Doubt Diaries

Jim Keyes is the former CEO of 7-Eleven and the last CEO of Blockbuster. He has been the chief executive of two Fortune 500 companies, which is something very few people in the world can claim. He also came home from school at age ten to find his family’s house literally condemned - he had to look the word up. We talk about that, and about the real story of what happened at Blockbuster (most of wh...

Tara Mohr is the bestselling author of Playing Big, an Apple Book of the Year, and one of the most quietly influential voices on women’s leadership today. I came across her work years ago and think she's incredible! We talk about why the entire confidence-building self-help industry might be solving the wrong problem - and the reframe that has stayed with me ever since. Originally released in...

Sara Jane Ho is the founder of China’s first finishing school and the host of the Emmy-nominated Netflix series Mind Your Manners. She is a Harvard Business School graduate and the author of Mind Your Manners: How to Be Your Best Self in Any Situation. We talk about why she genuinely doesn’t worry about failing, why etiquette can give you confidence, and what she does in the moment when she walks...

Rob Pierre is the co-founder and former CEO of Jellyfish, the digital media and marketing group he built over eighteen years and recently sold for, in his own words, ‘an eye-watering amount of money.’ He was named Media Week’s Media Leader of the Year in 2021. He is also one of the very few guests on this show with a fully thought-through framework for managing self-doubt. We talk about his ‘modul...

Joanna Flint is the Global Chief Commercial Officer at Mandarin Oriental Hotel Group. Before that she spent twelve years at Google, ending as Managing Director, Singapore. Like me, she’s originally British and has ended up in Singapore. We talk about the moment a colleague reframed an entire job application for her and why she nearly didn’t apply for the Google MD role. Originally released in 2024...

Rick Harshman is a senior tech leader who has held managing director roles across Asia Pacific at Google Cloud, UiPath and AWS. He has been based in Asia for nearly twenty years. I admit on this episode to a bias I didn’t know I had - and his answers thoroughly upended it. We talk about thirty years of imposter syndrome rooted in growing up in a family where greatness was the table stakes, and the...

Mollie Rogers Jean de Dieu is General Manager of Longchamp in Singapore and Malaysia, and the author of Emotional Inclusion: A Humanizing Revolution at Work. She coined the term 'emotional inclusion'. We talk about what it really takes to be human in a professional workplace, why everyone discusses emotional intelligence and almost no one discusses emotional inclusion, and what this means...

Tim Shriver is the chairman of Special Olympics - the world’s largest organisation for children and adults with intellectual disabilities, founded by his mother, Eunice Kennedy Shriver. He is the author of the New York Times bestselling memoir Fully Alive. His uncle was John F Kennedy. We talk about what it actually does to your sense of self to grow up in a family where the unspoken benchmark was...

Welcome to Doubt Diaries. A podcast about self-doubt, imposter syndrome, and the people you'd never expect to have either. Host Pippa Woodhead has spent the last seven years and over 2,000 interviews talking to the people we'd assume are endlessly confident: CEOs, Olympic athletes, Ivy League psychologists, and bestselling authors.  She assumed they'd all have it figured out. After all...