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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...
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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.
show less
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.
Episodes & Posts
Episodes
Posts
23 JUL 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: https://www.carlastickler.com
- Company website: https://www.creators.spotify.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
https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
9 JUL 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: http://opiniconinvestments.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
https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
25 JUN 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: https://www.whlalliance.org / https://www.ItsPersonalStories.com
- LinkedIn: https://www.linkedin.com/in/rachel-a-humphrey
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
https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
11 JUN 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: https://www.instagram.com/brightspotnetwork
- Facebook: https://www.facebook.com/BrightSpotNetwork/
- LinkedIn: https://www.linkedin.com/company/bright-spot-network/
- LinkedIn: https://www.linkedin.com/in/haley-pollack-78355410a/
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
https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
28 MAY 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
14 MAY 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: http://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.coTiktok:
https://www.tiktok.com/@clockingoutpodX:
http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videos
Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maUvA/viewform
30 APR 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: http://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
https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maU
16 APR 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.coTiktok:
https://www.tiktok.com/@clockingoutpodX:
http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videos
Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maUvA/viewform
2 APR 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/@TheHiddenSpeakerWebsite:https://thehiddenspeaker.com/
Follow Raymond:
LinkedIn:
https://www.linkedin.com/in/raymondmlee/Instagram:
https://www.instagram.com/raymondlee.coTiktok:
https://www.tiktok.com/@clockingoutpodX:
http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videos
Become a guest on Clocking Out:
https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maUvA/viewform
19 MAR 2025 · In this episode of Clocking Out, we dive into the inspiring journey of Amber Williams, a Brooklyn native with deep Caribbean roots. Growing up in a vibrant immigrant community, education and ambition were ingrained in her from a young age. Though she initially aspired to be a lawyer, a pivotal summer program introduced her to the world of television, setting her on a path toward media and storytelling.
Amber studied Film & Television at Hobart College, gained hands-on experience through internships, and landed a job in media advertising post-graduation. However, she craved creativity beyond spreadsheets, leading her to a career transition into production. By leveraging LinkedIn and networking at film sets, she transitioned into freelancing on major productions like Billions and Clifford the Big Red Dog. Yet, she knew there was still something missing. She wanted to be the person that creates the stories. From then on, that became her long term goal.
To make those dreams a reality, she applied to NBCUniversal’s East Coast Page Program and was accepted. Through that program, she landed a role at Peacock, where she helped launch key marketing campaigns. Around the same time, she earned her MFA in Screenwriting at Emerson College, further solidifying her path as a storyteller. After three years, Peacock let her go, but that hasn’t stopped her from pursuing her ultimate goal: writing and creating authentic stories for television.
Amber’s journey is a testament to resilience, strategic career transitions, and the power of pursuing your passion. Tune in for her remarkable story of navigating the entertainment industry on her own terms.
Connect with Amber at:
LinkedIn: https://www.linkedin.com/in/amber-williams-mfa-0632b99a/
Follow Raymond:
LinkedIn:
https://www.linkedin.com/in/raymondmlee/Instagram:
https://www.instagram.com/raymondlee.coTiktok:
https://www.tiktok.com/@clockingoutpodX:
http://twitter.com/hrentrepreneurYoutube: https://www.youtube.com/@clockingoutwithraymondlee/videos
Become a guest on Clocking Out: https://docs.google.com/forms/d/e/1FAIpQLSeSTQmww_Gvld1zfLzTmS16PDfZvltFna7Gh6iSYehL-maUvA/viewform
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...
show more
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.
show less
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.
Information
| Author | Peak Digital Media |
| Organization | Jeff Nadu |
| Categories | Careers , Entrepreneurship , Management |
| Website | careerminds.com |
| hello@andrewgormley.com |
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