15 Sep 2026 05:00
Jonathan Rogers: What Do You Do When Your Best Work Fails Completely?
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 Rogers
The Wilderking Trilogy by Jonathan Rogers
The Habit — Jonathan's membership community/organization for writers
*Watch this interview on Andrew’s YouTube channel!
*All episode music is by Andrew Osenga.
Guest’s Links:
Connect with Andrew:
