The Help Desk: As a writer, how do I get into another person's head?

Every Friday, Cienna Madrid offers solutions to life’s most vexing literary problems. Do you need a book recommendation to send your worst cousin on her birthday? Is it okay to read erotica on public transit? Cienna can help. Send your questions to

Dear Cienna,

I've done NaNoWriMo a few times and I have this one problem: My characters always turn out to be me, and it's boring the shit out of me. Last year, I tried to make the main character do some fun stuff: get into bar fights, go on a trip to the Middle East — I even tried to make him an undercover spy. But in the end, he snapped back to the same boring guy working at the same boring office. Why can't I engage my imagination? Am I cursed to always write what I know? Should I give up fiction forever?

Jeff, Magnuson Park

Dear Jeff,

You are in luck, as this is the perfect week to begin practicing escapism, much like my spiders do every time I try to contain their orgies to shoe boxes. Reading and writing are excellent ways to help people forget, however briefly, the practical (or carnivalesque) horrors of their daily lives.

You want to know how to write about someone other than yourself. I have two exercises for you:

1) Swap the gender of your main character – make her a woman, or LGBTQ, basically any type of person on the sexual or gender rainbow other than yourself. Instead of making your novel plot-driven, make it character driven. Explore how the world you've created perceives your character, how they navigate that world, how they interact with other characters you've created. (Tom Wolfe did this with the 2004 novel I Am Charlotte Simmons, which I personally thought was dull but other people went crazy for. I am confident you can do better than Tom Wolfe.)

2) Think of someone you personally know whom you actively dislike. Make them your main character, and, like the previous exercise, make your novel character driven as opposed to plot driven.

Both of these writing prompts are exercises in empathy. The best writing helps readers relate on some level to characters they don't understand or are even repulsed by. If you want your writing to resonate with an audience – or if you simply want to stop boring yourself – challenge yourself by writing about people and situations that make you uncomfortable.