Clocking Out with Raymond Lee

Raymond Lee
  • 5.0 (18)
  • CAREERS
  • UPDATED BIWEEKLY

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. 2D AGO

    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/johnfareed Website: 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

    55 min

  2. APR 1

    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

    48 min

  3. MAR 18

    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

    51 min

  4. MAR 4

    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

    52 min

  5. FEB 18

    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

  6. 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

  7. 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

  8. 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
See All (65)

Trailer

5
out of 5
18 Ratings

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.

Information