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My guest for Episode #301 of the My Favorite Mistake podcast is Jonathan Small, an award-winning journalist, editor, podcast host, and producer based in Los Angeles. As president of Strike Fire Productions, he has built a diverse career that spans magazine editing at top publications—from Child Magazine to Maxim—and pioneering roles in digital media and podcasting. Known for his candid storytelling and willingness to embrace risk, Jon has transformed professional setbacks into defining career moments, including leaving a cushy executive role to reinvent himself in a rapidly changing media landscape.
He's also the podcast of a podcast called “Write About Now.” Jon's also the author of a book with the same title.
In this episode, Jon recounts his bold decision to leave a high-flying magazine career in New York for a risky, low-paying production role in Los Angeles—a move that, despite its initial challenges (like parting with his beloved cat and facing financial uncertainty), ultimately redefined his career. He shares insights into the evolution of the publishing industry, the shift from print to digital media, and how even seemingly disastrous mistakes can pave the way for reinvention, new opportunities, and personal growth.
Jon also delves into his extensive experience as a writer and interviewer, offering practical advice on common pitfalls in writing and the art of “show, don’t tell.” He emphasizes the importance of embracing imperfect first drafts, the necessity of reading widely to hone one’s craft, and the value of authentic conversation in podcasting—whether as a host or a guest.
Throughout the episode, listeners are treated to vivid anecdotes from his career, tips for leveraging AI in writing, and reflections on how vulnerability and genuine curiosity fuel both compelling storytelling and effective interviews.
Questions and Topics:
- What is your favorite mistake?
- What prompted you to leave magazine editing for a role in film production?
- Did you consider returning to New York after the move?
- What was your role at the movie production company?
- What are the most common mistakes rookie writers make?
- Can you provide an example that illustrates the difference between showing and telling in writing?
- What tips do you have for becoming a more effective interviewer?
- Based on your experience, what advice would you offer to guests on a podcast?
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- Video version of the episode
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- Quotes
- Full transcript
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Automated Transcript (May Contain Mistakes)
Mark Graban:
Hi, welcome to My Favorite Mistake. I'm your host, Mark Graban. Our guest today is Jonathan Small. He is an award-winning journalist, editor, podcast host, and producer based in Los Angeles. He is the president of Strike Fire Productions, a podcast production company.
Mark Graban:
He's hosted podcasts, including one called Write About Now. So since he's a writer, it's spelled W-R-I-T-E. If you go searching for Write About Now, you'll find it features interviews with successful writers. Jon has written for publications including The New York Times, TV Guide, Cosmo, Details, Maxim, and Good Housekeeping. And he's the author of a book with the same title as that podcast, Right About Now.
Mark Graban:
So, Jon, welcome to the show and tell us about the award you just received.
Jon Small:
Oh yes, thanks. Just Breaking News just got voted one of the best indie books of the year by Kirkus Reviews magazine. That just came out—it was a really exciting moment.
Mark Graban:
Congratulations, congratulations for that. We're going to talk about writing, and we have a lot to cover in the episode. Before we get into your favorite mistake story, I've got a comment: looking at the list of publications like Cosmo and Maxim, that's really a full spectrum of publications, right?
Jon Small:
It is. And it's funny—in the early part of my career, I always say I evolved. I started my career in magazines at a publication called Child Magazine, which was a parenting magazine. Then eventually I started working for a teen magazine called Twist.
Jon Small:
Then, eventually, I graduated to working for women's magazines like Glamour and Cosmo, and finally found my actual place in life by working for a men's magazine, Maxim, and later at Stuff magazine. So I've kind of gone through every generation of growth in my magazine career.
Mark Graban:
Yeah, and you were writing for Child Magazine early in your career without having any children.
Jon Small:
Zero children. I had absolutely no clue what I was doing back then. Now I have two children, and I still can’t believe they let me have that job in retrospect. But I found my niche—I reviewed children's books and children's movies.
Jon Small:
I did travel, stayed at family-friendly hotels, and pretended to be a travel writer. So yeah, I made the best of it, but it was a ridiculous job for me.
Mark Graban:
Well, I'm glad you're here with us today. So I'm going to ask you the question we always start with: What's your favorite mistake?
Jon Small:
The favorite mistake I ever made professionally was when I was at the peak of my career. I was executive editor of Stuff magazine—the number two most popular magazine in America at the time. Everything was going great, and I decided to quit my job. My career was in a great place—I was even on track to possibly become editor-in-chief in the next few years.
Jon Small:
I had devoted 10 years of my life to being an editor, serving as executive editor (second in command) at one of the top men's magazines. And then I left to go to Los Angeles for a job that paid about a fifth of what I earned. The money had no security whatsoever. I didn’t really know anyone in Los Angeles; I was living in New York at the time.
Jon Small:
I actually had to leave my cat behind because they wouldn’t allow me to bring one. That was a big deal for me because I love cats. I started working for a fledgling movie production company. Within about two months of that major life shakeup, I lost that job at the movie company—because, believe it or not, working for an indie movie production company is a pretty tenuous career move.
Jon Small:
I found myself without my old cushy job at Stuff and without the security of my friends and my cat in New York. I thought, “Maybe this is the stupidest thing I’ve ever done.” But you know what? It ended up being probably the best decision I ever made in my life—aside from the cat issue, because I’ve always been upset that I had to leave my cat in New York. In retrospect, that decision also revealed that the magazine business would completely cease to be in the next few years.
Mark Graban:
What year was this taking place?
Jon Small:
We're talking about 2003, 2004. This was the end of the print magazine era, pretty much. And it was also a time when everything was shifting to digital. I found myself thinking, “Maybe this is the stupidest thing I’ve ever done”—and yet, finding a new job and a new career path in Los Angeles completely reinvented me.
Jon Small:
I became a digital online editor, got very involved in digital video, and embraced podcasting when it started taking off. Out of necessity, this mistake—something I thought was foolish—turned out to be one of the smartest moves I ever made because it put me in an entirely new frame of mind and forced me to reinvent myself. I also met my wife out here and ended up staying here. I still say “here” even though I’m a New Yorker—I wear my Dodgers cap here. So, yeah, a good mistake.
Mark Graban:
Yeah, you could say it was a mistake that worked out.
Jon Small:
It worked out.
Mark Graban:
For those who are just listening, you can’t see it, but Jon’s got a fashion-driven Dodgers hat. It looks like a factory mistake where it somehow became red and black.
Jon Small:
I don't know. But I'm so tired of wearing blue that I have all these different versions of LA caps in various colors. I think this one might be a mix—like the colors of the LA Angels meeting the LA Dodgers. I just didn’t want to wear blue.
Jon Small:
Maybe it's my way of saying I love the Dodgers, but I'm still a New Yorker, so I can’t fully commit to their full colors.
Mark Graban:
Yeah, I was in Japan in November with a Yankees hat.
Jon Small:
Exciting, right?
Mark Graban:
It was exciting—you know, a Yankees hat with that logo in every color under the sun, being sold and worn. I saw Dodger hats too, like something inspired by Otani.
Jon Small:
Yeah, that's what I would imagine. He's huge over in Japan.
Mark Graban:
But the Yankees brand is still…
Jon Small:
It really is a powerful brand.
Mark Graban:
So, can you walk us through what led you to shift from magazine editing to a job at a movie production company? In the moment, it seemed like a good idea—not a mistake. What prompted that decision?
Jon Small:
It always seemed a little risky. There were two mistakes I made. One was working for a friend—a high school friend, which I don't recommend. It turned out to be the only business he ever created that wasn’t hugely successful. He’s now retired and a multimillionaire with many other businesses. For some reason, the one business I got involved in was his only failure.
Mark Graban:
He doesn’t blame you for that, right?
Jon Small:
I hope he doesn't. I still thank him because he got me out there. But we were talking—I was burned out. I think we all reach that point in our careers. I was in my late 30s, very tired, not married, with few responsibilities holding me down. I probably couldn’t have made this decision as easily now with all the commitments I have.
Jon Small:
This was a time when I was relatively free, not in a committed relationship. It was shortly after 9/11, and living in New York was incredibly stressful. I was traveling back and forth to California for celebrity interviews, and I had carved out a niche as the guy who did those interviews. I kept thinking, “LA is amazing; it seems so far removed from the tenseness of New York.”
Jon Small:
So, it seemed like a mistake—but the real mistake was taking an insanely low pay cut. I took about a fifth of my previous salary. It was almost an unlivable wage. I had to live with a friend in a house, even though I previously had a really nice apartment in New York. I was living the magazine dream, and then this happened.
Jon Small:
I had no experience in movies other than enjoying going to them. Suddenly, I found myself calling agents about projects, and I quickly realized I was out of my depth. I even thought about going back after a couple of months, but it was too late.
Mark Graban:
What exactly was your role at the movie production company?
Jon Small:
I was head of production for a company called Ming Productions. A friend of mine, Peter, had raised money in Japan—independent Japanese financing—to start a production company that would produce American projects in Japan. It seemed like a great concept because people in Hollywood are always chasing money. But when you're a low-budget, non-studio operation, you start getting all the worst projects that no one else wants. Agents sent over scripts that were not very good or interesting, and the talent was very low level.
Jon Small:
I immediately knew that this was going to be a tough grind—unless we discovered an amazing indie flick, which we never did. My friend eventually got less interested as he became more involved in his work in China and started having real success there. So we parted ways, though we remain good friends.
Jon Small:
Suddenly, I found myself on my own, living with roommates in a Venice apartment, not really knowing what to do. It did seem like a mistake—like, “What have I done?” It was the only time I really blew up my life, but it ended up being a good thing because it led me down a new path.
Jon Small:
I sometimes tell people, if you're in a position where you can make a major change but you're just too scared, don’t do it if others depend on you. But if you’re free, then go for it—I did.
Mark Graban:
Did you consider going back to New York?
Jon Small:
I did. I can’t say I didn’t consider it completely, because I still freelanced—wrote stories for Maxim and kept contacts at Stuff magazine. Back then, magazines were still paying decent wages—around $2 a word for quality magazines, which is a lot more than today. So I could have returned, but the work was unstable and I lost benefits like health insurance. It was jarring for someone used to a secure, company-based life.
Jon Small:
Even though I’ve been freelancing for a while now, once you experience those “golden handcuffs,” it’s hard to let them go.
Mark Graban:
I'm glad you’ve found happiness in LA. I, too, have a favorite mistake story—I took a job in 1999 in Austin, Texas, which wasn’t the right fit, but I ended up meeting my wife there 20 years later.
Mark Graban:
So, Jon, tell us about your experience as an advice columnist at Glamour. I’m sure there's a fun story behind that.
Jon Small:
Well, back when I was at Child Magazine—one of my first jobs—I was working for a parenting magazine. Across the hall was a magazine called YM (Young & Modern, as they later rebranded), where the cool girls from the teen magazine worked. We’d hang out at the water cooler or grab drinks after work.
Jon Small:
They would share their sob stories about guys, and I’d say, “Why don’t you do this?” They told me I was good at giving advice—so I started writing advice stories for YM, and later for Cosmo and Glamour. It became my thing—I was the guy who could dole out advice. It’s ironic because I’m terrible at following my own advice. I never considered myself an expert, yet I spent a lot of my life pretending I was. Welcome to being a magazine editor.
Jon Small:
Later, when I got a staff position at Glamour, they asked me to take over a column called “Jake” (sometimes known as “Ask Jake”), which was a first-person advice column. Then, when I was freelancing in LA, Cosmo called and asked if I’d be their “Guy Guru” for a new column.
Mark Graban:
So you weren't hiding behind a female pseudonym like “Jake”?
Jon Small:
No, no. It was always as a guy—definitely a guy’s perspective. And interestingly, I still meet people who say they read my column back in high school. I always apologize and explain.
Mark Graban:
Very different times.
Jon Small:
Yeah.
Mark Graban:
So I want to tap into your experience as a writer on the theme of mistakes. What are some of the top mistakes rookie writers make?
Jon Small:
Oh, my goodness.
Mark Graban:
What are the most common mistakes that, if we haven't learned from them already, we need to overcome or avoid?
Jon Small:
There are many. One is trying to perfect the first draft—writers kill themselves trying to get it right immediately, even though the first draft is really just a “vomit draft” to get everything down. Writing is mostly rewriting afterward.
Another mistake is not understanding the principle of “show, don’t tell.” Writers often simply tell rather than illustrate their points.
And finally, many writers want to write without having read widely. To be a good writer, you need to read—to absorb what makes a good story and how sentences are structured effectively. Those are three major pitfalls I see. I even did a podcast episode with my friend Melissa Clark about the 20 mistakes new writers make—and we laughed because we did them too.
Mark Graban:
I’ll be sure to put a link to that episode. Was that episode on Right About Now or somewhere else?
Jon Small:
It was on Right About Now. I’ll definitely share the link.
Mark Graban:
I think it's especially important to understand the difference between “show” and “tell” in writing. Can you provide an example?
Jon Small:
Sure. For example, instead of saying “it was a really rainy day,” which is telling, you might describe the wetness of your shoes, the temperature, and how the rain felt on your skin. That brings the experience to life. When you dissect good writing, you see that a vivid description is more interesting than just stating facts. That’s the essence of “show, don’t tell.”
Mark Graban:
That’s very helpful. Even in non-fiction, good writing involves letting the reader experience the story rather than just reading the facts.
Jon Small:
Exactly. I often tell non-fiction writers, “Don’t just list the facts; show me how they apply to your life.” Otherwise, the story can feel flat.
Mark Graban:
I mentioned earlier that I sometimes run my writing through AI to evaluate if I’m showing or telling. I might even ask ChatGPT for a synopsis of this episode—clearly, it’s good at that. But sometimes it uses crutch words like “delve into.”
Jon Small:
Right. I always love it when it does that—it tends to sound like a marketing exec at Nike with words like “innovative.” It never sticks to one thing; it's always multiple adjectives.
Mark Graban:
I agree. Using AI as a thought partner is great, but you have to ensure it stays true to the source.
Jon Small:
Absolutely. I often tell it, “Stay true to the source material.” These generative AI platforms are only as good as the person monitoring them.
Mark Graban:
I sometimes ask ChatGPT for five compelling verbatim quotes from the transcript for social media. It’s a good exercise.
Jon Small:
Yes, but you have to be clear in your instructions to get exactly what you need.
Mark Graban:
Now, let’s talk about podcast hosting and interviewing. What have you learned about being a better interviewer? What advice do you have?
Jon Small:
You're doing great, Mark. But really, the most important thing is curiosity—and listening. Some podcasters, even with a prepared list of questions, miss out on following the conversation. I've learned that it's crucial to listen carefully so you can follow interesting tangents rather than just ticking off a list of questions.
Jon Small:
I learned a lot about listening from my early days when I wanted to be an actor in college. Acting is about listening and responding to your scene partner—not just reciting your lines. Podcasting is similar: you must respond to the answers you hear.
Mark Graban:
That’s great advice. Good guests also make an interviewer look good. What advice would you give to guests on a podcast?
Jon Small:
As a guest, I recommend being prepared with a few bullet points—don’t script your responses verbatim. You want to be natural. If you have a script, it comes off as reading, and that isn’t engaging. Have a general outline of your points, but then let the conversation flow naturally. Authenticity and vulnerability are key.
Mark Graban:
I’ve had experiences where guests clearly read their answers. It’s much better when you’re authentic.
Jon Small:
Exactly.
Mark Graban:
And, do you have kids? I mean, all these changes in your life—what about your family?
Jon Small:
I do. I watch my daughter—she’s 14 and plays volleyball. I hope she's not listening to us because, honestly, she's terrible at it! But she makes herself go to practice every day. She's very dedicated, and I often think, “I don’t know if I could do what she does,” because she makes so many mistakes—and yet, she keeps pushing forward.
Mark Graban:
Well, when you're new to a sport, that dedication teaches you a lot. And if she happens to be tall, well, you can’t really teach height.
Jon Small:
She is very tall, which definitely helps.
Mark Graban:
Or volleyball.
Jon Small:
Yeah, she is tall, which helps a lot.
Mark Graban:
Alright, so as we wrap up here, tell us a little bit about your book.
Jon Small:
Right About Now is a collection of origin stories. Over the years, I’ve interviewed hundreds of writers—including bestsellers like Ken Follett, Kristen Hannah, and David Grann—and I was always surprised that their stories were filled with mistakes, challenges, and doubts. I realized these imperfections make their journeys relatable, so I compiled the best origin stories from my interviews into one book.
Jon Small:
Origin stories have always fascinated me—whether they’re from real people or fictional characters. I see them everywhere, from the latest Lego Movie to a new Transformers film. People love to know how someone started from nothing and rose to the top.
Mark Graban:
I saw an ad yesterday for a new Dexter origin story.
Jon Small:
Right, exactly.
Mark Graban:
So I hope people will check out the book—there’s a lot to learn about writing, resilience, and finding your own unique path.
Jon Small:
Right, exactly. It’s inspiring whether you’re a writer or not. It shows that even those who started with nothing can succeed by learning from their mistakes.
Mark Graban:
And congratulations again on the Kirkus recognition for your book—top 100 indie books. Our guest today, Jonathan Small, has been fantastic. There will be links in the show notes to learn more about him and his work. Thank you so much for sharing your story.
Jon Small:
Thank you. It’s always a pleasure to be interviewed by a fellow podcaster and writer. I really appreciate it.
Mark Graban:
Thanks—and a fellow Dodger fan.
Jon Small:
Oh, and a Dodger fan indeed.
Mark Graban:
I lived in LA for two years. Shohei Ohtani has been my favorite player; I kind of followed him.
Jon Small:
He is absolutely amazing. Listen, I completely switched my loyalties—from being a Yankees fan in the 90s when I lived in New York to being all-in with the Dodgers now. I didn’t even hesitate about my loyalties this series.
Mark Graban:
It's a beautiful place to watch a game; you really feel that LA sunshine.
Jon Small:
Yeah, it really is. LA makes New York look so gray, boring, and even depressing—especially this year, even compared to the rapper Ice Cube or whoever they had perform before the game.
Jon Small (laughing):
It just wasn’t working out.
Mark Graban:
Yeah, not a good performance from Fat Joe—though he’s no longer fat, but still.
Jon Small:
Exactly. He just wasn’t cutting it.
Mark Graban:
Yeah, it's just Joe. All right, well, John. Not Fat Jon, Jon Small. Thank you for being here again today. I'm going to awkwardly wrap up and again say thanks.
Jon Small:
Thank you.
3 Actionable Takeaways from the Episode with Jon Small
Embrace Mistakes as Opportunities for Growth
Jon Small shares his story about leaving a promising editorial career at Stuff magazine for a risky move to Los Angeles—a decision he initially thought was a mistake, but later realized was a pivotal moment in his career. He mentions, “It ended up being probably the best decision…” because it opened new avenues in the digital and podcasting world (00:05:57 – 00:05:59). Listeners can reassess their past decisions and see how perceived mistakes may have led to unexpected opportunities.
The Value of Listening in Interviews
Jon highlights the importance of listening actively during podcasts, referencing some podcasters who miss pivotal moments because they don't listen enough, like Alec Baldwin's interview with Billy Joel. He stresses, “You should… listen to what the answers are because it might take you in a direction you didn’t necessarily plan on going” (00:33:17 – 00:33:29). Implementing active listening could improve communication skills in podcasting or any interview setting.
Utilize AI as a Collaborative Tool
Jon discusses using AI as a writing partner to identify clichéd phrases or improve writing by asking it to “filter out every cliché” or improve their storytelling by “showing, not telling” (00:27:01 – 00:27:09). By leveraging AI, listeners can enhance their writing or editing process, ensuring their content is engaging and well-structured.