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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
  • Linda Misegadis: The Identity You Built for Everyone Else

    Linda Misegadis: The Identity You Built for Everyone Else
    May 26 2026
    What happens when you've spent decades being the most reliable person in the room — and you finally stop to ask: reliable for whom? In this warm, wide-ranging episode of Leaderspace, host Cathleen O'Sullivan is joined by Linda Misegadis — senior government strategist at UKG, global DEI ambassador, certified payroll professional, and host of the Her Resources Podcast. Linda built her career the way many high-achievers do: nose down, hard work, always available, always solving. She led one of the most complex technology change projects in Denver's public sector history and then walked into the VP of Sales of the company whose software she'd just implemented and told him, clearly and directly, that she didn't think they understood the public sector space at all. He offered her a job. Linda and Cathleen explore what it costs to tie your identity to being the one everyone counts on, how introversion becomes a leadership superpower once you stop letting others use it as a label that limits you, and why the most important question in any career transition isn't what's next — it's who am I actually? They talk about the trap of availability culture, what burnout really looks like when you've built your reward system around being indispensable, and the slow, nonlinear work of separating your professional identity from your sense of self. They also go deep on what it means to lead through complexity without consensus paralysis, how COVID quietly pushed Linda from observer to connector, and the particular challenge women still face in corporate life in 2026 — not just in being heard, but in being seen for the right things. This is a conversation about the courage it takes to stop performing reliability and start building something that actually belongs to you. If you've ever been the go-to person, the Swiss Army knife, the one who always raises their hand — this one is for you. Cathleen's question for this episode: what is it costing you to keep staying quiet about something you've already noticed? Episode Timeline: 00:00:00 Welcome and Introduction 00:02:38 Introducing Linda Misegadis 00:07:04 Heritage, Roots, and Identity 00:11:09 What Has Shaped Your Identity? 00:15:10 The Trap of Being the Reliable One 00:19:09 Who Is Linda Now? 00:21:39 AI, Layoffs, and the Human Side of Work 00:31:36 How COVID Made Linda a Connector 00:34:17 Introversion as a Leadership Strength 00:40:29 Leading Without a Title 00:44:00 The Audacious Move That Changed Everything 00:48:00 The Risk of Always Being the Problem Solver 00:53:46 The Reward Behind Constant Availability 01:00:52 How the Reward Has Shifted 01:04:14 Approaching Complex Problems 01:11:24 Women's Voices in Corporate Life — Still Not There Yet 01:13:36 One Piece of Advice for Women Entering Leadership Key Takeaways: The Reliable One Is a Role, Not an Identity: Building your sense of self around being available to everyone is a reward system, not a foundation. Recognising what that role is costing you — in energy, in clarity, in career direction — is the first step to changing it. Introversion Is a Skill Gap, Not a Personality Sentence: Linda didn't network because she'd never been taught how, not because she was incapable. Once she separated the label from the limitation, she built a podcast, a community, and a career chapter on her own terms. Observation Is Underrated Leadership Data: Stepping back and watching — really watching — builds pattern recognition that others miss. The quietest person in the room often sees the most. Someone Has to Make the Call: Consensus has its place, but leadership means being willing to own a decision, not manage a committee. The people around you are counting on someone to choose. The New Reward Has to Be Real: When you stop being the one who solves everything, the satisfaction has to come from somewhere else. For Linda, it became the pride of watching her team step up. The reward needs to be replaced — not just removed. About Linda Misegadis: Linda Misegadis is a Senior Government Strategist at UKG and Global Diversity, Equity, Inclusion, and Belonging Ambassador, based in Colorado. She is a Certified Payroll Professional (CPP), Certified Public Manager (CPM), IPMA-CP, and Prosci Certified Change Manager who has spent her career helping organisations navigate complexity — and bring people with them through it. She previously served as Director of Citywide Payroll Operations and Administration for the City and County of Denver, where she led a workforce management deployment across 13,000 employees. Her defining career pivot came when she walked into the VP of Sales of the company whose software she had just implemented, told him plainly that she didn't think they understood the public sector space, and left with a job offer. She is also the co-host of the Her Resources Podcast. Connect with Linda Misegadis: LinkedIn: https://www.linkedin.com/in/lindamisegadis Website (Podcast...
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    1 hr and 19 mins
  • Confidence Is a Practice, Not a Personality Trait

    Confidence Is a Practice, Not a Personality Trait
    May 19 2026

    What if the confidence you've been waiting to feel is actually something you've been building all along—one small, imperfect action at a time? In this solo episode, host Cathleen O'Sullivan tackles one of the most common beliefs she encounters with clients: that confidence is something you either have or you don't.

    Drawing on psychology, client stories, and her own experience, Cathleen reframes confidence not as a fixed trait but as a skill—one that grows through action, repetition, and the willingness to show up before you feel ready. This episode is a practical, grounding reminder that you don't need to become a different person. You just need to start.

    Episode Timeline:

    01:01 Confidence is a skill, not a trait — here's why that matters

    05:43 The client who only spoke when she was certain (and what changed)

    08:05 Why you can't think your way into confidence

    09:48 Four micro practices that actually build the muscle

    16:13 Messy is normal — and often proof you're growing

    17:04 The keynote moment that felt like failure but wasn't

    18:51 Why confidence doesn't develop in isolation

    20:53 The one thing to take away from this episode

    Key Takeaway:

    • Confidence Is Built, Not Born: Confidence isn't a fixed personality trait. It grows through experience, repetition, and the willingness to act before you feel fully ready—and that means anyone can build it.

    • Action Comes First: Waiting to feel confident before you act is exactly what keeps you stuck. The evidence that builds self-belief only comes from doing, not from thinking about doing.

    • Small and Repeatable Wins: Treat confidence like a muscle. Prepare before meetings, speak early, keep a running note of small wins. Consistent, manageable actions compound over time.

    • Messy Doesn't Mean Lacking: Losing your place, your voice shaking, phrasing something imperfectly—these aren't signs of failure. Confidence isn't the absence of mistakes. It's how you stay with yourself when things don't go perfectly.​​​​​​​​​​​​​​​​

    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
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    23 mins
  • Scott Proposki: When the Business You Built Becomes the Life You Lost

    Scott Proposki: When the Business You Built Becomes the Life You Lost
    May 12 2026
    What if the success you spent three decades building disappeared overnight — and the hardest part wasn't the money, but knowing who you were without it? In this honest, unhurried episode of Legendary Leaders, host Cathleen O'Sullivan is joined by Scott Proposki — photographer, entrepreneur, author, and business coach based in Boston, Massachusetts. For nearly three decades, Scott built one of the most recognisable event photography businesses in North America: 52 people, eight-figure revenue, and a client list that included National Geographic, the White House, Sports Illustrated, and the NFL. Then 2020 arrived, and almost overnight, it was gone. Scott and Cathleen explore what it really costs to stop being the craftsperson and become the CEO, why growing fast can quietly hollow out the thing you loved, how depression after business loss is a grief that doesn't get enough airtime, and what a single conversation with a coach unlocked in his next chapter. They also go deep on his ADHD diagnosis in his early fifties, how understanding it reshaped the way he works and leads, and why his current lifestyle business — intentionally small, deeply profitable, and accessible from the Swiss Alps — is more aligned with who he actually is than the empire ever was. This is a conversation that will ask you to pause before you hit grow again and sit with the question Cathleen raises at the very start: is the size of your business, your ambition, your pace — something you actually chose? Or did you just keep going because stopping felt like failure?​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​ Episode Timeline: 00:00:00 The Cost of Becoming CEO 00:04:33 Introduction to Scott Proposki 00:07:02 The Blueberry Muffin Problem 00:12:42 Learning Leadership by Proximity 00:17:49 How You Show Up for the People You Lead 00:20:14 The Bigger Boat Trap 00:25:27 When COVID Took It All 00:29:24 Depression, Doubt, the Silence Underneath 00:34:02 The Conversation That Cracked Something Open 00:35:42 Life After the Empire 00:41:52 Helping Creators Build Profitable Businesses 00:44:50 Forty Levers, Not One Fix 00:48:19 The Compounding Power of Small Gains 00:55:11 ADHD, the Camera, the Superpower of Focus 01:04:25 The Five-Year Vision 01:09:22 One Step When You Feel Stuck​​​​​​​​​​​​​​​​ Key Takeaway: Becoming the CEO Means Leaving the Craft Behind: Scaling a business often means stepping away from the work that made you good in the first place. That shift needs to be a conscious choice, not something you drift into without noticing. Losing a Business Is a Grief Most People Don't Name: When the business disappeared, so did the identity, purpose, and daily rhythm built around it. Naming that loss for what it is makes rebuilding possible — pushing through without acknowledging it makes it harder. Profit Is a Strategy, Not a Side Effect: Most small business owners are busy without being profitable. Small improvements across multiple areas of a business compound quickly — and cost-cutting, unlike new revenue, goes straight to the bottom line. Own Your List Before the Platform Disappears: Social platforms can vanish or shut you out overnight. An organic email list built on consistent, genuine storytelling is one of the most durable assets a small business can hold. Choose Your Boat Size Before You Start Rowing: The most important question isn't how big you can grow — it's what size business supports the life you actually want. Answering that honestly before you scale can save years of chasing the wrong thing.​​​​​​​​​​​​​​​​ About Scott Proposki: Scott Proposki is a business coach, photographer, and author based in Haverhill, Massachusetts. Over nearly three decades, he built one of North America's leading event photography businesses — working with clients including National Geographic, the White House, Sports Illustrated, HBO, and Microsoft — before scaling to a team of 52. When COVID-19 effectively ended the events industry overnight, Scott lost the business he had spent his career building and spent the years that followed rebuilding with far greater intentionality. He is the author of multiple books including Camera Focus (2019) and Focus on the Profits, and the founder of the Camera Focus Method — a structured coaching framework that helps photographers and creative entrepreneurs build businesses that are genuinely profitable, not just busy. Connect with Scott Proposki: Website: https://businessfocusmethod.com Website: https://scottproposki.com LinkedIn: https://www.linkedin.com/in/scottproposki Instagram: https://www.instagram.com/scottproposki/ 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/ ...
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    1 hr and 10 mins
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