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.

Clocking Out with Raymond Lee is a business podcast hosted by Raymond Lee, with 47 episodes on record and a Required Pod Score of 80.

Raymond Lee hosts Clocking Out with Raymond Lee, a business show with 47 episodes published.

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  Clocking Out with Raymond Lee

  Carla Stickler: Broadway Star to Software Engineer

  Jul 23, 202556 minS0

  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.<br /><br />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 ego to take a back seat and ultimately reshaped her definition of success.<br /><br />That shift in perspective made her not only more gr...

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  Episode #45

  Dakota Barker: Physician Assistant to Entrepreneur and Real Estate Investor

  Jul 9, 202559 minS0

  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.<br /><br />Burnout crept in until it became overwhelming. Dakota found herself crying before shifts, questioning her future, and losing joy in both work and life. After trying everything from therapy to stress leave, she...

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  Episode #44

  Rachel Humphrey: Defense Attorney to Association Exec to Champion for Women in Hospitality

  Jun 25, 20251 hourS0

  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 rediscover what truly fueled her.<br /><br />That leap led her somewhere she never expected: the hospitality industry. Through a serendipitous conversation, Rachel discovered that the skills she honed in the...

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  Episode #43

  Haley Pollack: Educator to Nonprofit Founder for Families Facing Cancer

  Jun 11, 202553 minS0

  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.<br /><br />Haley’s career began in academia, with a PhD in U.S. history and a deep passion for teaching. After a decade in the adjunct “rat race,” she left higher education to work at the intersection of criminal justice...

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  Episode #42

  Lynne Thompson: Lawyer to Poet Laureate

  May 28, 202548 minS0

  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.<br /><br />A native Angeleno and daughter of Caribbean immigrants, Lynne grew up in where books, education, and ambition mattered — and she never let her four older brothers outpace her. Though she began writing at a y...

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