The Legendary Leaders Podcast

Cathleen O'Sullivan – Growth Accelerator for Leaders
  • 5.0 (14)
  • CAREERS
  • UPDATED BIWEEKLY

Welcome to the Legendary Leaders Podcast! This show aims to inspire you to start living your best life! My podcast guests will be sharing their own personal paths to success, the moments when they 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 professional and personal life. Our guests, who are all leaders in their own rights, will be talking about how they started their journey, what inspired and motivated them, along with the challenges they had to overcome in order to get to where they are now, having achieved a more content and liberated life. All episodes will cover an array of topics from the importance of self-care 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 as well as actors, business mentors, speakers and many, many more. They all faced tough challenges which served as motivation to live their best lives yet! Please enjoy listening to this 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.

  1. Augusta Vivian – Culture Starts in the Smallest Moments

    23H AGO

    Augusta Vivian – Culture Starts in the Smallest Moments

    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:  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.

    1h 16m
  2. Lena Sisco – Stop Giving Them Space in Your Head: Reclaiming Your Energy from Toxic People

    FEB 24

    Lena Sisco – Stop Giving Them Space in Your Head: Reclaiming Your Energy from Toxic People

    What if the person making your work life miserable isn't just difficult—but following a predictable pattern you were never taught to recognize? In this eye-opening episode of Legendary Leaders, host Cathleen O'Sullivan sits down with Lena Sisco—former military interrogator at Guantanamo Bay and expert in dark psychology—whose unflinching take on toxic workplaces will make you see that impossible boss in a completely different light.  Lena shares how she went from aspiring archaeologist to interrogating terror suspects, why her narcissistic boss threw a laptop across a C-suite meeting then got her fired while the company protected him, and why her neighbor's daughter stayed trapped in an abusive marriage for 10 years over an incident involving crackers. With striking honesty, she explains why she lived with anger for a year over that firing, why taking up physical space literally drops your stress hormones, and why kindness became her secret weapon in the interrogation room.  Together, Cathleen and Lena explore what manipulation actually looks like in daily interactions, why you cannot change someone with a personality disorder no matter how reasonable you are, and the hard truth about when systems protect bad behavior. This conversation is for anyone dealing with a boss who never gets held accountable, stuck doubting yourself in a toxic relationship, or ready to stop giving manipulative people free rent in your head—because sometimes the most powerful move isn't proving you can handle it, it's recognizing the pattern and walking away.   Episode Timeline: 00:08:10 Why she wrote The 13 Power Moves of Dark Psychology  00:14:04 What dark psychology actually is  00:22:14 The abuse cycle: fear, love bombing, and guilt trips  00:28:01 Her narcissistic boss threw a laptop in a C-suite meeting  00:32:38 Why she got fired for holding him accountable  00:40:55 Teaching empathy to a Marine Corps colonel  00:57:24 The physical shift that drops cortisol instantly  01:05:53 The SBIR feedback tool for accountability  01:12:42 Her first day at Guantanamo Bay  01:23:15 Why kindness became her interrogation superpower  01:33:50 Three accurate tells that someone is lying to you    Key Takeaway: You Can't Change a Narcissist—You Can Only Change How You Show Up: Personality disorders are in someone's DNA and neural pathways. No amount of reasoning, fairness, or empathy will change them. The only thing you control is whether you stay in that dynamic or protect yourself by setting boundaries and walking away.  Kindness Isn't Weakness—It's the Most Powerful Tool You Have: Lena's interrogation breakthrough came from taking off a detainee's handcuffs and offering tea, not from yelling or intimidation. Being kind to someone who's lying or manipulating you takes the strongest willpower—and it actually works because it disarms them while keeping you in control of the conversation.  Taking Up Physical Space Literally Drops Your Stress Hormones: When you uncross your arms, plant your feet, lift your chin, and open your palms, your cortisol drops and your confidence rises. Before any difficult conversation, reset your body first—because when you feel small physically, your whole demeanor gets smaller. Move your body, move your mind.  If Someone Can't Answer a Simple Yes or No Question, They're Probably Lying: Truthful people have no problem with direct answers. Liars dodge, embellish, and avoid committing because they can't take accountability. Watch for shoulder shrugs on definitive statements, head shakes that don't match their words, and rambling non-answers—these are the most accurate tells that someone isn't being honest with you.   About Lena Sisco: Lena Sisco is a communication and human behavior expert working with leaders and organizations navigating high-stakes conversations and complex decision-making. A former Department of Defense–certified military interrogator and Naval Human Intelligence Officer, Lena served during the Global War on Terror, conducting hundreds of interrogations that shaped her expertise in rapport-building, elicitation, and truth-seeking under pressure. She later founded The Congruency Group and Sector Intelligence, translating elite HUMINT tradecraft into practical tools for leadership, negotiation, and influence. Lena brings hard-won experience in reading behavior, managing uncertainty, and leading with clarity when the stakes are high. Today, she works with professionals who want to communicate with confidence and authority in moments that matter most.   Connect with Lena Sisco: Website: https://www.lenasisco.com/  Website: https://www.thecongruencygroup.com/  LinkedIn: https://www.linkedin.com/in/lena-sisco-8a31b451  Book: https://www.lenasisco.com/books  TruthScan AI: https://www.thecongruencygroup.com/truthscanai    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.

    1h 44m
  3. Clare Laycock – You Make It Look Too Easy: Leaving Status Behind to Redefine Success

    FEB 10

    Clare Laycock – You Make It Look Too Easy: Leaving Status Behind to Redefine Success

    What if your career success was never meant to be about the next promotion—but how free you feel every single day when you show up?  In this powerful episode of Legendary Leaders, host Cathleen O'Sullivan sits down with Clare Laycock—former SVP at Warner Brothers Discovery who spent 30+ years leading major UK television brands—whose honest account of walking away will make you question what you're actually chasing.  Clare shares how she fell into TV by grabbing someone else's unwanted placement, why her boss told her "you make it look too easy" when she asked for promotion, and why in television if you're not failing you're not trying hard enough. With disarming candor, she explains why she ran an Epic Fails Day with her team every year, why losing status hit harder than expected when people stopped returning her emails, and why she spent months dreaming about work even though her shoulders felt physically lighter the moment she left.  Together, Cathleen and Clare explore what it means to protect your team while the pressure crushes you, why "soft skills" being dismissed made her want to scream, and the shock of having to rehearse what to say at events when "I used to be..." doesn't work anymore. This conversation is for anyone navigating change, stuck at a crossroads, or binge-watching The Sopranos while processing what just happened to their identity—because sometimes the bravest thing isn't climbing higher, it's finally admitting you're done pretending easy work means it doesn't matter.    Episode Timeline:   00:06:24 Falling into TV by grabbing an unwanted placement  00:10:04 If you're not failing, you're not trying hard enough  00:14:21 Selling creativity to the bottom line  00:18:48 Protecting your team through brutal restructures  00:25:15 Vulnerability without losing strength  00:29:35 What difficult leaders taught her  00:31:45 Make a decision and make it the right one  00:35:09 Epic Fails Day and undervalued soft skills  00:43:06 You make it look too easy  00:50:28 When a culture just isn't right for you  00:59:53 Her shoulders felt instantly lighter  01:05:02 Redefining success beyond title and salary  01:10:59 Losing status and binge-watching The Sopranos  01:14:29 Introducing yourself without a big title   Key Takeaway: Walking Away Isn't Failure—Staying Stuck Is: Just because you've spent 30 years building success doesn't mean you can't choose differently. Clare's shoulders felt physically lighter the moment she left, even through the shock. The real trap isn't leaving—it's staying somewhere that crushes you when you know you're ready for something else.  "You Make It Look Too Easy" Is a Leadership Compliment—Not a Reason to Deny Promotion: When your boss tells you this, it means you've mastered the hardest skill: making complex work feel simple. But organizations undervalue leadership as a "soft skill," so you have to learn to dial up your profile by just 5%—not to brag, but to be seen for what you're actually delivering.  Failure Isn't Something to Hide—It's How You Innovate: Clare ran Epic Fails Day every year with her team. In TV, most programs fail—so if you're not failing, you're not trying hard enough. Getting failure out in the open takes the fear away and feeds into your strategy for next year. It's liberating when you stop pretending everything's perfect.  Losing Status Hits Harder Than You Think—And That's Okay to Admit: When you leave, people stop returning your emails. You have to rehearse new words at industry events because "I used to be..." doesn't work anymore. Clare dreamed about work for months even after leaving. Processing the identity shift takes time—and pretending it doesn't is what keeps people trapped.     About Clare Laycock:   Clare Laycock is a leadership coach working with media professionals navigating transition, growth, and change. A former SVP and Head of Content Networks & Streaming UK at Warner Brothers Discovery, Clare spent over 30 years leading major UK television brands. She launched channels during the digital revolution, managed multi-million dollar content strategies, and built fiercely loyal teams through brutal restructures and industry upheaval. Clare brings hard-won experience in protecting creative teams while managing business pressures and leading through ambiguity. Since retraining as a coach, she works with leaders who are stuck, burned out, or ready for something different—helping them redefine success beyond titles and build careers that feel aligned instead of crushing.   Connect with Clare Laycock: Website: https://www.clarelaycock.com/  LinkedIn: https://www.linkedin.com/in/clare-laycock-2200b821/  Email: clarelaycock5@gmail.com    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.

    1h 22m
  4. Fiona Fraser – From Stuck to Unstuck: Leaving the Performance of Professionalism to Lead on Your Own Terms

    JAN 27

    Fiona Fraser – From Stuck to Unstuck: Leaving the Performance of Professionalism to Lead on Your Own Terms

    What if the key to success wasn't fitting in—but finally giving yourself permission to stop trying? In this refreshingly raw episode of Legendary Leaders, host Cathleen O'Sullivan sits down with Fiona Fraser—founder of Power PR and former BBC publicist—whose unfiltered honesty about ADHD, identity, and the exhausting performance of "professionalism" will make you question everything you've been told about showing up. Fiona shares what it was like spending years learning to sit on her personality in corporate environments, the casual dinner party moment when two friends diagnosed her ADHD like it was obvious to everyone but her, and why she left TV during COVID to build her own agency. With trademark directness, she explains why she can't do small talk with senior executives when she's already defended their show all weekend, why anger was her go-to ADHD response, and why the spa isn't a luxury—it's nervous system regulation. Together, Cathleen and Fiona explore why "you're not sociable enough" often means "you didn't perform emotional labor we never asked for," the stop-and-drop cycle that leaves you sick on every holiday, and why Married at First Sight at 9pm might be the most important boundary you set. This conversation is for anyone who's ever felt like an alien in open-plan offices, been told to "try harder" with people who treat you terribly, or wondered if leaving corporate means failure—when really, staying stuck might be the only shame worth naming.     Episode Timeline:   00:11:02 From BBC to 19 years in television publicity 00:12:52 COVID, motherhood, and leaving TV to build Power PR 00:18:07 The biggest shame isn't failure—it's staying stuck 00:21:21 Breaking free from "work hard" culture 00:27:19 Ambitious vs. too ambitious: fear vs. self-protection 00:32:13 Hiring an assistant and letting go of instant email responses 00:36:32 The casual dinner party ADHD diagnosis 00:38:12 Energy waves with ADHD: ride it or drown 00:41:09 Sensory overload: coughing, sneezing, and rage responses 00:47:24 Feeling like an alien and never quite fitting in 00:50:09 "I can't do small talk"—relationship building for the sake of it 00:53:17 "You didn't try hard enough" after defending their show all weekend 01:01:45 The unashamed ADHD leader who gets results 01:09:09 PR without selling your soul: controlling your message 01:18:38 Final insight: Get yourself unstuck as quickly as possible​​​​​​​​​​​​​​​​   Key Takeaway: Staying Stuck Is the Real Shame—Not Changing Your Mind: Just because you've had success doesn't mean you can never change again. You can leave corporate, struggle, even go back—none of it is failure. The only shame is staying somewhere that drains you when your days are finite. If you're good, you'll get another job. If you feel stuck, get unstuck as quickly as possible. Boundaries Protect Your Energy—And Your Energy Determines Your Results: For Fiona with ADHD, energy comes in waves: 8-11am peak, 12-3pm crash, 4-6pm comeback. Working effectively means protecting those windows fiercely and accepting that if work doesn't happen during your peak, it won't happen. Boundaries aren't about being difficult—they're about understanding how you actually work and setting up your day so you can deliver. Whether it's hiring an assistant for email or taking Fridays (mostly) off, it's about giving clients better results by protecting what's finite. Recognizing Strengths Matters More Than Performative Relationships: Real leadership isn't about making people go to lunch with executives who treat them badly. It's understanding how your people work, what drives them, and what they're actually good at. Build teams around what clients need and who they'll work well with. When you respect people's strengths and working styles, you get loyalty and results—not resentment and burnout. Your Achievements Aren't Bragging—They're Taking a Moment to Actually See Yourself: When leaders can't recognize their own achievements, they create cultures where no one does. Sharing your story—the hard parts, the barriers you've overcome—isn't "too much information." It's what makes you human. Recognizing what you've created isn't arrogance. It's seeing yourself clearly instead of racing past your own life.   About Fiona Fraser: Fiona Fraser is the Founder and Director of POW PR, the UK's leading podcast-focused public relations agency, where creators, production companies, and niche experts turn standout shows into chart-topping media brands. A former television publicist with over a decade in the industry, Fiona has led PR campaigns for the BBC, Channel 4, and global production companies including Warner Bros., Fremantle, and Endemol. Since launching POW PR in 2020, she has helped clients secure multiple No. 1 podcast chart positions and drive audience growth through strategy-led PR alone. Fiona believes podcasts aren't just content—they're powerful platforms for influence, and when positioned correctly, they become impossible to ignore.   Connect with Fiona Fraser: Website: https://www.powpr.co.uk  LinkedIn: https://www.linkedin.com/in/fiona-fraser-powpr  Instagram: https://www.instagram.com/thepodcastexpert    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.

    1h 21m
  5. Anthony Abbagnano – From Reactive to Creative: Moving One Letter (and One Breath) to Transform Leadership

    JAN 13

    Anthony Abbagnano – From Reactive to Creative: Moving One Letter (and One Breath) to Transform Leadership

    What if the most powerful shift you could make as a leader wasn't another productivity hack—but simply learning to breathe? In this episode of Legendary Leaders, host Cathleen O'Sullivan sits down with Anthony Abbagnano—founder of the Alchemy of Breath and one of the world's leading voices in modern breathwork—whose calm presence and practical wisdom will make you rethink everything you thought you knew about resilience.  Anthony shares why most of us have unlearned how to breathe properly, and why that disconnection costs us more than we realize. He opens up about his midlife crisis in Ibiza, the moment he realized he'd abandoned his inner child for sixty years, and how inner child work isn't just playfulness—it's reconciling with the wounded parts we left behind. With disarming warmth, he explains why trauma can be our teacher, how the difference between "reactive" and "creative" is just moving one letter, and why ten breaths before a meeting might be the most productive thing you do all day.  Together, Cathleen and Anthony explore why we lose choice under stress, the neuroscience behind overwhelm, and how the Coherence breath—a simple five-second inhale, five-second exhale—can regulate your nervous system in five minutes. This conversation is for anyone racing through life, leading from chaos instead of calm, or wondering where they've been holding their breath—and what might happen if they finally let go.     Episode Timeline:   00:00:46 Why most people have unlearned to breathe properly 00:06:08 Inner child work: beyond playfulness to reconciliation 00:07:35 Anthony's midlife crisis in Ibiza and creating "the bridge" process 00:13:17 How trauma takes our breath away and embeds in the body 00:17:06 Restoring choice to a choiceless moment 00:22:15 Outer Chaos, Inner Calm: navigating today's messy world 00:28:11 Reactive vs. creative: moving one letter to transform leadership 00:31:19 Building community: the five-year Italy experiment 00:42:28 Why Western society lives in shallow breathing 00:47:02 The gradient of choice: how stress shrinks our options 00:48:07 Ten breaths that transformed a hostile boardroom meeting 00:53:06 Meet, prevail, acknowledge, celebrate: the four stages of growth 00:57:41 How breath creates space for creativity in business  01:08:26 The Coherence breath: a live demonstration  01:19:53 Take a breath before you react (and do a random act of kindness)     Key Takeaway:   Trauma Takes Your Breath Away—Healing Means Taking It Back: When we're wounded, we literally lose our breath in that moment of impact. The body absorbs the shock and stores it as chronic tension or disease. But trauma isn't something to erase—it's something to learn from. Mo Gowdat surveyed 12,000 trauma survivors and 99% said they'd keep their trauma for the growth it brought. The work isn't forgetting the wounded parts; it's restoring choice to the moments where breath—and power—were taken away. One Breath Creates Space—And Space Creates Choice: Write out "reactive." Move the "C" to the front and you get "creative." That's what one breath does. Under stress, we self-lobotomize—exporting processing power to our amygdala, leaving us with only fight, flight, or freeze. But one conscious breath creates space between stimulus and response. Ten breaths before a meeting can transform hostility into harmony. It's not about fixing the problem—it's about polishing your lens so you can see solutions that were there all along. The Coherence Breath: Five In, Five Out, Five Minutes, Three Times a Day: Breathe in through your nose for five seconds, out for five seconds. This practice—used by military and SWAT teams worldwide—regulates your nervous system and becomes your automatic response to tension. After two weeks, it stops being something you "do" and becomes how you breathe. When panic hits? Extend your exhale to counter rising stress. Practice it when you're calm so you can reach for it when you're not. Inspire Literally Means to Bring In Spirit—That's What Leadership Looks Like: Four-fifths of neural messages go from body to brain, not the other way around. Your body knows things your mind hasn't figured out yet. Conscious breathing slows your frontal lobe and creates space for insight beyond thinking. You're not just calming down—you're accessing what Anthony calls "spiritual resources." That's when quantum shifts happen: when you stop trying to think your way through and start breathing your way into clarity.     About Anthony Abbagnano:   Anthony Abbagnano is a visionary healer, breathwork pioneer, and the founder of Alchemy of Breath, where a global community of over 100,000 seekers turns a biological reflex into a tool for radical transformation. A former international entrepreneur—only to walk away from the corporate world to study under masters in India and the Amazon. He's trained facilitators in 40+ countries and shared stages with everyone from Deepak Chopra to Gabor Maté. His latest book, Outer Chaos, Inner Calm, explores trauma, addiction, and the art of "self-remembering," weaving in the philosophical influence of his uncle. Anthony teaches that "the breath is the bridge" to our forgotten parts, and that in a world designed to keep us in a state of "fight or flight," the most revolutionary act you can take is a conscious inhale.     Connect with Anthony Abbagnano: Website (Alchemy of Breath): https://alchemyofbreath.com/  Website (ASHA): https://www.asha.global  Book: https://alchemyofbreath.com/outer-chaos-inner-calm/      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.

    1h 26m
  6. Karen Salmansohn – Your To-Die For List: What Matters When Productivity Isn't the Point

    12/30/2025

    Karen Salmansohn – Your To-Die For List: What Matters When Productivity Isn't the Point

    What makes someone quit a six-figure advertising career to write books that help people think differently? In this episode of Legendary Leaders, host Cathleen O'Sullivan sits down with Karen Salmansohn—bestselling author, behavioral change expert, and the creative force behind NotSalmon.com—whose sharp wit and mortality-driven wisdom will make you rethink everything on your to-do list. Karen shares why fun isn't frivolous—it's fuel. She breaks down the science of why laughter literally shakes ideas loose, explains why her "e-pee-phanies" in the bathroom cracked more creative codes than caffeine ever did, and reveals the mortality marble jar that transformed how she spends every single month. With disarming honesty, she opens up about hiding her intelligence to be liked and finally "coming out" as a smart person in her sixties. Together, Cathleen and Karen explore the fatal flaw of to-do lists, why your identity is the puppet master of your habits, and how writing your own eulogy can wake you up from a "near-life experience." This conversation is for anyone who's tired of sleepwalking through their days and ready to design a life their future self will actually thank them for.   Episode Timeline: 00:05:36 How funny are you? Karen's son vs. Jon Stewart's verdict  00:06:34 Fun as a high-performance fuel (and meditation on steroids)  00:09:23 Manifestation, energy, and why confidence attracts results  00:14:48 From advertising to authorship: quitting the senior VP job her parents hated  00:19:38 The Häagen-Dazs theory on productivity: only pick what excites you  00:22:35 Procrastination strategies: turn your pain into purpose 00:27:03 Writing your eulogy: the wake-up call that changes everything  00:29:41 The fatal flaw of to-do lists (and why you need a to-die list)  00:33:31 The seven core values that minimize regret: A to G  00:38:31 Identity-based statements: "I am loving, so I find a way to Connecticut"  00:44:34 Feisty then, feisty now: how Karen sold the book her agent didn't want  00:46:33 Hiding her intelligence to be liked, then embracing it fully in her sixties 00:57:14 Hedonia vs. eudaimonia: why happiness isn't the goal  01:00:16 Life as a den of pleasure AND a laboratory for growth  01:12:51 Near-life experiences: when you're scrolling instead of living  01:16:07 The mortality marble jar: 437 marbles and a monthly reckoning   Key Takeaway: Your Identity Is the Puppet Master of Your Habits: Who you think you are determines what you actually do. If you walk around thinking "I'm sloppy," you'll do sloppy things. If you think "I'm a loving person," you'll find a way to get to Connecticut for your friend's birthday—even without a car. Studies show people who identified as "voters" were three times more likely to show up at the polls than those who just heard clever slogans. Change your identity statement, change your behavior.  To-Do Lists Prioritize Productivity, Not Meaning—That's Their Fatal Flaw: You can check off every box on your to-do list and still waste your life. Karen created a "to-die list" alongside her to-do list—a place for meaningful habits tied to core values, not just tasks. The top regrets of the dying? Working too hard, not spending time with friends, not allowing themselves to be happier, not living true to themselves. Your to-die list is the bridge between current you and the person your eulogy will describe.  Life Is a Den of Pleasure AND a Laboratory for Growth—You Need Both: We're addicted to instant gratification—scrolling, avoiding discomfort, waiting for "someday." But here's the truth: you can't seize every day. Aristotle said the goal isn't living pain-free; it's learning lessons that grow you into your best self. Emotional diversity is what makes you flourish. Instead of "seize the day," try "seize every other day." The moments in the laboratory of growth—where you get curious about your patterns and repair what keeps repeating—are what make the pleasure meaningful. The Mortality Marble Jar: Math That Shakes You Awake: Karen calculated how many months she has left if she lives to 100 (she promised her son). She bought that many marbles, put them in a jar, and every month she moves one marble to her "past" jar. The first time she did it, she couldn't remember what she'd done that month. Depressing. Now she intentionally plans meaningful experiences—dancing with friends, theater nights, time with her son—so when she holds that marble, she has something to report. The question that changes everything: "Is this really worth a marble of my life?"   About Karen Salmansohn: Karen Salmansohn is a bestselling author, behavioral change expert, and the founder of NotSalmon.com, where 1.5 million followers get their daily dose of psychology wrapped in wit. A former senior VP creative director who walked away from advertising in her twenties—despite her parents' protests—she's sold over 2 million books including How to Be Happy, Dammit and Think Happy, and her work has appeared everywhere from Oprah's platform to Psychology Today.Her latest book, Your To-Die-For Life, tackles mortality, regret, and the art of living intentionally—complete with a marble jar in her kitchen that tracks every month she has left if she lives to 100. Karen teaches that fun isn't a bonus, it's fuel, and that your identity is the puppet master of your habits.   Connect with Karen Salmansohn: Website (NotSalmon): https://www.notsalmon.com/  Book (Your To Die For Life): https://yourtodieforlife.com/  Instagram: https://www.instagram.com/notsalmon/  Twitter/X: https://x.com/Notsalmon  Facebook: https://www.facebook.com/Notsalmon/  YouTube: https://www.youtube.com/user/NotsalmonTV  Substack: https://notsalmon.substack.com/    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.

    1h 25m
  7. Stop Being So Damn Helpful: The Curse of the Over-Responsible Leader

    12/24/2025

    Stop Being So Damn Helpful: The Curse of the Over-Responsible Leader

    Are you the person everyone turns to because you'll "just handle it"? The one replying to emails at 11pm, rewriting your team's work, or silently resenting the people you keep rescuing? In this solo episode, Cathleen O'Sullivan tackles a behavior that's as exhausting as it is common: over-functioning in the name of being helpful.  Cathleen reveals why constant helpfulness isn't kindness—it's a control strategy that stifles growth, creates dependency, and keeps you small. She shares the story of a leader who was praised for being dependable but passed over for promotion because she wasn't seen as visionary, and unpacks why always being the fixer means you're losing time, energy, and strategic thinking space.  This punchy episode delivers four practical steps to shift from over-functioning to actual leadership: building awareness around guilt-driven yeses, replacing rescuing with coaching questions, using scripts that empower without abandoning, and practicing the useful discomfort of not jumping in. Your team doesn't need a hero. They need a leader. And you need your energy back.   Episode Timeline: 00:01:01 Why being helpful is actually a curse  00:01:44 "It's just quicker if I do it"—the trap of over-functioning  00:03:43 The exhausted leader who felt like a parent to her team  00:04:35 How helpfulness backfires: creating dependency, not ownership  00:05:59 The people pleaser passed over for promotion  00:06:45 Step 1: Build awareness—am I doing work that's not mine?  00:08:19 Step 2: Replace rescuing with coaching questions  00:10:09 Step 3: The script for letting go without guilt  00:12:00 Step 4: Practice useful discomfort—let them struggle and grow  00:14:08 The truth: over-helpfulness is a control strategy in disguise  00:14:42 Your challenge: find one moment this week and don't jump in   Key Takeaway: Step 1: Build Awareness—Notice When You're Over-Functioning Am I doing work that's not mine? Saying yes out of guilt? Secretly resentful? One leader kept rewriting her team's decks—not for quality, but out of fear of being judged. Keep asking "why" until you hit the root cause.  Step 2: Replace Rescuing with Coaching Questions Don't jump into fix-it mode. Ask: "What have you tried? Where did you get stuck? What do you think could work?" Put ownership back in their hands. Let them think first—then see where they really get stuck.  Step 3: Use a Script for Letting Go Without Guilt Try this: "I trust you to run with this. If you hit a wall, I'm here, but I know you've got this." Leadership isn't about perfection—it's about empowerment and growing together.  Step 4: Practice Useful Discomfort—Let Them Struggle Wait 24 hours before replying. Let someone struggle without stepping in—they'll figure it out. Ask yourself: Am I fixing this to help, or to feel needed? Growth is messy. If you never let them wobble, they'll never walk on their own.   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/    FOLLOW LEGENDARY LEADERS ON APPLE, SPOTIFY OR WHEREVER YOU LISTEN TO YOUR PODCASTS

    16 min
  8. Darryl Stickel – Share, Don't Scare: The Science of Building Trust When the World Feels Broken

    12/16/2025

    Darryl Stickel – Share, Don't Scare: The Science of Building Trust When the World Feels Broken

    What makes a complete stranger walk up to you on a bus and say, "I'm really having a hard time today"? In this episode of Legendary Leaders, host Cathleen O'Sullivan sits down with Darryl Stickel—trust researcher, founder of Trust Unlimited, and author of Building Trust—whose life's work reveals that connection isn't magic. It's a skill you can learn, practice, and pull off even when everything feels like it's falling apart.    Darryl shares why trust isn't just about certainty—it's about being willing to get hurt. He breaks down the formula, explains why leaders who admit they're not perfect inspire fierce loyalty, and walks through the exact steps he used to help warring union reps and board executives shake hands after five years in court. With disarming honesty, he opens up about surviving multiple concussions, navigating life as a legally blind leader, and discovering that accepting help isn't weakness—it's a gift you give other people.    Together, Cathleen and Darryl explore what it means to lead without pretending, why "share, don't scare" transforms relationships, and how pulling three specific levers can rebuild trust faster than you think. This conversation is for anyone who's tired of surface-level connections and ready to do the uncomfortable work that actually brings people closer.     Episode Timeline:   00:02:38 Why vulnerability is the part of trust everyone ignores  00:05:02 The trust equation: uncertainty × vulnerability = perceived risk  00:09:51 When not to be vulnerable: protecting yourself while staying open 00:15:54 Three levers every leader needs: benevolence, integrity, ability  00:26:35 Men, mental health, and the Aspirational Men's Program  00:30:53 Internal vs. external locus of control: what you actually control  00:39:43 The benevolence conversation: "What does success look like for you?"  00:50:41 Five years in court: how he got unions and executives talking again  00:57:48 "I feel uncertainty" vs. "I don't trust you": the language that neutralizes conflict  01:08:56 The one small step: start with a dose of vulnerability  01:14:09 The father who went from "they're scared of me" to "they fight over who sits next to me"  01:18:12 Hockey, concussions, and finding purpose in the wreckage     Key Takeaway:   Trust = Uncertainty × Vulnerability, and Both Are at All-Time Highs: Trust isn't just about predicting someone's behavior—it's about being willing to be hurt when you can't know for sure what they'll do. In deep relationships, uncertainty shrinks and vulnerability expands. But right now, with uncertainty spiking everywhere, even small asks for vulnerability feel like jumping off a cliff.  Refusing Help Is Selfish—You're Robbing People of Joy: Darryl told a room of executives: "You just shared how powerful it is to help someone. Now explain why you're so effing selfish—you never let anyone have that experience with you." When you never admit you need help or show vulnerability, you steal the gift of contribution from others. Even the struggling woman panhandling on the street felt meaning when she could help the blind guy cross.  Change the Story, Change Everything: Darryl's son wanted a baseball scholarship, so Darryl "nagged" him about eating well, practicing, studying, being a good teammate. But because they'd defined success together first, his son heard every nudge as "Dad has my back" instead of criticism. We interpret the world through stories—if you don't actively shape the narrative, 20 different versions will spread, and most won't work in your favor.  Start With One Small Dose of Vulnerability: Don't open the kimono. Don't pretend you're clueless. Just admit you made a mistake in the past, probably will in the future, or need someone's expertise on something. Leaders reach positions because of technical skill—that skill atrophies the moment you sit behind a desk. Tell people: "You're the expert now. I'm going to need your help." That small crack opens everything.     About Darryl Stickel:   Darryl Stickel is founder of Trust Unlimited and author of Building Trust: Exceptional Leadership in an Uncertain World. He holds a PhD from Duke University, where his doctoral thesis on building trust in hostile environments was so groundbreaking his advisors admitted he'd solved what they thought was impossible. After consulting at McKinsey & Company, Darryl founded Trust Unlimited in 2001 and has since worked with unions, military units, Fortune 500 companies, and nonprofits worldwide—from helping the Canadian military build trust with locals in Afghanistan to reuniting fathers with sons who'd given up hope. Legally blind and navigating the world with his guide dog Drake, Darryl teaches that vulnerability isn't weakness—it's the foundation of everything that matters.      Connect with Darryl Stickel: LinkedIn: ca.linkedin.com/in/darryl-stickel-phd  Website: https://www.trustunlimited.com/  Book: https://www.trustunlimited.com/book/  Facebook: https://www.facebook.com/people/Trust-Unlimited-Inc/61563450129818/ Instagram: http://www.instagram.com/darrylstickel  YouTube: http://www.youtube.com/@DarrylStickel_BuildingTrust Podcast: https://imperfectcafe.buzzsprout.com/      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/      FOLLOW LEGENDARY LEADERS ON APPLE, SPOTIFY OR WHEREVER YOU LISTEN TO YOUR PODCASTS

    1h 30m
See All (100)

5
out of 5
14 Ratings

About

Welcome to the Legendary Leaders Podcast! This show aims to inspire you to start living your best life! My podcast guests will be sharing their own personal paths to success, the moments when they 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 professional and personal life. Our guests, who are all leaders in their own rights, will be talking about how they started their journey, what inspired and motivated them, along with the challenges they had to overcome in order to get to where they are now, having achieved a more content and liberated life. All episodes will cover an array of topics from the importance of self-care 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 as well as actors, business mentors, speakers and many, many more. They all faced tough challenges which served as motivation to live their best lives yet! Please enjoy listening to this 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.

Information

  • Creator
    Cathleen O'Sullivan – Growth Accelerator for Leaders
  • Years Active
    2019 - 2026
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © Cathleen O'Sullivan (Merkel)
  • Show Website
    The Legendary Leaders Podcast