Clocking Out with Raymond Lee – Détails, épisodes et analyse

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Clocking Out with Raymond Lee

Clocking Out with Raymond Lee

Raymond Lee

Business & Entrepreneuriat
Business & Entrepreneuriat

Fréquence : 1 épisode/11j. Total Éps: 65

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

Saison 4 · Épisode 6

mercredi 8 octobre 2025 • Durée 46:17

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.

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Christopher Veal: Marine Corps Office to Vulnerability Vanguard

Saison 4 · Épisode 5

mercredi 24 septembre 2025 • Durée 55:54

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.

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Simon Rinne: From Silent Struggle to Social Impact

Saison 3 · Épisode 11

mercredi 14 mai 2025 • Durée 50:24

In this episode of Clocking Out, we meet Simon Rinne,  a former government worker who spent years navigating traditional career paths before realizing his deeper purpose was to support others in their healing. Now a mental health social worker and founder of Mindful Men, Simon helps men break the silence around mental illness, drawing from his own lived experience with undiagnosed OCD, depression, and anxiety.

Simon grew up in a working-class, hyper-masculine household in northern Adelaide, where emotional expression was rare and mental health wasn’t discussed. Behind his jokes and big smile was a young man silently struggling. From visual arts to anthropology to public service, Simon explored different paths but found himself stuck in toxic work environments, under controlling and unsupportive managers, and in roles that left him anxious, isolated, and eventually burned out.

After years of masking pain with alcohol, internal struggles, and bottled-up emotions, a series of personal and professional turning points led Simon to finally live more openly and honestly. A burnout during the pandemic pushed everything to the surface, forcing him to confront what he had carried for so long. As he began sharing his story - first on Instagram, then through his Mindful Men podcast, and ultimately as a lived-experience therapist - he saw firsthand how powerful and healing it is to speak the truth, both for himself and others.

Published in honor of Mental Health Awareness Month, this episode is a reminder that real strength lies in vulnerability — and that healing begins when we stop pretending we’re fine. Simon’s story is about courage, connection, and what’s possible when we finally clock out of survival mode and into something more authentic.

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Sarah Dale: Corporate Success to Women’s Empowerment Trailblazer

Saison 3 · Épisode 10

mercredi 30 avril 2025 • Durée 56:21

In this episode of Clocking Out, we meet Sarah Dale — a woman who spent years excelling in the world of media and advertising, helping brands like The Wall Street Journal and Fortune grow and thrive. Raised in a driven, adventurous family in New Jersey, Sarah learned early on that anything was possible — a mindset that carried her through multiple career pivots.

After building early career success and pursuing a new job opportunity, Sarah decided to take a much-needed break and traveled to Montana. There, she quickly fell in love with its adventurous spirit and wide-open way of life — so much so that she made the life-changing decision to leave everything behind and move there. During her years in Montana, she planted the first seeds of her dream: creating empowering outdoor experiences for women.

After personal upheaval eventually pulled her back into the corporate world, it was her strong network — and the relationships she had carefully nurtured — that helped her rebuild her career. Yet even after a decade of professional success, Sarah realized that true fulfillment wasn’t found at the top of the ladder. Inspired by the love for her children, she knew it was finally time to launch Project 1490, the mission that had lived in her heart for years.

Today, through Project 1490, Sarah helps professional women rediscover their confidence and strength by learning outdoor skills like fly fishing, archery, and horseback riding — while building deep, authentic connections that fuel both their personal and professional lives.

If you’ve ever dreamed of stepping off the traditional path and into something more authentic, Sarah’s story will inspire you to trust your gut, build your tribe, take the leap, and create a life you truly love.

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Jeremy Schifeling: Kindergarten Teacher to Founder of The Job Insiders

Saison 3 · Épisode 9

mercredi 16 avril 2025 • Durée 43:35

In this episode of Clocking Out, we sit down with Jeremy Schifeling, founder of The Job Insiders and author of the Amazon best-seller LinkedIn and ChatGPT for Job-Seeking.

Growing up in the working-class city of Buffalo and dreaming of playing for the Chicago Cubs, Jeremy learned early on how to hustle, adapt, and punch above his weight. Jeremy shares how his early days substitute teaching in Brooklyn classrooms—often a trial by fire—helped him discover his true passion: empowering others through technology and education. That small spark led him to roles impacting hundreds of thousands of learners and building new skills in marketing, research, and strategy.

But breaking into top tech companies wasn’t about perfect grades or a shiny resume — it was about building trust, finding insiders, and getting in through the side door. Jeremy shares how real relationships—not brand names—were the secret to unlocking the next stage of his career.

Eventually, he realized he wanted more than just a seat at someone else’s table. He wanted to build his own. So he stepped away from big tech to launch The Job Insiders, helping others find fulfilling work by rewriting the rules of job searching.This episode is packed with hard-won wisdom on how to find the right career path, navigating career pivots, and using your unique story as your greatest advantage.

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Christopher Chin: Acoustic Engineer to Founder & CEO of The Hidden Speaker

Saison 3 · Épisode 8

mercredi 2 avril 2025 • Durée 48:53

In this episode of Clocking Out, we meet Christopher Chin, a former data scientist turned communication coach who’s helping people transform information into impact.

Chris grew up in Queens, New York, in a household led by immigrant parents—both doctors—who encouraged him and his brother to follow traditional paths. But Chris had other ideas. His first bold pivot came in college, when he left pre-med to study music composition, turning a lifelong passion into a creative career.

After working as a freelance composer, Chris realized that while the work was fulfilling, it wasn’t financially sustainable. He pivoted again, earning a master’s in acoustic engineering to stay close to the world of sound while securing a more stable income. It’s a path he often recommends to those who want to remain in the music industry but also seek financial security. But for Chris, something still didn’t feel right. He taught himself to code and transitioned into tech—building a successful career in data, which he enjoyed for several years. But during the pandemic, everything shifted. Sitting in his office one day, he realized he had become good at something he no longer loved. Once again at a crossroads, Chris decided to bet on himself.

In 2023, he launched The Hidden Speaker, a company born from both risk and experience. His first music business had failed, but this time he identified a real and growing need in the professional world: communication. From storytelling to data delivery, Chris helps organizations present ideas with clarity, confidence, and heart. Through workshops, consulting, and TEDx talks, he now empowers others to find their voice—and use it to make an impact.

In this episode, Chris takes us through the rollercoaster of reinvention—from creative dreams to data science, tough choices to personal clarity. It’s a story about risk, resilience, and redefining success on your own terms.

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Amber Williams: Freelance Production Assistant to Content & Film Producer

Saison 3 · Épisode 7

mercredi 19 mars 2025 • Durée 55:53

In this episode of Clocking Out, we dive into the inspiring journey of Amber Williams, a Brooklyn native with deep Caribbean roots. Growing up in a vibrant immigrant community, education and ambition were ingrained in her from a young age. Though she initially aspired to be a lawyer, a pivotal summer program introduced her to the world of television, setting her on a path toward media and storytelling.

Amber studied Film & Television at Hobart College, gained hands-on experience through internships, and landed a job in media advertising post-graduation. However, she craved creativity beyond spreadsheets, leading her to a career transition into production. By leveraging LinkedIn and networking at film sets, she transitioned into freelancing on major productions like Billions and Clifford the Big Red Dog. Yet, she knew there was still something missing. She wanted to be the person that creates the stories. From then on, that became her long term goal.

To make those dreams a reality, she applied to NBCUniversal’s East Coast Page Program and was accepted. Through that program, she landed a role at Peacock, where she helped launch key marketing campaigns. Around the same time, she earned her MFA in Screenwriting at Emerson College, further solidifying her path as a storyteller. After three years, Peacock let her go, but that hasn’t stopped her from pursuing her ultimate goal: writing and creating authentic stories for television.

Amber’s journey is a testament to resilience, strategic career transitions, and the power of pursuing your passion. Tune in for her remarkable story of navigating the entertainment industry on her own terms.

Connect with Amber at:
LinkedIn: https://www.linkedin.com/in/amber-williams-mfa-0632b99a/

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Ronald Braver: Special Agent - Internal Revenue Service to Private Sector Investigator, Entrepreneur, & Partner

Saison 3 · Épisode 6

mercredi 5 mars 2025 • Durée 38:41

In this episode of Clocking Out, we explore the incredible career journey of Ronald H. Braver, a financial crime investigator who transitioned from government service to private sector success.

Ron grew up in the suburbs of Chicago and was fascinated by James Bond and dreamed of pursuing a career in investigative work. He followed that passion, earning a Bachelor’s Degree in Accounting and later a Master’s in Taxation from DePaul University.

After college, Ron embarked on a remarkable 25-year career as a Special Agent and Supervisory Special Agent with the IRS Criminal Investigation Division. Over the years, he took on high-profile investigations, leading major cases on money laundering, public corruption, Ponzi schemes, and organized crime. His expertise earned him numerous performance awards, including the Albert Gallatin Award and a Federal Employee of the Year nomination.

Following his IRS retirement, Ron transitioned to the private sector, working for a major accounting firm before launching his own forensic accounting and investigative consulting business. Today, he is a Partner at HKA, where he continues to apply his 40+ years of experience in financial investigations.

Join us as Ron shares his fascinating journey from public service to private sector, offering insights and advice for those looking to make a career transition. Whether you're considering a major career shift or are simply intrigued by the world of financial investigations, this episode is packed with inspiration and valuable takeaways.

Please enjoy Ron Braver and his Clocking Out story!

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Casey Brown: Chemical Engineer to Entrepreneur, TED Speaker, Author, & Pricing Geek

Saison 3 · Épisode 5

mercredi 19 février 2025 • Durée 46:29

In this episode of Clocking Out, we sit down with Casey Brown, a bold entrepreneur and founder of Boost Pricing, who walked away from the corporate world to help businesses sell at higher prices—and to give sales teams the confidence they need to succeed.

Growing up in a hardworking blue-collar town in Ohio, Casey was shaped by the values of persistence and education, instilled by her parents. With a dual degree in chemical engineering and Spanish, plus an MBA from Case Western Reserve University, she built a thriving corporate career before making the leap into entrepreneurship. Now, through Boost Pricing, she helps companies charge what they're truly worth—and teaches others to do the same.

Her powerful TED Talk, viewed over 4 million times, delivered the eye-opening message: "No one will ever pay you what you're worth. They'll only ever pay you what they think you're worth."

Listen as Casey shares how she found the confidence to step out on her own, the biggest pricing mistakes businesses make, and insights from her new book, Fearless Pricing. If you’re ready to stop undervaluing yourself and start owning your worth, this conversation is for you.

Tune in now to hear Casey’s inspiring “clocking out” story!

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Ginny Palmieri: Chief Human Resources Officer to CEO & Co-Founder of MyNextory

Saison 3 · Épisode 4

mercredi 5 février 2025 • Durée 44:36

In this episode of Clocking Out, Raymond welcomes Ginny Palmieri, a powerhouse leader who has mastered the intersection of HR, business strategy, and entrepreneurship. With a distinguished career spanning executive roles at Independence Blue Cross, Commerce Bancorp, and Bank of America, Ginny has built a reputation for driving transformation and inspiring growth. Now, as the CEO and Co-Founder of MyNextory, she’s on a mission to revolutionize career development through innovative, scalable solutions.

Ginny shares her insights on navigating change, embracing opportunity, and building a career aligned with personal values. Recognized as one of Main Line Today’s 2024 Power Women and Philadelphia Business Journal’s Women of Distinction, she is also the author of Unspoken: Finding Your Voice and Living Your Authentic Life, a book that champions authenticity and courage in professional and personal growth.

Tune in as Ginny reflects on her evolution from CHRO to CEO, the leadership lessons she’s learned along the way, and how she’s helping others take control of their careers—one step at a time.

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