What 500 Conversations Taught Me

At the end of almost every episode of Uncorking a Story, I ask the same question. If you could go back in time and whisper some advice into your younger self's ear, what would you say?

I've asked it of hundreds of people now — bestselling novelists, first-time memoirists, a neurosurgeon, a spiritual medium, the guy who launched the Xbox. You'd think that many people would give that many different answers.

They don't. One answer comes up more than any other. I'll get to it.

This week, Uncorking a Story hits episode 500. Here's what I've learned.

I started this show to get clients

In 2011 I was a new qualitative research moderator. Brands paid me to sit down with strangers and get them to tell me the truth. Every prospective client wanted to see examples of my work, and I had two problems. I didn't have much work yet. And what I did have was proprietary. You can't show Procter & Gamble the interviews you did for Unilever.

So I started a podcast. I could show I knew how to pull a story out of a stranger. And in 2011, simply having a podcast made me look ahead of the curve.

Episode one was "From Comedy Clubs to the Pulpit," with Father Dave Dwyer, who went from MTV and Comedy Central to the priesthood. The show notes said it paired well with a crisp white. I didn't record much that first year, and what I did was all over the map.

In 2013 my first novel came out, and I hired a publicist. She told me to make the show about authors. I'd learn the craft from people who had mastered it, the show would finally have a focus, and my books would sit in the same conversation as theirs. She was right on all three.

I like to say I interview authors to give them a platform. The truth is I wanted to pick their brains. Uncorking a Story became my MFA, with a new professor every week. Today the publicists find me, and I'm booked at least six months out.

The story starts long before the book

Ask an author where their story begins and almost nobody names a book deal. They name a library.

April Henry wrote a story about a six-foot frog when she was about nine and mailed it to Roald Dahl. He wrote back. Kaira Rouda's fifth-grade librarian laminated her first little book and put it on the shelf. If you've ever put a book in a kid's hands, you may have written the first chapter of somebody's career.

There's no such thing as an overnight success

April Henry's first book never found an agent. Her second found one but never sold. Her third didn't even earn nice rejection letters. Her fourth sold in three days. "So it was kind of like an overnight success," she told me. "So it took nine years."

Camille Di Maio's debut took four years, 43 rejections and 17 drafts. Kay Smith-Blum said she was still getting rejected, but she was getting better rejections. We only hear about the outliers who sell to the first agent who reads them. The real story is the person who keeps digging.

It's never too late

Some of my favorite guests started writing in their sixties and seventies. Iris Mitlin Lav retired at about 72, "still all there," and decided to write fiction. Lina Chern told me she was glad she came to it later, because life had taught her so much about people.

If you're sitting on a story because you think the window has closed, it hasn't.

Writing is therapy

I started this show to learn how to write a better book. I didn't expect to learn why so many people need to write one.

When I ask memoirists whether writing their book helped, I hear the same word again and again: cathartic. Jane McGuinness told me that until she wrote hers, she hadn't really owned her story. Therapists I've interviewed prescribe it. When you're upset, take a deep breath and write it down.

The writers who tell the hardest stories best aren't writing from the open wound. They wait until it scars over, and they write from the scar.

Writing through grief

In June 2023 my brother Greg died of lung cancer. He'd never smoked. A year and a month later, my mom was gone too. I was with them both at the end.

I kept recording through it, and I kept writing. Grief and comedy make strange bedfellows, but Greg was funny to the end, so I wrote fiction with both in it. When I finished, I actually felt better. I've come to believe the act of writing is where the healing comes from, and that's as true for fiction as it is for memoir.

It doesn't end the grief. Grief doesn't have an end date or an off switch. But writing gave me permission to feel it instead of numbing it.

Where stories come from

In November 2024, a guest mentioned authors who channel their books. I joked that it sounded a lot easier than what I was doing. To me, writing was discipline — daily reps, like logging miles.

About a month later, it happened to me. At three in the morning over Christmas, sick in the guest room, a story arrived in flashes, almost whole. That became The Waiting Room. Only afterward did I notice I'd named my characters Mary and Joseph, put them in Holy Family Hospital, and set the whole thing on Christmas Eve. None of it was on purpose.

I'm not the only one. Guest after guest has described a book arriving like a download in the middle of the night. As spiritual medium Anna Raimondi put it, "You reread it and say, wow, I don't remember writing that."

I grew up Catholic and I still practice. I don't know exactly where stories come from. But I've stopped thinking of writing as only a craft. There's a spiritual component to it. Some days it's closer to prayer: you show up, you get quiet, and you listen.

It's going to be okay

So, that question about your younger self. The most common answer, by far, is reassurance.

"You're gonna be okay." "Don't worry so much." "Hang in there." "Don't worry. Your future is assured. You'll be fine." Jane McGuinness passed along her best friend's version: it's all going to be okay in the end, and if it's not okay, it's not the end.

One guest apologized for giving that answer. "Isn't that an awful answer?" she asked. It isn't. It's a powerful one. My favorite came from Holly LaBarbera, who said she'd tell her younger self not to worry so much, "but I'd probably like to tell my current self that too, and I don't really listen now either."

When a friend turned the tables on me for episode 451, I said I wouldn't change anything, because it took me a while to like who I became. I added one thing: spend time with the people you love, because they won't always be there.

At 500, my answer is simpler: it's going to be okay. Run your own race. And treasure the little moments, like my brother waiting on his back porch for the hummingbirds.

Thank you to every guest who let me uncork their story, and to everyone who listens. Pour yourself something. Here's to the next 500.

Listen to episode 500 of Uncorking a Story on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts.