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
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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
  • 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
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    53 mins
  • Lynne Thompson: Lawyer to Poet Laureate

    Lynne Thompson: Lawyer to Poet Laureate
    May 28 2025
    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 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 young age, she followed a practical path, becoming a successful lawyer. Yet even with a full career, something was missing. She realized the law was feeding her head, not her heart. Seeking more space to create, she transitioned to lead labor and employee relations at UCLA — a demanding role, but one that gave her room to pursue poetry more intentionally. After 20 years, she took early retirement to fully commit to her passion.

    Lynne shares how she found her way back to poetry, how she transitioned with purpose (and a plan), and how her background in law shaped both her voice and her empathy as a writer. Without an MFA or literature degree, she gave herself permission to pursue the creative life she’d long imagined — immersing herself in workshops, readings, and writing groups to build a second career on her own terms. Along the way, she became not just a poet, but a literary leader: serving on the boards of major institutions, publishing widely, mentoring emerging voices, and proving that it’s never too late to follow the path that calls to you.

    This episode is a powerful reminder that your passions don’t expire — and that it’s never too late to write your own next chapter. Lynne’s story invites us to honor the dreams that never left us.

    Connect with Lynne at:
    Bluesky: https://bsky.app/profile/lynnet22.bsky.social
    LinkedIn: https://www.linkedin.com/in/lynne-thompson-76b53512/
    Instagram: https://www.instagram.com/letpms/

    Follow Raymond:
    LinkedIn: https://www.linkedin.com/in/raymondmlee/
    Instagram: https://www.instagram.com/raymondlee.co
    Tiktok: https://www.tiktok.com/@clockingoutpod
    X: http://twitter.com/hrentrepreneur
    Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos

    Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
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    48 mins
  • Simon Rinne: From Silent Struggle to Social Impact

    Simon Rinne: From Silent Struggle to Social Impact
    May 14 2025
    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.

    Connect with Simon at:
    Website: www.mindfulmen.com.au
    LinkedIn: https://www.linkedin.com/in/simon-rinne/
    Instagram: https://www.instagram.com/mindful.men.aus/
    Facebook: https://www.facebook.com/groups/2050441875316594/

    Follow Raymond:
    LinkedIn: https://www.linkedin.com/in/raymondmlee/
    Instagram: https://www.instagram.com/raymondlee.co
    Tiktok: https://www.tiktok.com/@clockingoutpod
    X: http://twitter.com/hrentrepreneur
    Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos


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    50 mins
  • Sarah Dale: Corporate Success to Women’s Empowerment Trailblazer

    Sarah Dale: Corporate Success to Women’s Empowerment Trailblazer
    Apr 30 2025
    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.

    Connect with Sarah at
    • LinkedIn: https://www.linkedin.com/company/project-1490
    • Instagram: @project_1490
    • Website: www.project1490.com
    Follow Raymond:

    • LinkedIn: https://www.linkedin.com/in/raymondmlee/
    • Instagram: https://www.instagram.com/raymondlee.co
    • Tiktok: https://www.tiktok.com/@clockingoutpod
    • X: http://twitter.com/hrentrepreneur
    • Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos

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    56 mins
  • Jeremy Schifeling: Kindergarten Teacher to Founder of The Job Insiders

    Jeremy Schifeling: Kindergarten Teacher to Founder of The Job Insiders
    Apr 16 2025
    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.

    Connect with Jeremy at:
    LinkedIn: https://www.linkedin.com/in/schifeling/
    Instagram: https://www.instagram.com/jobinsiders/
    X: https://twitter.com/2LinkedInGuys
    Website: https://www.thejobinsiders.com/
    LinkedIn and ChatGPT for Job-Seeking: https://www.amazon.com/Career-Coach-GPT-Complete-Interview/dp/B0C8QRMCFC

    Follow Raymond:
    LinkedIn: https://www.linkedin.com/in/raymondmlee/
    Instagram: https://www.instagram.com/raymondlee.co
    Tiktok: https://www.tiktok.com/@clockingoutpod
    X: http://twitter.com/hrentrepreneur
    Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos

    Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
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    44 mins
  • Christopher Chin: Acoustic Engineer to Founder & CEO of The Hidden Speaker

    Christopher Chin: Acoustic Engineer to Founder & CEO of The Hidden Speaker
    Apr 2 2025
    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.

    Connect with Chris at:
    LinkedIn: https://www.linkedin.com/in/cchiddenspeaker/
    YouTube: https://www.youtube.com/@TheHiddenSpeaker
    Website: https://thehiddenspeaker.com/

    Follow Raymond:
    LinkedIn: https://www.linkedin.com/in/raymondmlee/
    Instagram: https://www.instagram.com/raymondlee.co
    Tiktok: https://www.tiktok.com/@clockingoutpod
    X: http://twitter.com/hrentrepreneur
    Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos

    Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maUvA/viewform
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    49 mins