Overcoming Setbacks: Jonathan Small on the Career Mistake That Sparked His Success

My Favorite Mistake: Business Lessons from Failures and Success

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2M ago 45:22

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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.

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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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