Clocking Out with Raymond Lee

Carla Stickler: Broadway Star to Software Engineer

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  [https://www.tiktok.com/@sticklercarla] * Instagram: https://www.instagram.com/sticklercarla/  [https://www.instagram.com/sticklercarla/] * LinkedIn: https://www.linkedin.com/in/carlastickler/ [https://www.linkedin.com/in/carlastickler/] * Personal website: www.carlastickler.com [https://www.carlastickler.com] * Company website: www.creators.spotify.com [https://www.creators.spotify.com] Follow Raymond:  * LinkedIn: Raymond Lee [https://www.linkedin.com/in/raymondmlee/] * Instagram: @raymondlee.co [https://www.instagram.com/raymondlee.co] * Tiktok: @clockingoutpod [https://www.tiktok.com/@clockingoutpod] * X: @hrentrepreneur [http://twitter.com/hrentrepreneur] * Youtube: @clockingoutwithraymondlee [https://www.youtube.com/@clockingoutwithraymondlee/videos] Click Here to become a guest on Clocking Out [https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU]

Dakota Barker: Physician Assistant to Entrepreneur and Real Estate Investor

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/ [https://www.instagram.com/dakota.barker.rei/] * Facebook: https://www.facebook.com/dakota.w.7/ [https://www.facebook.com/dakota.w.7/] * LinkedIn: https://www.linkedin.com/in/dakota-barker-a6760645/ [https://www.linkedin.com/in/dakota-barker-a6760645/] * Website: opiniconinvestments.com [http://opiniconinvestments.com] Follow Raymond:  * LinkedIn: Raymond Lee [https://www.linkedin.com/in/raymondmlee/] * Instagram: @raymondlee.co [https://www.instagram.com/raymondlee.co] * Tiktok: @clockingoutpod [https://www.tiktok.com/@clockingoutpod] * X: @hrentrepreneur [http://twitter.com/hrentrepreneur] * Youtube: @clockingoutwithraymondlee [https://www.youtube.com/@clockingoutwithraymondlee/videos] Click Here to become a guest on Clocking Out [https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU]

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

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 [https://www.whlalliance.org] / www.ItsPersonalStories.com [https://www.ItsPersonalStories.com] * LinkedIn: https://www.linkedin.com/in/rachel-a-humphrey [https://www.linkedin.com/in/rachel-a-humphrey] Follow Raymond:  * LinkedIn: Raymond Lee [https://www.linkedin.com/in/raymondmlee/] * Instagram: @raymondlee.co [https://www.instagram.com/raymondlee.co] * Tiktok: @clockingoutpod [https://www.tiktok.com/@clockingoutpod] * X: @hrentrepreneur [http://twitter.com/hrentrepreneur] * Youtube: @clockingoutwithraymondlee [https://www.youtube.com/@clockingoutwithraymondlee/videos] Click Here to become a guest on Clocking Out [https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU]

Haley Pollack: Educator to Nonprofit Founder for Families Facing Cancer

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/ [http://www.brightspotnetwork.org/] * Instagram: @brightspotnetwork [https://www.instagram.com/brightspotnetwork] * Facebook: @brightspotnetwork [https://www.facebook.com/BrightSpotNetwork/] * LinkedIn: Bright Spot Network [https://www.linkedin.com/company/bright-spot-network/] * LinkedIn: Haley Pollack [https://www.linkedin.com/in/haley-pollack-78355410a/] Follow Raymond:  * LinkedIn: Raymond Lee [https://www.linkedin.com/in/raymondmlee/] * Instagram: @raymondlee.co [https://www.instagram.com/raymondlee.co] * Tiktok: @clockingoutpod [https://www.tiktok.com/@clockingoutpod] * X: @hrentrepreneur [http://twitter.com/hrentrepreneur] * Youtube: @clockingoutwithraymondlee [https://www.youtube.com/@clockingoutwithraymondlee/videos] Click Here to become a guest on Clocking Out [https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU]

Lynne Thompson: Lawyer to Poet Laureate

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 [https://bsky.app/profile/lynnet22.bsky.social]  LinkedIn: https://www.linkedin.com/in/lynne-thompson-76b53512/ [https://www.linkedin.com/in/lynne-thompson-76b53512/]  Instagram: https://www.instagram.com/letpms/ [https://www.instagram.com/letpms/]  Follow Raymond: LinkedIn: https://www.linkedin.com/in/raymondmlee/ [https://www.linkedin.com/in/raymondmlee/] Instagram: https://www.instagram.com/raymondlee.co [https://www.instagram.com/raymondlee.co] Tiktok: https://www.tiktok.com/@clockingoutpod [https://www.tiktok.com/@clockingoutpod] X: http://twitter.com/hrentrepreneur [http://twitter.com/hrentrepreneur] Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos [https://www.youtube.com/@clockingoutwithraymondlee/videos] Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU [https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU]