Letter To My Younger Self with Dame Stephanie "Steve" Shirley CH Tech Pioneer, Businesswoman & Philanthropist

In this powerful micro podcast episode, Holly reconnects with the remarkable Trinny Woodall, founder and CEO of Trinny London and a woman whose career in fashion and media has influenced and inspired for over 30 years. In a heartfelt letter to her younger self, Trinny shares the raw truths, hard-won wisdom, and deeply personal reflections that define her journey. With courage and honesty, she dives into moments of vulnerability, reminding us of the importance of speaking our truths—even when they might be unpopular. As Trinny reflects on navigating self-doubt, guilt, and the pressure to conform, her words resonate with anyone who has ever second-guessed their voice or values. Holly listens and reflects on the universal themes of self-acceptance and resilience, sharing her own realizations about the importance of standing firm in one’s beliefs. This episode is a powerful reminder to trust in your voice, as the right people will appreciate it. Whether you’re at the beginning of your journey or looking back with the wisdom of experience, Trinny’s letter is a true gift, filled with inspiration and courage.

What do you do when life, as you know it, shatters in an instant? In this episode, Holly speaks with Ed and Lois Jackson and explores the profound and life-altering journey that they have been on. Once living a dream life filled with athletic success and endless opportunities, their world was turned upside down when Ed, a former professional rugby player, suffered a catastrophic accident that left him paralyzed. What followed was not only a physical battle to defy the odds and regain movement but a mental and emotional transformation for both Ed and Lois. Together, they’ve faced the unimaginable, and through grit, resilience, and love, they've found a new purpose, helping others overcome adversity and reframe their mental health in the process. This is a raw, inspiring story of how Ed and Lois have turned a tragedy into a mission to uplift, empower, and show that even in our darkest moments, there is light, hope, and a way forward. This conversation will challenge you to rethink what it means to face hardship and how when life doesn’t go as planned, we are truly capable of much more than we know.

Get a glimpse into one of the most phenomenal entrepreneurial minds in the world with Greg Hoffman, author and former Chief Marketing Officer of Nike, a man who has not only led some of the most powerful marketing campaigns in history but one who has an awe-inspiring understanding of what makes human beings tick.  In this micro episode Greg reads a letter to his 7 year old self, sharing the insights and experiences that carved his path from humble beginnings to reaching the pinnacle of success. This is your micro shot of inspiration and an episode that brings to life the transformative power of a simple letter.

What if the key to a more just, compassionate world started in the classroom? In this powerful and thought-provoking episode, Holly speaks with award-winning filmmaker, human rights advocate, and education activist, Leslee Udwin. Known for her groundbreaking documentary India's Daughter and as the visionary behind Think Equal, Leslee shares her journey from confronting injustice on the screen to reshaping education for empathy, compassion, and social equality. Throughout their conversation, Leslee discusses the pivotal moments that inspired her to dedicate her life to creating an education system rooted in emotional intelligence and mutual respect. Think Equal imagines a world where empathy is as essential as numeracy or literacy, teaching children from a young age to appreciate and respect diverse cultures, genders, races, and religions. This episode is both inspiring and, at times, deeply raw, as Leslee speaks openly about the painful realities that have driven her mission. But her passion for creating a world where children learn empathy, respect, and emotional resilience shines through, offering hope for a more peaceful future. Trigger Warning: This episode addresses sensitive and potentially distressing topics, including discussions on race, sexual violence, child abuse, and violence against women. Listener discretion is advised, and we encourage you to prioritise your well-being. Please pause or skip sections that may be triggering for you.

What would you say to your 21 year old self? What advice and wisdom would you share? In this micro episode, we hear from Anya Hindmarch CBE, accessories designer, design and arts advocate, sustainability campaigner and Sunday Times bestselling author.  as she gives us a glimpse into the world through her eyes with an intimate letter written to her younger self. With an unique ability to make the ordinary, extraordinary, Anya’s letter is a love note to self, one that encourages and supports, advises and guides. This is your micro shot of inspiration and an episode that brings to life the transformative power of a simple letter.

What drives someone born into one of the UK’s most prominent aristocratic families to dedicate their life to prison reform, particularly advocating for the needs of women behind bars? In this episode, Holly speaks with the remarkable Lady Edwina Grosvenor, whose background might lead you to expect a life of privilege and tradition—but her story is anything but conventional. Edwina shares how, “From a really young age, I felt that injustice of the luck of birth,” an early realisation that sparked her commitment to the most marginalised members of society. From the impact of privilege on her perspectives to her work in addressing the systemic injustices faced by incarcerated women—like the lack of access to basic necessities—Edwina shares a rare, firsthand view of the hidden world of prisons. She dives into the complex relationship between domestic violence and incarceration rates, and why trauma-informed care is essential for breaking cycles of recidivism. She challenges us all: “Do we want our prisons to be warehouses for the incorrigible or greenhouses for the redeemable?” Her vision for a more compassionate justice system is clear: “Should we be helping people to lead a better life or should we be actively preventing it?” Listen now for a conversation that will open your eyes, challenge your assumptions, and inspire you to consider how empathy can drive real change. Join us in exploring the hidden world of prisons and the transformative power of hope. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to share? Enter for a chance to win your own ad break on this podcast. This opportunity is brought to you in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions. Exclusive Dell discount for Conversations of Inspiration listeners: Save up to 20% through Dell Exclusive Offers by using your email and the exclusive Holly & Co password: ‘HCO’. Trigger warning: This episode includes discussions about the deaths of babies, which may be distressing for some listeners. If you need to, please skip from 26 to 28 minutes. Take care while listening.

In this micro-episode, Holly revisits the extraordinary letter Sophie Morgan—TV presenter, author, and disability activist—wrote to her younger self. Sophie shares her powerful story of resilience after a life-altering car accident at 18 left her paralysed, yet propelled her towards a new, vibrant path. Through her letter, she reminds us that the tenacity and strength often labeled as "difficult" are the very qualities that help us overcome life’s toughest moments. This episode will leave you feeling empowered and inspired to embrace your inner strength, no matter the challenges you face. You’ll take away insights into: The power of resilience: Learn how Sophie turned adversity into triumph, showing that even life’s hardest moments can lead to a bright and colourful future. Embracing your true self: Discover why the very traits that others might see as difficult can become your greatest assets. A new perspective on hardship: Sophie’s wisdom will inspire you to find light in dark times and to keep moving forward, step by step. This episode is your micro-shot of inspiration, offering a heartfelt reminder that no matter where you are in life, you have everything you need within you to get through it all.

Imagine turning down a dream job, facing a mountain of debt, and surviving a life-or-death experience—only to emerge with a mission that’s transforming the world of giving. In this episode of Conversations of Inspiration, Matt Pohlson, co-founder of Omaze—a platform that offers life-changing experiences and prizes while raising funds for charitable causes—shares his remarkable journey. It’s packed with insights for anyone looking to make a difference. What you’ll learn: Turn fear into fuel – Matt reveals how he overcame $200,000 in debt and turned down a major job offer, staying true to his mission even when the challenges felt insurmountable. Build trust through vulnerability – Find out how embracing honesty and openness can forge deeper connections, whether in business or in life. Combine profit with purpose – Discover how Omaze has raised over £60 million for charities by harnessing the power of storytelling. Matt’s story is a powerful reminder that our toughest moments can become our greatest sources of strength. Tune in to see how these lessons could shape your own journey. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to share? Enter for a chance to win your own ad break on this podcast. This opportunity is brought to you in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions. Exclusive Dell discount for Conversations of Inspiration listeners: Save up to 20% through Dell Exclusive Offers by using your email and the exclusive Holly & Co password: ‘HCO’.

Dive into this inspiring micro episode of Letters to My Younger Self with Richard Reed CBE, co-founder of Innocent and Jam Jar Investments. In this heartfelt letter to his younger self, Richard shares invaluable life lessons that offer profound insights for anyone navigating their own journey. Listeners will gain: Empathy and Connection: Discover how Richard’s reflections on friendship and vulnerability resonate with your own experiences, fostering a deeper understanding of life’s challenges. Life Lessons: Gain practical wisdom about embracing sadness as an asset, learning to navigate fear-based thinking, and recognizing the importance of authenticity in building meaningful relationships. Inspiration for Growth: Feel motivated to reflect on your own journey and connect the dots of your past, realizing that every experience contributes to the person you are today. Join us to uncover the transformative power of self-reflection through Richard's heartfelt words. This episode promises to uplift and inspire, reminding you that you are not alone on this journey—your story matters.

Meet Patrick and Karen O’Flaherty, the dynamic husband and wife duo behind Pip Organic, a pioneering force in the organic food and drink industry. Their story began in the bustling heart of London, where their shared passion for health, sustainability, and community blossomed into a visionary business idea. United by their commitment to creating wholesome, organic products, Patrick and Karen embarked on a journey to transform the way people consume food and beverages. In this episode, Patrick and Karen reveal the intricacies of their entrepreneurial journey sharing the complexities of being an organic business and managing a sustainable supply chain all whilst ensuring that Pip Organic remains synonymous with purity and simplicity. But it’s not just a story about business, Patrick and Karen’s journey is also testament to the remarkable power of a family-run enterprise and of how they have woven their personal values into the fabric of their brand. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to tell? Enter for a chance to win your own ad break on this podcast. This competition is delivered in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions. Exclusive Dell discount code for Conversations of Inspiration listeners: You can save up to 20% off via Dell Exclusive Offers with your email and your exclusive Holly & Co password ‘HCO’.