Clocking Out with Raymond Lee

Raymond Lee
  • 5.0 (18)
  • CAREERS
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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. 1D AGO

    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

    48 min

  2. FEB 4

    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

    56 min

  3. JAN 21

    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

    54 min

  4. JAN 7

    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

    50 min

  5. 12/17/2025 · BONUS

    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.

    5 min

  6. 12/03/2025

    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

    57 min

  7. 11/19/2025

    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

    1 hr

  8. 11/05/2025

    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

    55 min
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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 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.

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