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.jessicathejungian.coach/
• LinkedIn: https://www.instagram.com/_jessicatracy
• Instagram: https://www.linkedin.com/in/jessica-tracy-gbds-clcs/

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• LinkedIn: https://www.linkedin.com/in/raymondmlee/
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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/
• LinkedIn: https://www.linkedin.com/in/matthew-devine-9296552/
• Instagram: https://www.instagram.com/heroesunleashed_ca/

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://bit.ly/46sqClq

Chrisa Zindros wanted to be an archaeologist. She never became one, and in a sense she never stopped being one either. She grew up in Waterbury, Connecticut, the daughter of immigrant parents who built their own version of the American dream through work they owned outright, including a father who ran an ice cream truck for decades and taught her that any position of influence carries an obligation to help someone else up. When a Barnes & Noble opened near her in middle school, she went there to read philosophy while her friends went to parties. She never quite found her crew. What she found instead was a lasting fascination with what lies beneath the surface of people and the artifacts they leave behind.

Archaeology gave way to business. Through college she held two jobs at once: admin work at an insurance company, and a keyholder shift at the mall, where she was the one working late enough to receive the shipments and lay out the floor sets. A relationship with the company's visual merchandising lead turned into trust, then into a job offer opening sixty stores. She picked the mall. From there came the circuit: nearly every brand you can name, remodels, rebrands, websites built for the first time, entire functions collapsing and being reinvented underneath her. Then came the morning she now describes to clients walking down Seventh Avenue toward a corner office, twelve-dollar coffee in hand, inexplicably irritated. She had everything she'd wanted. Something was off anyway.

There was no breaking point. When her company was bought and sold she took the package, assuming she'd land as a CMO somewhere. Walking out of the building that day, the CEO of the coaching firm she'd been moonlighting with for six years called. The role she took for a few months lasted ten years, at a fraction of her old salary, and led eventually to her own practice. The pay cut, she says, was never the hard part. The identity work was.

This conversation is about the quieter kind of reinvention, the kind that doesn't require a crisis. About restlessness as information rather than failure, and about what it takes to become someone new on purpose.

Connect with Chrisa at:

• Website: https://www.czbconsulting.com/
• LinkedIn: linkedin.com/in/chrisa-zindros-boyce

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://bit.ly/46sqClq

Jamie Jacobs spent two decades climbing the corporate HR ladder before walking away from it, and the thing that made the walk possible was courage she'd been quietly building since childhood. She grew up in the San Diego area with parents who stayed married and never finished college, and a father known around town as "Mr. Mercedes," a general sales manager at a Mercedes-Benz dealership for 25 years who could work any room. Her drive showed up early: her parents were called into her kindergarten class by a teacher worried they were pushing her too hard. They weren't.

She fell into HR at Four Seasons Hotels and Resorts, starting in front office roles before a position opened on the people side. Five years later she was at Ingersoll Rand, hired as a generalist and covering her boss's role two weeks in when she went on leave and never came back. A pattern emerged: she was the person called in to build something new or fix something broken, never to maintain it. Somewhere along the way she ran an environmental training division, got certified as an underground storage tank operator, and found herself on a plane to Houston to teach Shell Oil about California law, a lesson less about expertise than about walking into the room anyway.

The clocking out moment came at a fast-growing company where she was the first HR hire, scaling from roughly 150 employees to 675 in twelve months. When regulatory changes reversed the growth, she told the chairman of the board she didn't think they needed her role. She took three weeks alone to think, wrote a book on culture, started consulting, and in 2019 co-founded Gig Talent, buying out her co-founder at the end of 2024 and rebuilding it around a single question: what is this actually meant to become? She did much of it while raising a daughter as a single mom.

This conversation is about the difference between success that looks right and work that feels aligned. About holding a goal lightly enough that it can grow past what you imagined, about fear as a signal rather than a stop sign, and about what happens when you stop asking what the system rewards and start asking what you're actually here to build.

Connect with Jamie at:

• Website: https://gigtalentagency.com
• LinkedIn: https://www.linkedin.com/company/gig-talent/ and https://www.linkedin.com/in/jlatianojacobs
• Instagram: https://www.instagram.com/jamielatianojacobs/ and https://www.instagram.com/gigtalentagency/

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://bit.ly/46sqClq

Permission. It's the word that anchors this conversation, and few people have claimed it as fully as Bianca Alba. Born in Cochabamba, Bolivia, and brought to the US at six months old, she grew up in the DMV as the oldest of four girls, watching her parents work multiple jobs to keep food on the table. She became the first in her family to earn a college degree on a full scholarship after failed courses in microbiology and organic chemistry redirected her from the medical route toward public health.

That path led to the CDC, an internship during the Ebola outbreak, and a competitive fellowship that took her to Santa Fe, New Mexico, on a $20,000 salary. Alone in a new city, she learned to take herself on dates, hike, and travel solo, quietly laying the foundation for everything that came next. A deployment during the Zika response brought her to Puerto Rico, where she's lived for nearly a decade.

Then Covid hit. Deployed relentlessly to the front lines, living out of hotels and building test kits at night, Bianca reached a breaking point: she couldn't promote mental health while struggling with her own. She started a podcast on the side:This Latina Travels, moved to a remote federal role, and kept building an emergency fund just in case. When that position was eliminated in a reduction in force last year, her preparation met its moment. She chose herself, going all in on the platform she'd built, which now spans a blog, speaking engagements, and service-focused college programs in Puerto Rico that have put over $70,000 into local hands.

This conversation is about giving yourself permission,to start before you're ready, to grieve a career even as you outgrow it, and to trust that preparation, community, and purpose can turn an ending into a beginning.

Connect with Bianca at:

• Website: https://www.thislatinatravels.com/
• Instagram: https://www.instagram.com/thislatinatravels/
• Linkedin: https://www.linkedin.com/in/biancaalba/
• TikTok: https://www.tiktok.com/@thislatinatravels
• FB Group: https://www.facebook.com/groups/thislatinatravels
• Youtube: https://www.youtube.com/@ThisLatinaTravels

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• 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://bit.ly/46sqClq

Are you alive — not just breathing, but truly, deeply alive?" It's the question that anchors Eloise Skinner's work, and few people have chased it as far as she has. A psychotherapist and author specializing in existentialism, Eloise has lived more versions of herself than most people let themselves imagine; corporate lawyer, monastic, fitness instructor, writer, founder.

Raised in London by two musicians, she grew up immersed in music, playing piano above all. But at sixteen, in a quiet act of rebellion, she turned away from the family art and chose law, partly because it was a clean slate. She wanted a firm foundation under her feet, studied at Cambridge, and became a corporate tax lawyer at a US firm's London office. She loved it. Yet alongside the work, something else grew: she began writing and teaching, drawn less to the contracts than to helping others find their footing.

At twenty-six, still practicing law, she joined a one-year monastic community run out of Lambeth Palace, structured around a "rule of life" of poverty and silence. She kept her job and lived it in parallel, spending her annual leave on silent retreats. What the silence revealed didn't break her; it built her, forcing a confrontation with herself that modern life is designed to help us avoid. Then, in 2021, amid the Great Resignation, she left law — not out of bitterness, but from a conviction that every day on the legal path was another day too long away from a path she couldn't yet name.

Since then she's trained as an existential psychotherapist, founded The Purpose Workshop, and written The Purpose Handbook and But Are You Alive? This conversation is about living from a foundation of self-knowledge rather than a fixed plan about what stillness reveals, refusing to abandon yourself through a hard transition, and the courage to follow an inner pull you can't fully articulate, trusting that reinvention is a slow, ongoing act of becoming.

Connect with Eloise at:

Website: https://www.eloiseskinner.com

Instagram: https://www.instagram.com/eloiseallexia

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://bit.ly/46sqClq

In this episode of Clocking Out, we meet Hung Lee, a man whose path bears no resemblance to a plan, and who would be the first to tell you not to follow it.

Hung was born in the Netherlands to Hong Kong Chinese parents, the kind of family that ran a restaurant and finished school at fourteen, leaving him and his brother to figure out the rest. By three he was in Germany, by five in England, a third-culture kid who learned early that belonging was never guaranteed and otherness arrived young. As a boy he dreamed of becoming a zoologist, of living the David Attenborough life outside the office. Instead, academic realities pulled him toward the study of humans, and he majored in anthropology, only to grow disillusioned with the discipline and walk away from it entirely. He never worked a day in the field.

What followed was not a clean arc but a series of hard resets. Rejection after rejection in his job search. A serious car accident that left him convalescing for eighteen months, broken and isolated, with nothing to do but think. But it was in that forced stillness that the clarity came: he couldn't wait for a life to arrive, he had to go make one. He moved to London with three days' rent in his pocket and a single rule, that he would have a job by the end of it. He talked his way into recruiting and stayed for twenty-five years.

The defining moment wasn't loud. Hungover one morning, mid-screening call, he realized he had become so good at the job he could do it half-asleep, and felt a flash of pride, then a wave of shame. He had disrespected the candidate, the profession, and himself. He resigned that same day, with no plan and no fallback. What came after was a string of failed businesses, an 18-month rhythm of trying, failing, learning, and trying again, built on a philosophy he holds to this day: never run a plan B, just build another plan A. Out of the wreckage of a failing startup came Brainfood, a newsletter born from his own frustration at wading through internet noise to find anything worth reading. It quietly became a fixture of the recruitment industry.

This conversation is about living without a map. It's about what stillness can reveal when everything else has been stripped away, about treating rejection as information rather than a verdict, and about the strange freedom of having no fallback. Most of all, it's about the courage to listen when something inside tells you it's over, even when leaving makes no economic sense at all, and to keep putting energy into the world until something worth keeping emerges.

Connect with Hung Lee at:

LinkedIn: https://www.linkedin.com/in/hunglee

Newsletter: https://recruitingbrainfood.substack.com/

Website: https://www.recruitingbrainfood.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://bit.ly/46sqClq

In this episode of Clocking Out, we meet Terentia Browne, a woman who spent two decades mastering one of the most demanding technical disciplines in the world, before realizing that the most meaningful work she'd ever done had nothing to do with chemistry at all.

Terentia grew up in Durban, South Africa, during the final years of apartheid, the first grandchild on either side of her family to go to university. Her mother, a single parent who never got the opportunity herself, made the message unmistakable: education was the only thing that could break the cycle. So Terentia chose chemical engineering, thrived, and went on to build an ice cream factory alongside international teams, lead engineering at Johnson & Johnson, and earn the Healthcare Businesswoman's Association Rising Star Award. On the surface, a career in full ascent.

But beneath the promotions, something else had always been running. She was coaching people. Not formally, not for money, just because it was where she came alive. The pivot didn't arrive as a crisis. It arrived in a Dubai hotel room in February 2019, when a single question stopped her cold: what is the significant impact you want to make on this world? She resigned from J&J, flew home on the first of March 2020, and landed in a global lockdown with no clients and no office. She sat in her apartment and built a leadership program from scratch. The first sale was three hundred dollars. By year's end, she had sold the same program to Airbus OneWeb Satellites for sixty thousand.

Impel Talent now works with Fortune 500 companies across life sciences, space and tech, and renewable energy, developing the technically brilliant people nobody ever taught to lead.

This conversation is about a calling that doesn't announce itself loudly, but builds slowly and unmistakably over two decades. It's about telling your mother you're walking away from the degree she sacrificed everything for. It's about flying two planes at once, and knowing when to let go of the one you're on.

Connect with Terentia at:

LinkedIn: https://www.linkedin.com/in/terentia-browne/

TikTok: https://www.tiktok.com/@terentiabrowne

Instagram: https://www.instagram.com/terentia_browne

Website: https://www.impeltalent.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://bit.ly/46sqClq

In this episode of Clocking Out, we meet Paul Tasner, a man who spent four decades doing exactly what he was supposed to do, before getting fired at 64 and discovering that the most important chapter of his life hadn't started yet.

Paul grew up in Newark, the son of a postal worker who carried mail on his back and complained about it quietly for thirty years. Without anyone saying it out loud, the message was clear: find something stable, stay there, keep your head down. And Paul followed that script with remarkable dedication. He chose industrial engineering because it was the least intense option. He pursued a PhD in mathematics and walked away five years in because he couldn't see himself living that life. He took a job with his favorite uncle and left within two years because the man he'd idolized was impossible to work for. Then he landed at Clorox, where he stayed for fifteen years. The first five full of ambition, the middle five a plateau, and the last five quietly suffocating under a boss who wanted him gone.

At 64, fired and clear-eyed about his odds of being hired again, Paul didn't retire. He needed income, so he started consulting. But consulting felt like doing the same work for other people's companies, and he'd done enough of that. Over two years, an idea took shape: sustainable packaging made from waste pulp, a compostable replacement for the toxic plastic blister packs lining store shelves everywhere. He launched PulpWorks in 2011, at 66, into a market that wasn't ready for it. And he built it anyway, waiting for the world to catch up.

Fifteen years later, with nearly 3 million views on a TED Talk he thought had the worst title he'd ever heard, Paul is still at it. Still checking his email every morning with something close to excitement. Still convinced that doing your own thing feels fundamentally different when it belongs to you.

This conversation is about what it actually takes to start over late. Not with great courage or a grand plan, but with a financial need, a few good relationships, and the slow realization that the safe path was always a detour. It's about staying current, the unexpected gift of being let go, and what a Netherlands life insurance company told Paul after his TED Talk: that finding a passion in your senior years might be the single most powerful thing you can do for how long, and how well, you live.

Connect with Paul at:

LinkedIn: https://www.linkedin.com/company/2336787/admin/dashboard/

Facebook: https://www.facebook.com/search/top?q=pulpworks%2C%20inc

Website: https://pulpworksinc.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://bit.ly/46sqClq

In this episode of Clocking Out, we meet Lily Woi, a self-described shy, quiet, reserved, and awkward introvert who walked away from a prestigious consulting career at Deloitte three months before a promotion, with no business name, no clients, and no plan. What she had was the clarity that staying any longer would cost her something she couldn't get back.

Born and raised in a quietly entrepreneurial family, Lily grew up watching her parents model financial freedom while steering her toward the safer road: accounting, a chartered qualification, a recession-proof career. She followed the plan exactly. She joined Deloitte's graduate program, earned promotion after promotion, and was well on her way to manager. On paper, everything looked right. Underneath, the gap between what she was being rewarded for and what she actually cared about was quietly widening with every passing month.

The pivot came not from a crisis but from a moment of plain, unignorable clarity. One ordinary morning, she texted her manager and resigned. No backup. No business plan. Not even a name for what came next. She didn't tell her parents until after it was done, because she knew what they'd say, and she wasn't sure she was strong enough to hear it out loud and still go through with it.

What followed was the messy, exhilarating work of rebuilding from scratch. First clients through referrals. A speaking stage that went so badly she left the conference and had a quiet breakdown at a friend's place. And still she kept going. She wrote a book, Quiet Confidence, and discovered that the same introversion she'd spent years managing around was, in fact, her sharpest professional tool. The shy girl who used to hide in bathroom stalls to recover from the overstimulation of corporate networking is now a sought-after coach, speaker, and author, not because she became someone else, but because she finally stopped pretending to.

This conversation is about the quiet courage it takes to leave when nothing is visibly wrong, the identity loss no one warns you about when you trade a title for a blank page, and what it really means to build confidence, not as a destination you arrive at, but as evidence you accumulate one hard thing at a time.

Connect with Lily at:

LinkedIn: https://www.linkedin.com/in/lilywoi/

Website: https://lilywoi.com/

Book: https://bookboon.com/en/quiet-confidence-ebook

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://bit.ly/46sqClq