In today’s world, financial advice is everywhere—but rarely helpful. In Part Two , Michael Sakraida continues dismantling outdated ideas about wealth, offering a fresh framework that centers emotional intelligence and personal values. He explains why legacy isn’t just about what you leave behind, but how you live today. From the limits of “aggressive investor” labels to the chaos of unregulated financial influencers, Michael unpacks the hidden damage done by bad advice—and what real financial co...
May 13, 2025•23 min•Ep. 367
Michael Sakraida didn’t write a money manual. He wrote a mindset shift. In Part One , the author of Money, Balance and Joy shares how his upbringing, career in finance, and burnout led him to a new definition of wealth—one that includes time freedom and emotional fulfillment, not just financial metrics. He questions why Wall Street ignores the emotional toll of economic instability and how media-driven fear only adds to our sense of isolation and failure. This episode covers the emotional underb...
May 13, 2025•25 min•Ep. 366
You’re exhausted. The meetings are pointless, the politics are draining, and your boss sends Slack messages that trigger a fight-or-flight response. It feels like the only answer is to walk away. But what if there’s another way? In this episode, executive coach and author Darcy Eikenberg shares how to turn burnout into clarity without updating your résumé. Drawing from her book Red Cape Rescue: Save Your Career Without Leaving Your Job , Darcy walks us through how to reset how you think, revise ...
May 13, 2025•37 min•Ep. 365
What happens after you’ve lost everything—status, stability, and even your sense of self? In Part Two , Sihame El Kaouakibi goes deeper into her journey of rebuilding: not just her career, but her core identity. From leaving toxic environments to redefining ambition, Sihame breaks down how Women Leaders OS came from her own healing, and how she now helps high-achieving women across cultures do the same. She also opens up about why global coaching requires cultural fluency, why some success stori...
May 12, 2025•35 min•Ep. 364
What happens when a rising political star crashes—publicly, painfully, and all at once? In Part One , Sihame El Kaouakibi, Moroccan-born former Belgian MP and five-time founder, shares the deeply personal story behind her public unraveling. Once a celebrated social entrepreneur and national leader, Sihame faced burnout, betrayal, and bankruptcy—all while navigating racism, politics, and impossible expectations. But instead of disappearing, she rebuilt. This episode is a raw look at what it means...
May 11, 2025•27 min•Ep. 363
Starting a franchise isn’t just a business move—it’s a mindset shift. In Part Two , James Hilovsky—former athlete turned franchise consultant—goes beyond playbooks and into the real psychology of success. He explores why some athletes stumble when they let ego overtake strategy, how corporate professionals can regain control after layoffs, and why betting on yourself only works when you’re honest about what kind of help you need. From risk tolerance to leadership, coachability to due diligence, ...
May 11, 2025•28 min•Ep. 362
What happens after the cheering stops? For James Hilovsky, it meant trading his baseball uniform for business ownership—and helping other athletes do the same. In Part One , James shares how his short-lived pro sports career led to 25 years in restaurant franchising, including scaling Pieology from one store to over 100. Now, as a franchise consultant, James works with NFL and NBA players looking to invest wisely, build generational wealth, and transition from the field to the franchise world. H...
May 11, 2025•27 min•Ep. 361
If students are graduating into a broken job market, can we really call that success? In Part Two , Bridget Burns, CEO of the University Innovation Alliance, zooms out to expose the cracks between graduation and employment—and shares what it actually takes to close them. From outdated career services buried in basement offices to siloed AI initiatives happening in secret, Bridget makes the case for a total redesign of higher education’s operating system. With a blend of empathy and systems think...
May 10, 2025•28 min•Ep. 360
If higher education feels like the Hunger Games, Dr. Bridget Burns is building the resistance. In Part One , Bridget shares her journey from growing up in rural Montana to becoming CEO of the University Innovation Alliance—a national coalition of public research universities working together (yes, together) to improve outcomes for low-income and first-generation students. She pulls back the curtain on the real problem in academia: a culture of competition, hierarchy, and duplicated failure maske...
May 10, 2025•31 min•Ep. 359
Let’s be honest—today’s job search often feels like shouting into the void. In Part Three , Mary Shea—former General Manager at HireQuotient and co-CEO at Mediafly—tackles the modern job market from both sides of the table. She pulls back the curtain on how AI is reshaping recruitment: from sourcing passive candidates to fighting unconscious bias, automating outreach, and uncovering overlooked talent. But this isn’t a tech sales pitch—Mary gets real about what AI can’t do (like fix a broken cand...
May 10, 2025•43 min•Ep. 358
Is two better than one? In Part Two of this series, Mary Shea—former co-CEO of Mediafly and former General Manager at Hire Quotient—shares how she navigated one of the most unconventional leadership models in business: co-CEOship. From building trust with her co-leader to balancing responsibilities across time zones and product lines, Mary unpacks the human side of shared power—and why mutual respect beats ego every time. She also explores how AI is transforming sales effectiveness, not just eff...
May 10, 2025•26 min•Ep. 357
Mary Shea didn’t follow a traditional path. She composed her own. In Part One of this three-part series, Mary walks us through the bold decisions that took her from professional oboist to PhD to sales analyst—and eventually to co-CEO of Mediafly. Along the way, she’s picked up more than titles: she’s developed a philosophy that blends intellectual rigor, creative play, and social equity. She opens up about what it’s like to enter the business world a decade “behind” her peers, the financial free...
May 10, 2025•23 min•Ep. 356
Becoming Singapore’s youngest parliamentarian was just the beginning. In Part Two of this conversation, Tin Pei Ling reflects on how she’s evolved as a leader, mother, policymaker, and public voice. From walking the campaign trail just days after giving birth, to pursuing an MBA mid-term while managing a constituency, her path isn’t about having it all—it’s about knowing what to give, and when. She opens up about the guilt of missing milestones, the value of learning from older peers, and the re...
May 08, 2025•22 min•Ep. 355
What happens when your first job in politics comes with public ridicule, online harassment, and sky-high expectations? At 27, Tin Pei Ling became Singapore’s youngest female Member of Parliament. But what looked like a bold milestone from the outside was also the darkest chapter of her life. In Part One of this candid conversation, Pei Ling opens up about walking away from a stable consulting job, the backlash she faced as a “too young” candidate, and why she chose to fight for trust instead of ...
May 07, 2025•21 min•Ep. 354
Would you leave a powerful career in global banking, pack up your family, and start over in a developing country? That’s exactly what Fatou Sagna Sow did. Born and raised in Paris, she built a high-flying legal career at some of the world’s top banks—leading teams, managing billion-dollar deals, and thriving in the French system. But it wasn’t enough. In 2016, she returned to Senegal to write a new playbook—one rooted in identity, impact, and intercontinental connection. In this episode, Fatou s...
May 07, 2025•34 min•Ep. 353
Hybrid work was supposed to be the future—but it’s feeling more like a tug-of-war. Wayne Turmel, co-author of The Long-Distance Leader , has spent two decades studying how we lead across distance—and what falls apart when we don’t. In this episode, Wayne explains why most return-to-office plans are more negotiation than strategy, how unexamined proximity bias silently shapes promotions, and why hybrid leadership isn’t about place—it’s about intentionality . Whether you’re managing global teams o...
May 07, 2025•32 min•Ep. 352
The way we communicate is changing—but what does that mean for the humans doing the talking? Dr. Juliana Schroeder, associate professor at UC Berkeley Haas, has spent her career unpacking how we perceive other minds—both human and machine. In this episode, she breaks down how AI isn’t just reshaping tech—it’s reshaping the psychology of communication itself. From virtual assistants to algorithmic bias, and from voice cues to power dynamics, Juliana offers a grounded look at what we gain (and ris...
May 06, 2025•35 min•Ep. 351
Confidence might be the most overused word in leadership—but Lucy Gernon is here to give it teeth. After two decades in the pharmaceutical world, Lucy faced a moment of reckoning when a family tragedy pushed her to stop waiting and start living on her own terms. Now, as a multi-award-winning executive coach and founder of the Executive Presence Blueprint, she helps high-achieving women get out of their own heads—and into positions of power. In this episode, Lucy opens up about overcoming self-do...
May 06, 2025•30 min•Ep. 350
What happens when the dream job turns into a corporate casualty? Benedikt Oehmen spent nearly two decades at Blizzard—first as a support staffer, then a beloved team leader—only to watch the company’s gamer-first culture erode after its merger with Activision. When layoffs came, it wasn’t just a paycheck he lost. It was identity, community, and certainty. But Benedikt didn’t stay stuck. He pivoted from game development to career redevelopment—first coaching his own team through grief and transit...
May 06, 2025•30 min•Ep. 349
Ian Myers isn’t here to give you startup hacks—he’s here to tell the truth. At just 26, he became a CEO. By 30, he’d built Oceans, a $10 million agency connecting skilled professionals in Sri Lanka with U.S. startups. But his story isn’t a straight line—it’s an open map. From literature to venture capital, Japan to New York, success and failure, Ian has treated life like a Tintin adventure: follow the clues, embrace the chaos, and keep going. In this conversation, we dig into what really fuels a...
May 06, 2025•40 min•Ep. 348
For the first time, the Chief Change Officer podcast returns to its birthplace—Hong Kong—to spotlight local artist and community builder May Yeung. From doodling on walls at age two to sculpting giant dim sum steamers for public exhibitions, May’s journey is anything but typical. She swapped Goldman Sachs for gallery spaces, battled cancer with faith (and clay), and now leads Art of My Family , a charity that brings art, healing, and heritage to underprivileged youth across Hong Kong. Whether it...
May 05, 2025•34 min•Ep. 347
Vince Jeong isn’t your typical edtech founder—and this isn’t your typical training conversation. After immigrating to Canada at 12 and learning English from scratch, Vince chased uncertainty across five continents and a dozen careers—from McKinsey to NGOs in Tanzania to Latin American startups. That winding path led him to one insight: real learning happens when real people engage together, not alone. Now as CEO of Sparkwise, he’s scaling live group learning in ways that mirror the best of Harva...
May 05, 2025•37 min•Ep. 346
Sienna Jackson, the CEO of Nortera.io, walks us through her unexpected shift from entertainment executive to impact strategist. Rather than chasing a title, she followed a thread—registering an LLC, collecting ideas, and finally stepping into work that aligned with her values. Now, she’s helping professionalize the field of social impact by focusing on measurable outcomes, not slogans. From impact modeling to cross-sector coalitions, Sienna shows how complex change starts behind the scenes—with ...
May 05, 2025•23 min•Ep. 345
From film sets to SaaS, Sienna Jackson has lived through more than one reinvention. A two-time founder, former entertainment executive, and current tech CEO, she joins Chief Change Officer to break down what it means to build, to create, and to change—on your own terms. In Part 1, she shares what it was really like working in the music and production trenches at the Weinstein Company, how she navigated a high-glamour industry with clear-eyed curiosity, and why she never let a job title define he...
May 04, 2025•31 min•Ep. 344
Brian Sims, the CEO of Agenda PAC, walks us through what it was really like inside the halls of power—getting his mic cut on the House floor, confronting closeted anti-LGBTQ colleagues, and learning the limits of both strategy and ego. Now in the private sector, he’s using data to fight back—not with louder voices, but with smarter ones. Key Highlights of Our Interview: When the Mic Goes Dead “I got half a word out. Then it cut. They didn’t even pretend it was technical.” No Friends Across the A...
May 04, 2025•33 min•Ep. 343
From a military childhood to a college football captain, Brian Sims didn’t exactly grow up in activist circles. But a fiercely independent mother and a slow-burning coming-out story set the stage for something bigger. In Part One, Brian, the CEO of Agenda PAC, opens up about finding his voice, leaving law for civil rights work, and eventually winning his first election—becoming the first out gay man elected to Pennsylvania’s state legislature. Key Highlights of Our Interview: Raised by Leaders “...
May 04, 2025•26 min•Ep. 342
In this final installment, Gen X executive coach Jennifer Selby Long goes deep on the real decision behind office politics: should you stay or should you go? Drawing from decades of experience guiding leaders through complex change, she lays out the subtle dynamics that determine whether a culture is salvageable—or just stuck. From the hidden toll of hybrid models to bosses who subtly push out high performers, Jennifer offers tools for cutting through confusion. And with a memorable framework in...
May 03, 2025•26 min•Ep. 341
In this third installment with Gen X executive coach Jennifer Selby Long, we zoom in on one of the messiest, most misunderstood realities of modern work: office politics. Jennifer breaks down why politics often stem less from individual egos and more from structural dysfunction, emotional disconnection, and leadership blind spots—especially in hybrid teams. She explains how outdated views of leadership, chronic misalignment, and even cost-cutting decisions like slashed T&E budgets can quietl...
May 03, 2025•26 min•Ep. 340
Jennifer Selby Long is no stranger to messy transformations. With three decades of experience in executive coaching, digital change, and tech leadership, she helps seasoned professionals navigate the personal minefield that comes with professional change. In this second installment, Jennifer dives deep into neuroscience-backed insights on why we sabotage ourselves—and how to stop. She breaks down how our brains are wired for fear, how to spot the voice of the “judge,” and how misplaced loyalty t...
May 03, 2025•46 min•Ep. 339
Jennifer Selby Long has spent 30 years helping leaders navigate change—long before “change management” became a buzzword. In this episode, the Gen X executive coach reflects on how she stumbled into her calling during the early days of IT transformation, and why emotional intelligence—not just operational efficiency—is what drives successful digital change. Drawing from her own career pivots and coaching experiences, Jennifer explains how change must be mastered on a personal level before it can...
May 03, 2025•28 min•Ep. 338
