
S4E8 Rosie Wilby
06/19/24 • 26 min
In this episode of "The Longest Day," Rosie Wilby recounts her most challenging day, which also marked a pivotal moment in her life and career. On January 3, 2011, Rosie was abruptly dumped by her partner of five years via email. The shock and pain initially left her devastated and unable to process the breakup for years. Over time, however, this experience became the catalyst for a new creative direction.
Rosie eventually used this painful experience as the foundation for a trilogy of comedy shows focused on the psychology of love. This journey led her to create the podcast "The Breakup Monologues," write two books on relationships, and speak at various festivals about human connections and breakups. In the immediate aftermath, Rosie experienced a whirlwind of emotions and sought the support of friends. Remarkably, she performed a gig that evening, using her raw emotions to create a memorable and genuine comedy performance.
Rosie explores themes of communication, human connection, and the complex nature of grief in breakups. She reflects on how humour can serve as a defence mechanism and a way to process pain. She also discusses the societal implications of comedy, particularly for someone who doesn't fit the "default" comedian mold, and the challenge of balancing humour with self-compassion.
Using personal experiences in her art, Rosie acknowledges both the healing aspects and the potential for self-harm in revisiting painful memories. Despite the difficulties, she views breakups as opportunities for personal growth and transformation, allowing individuals to reinvent themselves and open up to new possibilities. Rosie's story is a testament to resilience and the power of creativity in overcoming personal challenges, finding joy and strength in unexpected places.
You can download Rosie's book, The Breakup Monologues: The Unexpected Joy of Heartbreak on Amazon here: https://www.amazon.co.uk/gp/aw/d/1472982282/
Don’t forget to subscribe, rate, and share this episode by following The Longest Day Podcast here:
- LinkedIn: https://www.linkedin.com/company/thelongestdaypodcast/
- Facebook: https://www.facebook.com/share/15QDqkhjZw/?mibextid=wwXIfr
- YouTube: https://www.youtube.com/@TheLongestDayPodcast-z1x
- X: @longestdaypod
- TikTok: @thelongestdaypodcast
- Instagram: https://www.instagram.com/thelongestdaypodcast
- Website: www.thelongestdaypodcast.com
- All previous episodes: https://pod.link/1684217939
In this episode of "The Longest Day," Rosie Wilby recounts her most challenging day, which also marked a pivotal moment in her life and career. On January 3, 2011, Rosie was abruptly dumped by her partner of five years via email. The shock and pain initially left her devastated and unable to process the breakup for years. Over time, however, this experience became the catalyst for a new creative direction.
Rosie eventually used this painful experience as the foundation for a trilogy of comedy shows focused on the psychology of love. This journey led her to create the podcast "The Breakup Monologues," write two books on relationships, and speak at various festivals about human connections and breakups. In the immediate aftermath, Rosie experienced a whirlwind of emotions and sought the support of friends. Remarkably, she performed a gig that evening, using her raw emotions to create a memorable and genuine comedy performance.
Rosie explores themes of communication, human connection, and the complex nature of grief in breakups. She reflects on how humour can serve as a defence mechanism and a way to process pain. She also discusses the societal implications of comedy, particularly for someone who doesn't fit the "default" comedian mold, and the challenge of balancing humour with self-compassion.
Using personal experiences in her art, Rosie acknowledges both the healing aspects and the potential for self-harm in revisiting painful memories. Despite the difficulties, she views breakups as opportunities for personal growth and transformation, allowing individuals to reinvent themselves and open up to new possibilities. Rosie's story is a testament to resilience and the power of creativity in overcoming personal challenges, finding joy and strength in unexpected places.
You can download Rosie's book, The Breakup Monologues: The Unexpected Joy of Heartbreak on Amazon here: https://www.amazon.co.uk/gp/aw/d/1472982282/
Don’t forget to subscribe, rate, and share this episode by following The Longest Day Podcast here:
- LinkedIn: https://www.linkedin.com/company/thelongestdaypodcast/
- Facebook: https://www.facebook.com/share/15QDqkhjZw/?mibextid=wwXIfr
- YouTube: https://www.youtube.com/@TheLongestDayPodcast-z1x
- X: @longestdaypod
- TikTok: @thelongestdaypodcast
- Instagram: https://www.instagram.com/thelongestdaypodcast
- Website: www.thelongestdaypodcast.com
- All previous episodes: https://pod.link/1684217939
Previous Episode

S4E7 Ashley Cox
Ashley Cox, Executive Director of Business Affairs and General Counsel, formerly interim CEO of Aquatics GB, shares the story of his longest day, which was filled with challenges and personal loss. Despite facing a series of unfortunate circumstances, Ashley remained calm and focused on his role as a leader. He credits his ability to handle pressure to his background in sports and his experience as a lawyer. Ashley emphasizes the importance of creating a positive and supportive environment within an organization and the role of mentorship in personal and professional development. He also discusses the need to process grief and the value of having people around who can provide honest feedback.
Next Episode

S4E09 - Rick Torrison
Rick Torrison shares his longest day story, which involves his son's struggles with anger, identity, and self-worth. Rick discusses the importance of addressing limiting beliefs and how they shape our behaviors and outcomes. He emphasizes the need to change beliefs, not just behaviors, in order to create sustainable change. Rick also talks about the transformative power of unconditional love and how it has impacted his relationship with his son. Throughout the conversation, Rick highlights the role of faith and spirituality in his journey.
Don’t forget to subscribe, rate, and share this episode by following The Longest Day Podcast here:
- LinkedIn: https://www.linkedin.com/company/thelongestdaypodcast/
- Facebook: https://www.facebook.com/share/15QDqkhjZw/?mibextid=wwXIfr
- YouTube: https://www.youtube.com/@TheLongestDayPodcast-z1x
- X: @longestdaypod
- TikTok: @thelongestdaypodcast
- Instagram: https://www.instagram.com/thelongestdaypodcast
- Website: www.thelongestdaypodcast.com
- All previous episodes: https://pod.link/1684217939
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