Hannah Sward’s publishing journey reads like a masterclass in persistence meets divine intervention.

After years of writing short stories for underground literary journals, she stumbled into a free writer’s group at a library—complete with homeless people sleeping on the sidelines.

That’s where she met Jill Sherry Robinson, an 80-year-old bestselling author who essentially kidnapped her and mentored her until she finished her book.

Through a comedy of errors involving three different agents (one retired three months after signing her), Sward eventually sold her book for a whopping $500 advance.

But here's the kicker: by the time her book Strip came out in 2022, Sward had built such authentic relationships in the recovery community that the book found its audience organically. No Instagram strategy needed—just good old-fashioned showing up. Now she's chronicling her sexual adventures after 50 on Substack, where she’s learned that—guess what?—vulnerability pays off when book deals may not.

Episode Highlights:

How Hannah's 14-year friendship with Anna led to confessing literary jealousy at an AA meeting
The serendipitous connection with 80-year-old mentor Jill Sherry Robinson at a free library writers group
Hannah's unconventional memoir structure: 75 short chapters designed for non-readers
The grueling agent search: 100 rejections and three failed agent relationships before going solo
Publishing with a small press for a $500 advance while her father was dying in hospice
How building authentic community relationships over years created organic publicity opportunities
The launch of "Summer of Men" Substack about sex after 50 that had readers paying to find out what happens next
Why Hannah refuses to repeat the traditional publishing process for her next book

Key Takeaways:

Jealousy among writers is normal and can be processed healthily through honest conversation
Mentorship can appear unexpectedly - stay open to guidance from unlikely sources
Persistence pays off: Hannah's father modeled being "the king of rejection" as a badge of honor
Community building matters more than platform building for authentic book promotion
The publishing process can be an "integrated experience" when you work through disappointments internally
Small press publishing with low advances can still lead to meaningful success and readership
Leading with credentials (blurbs from Nobel Prize winners) gets manuscripts read, not just good writing
Writing partnerships and accountability groups sustain creative work over years
Success doesn't fill the internal "hole" - there will always be compare and despair moments
Sometimes the journey to publication teaches more than the publication itself