Jeanne Darst's story is what happens when everything goes right—and then you realize "right" is more complicated than you thought.

After years of doing plays for 200 people in Vermont, she hit the publishing lottery: a bidding war sparked by a “This American Life” appearance that had publishers hunting her down by the next morning.

Riverhead Books won with serious money, the New York Times loved it, Vogue excerpted it, HBO optioned it and she wrote the pilot. It was the full fantasy—except the show didn't get picked up (Girls was coming out), and she spent the next decade in the Hollywood machine.

Her TV writing career was a success—she got a series of TV staff writing jobs—but her second book, Dad's Trying to Kill Me, couldn't find a publisher (despite glowing rejections). Now she's back to putting on shows while continuing to write, because sometimes the dream coming true teaches you what you actually want.

Episode Highlights:

• How Jeanne's This American Life story triggered a massive publishing bidding war overnight
• The strategic decision to write a proposal instead of submitting a completed manuscript
• Why Jeanne chose Riverhead and editor Sarah McGrath over the highest bidder
• The simultaneous media blitz: book launch, Vogue excerpt, and This American Life feature
• How HBO optioned the book before publication, leading to pilot writing opportunities
• The reality of post-success hustle: why the dream is "just the beginning of heartbreak"
• Jeanne's second book rejection and the lesson about going to small presses
• Why she's returning to grassroots theater after a decade in Hollywood
• The father-daughter dynamic when children outachieve their parents professionally

Key Takeaways:

• Two years of persistence can lead to overnight success 
• Agents and gatekeepers are "smart secretaries" - you must drive your own career
• Women wait 8 months to resubmit after rejection; men wait 3 days
• Big advances don't guarantee book tours or sustained marketing support
• Publishers only invest real marketing dollars in books that are already succeeding
• Hollywood packaging deals often benefit agencies more than the writers themselves
• Complete projects teach more than abandoned ones - finish what you start
• Traditional publishing success requires constant self-advocacy and hustle
• Family reactions to memoirs can be complicated, especially around professional jealousy