Clocking Out with Raymond Lee

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 thir...

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 t...

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...

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 entrepreneur...

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 plannin...

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 fath...

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 cou...

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 in...

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 t...

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 raise...

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 passi...

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 mini...

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. S...

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 ve...

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 woul...

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 ap...

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 m...

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 trap...

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...

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 NY...

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: st...

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....

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 succes...

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. Bu...

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 wit...