How To Fail With Elizabeth Day

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Jilly Cooper: On Failure, Love and Literature

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Oct 6, 2025

Guest

Jilly Cooper

Join the charismatic Dame Jilly Cooper, a best-selling novelist renowned for her Rutshire Chronicle series, as she shares her vibrant tales and insights. Jilly discusses her misconceptions about being labeled a popular author, her obsession with beauty reflected in her characters, and her harrowing experience of losing a 400,000-word manuscript on a bus. She also opens up about her struggles with technology, fertility, and the significance of friendship, all while celebrating a life filled with creativity and resilience.

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INSIGHT

Literary Status Is Time-Dependent

Jilly questions what qualifies as literature and suggests time decides whether work becomes literature.
She accepts being called a popular author and wonders if longevity determines literary status.

insights

INSIGHT

Class Remains A Quiet Force

Jilly sees class as a persistent social behaviour where people look up and down at others.
She notes class now may be less openly discussed but still influences how people judge each other.

question_answer

ANECDOTE

A Relentless Draft Hoarder

Jilly keeps roughly 15 drafts of every piece and stores them everywhere, admitting she can't throw things away.
Her house filled with notebooks, files, photos, and drafts, making her office very untidy.

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Jilly Cooper's Rise from Journalism to Bestseller

03:14 • 2min

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On Not Calling Herself Literary

05:11 • 1min

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Class and the Rutshire Chronicles' Social Insight

06:36 • 53sec

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Seeing the Rivals TV Adaptation

07:29 • 33sec

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Creating Rupert Campbell-Black

08:02 • 38sec

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Friendships with Royals and Politicians

08:41 • 1min

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Obsessed with Beauty and Masculinity

09:51 • 2min

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Family, Mother's Struggles, and Making People Happy

12:13 • 1min

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Failure: Hoarding Drafts and Cherishing the Past

13:27 • 4min

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Lost Manuscript on the Bus and Rewriting Rivals

17:53 • 1min

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Surviving the Paddington Train Crash

18:59 • 55sec

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Resilience, Deadlines, and Money Worries

19:55 • 12sec

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Thoughts on Death and Reuniting with Loved Ones

20:06 • 1min

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Regrets About Oxford and Knowing Yourself

21:10 • 1min

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Fertility Struggles and the Joy of Adoption

22:27 • 4min

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Failure to Stick to Diets and Body Image

26:01 • 4min

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Interviewing Margaret Thatcher and Public Figures

29:37 • 2min

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Technological Challenges and Typing Habits

31:26 • 1min

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Writing Process and Planning Books

32:27 • 1min

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Favourite Characters and Recurring Cast

33:36 • 25sec

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Driving Later in Life and Learning to Drive

34:01 • 1min

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The Importance of Friendship

35:10 • 1min

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Public Recognition, Fan Letters, and Social Media Views

36:17 • 1min

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Looking Back: Pride and Receiving a Damehood

37:23 • 37sec

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Legacy Over Literary Establishment Approval

38:00 • 40sec

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Listener Advice Segment Teaser

Polo is a novel by Jilly Cooper that immerses readers in the exhilarating and exclusive world of polo. The story follows the lives and loves of polo players, their families, and the social elite who surround the sport. Set against a backdrop of lavish estates and high-stakes matches, Polo explores themes of passion, rivalry, and the pursuit of success. Cooper's detailed descriptions of the polo matches and the lives of the characters create a vibrant and engaging narrative. The book captures the glamour and excitement of the polo scene, while also delving into the personal struggles and triumphs of its characters.

#8011

• Mentioned in 5 episodes

Riders

Jilly Cooper

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Class

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Rivals

Janet Dailey

Jilly Cooper's "Rivals" is a captivating novel set in the vibrant world of horse racing and the English countryside. The story follows the lives of several characters, their ambitions, and their relationships, all intertwined with the excitement of the races. The novel is known for its witty writing style, its engaging characters, and its depiction of social dynamics within a specific time period. It's a popular choice for readers who enjoy historical fiction with a focus on romance and social commentary. The series explores themes of love, rivalry, ambition, and the complexities of human relationships against the backdrop of the glamorous world of horse racing.

Today, we remember and celebrate the extraordinary life of Jilly Cooper, who has sadly passed away at the age of 88. A literary icon, Jilly captured hearts and imaginations with her wit, warmth, and unmistakable voice. Her novels, especially beloved titles like Riders and Rivals, sold over 11 million copies in the UK alone and most recently inspired the hit Disney+ adaptation that introduced her work to a whole new generation.

I had the immense privilege of speaking with Jilly just last October. She was everything I’d hoped she would be - funny, sharp, generous and inspiring. Today, in tribute to her legacy and the joy she brought to so many, I’m honoured to share the conversation with you again.

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Dame Jilly Cooper. What a legend. For the uninitiated (where have you been?) she’s a journalist and author most famous for her bestselling Rutshire Chronicle series which includes Riders, Polo and Rivals - the latter of which has now made into a hugely popular TV series starring David Tennant, Danny Dyer and Katherine Parkinson. In the past, Dame Jilly’s books have been unfairly dismissed as mere ‘bonkbusters’, charting the sex lives of the upper classes. But, as I discover, there’s much more to both her writing - and to her. We talk about her failures with technology, why she wishes she could throw more things away, as well as the terrifying time she lost an entire manuscript on the number 28 bus and had to rewrite it. Plus her experiences of interviewing Margaret Thatcher, her friendship with the Queen, her obsession with beautiful people and ‘macho men’ - and why she’d wholeheartedly recommend adoption to others.

Thank you Dame Jilly. A total sport (but we knew that).

✨ IN THIS EPISODE:

00:00 Remembering Dame Gili Cooper

03:43 Personal Reflections and Literary Success

07:37 Exploring Themes of Masculinity and Beauty

10:15 Family, Loss, and Resilience

11:28 Failures and Fertility Challenges

21:18 Dieting and Body Image

25:12 Interviewing Margaret Thatcher

26:46 Technical Challenges and Writing Process

30:27 Friendship and Social Media

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