The inspiration for the 50-Headline Challenge that I introduced back in Episode 50 came from an interview with Jon Morrow, who wrote 100 headlines a day for two years.

One of the things Jon brought up in that original interview with Duct Tape Marketing is that he likes to focus on the emotion he wants to bring out in the reader. The interviewer asked about his practice for finding that target emotion, and Jon explained that writing the 100 headlines a day helped him a) get better at writing headlines; and, b) find the ideas that seemed to generate emotion.
Headlines with Emotion
Those are the headlines he uses to write his posts: The ones that start with a target emotion, that make you feel something. He wants to write something that might make you cry or get mad. Jon stressed that sometimes you want a reader to get angry because, for example, let's say something is holding a reader back and he or she needs to push past that—Jon argues the reader should get angry at that block or resistance, so bringing out that emotion can be a good gift to the reader.

The interviewer asked Jon how it all worked, and Jon said he has to get himself into the state he wants the reader to be in. To do so, he might watch some YouTube videos or read a passage in a book or draw up a memory. And when the emotion is stirred inside him so strong that he can no longer contain it, he dumps it onto the page.

When people read and begin to feel that emotion, you create a connection—maybe even form a bond— between writer and reader. This reminds me of Robert Frost's famous quote:
No tears in the writer, no tears in the reader. No surprise for the writer, no surprise for the reader.
When I work on little snippets of memoir in an article or book, I take myself back and try to not only remember what happened but how I felt. Chapter 8 of On Being a Writer: 12 Simple Habits for a Writing Life That Lasts is titled "Discover (When I write, I discover myself)."

When working on that chapter, I took myself back to a formative stage in my teens and tried to pull up the circumstances and feelings. I keep the emotion understated, but here’s a portion of what I wrote.
Excerpt from On Being a Writer, Chapter 8 - "Notice"
By the time I (Ann) was 14, I realized the children’s department of the local library couldn’t provide the depth I yearned for. Shyly, I made it a habit to browse the adult nonfiction shelves for exercise books, vegetarian cookbooks, drawing tutorials, and a series that taught survival skills, in case I ever acted on my dream of living by myself in the woods, like the kid in My Side of the Mountain.

One afternoon I glanced through books on writing. A title caught my eye: Write to Discover Yourself, by Ruth Vaughn. I looked both ways and plucked it from the shelf, running my fingers over the green cover with a fuchsia Gerbera daisy poking out of a pencil cup. It seemed a little wacky, but . . .

Write. Discover.

I desperately wanted to understand myself, unearth who I was meant to become. And deep down, I wanted to write.

Cheeks flushed, heart thumping, I tucked the book under my arm to hide the title from anyone who might question my desire to write, or ridicule my search for self. I feared my family’s response most of all. In a household of word-people—both parents were journalists and my brother would eventually become an advertising executive—I was the vegetarian runner who asked for art supplies at Christmas. Compared with my family, I had never demonstrated noteworthy writing talent. I lost every game of Scrabble®.

Nevertheless, I retreated to my room, tiptoeing up the staircase, and secretly penned responses to the author’s writing exercises. I stuffed the spiral-bound notebook far back in my closet so no one would peek.

Over time, I kept a journal and followed instructions to “portrait” the important people in my life, exploring memories, capturing life. I sat on the hardwood floor of my bedroom and composed a w...