The Pivot

Jonathan Rogers: What Do You Do When Your Best Work Fails Completely?

September 15, 2026·1h 5m
Episode Description from the Publisher

Description: Sixteen years ago, Jonathan Rogers finished the novel he was proudest of — and watched it fail so completely that it never made it onto a single bookstore shelf. In this conversation with Andrew Osenga, Jonathan revisits that heartbreak as he re-releases The Charlatan's Boy with a new cover and new illustrations, and traces how the experience forced him to ask an uncomfortable question: why did he need strangers he'd never meet to tell him he mattered? That reckoning eventually pulled him out of a lonely writing life and into founding The Habit, a community built on the idea that writers don't need to compete to do good work — they just need someone in their corner. Thought-Provoking Quotes: "Why is it so important to me that people I don't know admire me? Why do I need to be loved by people I can't love back?" - Jonathan Rogers  "It's the loneliest thing in the world when the book comes out and the world doesn't stop and notice."  - Jonathan Rogers  "You don't have to prove yourself. You don't have to make a name for yourself. You've got a name and you've got an identity."  - Jonathan Rogers  "I'm not nearly as afraid of failure as I used to be."  - Jonathan Rogers  “Writing is a good thing to do whether you get published or not” - Jonathan Rogers Links, Products, and Resources Mentioned:The Charlatan's Boy by Jonathan RogersThe Wilderking Trilogy by Jonathan Rogers The Habit — Jonathan's membership community/organization for writers The Habit's "Focus Retreat"  *Watch this interview on Andrew’s YouTube channel!  *All episode music is by Andrew Osenga.  Guest’s Links: The HabitFacebookInstagramX Connect with Andrew: WebsiteYouTubeSubstackSpotifyFacebookInstagramHow to Remember by Andrew OsengaHo

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