A cure for story paralysis

Lane DeGregory's advice on not playing it safe, plus: how to interview shy people

August 1, 2025

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Dear Storyboard community,

Midway through my podcast conversation with Pulitzer Prize-winning journalist Lane DeGregory, I told her about a problem I've had in the past with reporting and writing projects: I would sit on multiple story ideas, in a state of paralysis, unable to decide which one to pursue. What if I chose the wrong one?

DeGregory said she didn't have that problem. "I think we're always waiting for the perfect story, and it's kind of like waiting for the perfect time to have a kid.”

In other words, decide, and get on with it. Picking one subject or angle isn’t the only decision you'll ever make, as DeGregory has proved during her 25-year career at the Tampa Bay Times. She's a prolific storyteller, an inspiring teacher, and there are lessons from every piece she writes. Her 2023 anthology, "The Girl in the Window and Other True Tales," includes specific notes and annotations on how she reported and wrote some of her classic pieces, including the title story, which won the Pulitzer Prize for Feature Writing in 2009.

On her website, DeGregory shares "a letter to young journalists," but really it's timeless advice for all of us:

I wish I had known that it was okay to make mistakes, that no matter how brilliant — or bad — your story is, another paper will come out tomorrow, so it’s okay to try something that might not work. But it’s not okay not to try. Or to bore yourself by always doing what’s safe. Or to think your readers will care if you don’t.

Thank you, Lane. Here's to the next story.

Pulitzer winner Lane DeGregory on the power of local storytelling

Lane DeGregory interviews Kalin Stokes. Photo by Dirk Shadd — Lane DeGregory interviews Kalin Stokes about a housing experiment in St. Petersburg. Photo by Dirk Shadd, courtesy Tampa Bay Times

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Links of note

When data-gathering is part of the story: ProPublica has created a database with individual narratives from the more than 230 Venezuelan immigrants who were taken from the U.S. and sent to the CECOT prison in El Salvador. This month, more than 200 of them were released and sent to Venezuela. “We spent four months without any contact with the outside world,” Arturo Suárez told Mother Jones. “We were kidnapped.”
On interviewing shy people: “Some people just take longer to open up. It can help if you record something in the field with them. Feel free to ask the same (or similar) question many times. It just gives them a chance to reflect more. Ira Glass has said he’ll often ask someone the same thing 4 or 5 times. That made me feel better because I do this a lot.” This is from Erika Lantz, who with her sister, Elin Lantz-Lesser, interviewed former nuns in Mother Teresa’s order for the podcast “The Turning: The Sisters Who Left.”
For Defector, Eva Holland writes about a National Geographic documentary that has gone missing — many questions, no definitive answers, and few willing to speak or go on the record.
Let's wrap this week by looking at how Storyboard contributor Kim Cross sets up her characters and their obstacles. It's a story for ESPN about her family's longtime tradition of riding in Bo Jackson's charity bike race:

[Cross's son] Austin was 6 the first time he did Bo Bikes Bama. I towed him in a Burley bike trailer as he passed out Easter eggs. At 8 he was the youngest rider to pedal the 20-mile loop around Auburn, crushing the hills and becoming an unofficial mini-mascot. At 9, he raced a boy up the climbs, shook Bo's hand, and mailed him a hand-written thank you note:

I think it is great that an NFL ~~player~~ star like you takes the time and energy out of your day to do this. In a few years I might be able to catch up to you! ... Thank you for putting on Bo Bikes Bama. Your ~~fre~~ friend, Austin Freyer

Then we moved to Idaho. Seven years flew by. Austin elongated into a lean, taut 17-year-old cyclist on a national devo team, training 15 hours a week for mountain bike nationals. He'll finally be able to catch up to Bo. That is, if it doesn't storm.

"One hundred percent chance of rain," a volunteer says. "Like an inch. At least."

If lightning strikes, the ride will be cancelled. If not, we'll ride in the rain. In 14 years of Bo Bikes Bama, they've never once had bad weather. Maybe the lucky streak has run out for an outdoor event held at the peak of tornado season in the heart of Dixie Alley.