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Clocking Out with Raymond Lee

Clocking Out with Raymond Lee

Written by: Raymond Lee
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About this listen

 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.
Raymond Lee Careers Economics Leadership Management Management & Leadership Personal Success
Episodes
  • Carla Stickler: Broadway Star to Software Engineer

    Carla Stickler: Broadway Star to Software Engineer
    Jul 23 2025
    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 ego to take a back seat and ultimately reshaped her definition of success.

    That shift in perspective made her not only more grounded but also a better colleague, and it led to a decade on stage. Landing big roles on Broadway and building a career many people dream about. But behind the curtain, the reality was far more complicated. The physical toll of performing eight shows a week mounted, and when Carla transitioned to teaching at the college level, she found herself struggling to inspire students to enter an industry she no longer felt supported by.

    Burnout, financial instability, and a deepening disillusionment led her to make a bold pivot: software engineering. With no tech background but plenty of grit, Carla enrolled in a coding bootcamp and discovered a surprising new outlet for her creativity. Today, she thrives in tech and champions artists looking to reinvent their careers. She proves that there’s always overlap in every profession, no skill or experience is ever wasted. When you set your mind to it, you really can do anything.

    In this conversation, Carla reflects on ambition, ego, rejection, and what it means to let go of the dream you thought you had to chase. If you’ve ever questioned whether it’s too late, or too risky, to start over. Carla’s story is your proof that it’s not. Tune in for a masterclass in reinvention.

    Connect with Carla at:
    • TikTok: https://www.tiktok.com/@sticklercarla
    • Instagram: https://www.instagram.com/sticklercarla/
    • LinkedIn: https://www.linkedin.com/in/carlastickler/
    • Personal website: www.carlastickler.com
    • Company website: www.creators.spotify.com


    Follow Raymond:
    • LinkedIn: Raymond Lee
    • Instagram: @raymondlee.co
    • Tiktok: @clockingoutpod
    • X: @hrentrepreneur
    • Youtube: @clockingoutwithraymondlee

    Click Here to become a guest on Clocking Out
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    56 mins
  • Dakota Barker: Physician Assistant to Entrepreneur and Real Estate Investor

    Dakota Barker: Physician Assistant to Entrepreneur and Real Estate Investor
    Jul 9 2025
    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 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 made the hardest decision of her life: to walk away.
    With grit, heart, and a little help from HGTV, Dakota and her partner started a small real estate side hustle while still working full-time. As their passion and knowledge grew, they made the bold decision to quit their stable, six-figure jobs and go all in. Committed to making it work, they got resourceful by renting out unused rooms, exploring new income streams, and learning how to build wealth in unconventional ways.

    Today, Dakota acquires and manages multifamily properties, provides safe housing in her community, and helps families build generational wealth—all while staying true to her lifelong drive to make a difference.

    In this conversation, Dakota shares the truth about burnout, the identity shift of leaving a "stable" profession, and how seemingly unrelated skills like empathy and communication can become your greatest assets. Her story is a powerful reminder that reinvention is possible for anyone willing to bet on themselves.

    If you’ve ever wondered whether it’s too late to start over, this episode is your sign that it’s not. Dakota’s experience shows how the bravest moves often start with saying, "This isn’t working anymore," and then daring to build something better. Tune in now to learn how Dakota turned burnout into freedom—and how you can too.

    Connect with Dakota at:
    • Instagram: https://www.instagram.com/dakota.barker.rei/
    • Facebook: https://www.facebook.com/dakota.w.7/
    • LinkedIn: https://www.linkedin.com/in/dakota-barker-a6760645/
    • Website: opiniconinvestments.com

    Follow Raymond:
    • LinkedIn: Raymond Lee
    • Instagram: @raymondlee.co
    • Tiktok: @clockingoutpod
    • X: @hrentrepreneur
    • Youtube: @clockingoutwithraymondlee

    Click Here to become a guest on Clocking Out
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    59 mins
  • Rachel Humphrey: Defense Attorney to Association Exec to Champion for Women in Hospitality

    Rachel Humphrey: Defense Attorney to Association Exec to Champion for Women in Hospitality
    Jun 25 2025
    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.

    That leap led her somewhere she never expected: the hospitality industry. Through a serendipitous conversation, Rachel discovered that the skills she honed in the courtroom — advocacy, negotiation, and leadership — could translate far beyond the law. She soon joined AAHOA, the largest hotel owners association in the country, and ultimately rose to interim CEO.

    Throughout her career, Rachel quietly carried a lifelong battle with self-doubt — often feeling the need to prove she belonged. But time and again, others saw something in her before she did. Their faith, combined with her relentless curiosity and drive, helped her rise to heights she never imagined for herself.

    From that experience, a new mission emerged: Fueled by a passion for equity, Rachel went on to found the Women in Hospitality Leadership Alliance, a consortium dedicated to amplifying women’s voices across the industry. Today, she mentors rising leaders, co-hosts a podcast spotlighting the human side of leadership, and speaks openly about reinvention, resilience, and learning to bet on yourself.

    Rachel’s story is a powerful reminder that we’re often more capable than we think — and that the most fulfilling chapters begin the moment we step outside the story we thought we had to live.

    Connect with Rachel at:
    • Website: www.whlalliance.org / www.ItsPersonalStories.com
    • LinkedIn: https://www.linkedin.com/in/rachel-a-humphrey
    Follow Raymond:
    • LinkedIn: Raymond Lee
    • Instagram: @raymondlee.co
    • Tiktok: @clockingoutpod
    • X: @hrentrepreneur
    • Youtube: @clockingoutwithraymondlee
    Click Here to become a guest on Clocking Out
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    1 hr
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