Clocking Out with Raymond Lee

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...

In this episode of Clocking Out, we meet John Fareed, a man who has lived more lives than most people dare to imagine and turned each one into raw material for the next.

Growing up in rural Georgia and summers spent in Egypt, John learned early that identity is fluid and the world contains far more possibility than the circumstances you're born into.

What followed was a life shaped less by planning than by honest reckoning. Six years in the U.S. Marines, kept only because of a private negotiation with his Egyptian grandfather, where...

In this episode of Clocking Out, we meet Natalie Nixon, a creativity strategist, global keynote speaker, author, and CEO of Figure 8 Thinking. A woman who built a career not by following a map, but by trusting the thread that connected every unexpected turn along the way.

Growing up in Mount Airy, Philadelphia, Natalie moved through three very different schools, a mother who wove and sewed, a father who worked two jobs, and a childhood spent figuring things out on the stoop. That's where her curiosity was born.

When it came time to declare her college...

In this episode of Clocking Out, we meet Henry Wong, a brand strategist, author, and former global advertising executive who spent years helping organizations shape powerful narratives, only to realize the most important story he needed to shape was his own.

Growing up in Toronto, Henry spent much of his childhood working in his parents’ Chinese restaurant. By age 11, he had moved to the front counter, where interacting with customers from all walks of life taught him how to read people, build connections, and understand the power of story — lessons that would quietly shape his future care...

In this episode of Clocking Out, we meet Scott Ramey, a former Division I athlete and Fortune 100 executive who spent decades looking steady on the outside while quietly unraveling on the inside.

Raised in a small Indiana town in a home that welcomed more than 35 foster children, Scott learned early to compete, lead, and fix what was broken. Basketball became his identity, until a career-ending injury at 19 triggered his first panic attack and the start of decades of silent anxiety.

He carried that anxiety into a 30-year career in financial services, rising from intern to...

In this episode of Clocking Out, we meet Rick Bleiweiss, a man who has reinvented himself not once, but five times.

Rick’s career reads like a masterclass in creative evolution: rock musician, record producer, senior music executive, publishing leader, and at age 77, debut novelist. Today, he has added podcaster and award-winning author to the list. What makes Rick’s story remarkable isn’t just the titles. It’s the mindset behind them.

Raised in New York by parents who encouraged him to follow his passion, Rick fell in love with music at an early...

In this episode of Clocking Out, we sit down with Sabrina DeVito, a visionary strategist, builder, and longtime leader whose career proves that success doesn’t always mean alignment.

Sabrina spent decades in financial services, moving across roles, cities, and companies not out of obligation, but out of a deep desire for growth, creativity, and challenge. A first-generation college graduate raised in Lancaster, Pennsylvania, she grew up surrounded by examples of reinvention. Her mother built a real estate business and later made a bold late-career pivot into public office, while her father’s steady accounting career offe...

In this episode of Clocking Out, we meet Christy Linn, founder of Second Nature Home Organizing, whose career journey proves that some of the biggest pivots happen quietly, one small decision at a time.

Christy grew up just outside Baltimore in a close-knit childhood shaped by sports, Girl Scouts, and weekends with family. Her mom stayed home when she was young and later rediscovered her own passion as a school photographer. Her dad was an accountant, and the path he modeled was simple and practical: go to school, study the thing, then go do the job. That...

In this episode of Clocking Out, Raymond sits down with Bronson Hill, host of the Mailbox Money podcast and founder and CEO of Bronson Equity, to unpack what it really means to “design your freedom.”

Bronson’s path is anything but typical. Raised middle-class by a single parent, he learned early that if he wanted something, he had to build a way to earn it. That mindset carried him from youth ministry to a high-performing career in medical sales, where the pay was great, but the treadmill never stopped. Even watching high earners burn out around him made o...

As the year winds down and the holidays settle in, lets take a moment to pause—not to interview a guest, but to reflect.

After more than 50 deeply honest conversations on Clocking Out, this episode looks back at the last two years of stories about burnout, identity, misalignment, and the quiet signals many of us ignore for far too long. These weren’t just career pivots. They were slow erosions. Subtle burnout. Success on paper paired with exhaustion, anxiety, and a nagging sense that something wasn’t right.

Raymond reflec...

In this episode of Clocking Out, we meet Lia James, founder of &Human and creator of The Traveling Table, an experience design and storytelling studio focused on one big idea: conversations are infrastructure.

Lia’s career has never followed a straight line. After graduating into a recession, she landed her first real role at a community college by A/B testing her own résumé, submitting one version with her full name, Aurelia, and one with her nickname, Lia. That bold move led to a tough, brilliant mentor who not only hired her but helped her launch her...

In this episode of Clocking Out, we meet Anna McDougall — an award-winning engineering leader, author, and former opera singer whose career is anything but ordinary.

Born in Sydney and raised by an academic mother and a creative father, Anna was a curious child who loved writing, performing, and—at just eight years old—taught herself to code from a book on HTML. That early spark of curiosity would guide her through a remarkable life of reinvention: from corporate boardrooms to opera stages, and eventually, to the world of tech.

Her path was anything but linear...

In this episode of Clocking Out, we meet Cate Luzio, a former banking executive who turned two decades in global finance into a mission to empower and connect women through community.

Cate’s path began in Ohio, shaped by parents who embodied service: her mother a teacher, her father an FBI agent. As a child, she dreamed of following in his footsteps until one honest answer on an FBI internship application changed her course forever. That detour led her to Washington D.C., a nonprofit, and eventually to the world of banking, where she spent twenty years ri...

In this episode of Clocking Out, we meet Benedict Beaumont, a former IT professional and high school teacher who traded the classroom for a deeper kind of teaching: helping others heal through breathwork.

Benedict grew up in Brighton, a seaside city on England’s south coast known for its creativity and openness. From an early age, he was curious about life’s big questions — why we’re here, what makes us whole — but found few answers in conventional paths. After university, he followed expectation rather than instinct, landing a well-paid IT job in London. From the outside, it looked...

In this episode of Clocking Out, we dive into the inspiring journey of Robert Markowitz. Once a criminal lawyer, now a children’s musician, author, and performer whose story proves it’s never too late to choose joy.

Robert spent years chasing a traditional definition of success: Duke Law, criminal trials, and the prestige of a respected profession. But behind the courtroom victories, he felt trapped, weighed down by family expectations, office walls, and a career that didn’t fit his temperament. After just a few years in practice, he walked away, leaving behind a decade of prepar...

What happens when a former Marine officer and combat veteran trades his uniform for emotional honesty?

In this episode of Clocking Out, we sit down with Christopher Veal, who is on a mission to challenge what leadership and masculinity really look like—starting with himself.

After a chance encounter opened a new door, Christopher left college to pursue a career with the Marine Corps, setting him on a path that would shape his future. He served for nearly a decade, deploying to Iraq, leading troops, and achieving his goal of becoming a company commander. Bu...

In this episode of Clocking Out, we meet Vanessa K. De Luca, a journalist and media executive whose career has been defined by bold pivots, perseverance, and a commitment to amplifying Black women’s voices.

Vanessa didn’t start in publishing. She spent seven years in retail management before answering the pull she’d always felt toward storytelling. Trading stability for possibility, she took an NYU summer course, built her writing chops, expanded her network, and eventually landed an entry-level publishing role at Glamour. From there, she climbed the ranks; first at Life magazine, then Essence, where...

In this episode of Clocking Out, we meet Ling Yah Wong — once a litigator at Malaysia’s top law firm, now the voice behind the So This Is My Why podcast and a sought-after LinkedIn strategist. For nearly a decade, Ling Yah followed the traditional path of prestige and stability, even as she quietly questioned whether law was truly for her.

When she discovered podcasts, she found a new passion: storytelling. In 2020, she made a deal with herself — after climbing Everest Base Camp that March, she would finally launch her own podcast. What started as a side p...

In this episode of Clocking Out, we meet Julia Skupchenko. An award-winning entrepreneur, sustainability leader, and co-founder of the global think tank AlterContacts. Recognized by the United Nations and the European Parliament for her work accelerating progress toward the Sustainable Development Goals, Julia designs bold social-impact initiatives and teaches the next generation of changemakers. But her journey to this point began far from the global stage. She grew up in the Arctic, raised by a family of academics and learning responsibility from an early age.

From her first dreams of becoming a detective to presenting at...

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 mo...

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...

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 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...

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 writin...

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 sil...

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...

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 lear...

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 financ...

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...

In this episode of Clocking Out, we explore the incredible career journey of Ronald H. Braver, a financial crime investigator who transitioned from government service to private sector success.

Ron grew up in the suburbs of Chicago and was fascinated by James Bond and dreamed of pursuing a career in investigative work. He followed that passion, earning a Bachelor’s Degree in Accounting and later a Master’s in Taxation from DePaul University.

After college, Ron embarked on a remarkable 25-year career as a Special Agent and Supervisory Special Agent with the IRS Criminal Investigation Divi...

In this episode of Clocking Out, we sit down with Casey Brown, a bold entrepreneur and founder of Boost Pricing, who walked away from the corporate world to help businesses sell at higher prices—and to give sales teams the confidence they need to succeed.

Growing up in a hardworking blue-collar town in Ohio, Casey was shaped by the values of persistence and education, instilled by her parents. With a dual degree in chemical engineering and Spanish, plus an MBA from Case Western Reserve University, she built a thriving corporate career before making the leap into entrepreneurship. No...

In this episode of Clocking Out, Raymond welcomes Ginny Palmieri, a powerhouse leader who has mastered the intersection of HR, business strategy, and entrepreneurship. With a distinguished career spanning executive roles at Independence Blue Cross, Commerce Bancorp, and Bank of America, Ginny has built a reputation for driving transformation and inspiring growth. Now, as the CEO and Co-Founder of MyNextory, she’s on a mission to revolutionize career development through innovative, scalable solutions.

Ginny shares her insights on navigating change, embracing opportunity, and building a career aligned with personal values. Recognized as one of Main Line Today’s 20...

In this episode of Clocking Out, Raymond is joined by Dr. Fiona Jamison, a seasoned leader in people analytics and organizational research. Fiona’s remarkable career spans over 25 years and includes exiting and selling her company Spring International.

Fiona was born in the UK and moved to the US after college. With a Ph.D. in Human Resource Management from the University of Bristol, she’s a true expert in transforming complex data into actionable insights that drive business performance.

Fiona’s story is anything but conventional. She started at Spring International as a researcher with n...

In this episode of Clocking Out, Raymond is joined by Aurelie Foucart, the founder of Affirmed Leadership, a company dedicated to executive coaching and leadership training. Born and raised in Paris, France, Aurelie's early life was filled with a love for writing and playing the piano, but she ultimately followed her mother’s advice to pursue a more traditional path and earned a law degree.

Aurelie’s career took a fascinating turn after spending over a decade in management consulting, working in various roles at major international organizations. Over time, her passion for leadership development led her to s...

In this episode of Clocking Out, Alice Rush, a certified Master Career Counselor, shares her inspiring journey from starting her career as a sales leader to becoming a leading expert in career coaching and counseling. Born in Palo Alto, CA, her father spent 30 years at IBM as an engineer and her mother was a concert pianist and entrepreneur. Alice learned early on the importance of both stability and the pursuit of passion. After working in a sales job at NCR with a grueling daily commute, Alice realized she was not living the life she wanted, so she took a...

In this inspiring episode of Clocking Out, Kate Lingoni, shares her amazing story of being a researcher, entrepreneur, actor, mom, and business owner whose career journey has been anything but conventional. Born in Metairie, Louisiana, Kate went to Archbishop Chapelle High School and later graduated from Louisiana State University. Kate’s early aspirations were rooted in a desire to serve others, initially wanting to become a police officer, but she later shifted her focus to Forensics and ultimately found her calling in Biology, specializing in Oceanography.

Kate’s career took a pivotal turn when she was assigned to t...

In this episode, we hear the inspiring journey of Wes Ehnert Carfi, a former sales leader who made a bold leap from a successful career in advertising sales to embracing his true passions for coaching, music, and comedy. Born and raised in New Jersey to a large Italian family with over 40 cousins, Wes was an entertainer at heart from an early age—whether it was through music, comedy, or sports. He was inspired by his mom’s unique ability to make people laugh.

After decades of sales experience, Wes began to recognize his true calling as a coac...

In this episode of Clocking Out, Raymond sits down with Sairan Aqrawi, who shares her inspiring journey of transformation and self-discovery. Born in Iraq, Sairan left her home country in 1997 to pursue the American Dream. Influenced by her father, she chose a career in Civil Engineering, dedicating herself to the field and excelling in systems integration and project delivery.

But despite her success, Sairan found herself drawn to a new path—one that would allow her to tap into her true passion for empowering others. After years of working as an engineer, Sairan made the bold decision to...

In Episode 27 of Clocking Out, Raymond Lee sits down with Kayla McDaniel, a tech leader whose career journey has taken unexpected—and ultimately rewarding—turns. Originally set on becoming a nurse, Kayla pivoted to pursue degrees in computer science and international business. Her path wasn’t without challenges; a trio of layoffs pushed her to reconsider her career trajectory, eventually leading her into software client success, where she has thrived by applying her technical expertise and leadership skills.

With over a decade in global operations and data analytics, Kayla has become an experienced, results-driven leader, specializing in operat...

In this episode of Clocking Out, host Raymond Lee sits down with Tammi Marks, a seasoned healthcare professional who recently took a bold step toward fulfilling her lifelong passion. After a 30-year career spanning clinical roles and healthcare IT, Tammi found herself at a crossroads when she was unexpectedly laid off from her position at Common Spirits. Rather than letting this setback define her, she embraced it as an opportunity to "clock out" of her former role and dive into something she had always dreamed of: aesthetics.

In this episode, Tammi shares her candid experience with the...