Clocking Out with Raymond Lee

About Clocking Out with Raymond Lee

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.

Publisher

Raymond Lee

Category

business · business

Language

en

Explicit

No

First episode

13 May 2024

Latest episode

14 Oct 2026

Latest episodes

1 of 76 episodes have a transcript.

1. 

   14 Oct 2026

   Jan Hunter: HR Executive to Career Coach & Author

   In this episode of Clocking Out, we meet Jan Hunter, who grew up in New Albany, Indiana, watching Goldie Hawn movies and knowing she wouldn't stay in the Midwest. A marketing degree from Ball State led to a short stint in fashion merchandising, then furniture sales. At 27, a friend's call took her to San Francisco to open a consulting firm's office, and into human resources. There, Jan learned she was paid less than colleagues because she wasn't married with children. That disappointment pushed her to name her core values: leadership transparency, mutual respect, risk-taking, and giving back. Those values led her to a community healthcare system, where she spent a decade with a CEO who backed her and paid for her MBA at Kellogg. The clocking out moment came after he retired. The leadership team moved on, the values shifted toward the bottom line, and a move to a new health system in Arizona brought several new bosses in six months. When she heard who would be next, Jan said, "I'm not going to work for her," and left without a plan. She began writing résumés for an outplacement firm and, in her 50s, rebuilt her career as a career coach with her own practice. A handout for overwhelmed job seekers eventually grew into her book, Starting From Experience. This conversation is about repositioning as a way of life. It explores why values decide whether you thrive at work, why careers rarely move in a straight line, and why experienced professionals are never starting from scratch. Connect with Jan at: Website: (https://www.heroesunleashed.ca/)https://www.modernjobseekersguide.com/ (https://www.modernjobseekersguide.com/) LinkedIn: https://www.linkedin.com/in/janhunter2026/ (https://www.linkedin.com/in/janhunter2026/) Follow Raymond: LinkedIn: (https://www.linkedin.com/in/raymondmlee/)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 (https://www.instagram.com/raymondlee.co) Tiktok: (https://www.tiktok.com/@clockingoutpod)https://www.tiktok.com/@clockingoutpod (https://www.tiktok.com/@clockingoutpod) X: (http://twitter.com/hrentrepreneur)http://twitter.com/hrentrepreneur (http://twitter.com/hrentrepreneur) Youtube: (https://www.youtube.com/@clockingoutwithraymondlee/videos)https://www.youtube.com/@clockingoutwithraymondlee/videos (https://www.youtube.com/@clockingoutwithraymondlee/videos) Become a guest on Clocking Out: (https://bit.ly/46sqClq)https://bit.ly/46sqClq (https://bit.ly/46sqClq)

2. 

   23 Sept 2026

   Jessica Tracy: Sales Executive to Jungian Coach & Psychedelic Integrator

   In this episode of Clocking Out, we meet Jessica Tracy, who is a Jungian Transformational Coach who applies Jungian psychology within an empowering coaching framework. Raised outside Philadelphia as the oldest girl of five, she became a second mother early and grew up feeling everything intensely. In her twenties she decided that was a liability and turned the volume down on it, leaning instead toward her father, an accountant and insurance broker who genuinely loved his work. She followed him into the industry, starting in underwriting to learn the financial mechanics from the inside and networking on her lunch breaks until she could move into production. It worked. She became a top producer with well-known Philadelphia clients and multiple six figures in income. The cost arrived quietly and then all at once. Sales rewarded exactly the things she had never examined: perfectionism, the hunt for external validation, the sense of never being quite enough. The bigger her book got, the less free she felt. By her early thirties she was carrying anxiety, insomnia, panic attacks, and a medicine cabinet answering each one separately. She left for a Silicon Valley startup in DNA sequencing and spent about six years there, but a marriage ended, wine became a habit, and the company shifted toward a focus she no longer wanted to spend her days inside. The turning point came during a psychedelic journey in another country. She watched the walls she had built come down, felt what it was like to live without the shoulds and shouldn'ts, and asked herself when she had ever agreed to any of them. Then she watched them come back up and understood that the experience was not the work. The work was integration. She got off the medications, quit drinking, trained as a facilitator in Philadelphia and in Peru, and founded The Sage Collective to help widen legal access to these medicines. Today, Jessica practices as a certified Jungian coach and is certified through the International Jungian Coaching School and holds ACC accreditation from the International Coaching Federation. Jessica has also trained in Jungian Expressive Arts, Gestalt Therapy, Celtic Shamanism, Psychedelic Assisted Therapy, Trauma-Informed Kundalini Yoga, Sound Healing, and Won Buddhism. Jessica is a Doctoral Student of Acupuncture & Chinese Medicine. This conversation is about what happens when the self you built to survive becomes the thing you have to dismantle. It is about fear as a portal rather than a warning, curiosity as the antidote to catastrophic thinking, and the slow, unglamorous labor of integration that turns a moment of clarity into an actual life. Connect with Jessica at: Website: (https://www.heroesunleashed.ca/)https://www.jessicathejungian.coach/ LinkedIn: https://www.instagram.com/_jessicatrac (https://www.instagram.com/_jessicatracy_?utm_source=qr)y Instagram: https://www.linkedin.com/in/jessica-tracy-gbds-clcs/ (https://www.linkedin.com/in/jessica-tracy-gbds-clcs/) Follow Raymond: LinkedIn: (https://www.linkedin.com/in/raymondmlee/)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 (https://www.instagram.com/raymondlee.co) Tiktok: (https://www.tiktok.com/@clockingoutpod)https://www.tiktok.com/@clockingoutpod (https://www.tiktok.com/@clockingoutpod) X: (http://twitter.com/hrentrepreneur)http://twitter.com/hrentrepreneur (http://twitter.com/hrentrepreneur) Youtube: (https://www.youtube.com/@clockingoutwithraymondlee/videos)https://www.youtube.com/@clockingoutwithraymondlee/videos (https://www.youtube.com/@clockingoutwithraymondlee/videos) Become a guest on Clocking Out: (https://bit.ly/46sqClq)https://bit.ly/46sqClq (https://bit.ly/46sqClq)

3. 

   9 Sept 2026

   Episode 73: Matthew Devine: Corporate CEO to Transformation Coach and Co-Founder of Heroes Unleashed

   In this episode of Clocking Out, we meet Matt Devine, who learned discipline the Canadian way: on the ice, and later in the ring. Hockey gave way to kickboxing, kickboxing gave way to ambition, and ambition carried him up the corporate ladder, through project management and multimillion-dollar initiatives all the way to CEO. On paper, it worked. His body disagreed first. Carrying more than 100 extra pounds, he got a doctor's warning that he was at high risk of a heart attack or stroke. He took it seriously, lost the weight, and rebuilt his health from the ground up. Then his mind disagreed too. Fit, successful, and outwardly thriving, Matt sank into a depression so deep he gave it a name: the gray monster. What followed was a search for a way out, conducted at extreme scale. He ran 300 kilometers through the Canadian Rockies. He completed seven marathons in seven days. He cycled 12,500 kilometers across Canada in the Ride for Change, and later led the Heroes Unleashed Cross-Canada Challenge. Along the way he raised over $250,000 for children's charities, including The Rainbow Society of Alberta, You Can Ride 2, and Little Warriors. The money was real, and Matt is honest about the other thing those feats were feeding: his ego. Looking back, he can see he was chasing significance and recognition, hoping an achievement big enough might finally fix something internal. It never did. The clocking out moment came quietly, in an office. Returning to his corporate job after one of those runs, Matt had what he describes as a Matrix-like realization: he was standing in a world he no longer belonged to. He resigned, left corporate life entirely, and went looking for real answers, this time in books instead of miles, immersing himself in neuroscience, psychology, and philosophy to understand the human condition from the inside out. That study became Heroes Unleashed, the company he co-founded to help individuals and organizations break through limitations, blending neuroscience-backed coaching with hard-won experience, and encouraging people to share their struggles openly enough to create what he calls a groundswell of change. This conversation is about the difference between transformation and escape. About why identity built on values and growth outlasts identity built on labels and dopamine, why rock bottom can arrive twice, and what it takes to stop running toward recognition and start running toward yourself. Connect with Matt at: Website: (https://www.heroesunleashed.ca/)https://www.heroesunleashed.ca/ (https://www.heroesunleashed.ca/) LinkedIn: (https://www.linkedin.com/in/matthew-devine-9296552/)https://www.linkedin.com/in/matthew-devine-9296552/ (https://www.linkedin.com/in/matthew-devine-9296552/) Instagram: (https://www.instagram.com/heroesunleashed_ca/)https://www.instagram.com/heroesunleashed_ca/ (https://www.instagram.com/heroesunleashed_ca/) Follow Raymond: LinkedIn: (https://www.linkedin.com/in/raymondmlee/)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 (https://www.instagram.com/raymondlee.co) Tiktok: (https://www.tiktok.com/@clockingoutpod)https://www.tiktok.com/@clockingoutpod (https://www.tiktok.com/@clockingoutpod) X: (http://twitter.com/hrentrepreneur)http://twitter.com/hrentrepreneur (http://twitter.com/hrentrepreneur) Youtube: (https://www.youtube.com/@clockingoutwithraymondlee/videos)https://www.youtube.com/@clockingoutwithraymondlee/videos (https://www.youtube.com/@clockingoutwithraymondlee/videos) Become a guest on Clocking Out: (https://bit.ly/46sqClq)https://bit.ly/46sqClq (https://bit.ly/46sqClq)

Inside a recent episode

Cate Luzio: Banking Executive to Empowerment Leader & Founder of Luminary

Published 5 Nov 2025 · Transcript excerpt

[…] So when you were a young girl, what did you dream about being? So my mom found something pretty recently in the fourth grade. I wanted to be the president of the United States. I'm sure lots of kids think that way. I think it was because my parents gave me this sort of like the roadmap to say dream and be whatever you want. It's why I played sports again for most of my young life and then all the way up through high school and then into college. But I knew I wanted to have an impact. That's why I wanted to play sports and play on team sports. I wanted to become a leader. And I also knew that I wanted to just learn as much as I possibly could. […]

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