Clocking Out with Raymond Lee podcast artwork

PODCAST · business

Clocking Out with Raymond Lee

Clocking Out is a podcast about bold moves and personal breakthroughs. Each episode spotlights people who’ve made the life-changing decision to walk away from jobs, careers, or situations that no longer served them in pursuit of something more meaningful.Through candid conversations, we explore the pivotal moments, mindset shifts, and personal values that fuel these transformations. Guests share the setbacks, surprises, and self-discoveries that helped shape their new paths, with themes of resilience, reinvention, and purpose woven throughout.Created as a tribute to Raymond's mother, who inspired the show by chasing her own dream of career fulfillment, Clocking Out is a reminder that it’s never too late to choose yourself.

  1. 65

    Lily Woi: Deloitte Management Consultant to Entrepreneur & Author

    In this episode of Clocking Out, we meet Lily Woi, a self-described shy, quiet, reserved, and awkward introvert who walked away from a prestigious consulting career at Deloitte three months before a promotion, with no business name, no clients, and no plan. What she had was the clarity that staying any longer would cost her something she couldn't get back.Born and raised in a quietly entrepreneurial family, Lily grew up watching her parents model financial freedom while steering her toward the safer road: accounting, a chartered qualification, a recession-proof career. She followed the plan exactly. She joined Deloitte's graduate program, earned promotion after promotion, and was well on her way to manager. On paper, everything looked right. Underneath, the gap between what she was being rewarded for and what she actually cared about was quietly widening with every passing month.The pivot came not from a crisis but from a moment of plain, unignorable clarity. One ordinary morning, she texted her manager and resigned. No backup. No business plan. Not even a name for what came next. She didn't tell her parents until after it was done, because she knew what they'd say, and she wasn't sure she was strong enough to hear it out loud and still go through with it.What followed was the messy, exhilarating work of rebuilding from scratch. First clients through referrals. A speaking stage that went so badly she left the conference and had a quiet breakdown at a friend's place. And still she kept going. She wrote a book, Quiet Confidence, and discovered that the same introversion she'd spent years managing around was, in fact, her sharpest professional tool. The shy girl who used to hide in bathroom stalls to recover from the overstimulation of corporate networking is now a sought-after coach, speaker, and author, not because she became someone else, but because she finally stopped pretending to.This conversation is about the quiet courage it takes to leave when nothing is visibly wrong, the identity loss no one warns you about when you trade a title for a blank page, and what it really means to build confidence, not as a destination you arrive at, but as evidence you accumulate one hard thing at a time.Connect with Lily at:LinkedIn: https://www.linkedin.com/in/lilywoi/Website: https://lilywoi.com/Book: https://bookboon.com/en/quiet-confidence-ebookFollow Raymond:LinkedIn: https://www.linkedin.com/in/raymondmlee/ Instagram: https://www.instagram.com/raymondlee.co Tiktok: https://www.tiktok.com/@clockingoutpod X: http://twitter.com/hrentrepreneur Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos Become a guest on Clocking Out: https://bit.ly/46sqClq

  2. 64

    John Fareed: Marine & Magician to Global Hospitality Chairman and Author

    In this episode of Clocking Out, we meet John Fareed, a man who has lived more lives than most people dare to imagine and turned each one into raw material for the next.Growing up in rural Georgia and summers spent in Egypt, John learned early that identity is fluid and the world contains far more possibility than the circumstances you're born into.What followed was a life shaped less by planning than by honest reckoning. Six years in the U.S. Marines, kept only because of a private negotiation with his Egyptian grandfather, where an eighteen-year-old passed on the car and asked instead for his mother to be welcomed back into the family. Fifteen years as a professional magician performing at the famed Magic Castle in Hollywood, on cruise ships, and in casino showrooms, until a trusted friend quietly walked him through the math. Not a failure. Not a breakdown. Just the ceiling, made visible by someone who cared enough to show it.The pivot into hospitality consulting came with nothing but nerve, no degree, no industry experience, no roadmap. For a while, it worked. Then 9/11 arrived and took most of it in a week. What looked like rock bottom turned out to be a blueprint. He worked inside a hotel, joined a prestigious firm, and in his forties moved to Dublin to earn a master's degree, graduating inside Saint Patrick's Cathedral and so moved by the experience that he went back a second time just to feel it again.Today, John serves as Global Chairman of Horwath HTL and is the author of From Invisible to Icon, distributed by Simon & Schuster, drawn from his experience of building authority from scratch in a field he entered as a complete outsider.This conversation is about reinvention without a safety net, the clarity that catastrophe can bring, and what it means to keep performing on a bigger and bigger stage. It is about the courage to look ridiculous to the people who know you, and the wisdom of dreaming large enough that even your regrets point somewhere worth going.Connect with John at:LinkedIn: https://www.linkedin.com/in/johnfareedWebsite: www.horwathhtl.com Follow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/ Instagram: https://www.instagram.com/raymondlee.co Tiktok: https://www.tiktok.com/@clockingoutpod X: http://twitter.com/hrentrepreneur Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos Become a guest on Clocking Out

  3. 63

    Natalie Nixon: Professor to Creativity Strategist, Speaker, & Author

    In this episode of Clocking Out, we meet Natalie Nixon, a creativity strategist, global keynote speaker, author, and CEO of Figure 8 Thinking. A woman who built a career not by following a map, but by trusting the thread that connected every unexpected turn along the way.Growing up in Mount Airy, Philadelphia, Natalie moved through three very different schools, a mother who wove and sewed, a father who worked two jobs, and a childhood spent figuring things out on the stoop. That's where her curiosity was born.When it came time to declare her college major, she called home bracing for disappointment. Instead, her father offered one of the most liberating sentences she'd ever hear: if you study what you love, you'll have to turn away opportunities. That statement became her north star.What followed was anything but linear. Middle school English teacher, hat designer, global fashion sourcing executive, professor and MBA program director. Each chapter fed the next in ways she couldn't have engineered.But the leap didn't come from inspiration. It came from exhaustion. The breaking point wasn't a dramatic resignation. It was an involuntary moment of honesty, walking down a hallway, arms full of papers, hearing herself say through clenched teeth, I don't want to do this.What she didn't realize was that she had already been building her next chapter. A small consulting practice called Figure 8 Thinking had quietly become proof of concept. The leap, when it came, was a step onto ground she had already been preparing.Today, Natalie advises leaders through her Wonder Rigor methodology, pairing imaginative curiosity with the discipline of testing and prototyping. Through keynote speaking, Leap Lab events, and two award-winning books, The Creativity Leap and Move. Think. Rest., she helps people build creative capacity for consistent innovation.This conversation is about nonlinear paths, the courage to follow your curiosity before you can justify it, and what it means to finally stop masking the voice that's been telling you it's time.Connect with Natalie at:LinkedIn: https://www.linkedin.com/in/natalienixonphd/ Website: https://www.figure8thinking.com/Follow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/ Instagram: https://www.instagram.com/raymondlee.co Tiktok: https://www.tiktok.com/@clockingoutpod X: http://twitter.com/hrentrepreneur Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos Become a guest on Clocking Out

  4. 62

    Henry Wong: Advertising Executive to Brand Strategist & Author

    In this episode of Clocking Out, we meet Henry Wong, a brand strategist, author, and former global advertising executive who spent years helping organizations shape powerful narratives, only to realize the most important story he needed to shape was his own.Growing up in Toronto, Henry spent much of his childhood working in his parents’ Chinese restaurant. By age 11, he had moved to the front counter, where interacting with customers from all walks of life taught him how to read people, build connections, and understand the power of story — lessons that would quietly shape his future career.After university, Henry followed his strength as a writer into journalism before moving into advertising, where his creativity led him to leadership roles at Saatchi & Saatchi. The work was exciting, prestigious, and full of recognition. But over time, he began to see the cost of chasing the next campaign, the next award, and the next win.As his career accelerated, Henry realized the trade-off was becoming clearer: the more he invested in the work, the further he drifted from his family and the life he wanted to build. Instead of continuing on the traditional corporate path, Henry stepped away, joined a smaller firm, became a partner, and built a career that gave him both meaningful work and greater balance.Today, Henry advises leaders on Narrative Intelligence — the ability to shape the stories that influence teams and culture. Through his consulting and his book Telling Your Story, Building Your Brand, he helps people clarify what they stand for, distill it into a defining word, and align how they show up with that truth. He now describes his own journey in three chapters: learning, earning, and returning.This conversation is about identity, authenticity, and the courage to redefine success on your own terms.Connect with Henry at:LinkedIn: https://www.linkedin.com/in/henrywongbrand/Website: henrywong.coFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/ Instagram: https://www.instagram.com/raymondlee.co Tiktok: https://www.tiktok.com/@clockingoutpod X: http://twitter.com/hrentrepreneur Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos Become a guest on Clocking Out

  5. 61

    Scott Ramey: Fortune 100 Executive to Entrepreneur & Founder

    In this episode of Clocking Out, we meet Scott Ramey, a former Division I athlete and Fortune 100 executive who spent decades looking steady on the outside while quietly unraveling on the inside.Raised in a small Indiana town in a home that welcomed more than 35 foster children, Scott learned early to compete, lead, and fix what was broken. Basketball became his identity, until a career-ending injury at 19 triggered his first panic attack and the start of decades of silent anxiety.He carried that anxiety into a 30-year career in financial services, rising from intern to senior executive. Known as the steady hand in moments of crisis, Scott built high-performing teams and led through uncertainty. But behind the calm exterior, he was paying what he calls the “masking tax”; appearing composed while internally redlining.A health scare forced him to confront what he had long ignored. Burnout wasn’t random. It was cumulative.Around the same time, Scott made a life-changing decision: he told his daughter about his lifelong anxiety. That conversation unburdened him and reshaped his understanding of leadership, strength, and legacy. Soon after, he gathered his family on the back porch and told them he was taking a leap into entrepreneurship.Today, Scott helps leaders and sales teams communicate with clarity and authenticity, building trust instead of control. But his most important leadership breakthrough came when he stopped copying toxic models and started leading as himself.This conversation is about identity, the hidden cost of pretending, and the courage to let go of who you thought you had to be. It’s about redefining strength, breaking the fixer cycle, and realizing that legacy isn’t what you leave behind — it’s how you show up every single day.Connect with Scott at:Website: https://thescottramey.com/ LinkedIn: https://www.linkedin.com/in/scott-ramey/ Facebook: https://www.facebook.com/profile.php?id=61567936481441 Instagram: https://www.instagram.com/the.scottramey/ Follow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/ Instagram: https://www.instagram.com/raymondlee.co Tiktok: https://www.tiktok.com/@clockingoutpod X: http://twitter.com/hrentrepreneur Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos Become a guest on Clocking Out

  6. 60

    Rick Bleiweiss: Record Executive to Award-Winning Novelist at Age 77

    In this episode of Clocking Out, we meet Rick Bleiweiss, a man who has reinvented himself not once, but five times.Rick’s career reads like a masterclass in creative evolution: rock musician, record producer, senior music executive, publishing leader, and at age 77, debut novelist. Today, he has added podcaster and award-winning author to the list. What makes Rick’s story remarkable isn’t just the titles. It’s the mindset behind them.Raised in New York by parents who encouraged him to follow his passion, Rick fell in love with music at an early age. That love led to a 15-year run as a professional musician before he transitioned into the business side of the industry, helping break major artists and producing hit records. Over time, he rose through the ranks of record labels, blending creativity with corporate leadership.When Napster and industry consolidation transformed the music business into something unrecognizable, Rick made a bold decision. He retired.It didn’t stick.After volunteering, serving on nonprofit boards, and doing retirement “right,” he realized something important: creative energy doesn’t expire. In his late seventies, Rick published his first novel. It became an award-winning, number one Amazon bestseller. He hasn’t slowed down since.Now Head of New Business Development at Blackstone Publishing and an acclaimed novelist, Rick proves that meaningful work, impact, and reinvention are available at every age.This conversation is about curiosity, courage, and refusing to let a number define your next chapter.Connect with Rick at:Website: https://www.rickbleiweiss.com/ Youtube: https://www.youtube.com/@rickbleiweiss7703 Instagram:https://www.instagram.com/rickbleiweissauthor/ His books: https://www.amazon.com/stores/author/B09DGLR9TD Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  7. 59

    Sabrina DeVito: Banking Executive to Entrepreneur and Freedom Mentor

    In this episode of Clocking Out, we sit down with Sabrina DeVito, a visionary strategist, builder, and longtime leader whose career proves that success doesn’t always mean alignment.Sabrina spent decades in financial services, moving across roles, cities, and companies not out of obligation, but out of a deep desire for growth, creativity, and challenge. A first-generation college graduate raised in Lancaster, Pennsylvania, she grew up surrounded by examples of reinvention. Her mother built a real estate business and later made a bold late-career pivot into public office, while her father’s steady accounting career offered a very different model. That blend of entrepreneurship and practicality quietly shaped how Sabrina approached her own path.Early on, she discovered a love for communication, storytelling, and rallying people around ideas. That instinct carried her through a long career in banking and fintech, including multiple early-stage companies and acquisitions, where she thrived in the messy, build-it-from-scratch phase and felt increasingly restless once structure and bureaucracy took over.Sabrina describes her career in three chapters: the learning years, the earning years, and what she calls the returning years. Her first true “clocking out” moment came when she left the safety of banking to join an early-stage startup in a completely different industry, trading polish for possibility. That leap sparked a deeper realization: climbing higher was no longer the goal. Designing a life that felt true was.Today, Sabrina is intentionally writing her next chapter, one rooted in flexibility, purpose, and impact. In this conversation, she reflects on trusting the clues, letting go of what looks good on paper, and choosing what feels right in your gut.If you’ve ever wondered what comes after success, this episode is for you.Connect with Sabrina at:Website: https://www.sabrinadevito.com/ LinkedIn: https://www.linkedin.com/in/sabrinadevito/ Instagram:https://www.instagram.com/sabrinadevit0 Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  8. 58

    Christy Linn: Management Consultant to Home Organizing Entrepreneur

    In this episode of Clocking Out, we meet Christy Linn, founder of Second Nature Home Organizing, whose career journey proves that some of the biggest pivots happen quietly, one small decision at a time.Christy grew up just outside Baltimore in a close-knit childhood shaped by sports, Girl Scouts, and weekends with family. Her mom stayed home when she was young and later rediscovered her own passion as a school photographer. Her dad was an accountant, and the path he modeled was simple and practical: go to school, study the thing, then go do the job. That mindset stuck with Christy early on.In high school, she decided she would become a lawyer and never looked back. She joined a mock trial, loved reading, writing, and debating, and headed to Syracuse with a clear plan. But during college, after studying abroad, something shifted. She realized law was not the future she wanted after all, and suddenly she had no backup plan. That uncertainty created real tension, especially with her dad, who worried she would graduate with a liberal arts degree and be unemployable.Determined to prove she could still build a stable career, Christy leaned into recruiting and landed a job offer with Accenture before graduation, a turning point that eased her dad’s fears. From there, she spent years in consulting, including a long chapter at Booz Allen.As she became a mom, the pressure of balancing career demands with family life grew heavier, especially in roles with little flexibility. Eventually, Christy made a choice many people don’t talk about openly: she stepped away from the corporate world, not to jump into another job, but to fully step into life at home. For a season, it worked beautifully.Until life changed again.A cross-country move during Covid brought loneliness, boredom, and a new restlessness. Christy found herself asking: What now? What began as an itch for purpose grew into something bigger. Drawing from the organizing systems she’d built for her own family, she began helping others create homes that support real life.Today, Christy helps families create realistic systems that reduce stress and make everyday life feel easier through Second Nature Home Organizing, turning life experience into a business that finally feels like the right fit.Connect with Christy:Website: https://second-nature.us LinkedIn: https://www.linkedin.com/in/christy-linn/ Instagram: https://www.instagram.com/secondnaturehomeorganizing/ Facebook: https://www.facebook.com/SecondNatureHomeOrganizing Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  9. 57

    Bronson Hill: Youth Pastor & Medical Sales to Financial Freedom Creator

    In this episode of Clocking Out, Raymond sits down with Bronson Hill, host of the Mailbox Money podcast and founder and CEO of Bronson Equity, to unpack what it really means to “design your freedom.”Bronson’s path is anything but typical. Raised middle-class by a single parent, he learned early that if he wanted something, he had to build a way to earn it. That mindset carried him from youth ministry to a high-performing career in medical sales, where the pay was great, but the treadmill never stopped. Even watching high earners burn out around him made one thing clear: money is not the same as freedom.Bronson shares the moment that sparked his decision to “fire himself,” how he reframed failure as useful data, and why low-risk experiments can change everything. Today, he teaches others how to pursue time freedom through passive investing, while staying grounded in faith, family, and impact.Connect with Bronson at:LinkedIn: https://www.linkedin.com/in/bronsonhill/ Instagram: https://www.instagram.com/bronsondavidhill/ Youtube: https://www.youtube.com/channel/UCc1KYJL8ZjF3GC3Wh5lYNfg Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  10. 56

    Reflections and A Look Forward

    As the year winds down and the holidays settle in, lets take a moment to pause—not to interview a guest, but to reflect.After more than 50 deeply honest conversations on Clocking Out, this episode looks back at the last two years of stories about burnout, identity, misalignment, and the quiet signals many of us ignore for far too long. These weren’t just career pivots. They were slow erosions. Subtle burnout. Success on paper paired with exhaustion, anxiety, and a nagging sense that something wasn’t right.Raymond reflects on what kept coming up again and again: how long people stayed, how burnout rarely arrives all at once, and the moments—big or small—when staying began to cost more than leaving.He also shares what’s coming next. In 2026, Clocking Out expands into a research-driven project, developed in collaboration with researcher Chris Castile, Associate Professor at Nicholls State University. Together, they’ll analyze these conversations to identify patterns: early warning signs, forces that keep people stuck, and how individuals make sense of their decisions on the other side. Not to tell anyone what to do—but to help people recognize themselves sooner.This episode is both a thank you and an invitation: to rest, to reflect, and to listen more closely to what your own experience might be trying to tell you.Take care of yourselves. Happy holidays, and here’s to a more intentional year ahead.

  11. 55

    Lia James: Career Coach to Connection Architect

    In this episode of Clocking Out, we meet Lia James, founder of &Human and creator of The Traveling Table, an experience design and storytelling studio focused on one big idea: conversations are infrastructure.Lia’s career has never followed a straight line. After graduating into a recession, she landed her first real role at a community college by A/B testing her own résumé, submitting one version with her full name, Aurelia, and one with her nickname, Lia. That bold move led to a tough, brilliant mentor who not only hired her but helped her launch her early ventures and lean into entrepreneurship.From there, Lia’s path unfolded in surprising ways. She became the kind of person who follows her curiosity wherever it leads, whether that meant building digital communities, guiding career changers through reinvention, or learning to work with her hands simply because it brought her back to herself. Over time, she realized a pattern: people sought her out not for her job titles, but for her ability to create spaces where they felt understood. And after supporting hundreds of people through major life transitions, she hit her own breaking point and began asking a deeper question: What would it look like to design environments where real connection isn’t an accident, but the purpose?Today, Lia designs transformational gatherings and facilitates high-stakes conversations for foundations, nonprofits, local governments, and corporate teams who are struggling to connect across differences.In this conversation, she shares how she walked away from the predictable path, packed a literal table in her car, and built a life around intentional connection. If you have ever felt the pull to create something more meaningful, this episode will give you a new way to think about work, community, and the power of being in the same conversation.Connect with Lia at:LinkedIn: https://www.linkedin.com/in/liajames/Instagram: https://www.instagram.com/thetraveling_table/YouTube: https://www.youtube.com/@thetravelingtableWebsite: www.andhuman.spaceFollow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  12. 54

    Anna McDougall: Opera Singer to Engineering Leader & Author

    In this episode of Clocking Out, we meet Anna McDougall — an award-winning engineering leader, author, and former opera singer whose career is anything but ordinary.Born in Sydney and raised by an academic mother and a creative father, Anna was a curious child who loved writing, performing, and—at just eight years old—taught herself to code from a book on HTML. That early spark of curiosity would guide her through a remarkable life of reinvention: from corporate boardrooms to opera stages, and eventually, to the world of tech.Her path was anything but linear. There were moments of burnout, side jobs, and starting over from scratch in a new country. She’s lived through long nights balancing ambition with survival, chasing both purpose and stability in equal measure. But whenever Anna dives into something, she’s all in—and each leap taught her something new about resilience, creativity, and courage. Today, she leads global engineering teams and mentors others navigating transformation. In this conversation, Anna shares how she built a career that feeds both her heart and her mind—and what it truly takes to follow curiosity wherever it leads. Her story is a reminder that your next chapter might be the one that finally feels like home.Connect with Anna at:Website: https://www.annamcdougall.com/ LinkedIn: https://www.linkedin.com/in/annajmcdougall/ Book: https://www.amazon.com/You-Belong-Tech-Programming-Knowledge/dp/3982435811Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  13. 53

    Cate Luzio: Banking Executive to Empowerment Leader & Founder of Luminary

    In this episode of Clocking Out, we meet Cate Luzio, a former banking executive who turned two decades in global finance into a mission to empower and connect women through community.Cate’s path began in Ohio, shaped by parents who embodied service: her mother a teacher, her father an FBI agent. As a child, she dreamed of following in his footsteps until one honest answer on an FBI internship application changed her course forever. That detour led her to Washington D.C., a nonprofit, and eventually to the world of banking, where she spent twenty years rising through the ranks at some of the world’s largest financial institutions, including Bank of America, JPMorgan Chase, and HSBC.Even as she climbed the corporate ladder, Cate stayed rooted in mentorship, leading women’s networks and championing workplace inclusion long before it was mainstream. But in 2018, she decided to take those lessons outside the boardroom. Trading stability for purpose, she launched Luminary, a New York–based collaboration hub designed to uplift, develop, and connect women across industries.When the pandemic hit just a year later, Cate refused to back down. She adapted, expanding Luminary into a thriving hybrid community that continues to grow worldwide.Today, Cate is more than a founder; she’s a builder of belonging, proof that leadership isn’t just about climbing ladders but creating new ones for others. Join us as Cate shares what it means to bet on yourself, redefine success, and light the way for those who follow.Connect with Cate at:Website: https://www.weareluminary.com/home LinkedIn: https://www.linkedin.com/in/cluzio/  Instagram: https://www.instagram.com/cateluzio/Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  14. 52

    Benedict Beaumont: IT Engineer to Breathwork Facilitator, Teacher and Founder of Breathing Space

    In this episode of Clocking Out, we meet Benedict Beaumont, a former IT professional and high school teacher who traded the classroom for a deeper kind of teaching: helping others heal through breathwork.Benedict grew up in Brighton, a seaside city on England’s south coast known for its creativity and openness. From an early age, he was curious about life’s big questions — why we’re here, what makes us whole — but found few answers in conventional paths. After university, he followed expectation rather than instinct, landing a well-paid IT job in London. From the outside, it looked like success. Inside, it felt empty.When his rock-and-roll dreams collided with his corporate life, Benedict chose passion over predictability and quit his job to pursue music full time. But when the record deal fell through, everything he’d built unraveled. With no job, no band, and no plan, he escaped to California to clear his head. In the stillness of the desert, he realized it was time to rebuild, this time with purpose. He became a high school teacher, dedicating his career to helping students in some of England’s toughest schools. But after years of giving everything to others, he hit another wall: burnout. Searching for renewal, he set off to India, a trip that would nearly cost him his life but ultimately gave him a new one.There, and later in Bali, Benedict discovered breathwork, a practice that reconnected him to purpose and presence. Today, as the founder of The Breathing Space, he trains facilitators and leads retreats around the world, empowering others to use the breath as a tool for transformation.In this conversation, Benedict shares how burnout, curiosity, led him back to himself and why every breath is a chance to begin again.Connect with Benedict at:Website: https://www.makesomebreathingspace.com/ LinkedIn: https://www.linkedin.com/in/benedict-beaumont-92860631/   Instagram: https://www.instagram.com/makesomebreathingspaceFacebook: https://www.facebook.com/makesomebreathingspace Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  15. 51

    Robert Markowitz: Criminal Defense Lawyer to Party Clown and Children’s Musician

    In this episode of Clocking Out, we dive into the inspiring journey of Robert Markowitz. Once a criminal lawyer, now a children’s musician, author, and performer whose story proves it’s never too late to choose joy.Robert spent years chasing a traditional definition of success: Duke Law, criminal trials, and the prestige of a respected profession. But behind the courtroom victories, he felt trapped, weighed down by family expectations, office walls, and a career that didn’t fit his temperament. After just a few years in practice, he walked away, leaving behind a decade of preparation and a stable paycheck for what many dismissed as unrealistic: performing for children.The leap wasn’t easy. Friends drifted away, family questioned his choices, and doors slammed in his face. But Robert persisted, first as “Bobo the Clown,” then as a musician singing to toddlers in libraries and schools across New York. What began as a radical pivot turned into a decades-long career rooted in joy, presence, and connection. Along the way, he also embraced writing, publishing essays in The New York Times and most recently his novel Clown Shoes, now adapted into a stage play.In this conversation, Robert reflects on ego, family pressure, reinvention, and the messy but meaningful journey of leaving behind a life that looks right on paper for one that feels right in your heart. If you’ve ever wondered what might happen if you truly followed your bliss, this episode is for you.Connect with Robert at:Free Substack blog: https://markowitz.substack.com/‘Clowns Shoes’ on Amazon: https://www.amazon.com/Clown-Shoes-Robert-Markowitz/dp/1956474307 ‘Clown Shoes, The Musical’: https://clownshoesthemusical.my.canva.site/ Facebook: https://www.facebook.com/robert.markowitz.77 Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  16. 50

    Christopher Veal: Marine Corps Office to Vulnerability Vanguard

    What happens when a former Marine officer and combat veteran trades his uniform for emotional honesty?In this episode of Clocking Out, we sit down with Christopher Veal, who is on a mission to challenge what leadership and masculinity really look like—starting with himself.After a chance encounter opened a new door, Christopher left college to pursue a career with the Marine Corps, setting him on a path that would shape his future. He served for nearly a decade, deploying to Iraq, leading troops, and achieving his goal of becoming a company commander. But when military life began to feel more political than purposeful, he made the bold decision to walk away.What followed wasn’t instant clarity. He spent six years in construction, working on tower cranes and learning the ropes, but slowly realized that while the work fit his skills, it didn’t feed his soul. It wasn’t until he became a father and faced outdated backlash for taking parental leave that he began to question not just his career, but his identity. What did leadership mean? What did it mean to be a man? What was the connection between vulnerability and masculinity?So, he pivoted again.Christopher returned to school, earned a master’s in organizational leadership, and discovered his true calling in coaching, facilitation, and leadership development. He built a new career in organizational development and eventually founded Echelon Left, where he now helps senior leaders show up with more clarity, courage, and connection.The inner work and curiosity about vulnerability and masculinity led him to launching: The Vulnerable Man podcast, where he hosts raw, real conversations about connection, identity, and healing.In this episode, Christopher shares how he reshaped his life and work to center vulnerability, how to recognize when it’s time to leave, and why letting go of the wrong fit can lead you to the work you’re meant to do.Connect with Christopher at:LinkedIn: https://www.linkedin.com/in/christopherveal/ Website: https://www.echelon-left.com/  Podcast: https://www.vulnerable-man.com/  Book: https://www.wholemanjourney.com/ Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  17. 49

    Vanessa K. De Luca: Retail Management to Editor in Chief & Content Strategist

    In this episode of Clocking Out, we meet Vanessa K. De Luca, a journalist and media executive whose career has been defined by bold pivots, perseverance, and a commitment to amplifying Black women’s voices.Vanessa didn’t start in publishing. She spent seven years in retail management before answering the pull she’d always felt toward storytelling. Trading stability for possibility, she took an NYU summer course, built her writing chops, expanded her network, and eventually landed an entry-level publishing role at Glamour. From there, she climbed the ranks; first at Life magazine, then Essence, where perseverance paid off after being passed over twice for Editor-in-Chief. In 2013, she finally took the helm, transforming the brand digitally and launching bold initiatives like the Woke 100 and Black Women in Hollywood.Her leadership journey didn’t end there. Vanessa went on to serve as Editor-in-Chief at ZORA and later at The Root, cementing her place as a powerful voice in Black media. But as the industry shifted, she found herself further from the creative spark that first drew her in. The mounting pressures of business, investors, and rapid change forced her to reflect on what she truly wanted.Now, Vanessa has returned to her roots in storytelling through platforms like Substack, reclaiming the freedom to write, mentor, and experiment without the weight of corporate pressures but with the joy of storytelling. In this conversation, she opens up about the courage to pivot, the lessons in perseverance, and what it takes to return to the work that feels most authentic.Connect with Vanessa at:LinkedIn: https://www.linkedin.com/in/vanessakdelucaInstagram: https://www.instagram.com/vanessa_kdeluca/ Email: [email protected] Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  18. 48

    Ling Yah Wong: Ex-Lawyer turned Personal Branding Strategist & Podcaster

    In this episode of Clocking Out, we meet Ling Yah Wong — once a litigator at Malaysia’s top law firm, now the voice behind the So This Is My Why podcast and a sought-after LinkedIn strategist. For nearly a decade, Ling Yah followed the traditional path of prestige and stability, even as she quietly questioned whether law was truly for her.When she discovered podcasts, she found a new passion: storytelling. In 2020, she made a deal with herself — after climbing Everest Base Camp that March, she would finally launch her own podcast. What started as a side project quickly became her way of connecting with extraordinary people from around the world, reverse-engineering their successes, and reimagining her own future. Along the way, she tapped into the power of LinkedIn, where her posts went viral, reaching millions, and where she began helping others craft their personal brands.By 2023, things had truly taken off. Ling Yah made the leap, leaving law behind for good and embracing what she calls her “Year of Yes.” Today, she runs a successful podcast, a YouTube channel, and a LinkedIn strategy business that has already helped clients gain recognition as LinkedIn Top Voices. Her story proves you don’t have to have it all figured out before starting over. Curiosity, consistency, and courage can take you further than you think.Join us as Ling reflects on identity, risk, and the freedom of walking away from a career that looks successful on the outside but feels misaligned on the inside. If you’ve ever wondered whether you’re “allowed” to change paths, Ling Yah’s journey is the reminder you need.Connect with Ling:Website: www.sothisismywhy.comInstagram: https://www.instagram.com/sothisismywhy/ LinkedIn: www.linkedin.com/in/lingyahYoutube: https://www.youtube.com/channel/UCSZlcS5ooyCjj_MkrmH_WhQSpotify: https://open.spotify.com/show/1ZK3NFTEX2EWXTvwelWHA7?si=rhU70hzZTSaRWrphIBe-7gApple podcast: https://podcasts.apple.com/my/podcast/so-this-is-my-why/id1521191442Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

  19. 47

    Julia Skupchenko: Corporate Oil & Gas Liaison to Social Impact Entrepreneur

    In this episode of Clocking Out, we meet Julia Skupchenko. An award-winning entrepreneur, sustainability leader, and co-founder of the global think tank AlterContacts. Recognized by the United Nations and the European Parliament for her work accelerating progress toward the Sustainable Development Goals, Julia designs bold social-impact initiatives and teaches the next generation of changemakers. But her journey to this point began far from the global stage. She grew up in the Arctic, raised by a family of academics and learning responsibility from an early age.From her first dreams of becoming a detective to presenting at international conferences in her early twenties, Julia chased opportunities with relentless energy. A chance encounter with Shell executives led to an internship that would open the door to the corporate world and also reveal its “golden cage.” After rising quickly, she faced the harsh reality of hierarchical leadership, questioned the meaning of her work, and walked away to forge her own path.Her leap into entrepreneurship wasn’t smooth. A failed translation business became a crash course in sales, branding, and resilience. But staying open to every opportunity led to strategic consulting work, a strong partnership with her future co-founder, and eventually the launch of AlterContacts. When the pandemic hit, which changed everything and her life split for a second time in before and after. Her drive to help people resulted in the founding of the Lockdown Economy, uniting volunteers from 42 countries to support small businesses in crisis. The success and global reach of that initiative became the foundation for Think Thank AlterContacts, where she now leads large-scale sustainability projects.In this conversation, Julia shares what it takes to break free from comfort, turn setbacks into stepping stones, and find purpose in helping others. If you’ve ever wondered how to align ambition with impact, this episode will inspire you to start — wherever you are.Connect with Julia:Website: https://www.altercontacts.org/Instagram: https://www.instagram.com/julia.skupchenkoLinkedIn: https://www.linkedin.com/in/juliaskupchenko/Company LinkedIn: https://www.linkedin.com/company/altercontacts/Follow Careerminds: LinkedIn: https://www.linkedin.com/company/careermindsInstagram: https://www.instagram.com/careerminds/Facebook: https://www.facebook.com/CareermindsYoutube: https://www.youtube.com/@CareermindsFollow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/Instagram: https://www.instagram.com/raymondlee.coTiktok: https://www.tiktok.com/@clockingoutpodX: http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videosVisit Raymond’s website: https://www.raymondlee.co/Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 Become a guest on Clocking Out

Type above to search every episode's transcript for a word or phrase. Matches are scoped to this podcast.

Searching…

We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.

No matches for "" in this podcast's transcripts.

Showing of matches

No topics indexed yet for this podcast.

Loading reviews...

ABOUT THIS SHOW

Clocking Out is a podcast about bold moves and personal breakthroughs. Each episode spotlights people who’ve made the life-changing decision to walk away from jobs, careers, or situations that no longer served them in pursuit of something more meaningful.Through candid conversations, we explore the pivotal moments, mindset shifts, and personal values that fuel these transformations. Guests share the setbacks, surprises, and self-discoveries that helped shape their new paths, with themes of resilience, reinvention, and purpose woven throughout.Created as a tribute to Raymond's mother, who inspired the show by chasing her own dream of career fulfillment, Clocking Out is a reminder that it’s never too late to choose yourself.

HOSTED BY

Raymond Lee

Frequently Asked Questions

How many episodes does Clocking Out with Raymond Lee have?

Clocking Out with Raymond Lee currently has 19 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Clocking Out with Raymond Lee about?

Clocking Out is a podcast about bold moves and personal breakthroughs. Each episode spotlights people who’ve made the life-changing decision to walk away from jobs, careers, or situations that no longer served them in pursuit of something more meaningful.Through candid conversations, we explore the...

How often does Clocking Out with Raymond Lee release new episodes?

Clocking Out with Raymond Lee has 19 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Clocking Out with Raymond Lee?

You can listen to Clocking Out with Raymond Lee on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Clocking Out with Raymond Lee?

Clocking Out with Raymond Lee is created and hosted by Raymond Lee.
URL copied to clipboard!