Ask Why 5 Times

ask why 5 timesI struggle with backstory. I’m never sure how deep to go into my characters. I’ve heard people say that you need to know everything about them, and there’s a certain logic to that, but EVERYTHING? Do I really need to know what kind of ice cream my antagonist enjoys? Maybe. Or maybe not. Who can say?

Well, I stumbled across this little trick I’m calling “Ask Why 5 Times.” I overheard someone talking about it at the Writer’s Digest conference, so I’m sorry I can’t cite my source, but stay with me here. It’s a good idea (I wish it were mine).

Ask Why 5 Times

The basic idea is to make like a toddler and just keep asking why. Start with something that your character does. All writers know how this goes: You’re writing a scene and your character says or does something you didn’t expect. For instance, I’m working with a character right now in my second novel who is a jerk to women. He just kind of came out that way. So I asked why.

  • Well, he had his heart broken recently.

Why was his heart broken?

  • He was naive and young and out in the world on his own and kind of latched onto this girl who was much more worldly and she just wasn’t that into him.

Why was he out in the world at such a young age?

  • Because his parents died, and he didn’t have anyone to take him in.


  • His parents died because they were in an accident. No one would take him in because times are tough, and his one aunt simply couldn’t afford another mouth to feed.

Why are times so tough?

  • It is the middle of the Great Depression.

What We Can Learn

Okay, so now I have a better sense of this guy. He’s not just a dick. He had a really rough childhood marred by the death of his parents and rejection by his aunt. He is (or at least was) really lonely and fell hard for a girl who brushed him aside. So he has repeatedly turned to women for comfort and been rejected. It doesn’t excuse his behavior, but it does help me understand it.

Each answer in the above sequence could be a story all it’s own. In fact, I get little glimpses of scenes as I re-read my answers. I’m not going to write out all those details, not for this minor character, but I could. And if this were one of my main characters, I totally would.

It’s an interesting exercise to bring to my writing, especially now that I find myself at the beginning of a new project. It’s not so fun with the manuscript I just finished. When I ask why 5 times of my first novel it’s less exciting because I know all the answers already. I figured them out without this little trick, it just took me nine years to do it.

So there you go. May my eavesdropping save you a few years of floundering.

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