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.
Episodes
July 23, 2025 • 56 mins
In this episode of Clocking Out, we meet Carla Stickler, a former Broadway actor who once brought Elphaba to life in Wicked and now writes code as a web engineer at Spotify.
After landing her first big tour right out of college, Carla returned to New York expecting stardom. Only to find herself waiting tables, battling rejection, and facing the hard truth that talent alone doesn’t guarantee success. That humbling chapter forced her ...
After landing her first big tour right out of college, Carla returned to New York expecting stardom. Only to find herself waiting tables, battling rejection, and facing the hard truth that talent alone doesn’t guarantee success. That humbling chapter forced her ...
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July 9, 2025 • 59 mins
In this episode of Clocking Out, we meet Dakota Barker, a former medical professional who once believed her future was in hospitals and healing. For years, she poured her heart into caring for pediatric cancer patients, driven by a deep passion for helping others. But when the COVID-19 pandemic hit, the cracks in the healthcare system widened, and the emotional toll became impossible to ignore.
Burnout crept in until it became overw...
Burnout crept in until it became overw...
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June 25, 2025 • 60 mins
In this episode of Clocking Out, we meet Rachel Humphrey — a former trial attorney who once believed she'd spend her entire life arguing cases in court. But after two decades in law and a major cross-country move, Rachel found herself at a crossroads: unfulfilled and reevaluating her life’s direction. When her longtime nanny unexpectedly resigned, Rachel made a bold decision — she quit her job without a backup plan, determined to r...
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June 11, 2025 • 53 mins
In this episode of Clocking Out, we meet Haley Pollack — a former academic and educator whose life took a dramatic turn when she was diagnosed with Stage III colon cancer at age 37. A mother of two, including a six-month-old at the time, Haley found herself navigating not only a devastating diagnosis but also the emotional complexity of parenting through it.
Haley’s career began in academia, with a PhD in U.S. history and a deep pas...
Haley’s career began in academia, with a PhD in U.S. history and a deep pas...
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May 28, 2025 • 48 mins
In this episode of Clocking Out, we meet Lynne Thompson — a former lawyer who spent over 20 years in the legal world before answering a call that had echoed since childhood: poetry. Lynne pivoted from litigation to literature, ultimately becoming Los Angeles’ 4th Poet Laureate, a nationally recognized advocate for the power of poetry, and the author of four acclaimed collections, including Blue on a Blue Palette.
A native Angeleno a...
A native Angeleno a...
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May 14, 2025 • 50 mins
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 wor...
Simon grew up in a wor...
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April 30, 2025 • 56 mins
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,...
After building early career success and pursuing a new job opportunity,...
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April 16, 2025 • 43 mins
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 fi...
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 fi...
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April 2, 2025 • 48 mins
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, turn...
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, turn...
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March 19, 2025 • 55 mins
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 & Telev...
Amber studied Film & Telev...
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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 Un...
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 Un...
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February 19, 2025 • 46 mins
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 engineer...
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 engineer...
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February 5, 2025 • 44 mins
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 re...
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January 22, 2025 • 53 mins
In this episode of Clocking Out, Raymond is joined by Dr. Fiona Jamison, a seasoned leader in people analytics and organizational research. Fiona’s remarkable career spans over 25 years and includes exiting and selling her company Spring International.
Fiona was born in the UK and moved to the US after college. With a Ph.D. in Human Resource Management from the University of Bristol, she’s a true expert in transforming complex data ...
Fiona was born in the UK and moved to the US after college. With a Ph.D. in Human Resource Management from the University of Bristol, she’s a true expert in transforming complex data ...
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January 8, 2025 • 41 mins
In this episode of Clocking Out, Raymond is joined by Aurelie Foucart, the founder of Affirmed Leadership, a company dedicated to executive coaching and leadership training. Born and raised in Paris, France, Aurelie's early life was filled with a love for writing and playing the piano, but she ultimately followed her mother’s advice to pursue a more traditional path and earned a law degree.
Aurelie’s career took a fascinating turn ...
Aurelie’s career took a fascinating turn ...
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December 18, 2024 • 40 mins
In this episode of Clocking Out, Alice Rush, a certified Master Career Counselor, shares her inspiring journey from starting her career as a sales leader to becoming a leading expert in career coaching and counseling. Born in Palo Alto, CA, her father spent 30 years at IBM as an engineer and her mother was a concert pianist and entrepreneur. Alice learned early on the importance of both stability and the pursuit of passion. After w...
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December 11, 2024 • 49 mins
In this inspiring episode of Clocking Out, Kate Lingoni, shares her amazing story of being a researcher, entrepreneur, actor, mom, and business owner whose career journey has been anything but conventional. Born in Metairie, Louisiana, Kate went to Archbishop Chapelle High School and later graduated from Louisiana State University. Kate’s early aspirations were rooted in a desire to serve others, initially wanting to become a polic...
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December 4, 2024 • 39 mins
In Episode 29 of the Clocking Out podcast, we hear the inspiring journey of Wes Ehnert Carfi, a former sales leader who made a bold leap from a successful career in advertising sales to embracing his true passions for coaching, music, and comedy. Born and raised in New Jersey to a large Italian family with over 40 cousins, Wes was an entertainer at heart from an early age—whether it was through music, comedy, or sports. He was insp...
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November 20, 2024 • 49 mins
In Episode 28 of Clocking Out, Raymond sits down with Sairan Aqrawi, who shares her inspiring journey of transformation and self-discovery. Born in Iraq, Sairan left her home country in 1997 to pursue the American Dream. Influenced by her father, she chose a career in Civil Engineering, dedicating herself to the field and excelling in systems integration and project delivery.
But despite her success, Sairan found herself drawn to a ...
But despite her success, Sairan found herself drawn to a ...
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November 13, 2024 • 41 mins
In Episode 27 of Clocking Out, Raymond Lee sits down with Kayla McDaniel, a tech leader whose career journey has taken unexpected—and ultimately rewarding—turns. Originally set on becoming a nurse, Kayla pivoted to pursue degrees in computer science and international business. Her path wasn’t without challenges; a trio of layoffs pushed her to reconsider her career trajectory, eventually leading her into software client success, wh...
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