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Clocking Out With Raymond Lee

Clocking Out With Raymond Lee

By: Raymond Lee
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About this listen

 Clocking Out is an inspirational podcast about individuals who have taken the leap of faith to “clock out” of a job, career or personal situation that wasn’t bringing them career fulfillment.

The show will do a deep dive into the personal stories and journey that highlight adversity and setbacks that contribute to the success of their overall career path with an emphasis on personal choice, mindset, agility, and trust.

Clocking Out is a podcast dedicated to his mom who has been an inspiration to him and has taken her own leap of faith to follow her dreams of career fulfillment.
Copyright Raymond Lee Career Success Economics Leadership Management Management & Leadership
Episodes
  • 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
    Show More Show Less
    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
    Show More Show Less
    1 hr
  • Haley Pollack: Educator to Nonprofit Founder for Families Facing Cancer

    Haley Pollack: Educator to Nonprofit Founder for Families Facing Cancer
    Jun 11 2025
    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 passion for teaching. After a decade in the adjunct “rat race,” she left higher education to work at the intersection of criminal justice and education, teaching English and literature to incarcerated students at San Quentin. The work was humbling, eye-opening, and deeply transformative. It challenged her assumptions, expanded her empathy, and reminded her of the power of education to change lives. It was some of the most meaningful work of her life — until illness steered her toward a different mission.

    Her diagnosis left her searching for support — not just as a patient, but as a parent. That search led to a transformative friendship and, ultimately, the founding of Bright Spot Network, a nonprofit that supports young families navigating a parent’s cancer diagnosis. Today, Bright Spot serves thousands of families each year through peer support groups, parenting resources, financial assistance, and community-building tools.

    Haley shares how her personal crisis reshaped her professional purpose, why she believes connection is key to healing, and how her work is bringing light to others in their darkest moments. Her story is a powerful reminder that even in hardship, we can build something hopeful — for ourselves and for others.

    Connect with Haley at:
    • Website: http://www.brightspotnetwork.org/
    • Instagram: @brightspotnetwork
    • Facebook: @brightspotnetwork
    • LinkedIn: Bright Spot Network
    • LinkedIn: Haley Pollack

    Follow Raymond:
    • LinkedIn: Raymond Lee
    • Instagram: @raymondlee.co
    • Tiktok: @clockingoutpod
    • X: @hrentrepreneur
    • Youtube: @clockingoutwithraymondlee
    Click Here to become a guest on Clocking Out
    Show More Show Less
    53 mins

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