Command Palette

Search for a command to run...

PodMine
How To Academy Podcast
How To Academy Podcast•October 16, 2025

Philippa Gregory - Jane Boleyn Reimagined

In this episode, Philippa Gregory discusses her novel about Jane Boleyn, exploring how historical fiction can reveal the internal life of a woman often misunderstood by Victorian historians, offering a nuanced perspective on her role in the Tudor court as a possible spy for Thomas Cromwell.
Cultural Criticism
History Deep Dives
Storytelling
Philippa Gregory
Jane Boleyn
Henry VIII
Thomas Cromwell
Catherine Howard

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
0:00/0:00

Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.

0:00/0:00

Podcast Summary

In this captivating episode of the How To Academy podcast, renowned Tudor novelist Philippa Gregory discusses her latest work "The Tainted Queen" with host Amy Morris. Gregory explores the fascinating and misunderstood figure of Jane Boleyn, wife of George Boleyn and sister-in-law to Anne Boleyn, who survived multiple Tudor scandals only to meet her tragic end during Catherine Howard's downfall. (01:01) The conversation delves deep into how historical prejudices have shaped our understanding of Tudor women, with Gregory arguing that Jane has been unfairly maligned by both Victorian and modern historians who projected their own biases onto her story. (01:27)

  • Main themes include the power of historical fiction to reveal women's inner lives, the dangers of tyranny in both Tudor times and modern politics, and the sophisticated spy networks that operated within Henry VIII's court

Speakers

Philippa Gregory

Philippa Gregory is one of Britain's most beloved historical novelists, best known for her bestselling Tudor series including the modern classic "The Other Boleyn Girl." She holds a PhD in interdisciplinary history and English literature and spent ten years writing her comprehensive history book "Normal Women," covering nine centuries of women's history from 1066 to 1966. Gregory's unique position as a successful novelist has allowed her the financial independence to undertake massive historical research projects that traditional academics couldn't afford to pursue.

Amy Morris

Amy Morris serves as the host for this episode of the How To Academy podcast. She conducts an insightful interview that draws out Gregory's expertise on both historical research methods and the parallels between Tudor tyranny and modern political movements.

Key Takeaways

Historical Fiction Reveals What Records Cannot

Gregory emphasizes that while history assembles records and makes interpretations based on evidence, fiction's unique power lies in exploring the internal lives of historical figures. (05:45) She explains that fiction can take you "behind the bedroom door" and into characters' secret private lives, providing entry into what would otherwise be a completely opaque internal world. For professionals, this highlights the importance of understanding that documented facts often tell only part of any story—whether in business dealings, team dynamics, or organizational history—and that developing empathy and insight into unrecorded motivations can be crucial for leadership and decision-making.

Survival Requires Strategic Adaptation and Hidden Alliances

Jane Boleyn's remarkable survival through multiple Tudor scandals illustrates the power of strategic thinking and cultivating secret alliances. (10:49) Gregory reveals how Jane likely survived by becoming part of Thomas Cromwell's spy network, trading information for protection and advancement. This demonstrates that in high-stakes environments, success often depends on understanding the hidden power structures and finding ways to make yourself valuable to those who truly hold influence, even when that influence isn't publicly acknowledged.

Recognize Tyranny Early Before It's Too Late

Gregory draws powerful parallels between Henry VIII's gradual consolidation of power and modern political situations, emphasizing that tyranny is often recognized too late. (29:34) She references Pastor Niemöller's famous poem about Nazi Germany to illustrate how people often fail to speak up when tyranny doesn't initially affect them directly. For professionals, this serves as a crucial reminder to stay vigilant about organizational or political changes that concentrate power, eliminate checks and balances, or silence dissent, and to speak up early rather than waiting until you're personally affected.

Question Historical Narratives and Seek Multiple Perspectives

Gregory demonstrates how historical figures like Jane Boleyn have been consistently mischaracterized due to the biases of different eras—Victorian morality, modern assumptions about sexual behavior, and male-dominated historical perspectives. (01:27) This teaches professionals the critical importance of questioning established narratives in their own fields, seeking out diverse perspectives, and recognizing how current biases might be shaping interpretations of events, whether in market research, performance reviews, or strategic planning.

The Danger of Centralizing Power in One Individual

The conversation reveals how Henry VIII's narcissistic personality became catastrophically dangerous when combined with absolute power, creating a system where "the king's happiness is what determines the safety of the kingdom." (19:54) Gregory explains how this made the political deeply personal in immediate and dangerous ways. For modern professionals, this highlights the risks of organizational structures that concentrate too much decision-making authority in single individuals, especially those with narcissistic tendencies, and the importance of maintaining checks, balances, and distributed leadership even in fast-moving business environments.

Statistics & Facts

  1. It took Philippa Gregory ten years to write "Normal Women," her comprehensive history covering nine centuries of women's history from the Norman Conquest in 1066 to 1966. (07:56) She notes that this was only possible because she was financially independent from her novel-writing success, as no academic historian could afford to spend that much time on a single project that might never see publication.
  2. It has been twenty-five years since the publication of "The Other Boleyn Girl," during which time historical understanding of Henry VIII and his wives has significantly evolved. (26:51) Gregory explains that new medical research has explored whether Henry was a psychopath, had genetic disorders, or suffered from Cushing's disease, fundamentally changing how historians view his behavior.
  3. Catherine Howard is now believed to have been much younger than previously thought - possibly only 17 years old when she was executed - and historians have established that she was sexually abused while in her grandmother's negligent care. (27:15) This has shifted the historical narrative from viewing her as an immoral mature woman to understanding her as a victim of abuse.

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

More episodes like this

a16z Podcast
January 13, 2026

Ben Horowitz on Investing in AI: AI Bubbles, Economic Impact, and VC Acceleration

a16z Podcast
Plain English with Derek Thompson
January 13, 2026

Plain English BEST OF: The Modern World Is Changing America’s Personality for the Worse

Plain English with Derek Thompson
The Art of Manliness
January 13, 2026

Money and Meaning — What Faith Traditions Teach Us About Personal Finance

The Art of Manliness
The Game with Alex Hormozi
January 13, 2026

The Mathematics of Business, Explained | Ep 990

The Game with Alex Hormozi
Swipe to navigate