characters suffers, we understand. It makes them more alive. It makes them more likable. It makes us care about them. When they are in pain, the readers are in pain. When they achieve a success, the readers share in the enjoyment. As readers, when a character we care about succeeds in overcoming amazing challenges, we literally feel the triumph alongside them.

Regarding the book I mentioned at the start of this article, if the main character had died halfway through the book, I probably would howled in laughter! Unfortunately, the twerp lived, and I think a sequel is in the works.

But with Frodo and Sam, did we not all hang on the edge of our seats as they “simply” walked into Mordor? With Harry Potter, did we not relate to him being bullied at school, struggle with certain teachers, fight to make and keep friends, and make tough decisions when deciding between right and wrong? And he did this while forming an army and taking down the bad guy (oh, spoiler alert there too, sorry).

And Rudy? I’ll admit, I can’t make it through that movie without cryingtearing up. I feel completely emotionally invested into that story, and Rudy is the one doing all the hard work. If you haven’t seen it, go pick up a copy and thank me later.

Create a character arc

Like I said earlier, the “hero” of that book didn’t change. The protagonist was the same guy on page one that he was on the last page, except he had picked up a few facts about his genealogical lineage. True character stories have characters who change from the beginning to the end.

Frodo changed so much that he no longer felt like he belonged in his beloved Shire he worked so hard to save. Harry Potter went from a pitiful, unloved orphan boy with no prospects to becoming a powerful auror with a loving family of his own. Rudy achieved his dream and is now a public speaker, helping others achieve theirs.

Make the book more interesting

Characters make great books, but so do great plots. By raising the stakes, it not only helps your characters grow, but it helps move the story. I didn’t mind the protagonist from the unnamed book above being a leaf in the wind, being pushed around by circumstance, but what would have really made the story great was if he stopped being the leaf…and became the wind. If he actually did things to make a difference.

Frodo was supposed to take the ring to Rivendell, and spent the first hobbits-hiding-from-nazgulhalf of Fellowship doing nothing but running for his life. Heck, he had to be carried into Rivendell. However, in Rivendell, he stepped forward to be the one to take the ring to Mount Doom. While the first few books of Harry Potter were fun, the plot really picked up for me in the fourth and fifth books when Harry decided to start taking his magical studies more seriously in The Goblet of Fire and when he formed Dumbledore’s Army in Order of the Phoenix. As Harry got more on the offensive, I got more engrossed and intrigued by the series.

Tip on how to do it: Try/Fail Cycle

When writing, make sure it takes a few tries to solve a problem. Three is the preferred number of tries… any less, and the problem doesn’t seem difficult. You can have more, but it might make the story drag on a bit. It’s best to have them solve the problem in three tries and then move on to another problem.

Oh, and each time, make the problem worse! Keep amping it up!

Frodo thought he was bringing the ring to Rivendell. Oops, now he’s frodosamgollum3taking it to Mount Doom, and he gets a fellowship to take him there. Oops again, somebody on the team turns on him and he decides to do it alone. Ah, easy sailing now, especially since he has a helper and finds a guide to take him there. No, no, no… not quite. The guide tries to turn him into spider-food, and his helper seems a little too eager, to the point that Frodo thinks he is just trying to get the ring all to himself. He finally reaches his destination, only to be overcome by the power of the ring and abandoning his quest. Can it get worse? Oh yes, the guide is back and ready to do anything to claim the ring for himself.

Next time you watch a show or a movie, or read a book, look for this. You’ll notice that they often run into problems and it takes at least three times to get it right, and after each failed attempt, new information is learned, e.g., oh, there’s a large three-headed dog guarding the entryway to a certain character’s goal, and the stakes get raised, e.g., the professor our character is trying to outmaneuver seems to have a head start.

Now, go ahead and sit down with your book, and if your character isn’t suffering, take away their true love, throw them into the pit of despair, and suck their entire life away with a water-powered machine. You’re characters—and your readers—will thank you later.

Sidenote: The obstacle mentioned in the previous paragraph MIGHT have already been used.

Princess Bride 5

About James Duckett

James is a geeky, nerdy dude. He writes, sometimes. He blogs, sometimes. He's helpful to people, sometimes. He doesn't like to repeat himself, sometimes. He's funny... looking... always.

His hopes and aspirations of the future is to one day find a way that people will pay him while he sleeps. It is his dream job.


Funny that for me I stopped being interested in the Harry Potter books around the 4th and 5th books because I felt that the world of wonder he was discovering had become mundane. I mean I get your point, that many endearing stories are about overcoming hardships and therefore your beloved characters are going to necessarily experience hardships. But that's not the only reason people read stories. Some of us like to enjoy the world around the characters. Some of us like to laugh at awkward situations or are looking for a hint of sexyness. I'm thinking of an Anime and Manga series right now called "Tenchi Muyo", of the "harem" variety of anime. Just saying that you wrote this from a "this is the only way" perspective. If you are bored with stories where the main character isn't sadistically tortured don't write stories where you don't torture your character. But some of us enjoy when Captain Mel doesn't know why his moral compass is always set on the right course or when the Doctor can tie up the loose ends with his magic sonic screwdriver and get kind of annoyed when these characters are tormented by contrived demons.

David Haskell
David Haskell

Very interesting and on-point article. I have a new blog to follow now, thanks!

Rebecca Blevins
Rebecca Blevins

A character who has things dropped in his lap is boring! Makes a book lose the will to live.

Suzanne Warr
Suzanne Warr

Great post! I'm with you that nothing kills a book faster than the molly-coddling of characters. And even if we don't like put them on the rack, it is pretty cool to help them get themselves off! So I guess reluctant writers can dangle that reward. PS I love Rudy!