The Legendary Leaders Podcast Podcast By Cathleen O'Sullivan – Growth Accelerator for Leaders cover art

The Legendary Leaders Podcast

The Legendary Leaders Podcast

By: Cathleen O'Sullivan – Growth Accelerator for Leaders
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Welcome to the Legendary Leaders podcast series! This podcast aims to inspire thousands and thousands of people to start living their best lives! My podcast guests will be sharing their own personal paths to success, the moments when they may have hit a wall that turned into their biggest breaking point, and we will be sharing some top tips on how to proactively create some exciting changes in your life. These leaders will be talking about how they started their journey, what inspired and drove them, along with the challenges they had to overcome along the way to get to where they are now, having achieved a more content and balanced life. The podcasts will cover an array of topics from the importance of selfcare and mindset, through to bravery and authenticity, and the importance of building communities and support networks. I have interviewed leaders who have all taken varied and interesting paths, from content creators, journalists through to designers, coaches, musicians and actors a business mentors, speakers and many, many more. They all faced tough challenges which served as motivation to live their best lives yet! I hope you enjoy listening to my series of podcasts as much as I have done creating them, and I really hope you take away lots to inspire, encourage and motivate you on your journey to becoming a Legendary Leader.Cathleen O'Sullivan (Merkel) Career Success Economics Leadership Management & Leadership
Episodes
  • Lorraine Whale – Roots, Reinvention and a Really Good Plan

    Lorraine Whale – Roots, Reinvention and a Really Good Plan
    Mar 24 2026
    What if the key to reinventing your career isn't a dramatic leap—but a quiet, stubborn plan built one small step at a time? In this warm, deeply honest episode of Legendary Leaders, host Cathleen O'Sullivan is joined by Lorraine Whale, qualified genealogist, house historian, and founder of Time Flies Ancestry—who spent over 25 years in HR and leadership roles before following a passion she'd been nurturing for decades. Their conversation spans career reinvention, the emotional cost of falling out of love with a profession, the underrated power of a good plan, and what it really means to lead yourself forward when nobody else is handing you a roadmap. Lorraine opens with something that will resonate with many—she doesn't see herself as a leader at all. But as the conversation unfolds, it becomes clear that her definition of leadership, building trust, giving others confidence, showing up with tenacity—is exactly what she has been doing all along, in boardrooms, in genealogy archives, and at home as a single mum raising a son she is quietly and fiercely proud of. She shares how she mapped her escape from HR with an Excel spreadsheet worthy of Andy Dufresne, why redundancy felt like liberation, and how a squiggly career can be the most intentional one of all. They also get into the human side of HR—why it too often becomes a ticketing system rather than a true business partner, what real people functions should look like, and the question that changed everything for Lorraine: Do you want to retire working in this? And for anyone wondering whether it's too late to start over, Lorraine's answer is simple: find the thing that lights you up, make a plan, and don't just do nothing. This is a conversation that will meet you with grace wherever you are in your career—and quietly nudge you to take that first step. Episode Timeline: 00:03:54 "I've never seen myself as a leader" 00:06:38 From admin to HR to genealogy — finding her place 00:16:39 Solitude, community, and the AGRA network 00:18:38 Falling out of love with a profession 00:21:19 What great HR actually looks like 00:29:02 The Andy Dufresne escape plan 00:34:02 Squiggly careers and waiting for what's next 00:40:13 The first small step 00:43:32 Loving the problem-solving of genealogy 00:49:43 The village it takes to raise a child 00:56:13 Self-care when there's no time for it 00:58:26 Find the thing that lights you up 00:59:13 How to find Lorraine and Time Flies Ancestry Key Takeaway: Reinvention Isn't a Leap — It's a Long Game: Changing direction doesn't mean scrapping everything overnight. Lorraine spent years qualifying, downsizing, and planning while still in her HR role. The most meaningful career shifts are built slowly, deliberately, and with a very clear goal in sight. Your Whole Career Is the Foundation, Not the Obstacle: A squiggly path isn't a weakness — it's a toolkit. Every function, every stakeholder, every challenge you've navigated gives you a perspective that a linear career never could. Don't discount it. Build on it. Ask Yourself the Uncomfortable Question: Lorraine's turning point came from one honest question — would I want to retire doing this? Sitting with that discomfort is where real clarity begins. If the answer is no, that's not a crisis. That's a starting point. If You Have a Goal, Make It Visible: Good intentions don't create change — a plan does. Whether it's an Excel spreadsheet, a timeline, or a milestone tracker, seeing your progress move is what keeps you going when the goal still feels far away. About Lorraine Whale: Lorraine Whale is a professional genealogist and family history researcher who helps people uncover their ancestral stories and preserve family and house histories. As Founder of Time Flies Ancestry, she specialises in detailed genealogical research that goes beyond online records to include archives, museums, and local history resources across southern England. Lorraine holds a Diploma in Genealogy and is a member of the Association of Genealogists & Researchers in Archives (AGRA) and the Register of Qualified Genealogists, and she also serves on the tutorial team of the Institute of Heraldic and Genealogical Studies. Today, she works with clients around the world to trace their roots and bring forgotten family narratives to life, drawing on decades of experience and a deep passion for the past. Connect with Lorraine Whale: Website: https://www.timefliesancestry.co.uk/ LinkedIn: https://www.linkedin.com/in/lorraine-whale-75634a1b/ Association of Genealogists and Researchers in Archives (AGRA): https://www.agra.org.uk/ Connect with Cathleen O'Sullivan: Business: https://cathleenosullivan.com/ LinkedIn: https://www.linkedin.com/in/cathleen-osullivan/ Instagram: https://www.instagram.com/legendary_leaders_cathleenos/ YouTube: https://www.youtube.com/@LegendaryLeaderswithCathleenOS FOLLOW LEGENDARY LEADERS ON APPLE, ...
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    1 hr and 2 mins
  • From One Conversation to Many

    From One Conversation to Many
    Mar 10 2026

    What if the biggest breakthrough in your leadership journey wasn't about having all the answers—but about showing up anyway, doubts and all? In this milestone solo episode, host Cathleen O'Sullivan celebrates 200 episodes by sharing the raw truth behind her podcasting journey—a masterclass in self-leadership, persistence, and knowing when to hold on versus when to let go.

    Cathleen opens up about crippling self-doubt, struggling with her accent, and balancing motherhood with building a business. Through it all, she discovered that impact doesn't need to be loud to be meaningful, and that starting small can lead to extraordinary ripples. This episode is your permission slip to take that brave step you've been holding back on.

    Episode Timeline:

    01:01 A journey of ups, downs, and contemplating quitting

    06:08 Battling the inner critic: "Who do you think you are?"

    08:07 What does it really mean to lead well?

    11:44 What felt tremendously hard: vulnerability and overthinking

    15:51 The power of starting small

    19:23 Freezing at the first recording: the fear of judgment

    21:30 Small steps that helped pushing through

    25:15 Key highlights from 200 episodes and extraordinary guests

    27:47 What's next: more unpolished truth and deeper solo episodes

    Key Takeaway:

    • The Power of Starting Small: You don't need perfection or a grand plan. Leadership begins with leading yourself out of fear and into your next step—one question, one voice, one brave move.

    • Vulnerability Is Strength: The most powerful leaders often have the deepest doubts. Being visibly human—doubt and all—isn't a weakness; it's your greatest asset and what builds trust.

    • One Person at a Time: Impact doesn't have to be loud to be meaningful. If one person feels less alone or more understood, it's worth it. Small, consistent changes create ripples.

    • Alignment Over Approval: Real leadership is about energy, behavior, and intention—not status or perfection. Choose what truly matters over what looks impressive.

    Connect with Cathleen O'Sullivan:

    Business: https://cathleenosullivan.com/

    LinkedIn: https://www.linkedin.com/in/cathleen-osullivan/

    Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

    YouTube: https://www.youtube.com/@LegendaryLeaderswithCathleenOS

    FOLLOW LEGENDARY LEADERS ON APPLE, SPOTIFY OR WHEREVER YOU LISTEN TO YOUR PODCASTS
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    31 mins
  • Augusta Vivian – Culture Starts in the Smallest Moments

    Augusta Vivian – Culture Starts in the Smallest Moments
    Mar 3 2026
    What if the culture your organisation is trying to build isn't hiding in a values poster or a strategy deck—but in the smallest things you do every single day? In this warm, deeply practical episode of Legendary Leaders, host Cathleen O'Sullivan is joined by Augusta Vivian, CEO of Higson, a people development consultancy helping senior teams lead through change, build inclusive workplaces, and embed culture that actually lasts. Their conversation spans parenting and leadership, kindness as a performance tool, the hard work of real inclusion, and why stubborn values might be the most underrated leadership quality of all. Augusta opens with something personal—how raising her 17-month-old daughter has sharpened her understanding of presence, trust, and the power of micro moments. From there, the conversation moves into the heart of her work: how the tiny, consistent behaviours we model become the architecture of how we treat each other at scale. She shares how Higson builds change-ready cultures, why clarity is an act of kindness, and how vulnerability from a leader doesn't weaken authority—it creates the conditions for real trust. They also tackle inclusion head-on—unpacking the critical difference between diversity and inclusion, the unconscious bias we all carry, and how even the language we use with toddlers is quietly shaping future leaders. And Augusta makes a compelling case that fun, charity, and giving back aren't soft add-ons—they're non-negotiables, built into processes and calendars precisely because life is busy and good intentions alone don't get it done. This is a conversation that will nudge you to look differently at how habits, tone, and attention shape the people around you—at home, in your community, and at work. Episode Timeline: 00:04:18 Parenting as a leadership practice 00:06:41 Why micro moments are the real culture builders 00:09:31 Building a change culture, not just surviving change 00:12:59 The importance of kindness and vulnerability 00:18:02 Financial transparency, strategy days 00:21:24 Culture add, not culture fit 00:23:56 Core values of of Higson 00:29:06 Making the values a non-negotiable 00:34:38 The people behind the passion and authenticity 00:36:35 Stubbornness as a values-led superpower 00:41:14 The impact of her Oxford days 00:43:10 Diversity vs inclusion – what leaders get wrong 00:52:26 Why culture change stalls at the poster 00:58:44 Intelligent failure and the Rose, Thorn, Bud tool 01:04:57 What a parenting book teaches us about leadership 01:08:16 Boundaries over balance Key Takeaway: Culture Lives in Behaviour, Not Slogans: Values on a wall mean nothing without the layer below them. Define what your values look like in practice, build them into how you hire, appraise and recognise people—then they become culture. Most organisations skip that step. Kindness is a Performance Tool, Not a Nice-to-Have: Honest communication, genuine recognition and psychological safety aren't soft—they're the foundation of high performance. Teams that trust their leader navigate change faster, stay longer and go further above and beyond. Diversity Gets People in the Room. Inclusion Keeps Them There: A diverse team without an inclusive culture doesn't outperform—it underperforms. Around 70% of how included someone feels comes directly from their leader. Check your language, challenge your biases, and make sure people feel heard—not just present. If It Matters, Build It In—Don't Just Intend It: Charity work, fun, wellbeing check-ins, strategy days—none of it happens on good intentions alone. If something is a value, make it a non-negotiable: schedule it, process it, protect it. Otherwise, busy wins. About Augusta Vivian: Augusta Vivian is a people development and organisational culture expert who works with leaders and teams to build inclusive, high-performing workplaces and lead through change. As Founder and CEO of the people consultancy Higson, she specialises in designing leadership frameworks, behavioural change programmes, and talent practices rooted in psychological insight that help organisations communicate better, innovate, and thrive. With a degree in Psychology from the University of Oxford, Augusta combines deep expertise in human behaviour with a mission to create positive social and environmental impact — including donating a significant portion of Higson's profits to charity and achieving B Corp certification. Today, she partners with professionals who want to transform culture, strengthen leadership, and drive lasting results in their organisations. Resources Mentioned: The Right Kind of Wrong: https://a.co/054z87s9 The Whole-Brain Child: https://drdansiegel.com/book/the-whole-brain-child/ Connect with Augusta Vivian: Website: https://consulthigson.com/ LinkedIn: https://www.linkedin.com/in/augustavivian/ Connect with Cathleen O'Sullivan: ...
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    1 hr and 16 mins
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