The Unstuck Career

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Chapter 3: The Rationalizer

The conversation focused on the voice that sounds reasonable while quietly keeping you stuck. In Chapter 3, “The Rationalizer,” the central belief is “I’m just being realistic,” but the stories created by the rationalizer may be believable without being true.

A cliff jump into a lake becomes a lesson in how excuses can grow larger than the fear behind them 02:38. A delayed response to a networking opportunity reveals how self-doubt can disguise itself as practicality, even when the opportunity is exactly what you want 06:44. The discussion explores t...

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This week, I sit down with Lori, who has spent more than two decades in SBA lending and has reached a point where the Sunday evening dread, 10 to 14-hour workdays, and constant exhaustion have made staying stuck impossible. She’s ready to trade the W-2 and alarm clock for work that gives her room to serve people, pursue her faith, and be present with her four grandchildren.

We talk about reinventing skills, exploring AI and remote work, writing a book about her faith journey, and turning her strengths in budgeting, organization, co...

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Ch2: Fear Makes Predictions, Not Promises

Fear can feel like evidence, especially when the future is uncertain. This episode explores how fear, doubt, and anxiety can distort decisions, from asking for the life you want to trusting your instincts in the cockpit.

One concept discussed was the difference between feelings and reliable information. In flight training, instruments reveal what the body can’t. The same principle applies to career and life decisions: fear may predict rejection, failure, or danger, but it can’t guarantee any of those outcomes. At 10:29, the...

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This week, I talk with Aryana about leaving a full-time job that promised stability but delivered 166-hour workweeks, burnout, and benefits she couldn’t afford. After grad school, she returned to freelancing in costume and contour design, creating everything from wedding gowns and corsets to dancewear, sportswear, and wearable technology.

We unpack what it takes to build a business around the life you actually want, including the discipline to schedule breaks, the courage to say no to poor-fit clients, and the value of having someone check in to make sure you’re “...

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 This week, I explore the limits we accept without ever testing them. A dentist’s recurring problem, a numbed mouth, and a surprising product that may reverse Novocaine’s effects reveal how often we simply put up with frustrations because we don’t know an alternative exists.

I’ll take you from a moving truck on the highways of Wyoming to Harry Houdini’s supposedly locked jail cell, which turned out to be unlocked all along. What if some of the barriers holding you back are assumptions rather than facts? And what could...

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This week, I sit down with Susan, who found me on TikTok and bravely reached out in the midst of her own messy "what’s next" journey. After a pivotal four-year reboot—relocating solo, embracing huge physical changes, and diving deep into self-discovery—Susan is now staring down her last big pivot: finding work that actually feels good. Together, we get real about the exhausting loop of taking jobs out of necessity rather than choice, and the sneaky fears that keep us stuck—even when everything else in life is finally clicking into place.<...

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This week, I’m asking a question that exposed more than a coolant leak: What am I tolerating simply because I’ve forgotten that I have options? I share how I ignored a problem with my car for months, only to discover that a five-minute test and a small repair could fix it. The same thing happened with electrical problems I had tolerated for years, because I was afraid to find out what the diagnosis might be.

You’ll be invited to take inventory of the parts of your life you’ve quiet...

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This week, we're taking you behind the scenes with Lucy, whose path from family-run businesses to independent hospitality entrepreneur will leave you rethinking everything you thought you knew about “safe” career choices. Lucy shares how leaving a so-called stable job led her to building a life and business filled with passion and flexibility, despite setbacks and the constant uncertainty of working for herself.

You'll hear Lucy get real about fears—like health insurance, business failures, and trading your time for money—and why none of these should hold you back from living y...

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This week, I sit down with Dan for a whirlwind journey through the ups and downs of an unconventional career path shaped by resilience and adaptability. From small-town roots in rural Oregon to living in five states and two Caribbean countries, Dan shares what it’s really like to reinvent yourself again and again in the face of layoffs, industry changes, and personal challenges. You’ll get the inside story of how losing his job to a robot—before it was “cool”—set him on a path from civil engineering to software development, with plenty...

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Welcome to the Unstuck Career Podcast. In this episode, Ken Williams explores a question most of us have never truly considered: who is really making the decisions about your career and your life? We assume that we’re in control, but as Ken Williams points out, too often we delegate that authority to our jobs, our bosses, societal expectations, or even an unwashed bathroom. Through relatable stories and introspective exercises, Ken Williams challenges you to reclaim your direction, take ownership of your decisions, and break free from invisible expectations. Tune in as we un...

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Every decision adds a new line to your life story, but who’s really holding the pen? In this episode, I lay bare the real reasons so many of us stay stuck in our careers and lives. We dig past the surface—fear of failure, fear of the unknown, imposter syndrome—and reveal the hidden force that keeps us spinning in place: authority. I share eye-opening stories, including the moment I realized my boss’s opinion could paralyze me in ways my own kids’ couldn't, and why it matters who you allow to define you...

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This week, I sit down with Sharyn Abbott, an unstoppable force in helping people break free from soul-crushing jobs and discover fulfilling work that truly fits who they are. We dig into why so many people feel trapped in jobs they hate and how you can reignite possibility in your career, even if you think you don’t have the resources or options. Sharyn shares the surprising power of tapping into your innate strengths, revealing simple strategies for starting fresh—sometimes with as little as a couple thousand dollars or just a few extr...

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This week, we dig into the overwhelm of decision-making in a world packed with endless information and opinions. Have you ever found yourself paralyzed by choices, unsure if you’re picking the right path or just following what others expect? I share a late-night conversation with my 19-year-old son, as he wrestles with whether to pursue art, psychology, or sign language, all while everyone—from managers to friends—weighs in with their own advice.

You’ll get a front-row seat as we unpack the real reason so many of us stay stuck: W...

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This week, I sit down with Andrea, a master of joy and transformation who turned life’s setbacks into a thriving singing telegram business. Ever wondered what it takes to move from playing small to leaving a lasting impact? Andrea shares how a major life change led her to follow her creative spark, start “Singagram” in the heart of the pandemic, and bring unforgettable celebrations to people in both the virtual and real worlds.

We unpack the courage it takes to break free from the “follow the rules” mentality and step into your...

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This week, we're tackling a question that’s been haunting so many of us: Is fear really about not knowing something, or is it about not truly knowing yourself? If you’ve ever caught yourself thinking, “Something’s got to change—I can’t keep doing this,” you’re in the right place. I open up about my own journey dealing with fear, from stumbling through podcast recordings with my cat as a surprise guest, to agonizing over what people (and yes, even my mom) would think when I took the leap into coaching and ent...

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This week on Unstuck Career, I sit down with Maria, aka “the Spicy Chef,” for a raw, honest conversation about what it really takes to leap out of a toxic work environment and into the unknown. Maria shares her journey from feeling trapped as an executive chef—even when she was “winning” by all traditional measures—to boldly starting her own hot sauce business and food consulting practice. If you’ve ever felt stuck in a job because of the paycheck or because you’re afraid of the unknown, Maria’s story will resonate.

Yo...

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This week, we break down one of the most misunderstood roadblocks in your career: the fear of failure. But here’s the twist—what if it’s not really failure you’re afraid of? I challenge the “fear of failure” myth and reveal the deeper anxiety that keeps so many of us from making bold career moves. (Hint: it’s about other people knowing you didn’t succeed.)

You’ll hear why the real fear might be about being seen as incompetent or about inviting criticism—especially from yourself, not others. I open up about my o...

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This week on Unstuck Career, I sit down with Matt, who shares his powerful journey from burnout in a niche, soul-draining job to truly thriving in a role where growth and fulfillment are finally possible. We unpack what it feels like when every day at work is just “going through the motions,” how the constant repetition and stress can creep into your home life, and how Matt reached the turning point that led him to choose something radically different for himself and his family.

You’ll hear how Matt overcame the anxiet...

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This week, we tackle a myth that keeps too many professionals stuck in place: the belief that you’re “too old” to change careers, go back to school, or start over. Have you ever caught yourself thinking that you’ve missed your chance or that it’s simply too late? I open up about the real fears behind this mindset—including my own hesitation about pursuing a master’s degree and the realization, at age 55, that it was time to reclaim ownership of my career.

We dig into some powerful truths: the time will...

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This week, I sit down with Jon for a raw, relatable conversation about the uneasy tension between career success and personal fulfillment. Jon opens up about what it’s really like to be a top performer in digital advertising sales—crushing quotas, earning well, and working with smart colleagues—yet feeling that nagging sense something’s missing at the end of each day. We break down the “golden handcuffs” dilemma: what happens when the perks of your job keep you stuck, even as you wonder if you’re settling for less than you deserve.

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Do you constantly put things off until you finally “feel ready”? This week’s episode tackles the myth of ever being 100% ready before making a big move in your career or life. I open up about my own struggles with procrastination and perfectionism, sharing why waiting to feel ready is actually just another form of staying stuck. From the hesitation to start a new workout routine to the much bigger leap of making a career pivot, we explore the real reason we freeze: we’re trying to predict the future—and that’s impossible.<...

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This week, I sit down with Clint, a relentless dreamer who ditched stability for a shot at building something meaningful. Ever wonder what it really takes to reinvent your life after 50? Clint shares his raw, honest story: selling a thriving business, moving cross-country, and discovering that changing your zip code doesn’t change your patterns. We unpack the moment he realized chasing his dreams meant taking real ownership, not just making excuses or waiting for the “perfect time.”

You’ll hear how Clint faced the scary crossroads of leaving a job, confront...

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This week on Unstuck Career, we tackle the paralyzing fear of making the “wrong” decision—a mindset that leads so many smart professionals into analysis paralysis and a life they never truly chose. I share the all-too-relatable ice cream saga (yes, Chocoholic Chunk is still the star!), showing how second-guessing, detours, and even dead ends aren’t proof that you made a bad choice—they’re just part of the journey.

You’ll learn why chasing perfect certainty is an illusion, and how treating every choice as “right” can liberate you from the anxiety o...

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This week, we're joined by Michael, whose journey is a masterclass in perseverance through radical change. From life on submarines and a dream engineering career to surviving a ruptured brain AVM that wiped out most of his memory, Michael’s story will grab you from the first minute. He opens up about what it’s really like to relearn everything—walking, thinking, and even basic daily activities—after a life-changing event, and how he learned to let go of what he lost so he could explore new possibilities instead of settling for less.

You...

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This week, we’re tackling one of the scariest—yet most liberating—moves you’ll ever make in your career: finding the courage to quit when you know it’s time. Are you living with that nagging voice that says, “Something has got to change”? I open up about my own struggles with the decision to leave a job that no longer fit, sharing what it really felt like to write my resignation, confront my boss, and walk away from a place I’d invested years into.

We unpack the myth of fear, from “F...

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What if you could keep your 9-to-5 and still build something deeply meaningful on the side? In this episode, I sit down with Mateo Platsidakis, the founder of The Forward Kind, to talk about what it means to chase “more” out of life without blowing up everything you already have. Mateo’s story is one so many of us can relate to—a job he enjoys, but a sense that something important was missing, leading him to launch a brand built on mental health awareness, resilience, and community.

We dig into the powe...

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This week, we challenge one of the biggest myths out there—the idea that a traditional job is supposed to make you feel safe and secure. Have you ever caught yourself thinking, “If I just made more money, then I’d finally feel safe”? I unpack why that sense of security you’re searching for will never come from your job title, paychecks, or even the size of your bank account.

We’ll explore real stories and insights from a recent coaching call that illustrate how chasing external safety is a moving targe...

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This week, I sit down with Shruti, a fellow coach, to explore what really happens when you're handed an unexpected chance at a fresh start. Shruti opens up about her abrupt transition from IT operations—13 years strong—to making coaching her full-time pursuit after getting laid off. She shares the vulnerable truth about ignoring her mental health for over a decade, the stigma she faced around therapy in the workplace, and the powerful moment she realized being let go might just be the freedom she always wanted.

We dig into how pers...

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Feeling lost or uncertain in your professional life? You’re not alone. In this episode of Unstuck Career, Ken Williams explores the concept of “career confusion”—that nagging realization that your current path might not be what you truly want. Drawing from his own winding journey through roles in sales, HR, and sixteen years at FedEx, Ken Williams shares personal stories and honest conversations about how easy it is to find your career ladder propped against the wrong wall. If you’re tired of settling and ready to pivot toward a more fulfilling direction...

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This week, I’m joined once again by Dave, whose leap from a high-powered executive role to founder of his own watch brand is nothing short of inspiring. Ever wonder what it’s like to step away from the “security” of corporate life—migraines and all—to chase a dream you never put on the front burner? Dave takes us inside his journey, from anxiety-ridden 4am wakeups and endless interview loops to the moment he went all in on LT, his creative outlet-turned-full-time business.

You’ll hear how a string of rejections and...

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In today’s episode, we’re tackling a question many wrestle with: Is it too late to make a change? After decades in corporate jobs, I faced this same crossroad myself and discovered it’s never too late to pursue work that aligns with your true goals. Whether you’re in your 30s, 40s, 50s, or beyond, age and shifting economic landscapes don’t have to hold you back. Today, I’ll debunk common myths about timing and opportunity, share stories and actionable steps, and remind you—the best time to start is now. Let’s get...

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This week on Unstuck Career, I sit down with Drew, a hot sauce entrepreneur whose inspiring journey is anything but ordinary. You might have seen him on the Kelly Clarkson Show or blowing up on TikTok, but what you haven’t heard is how a school project and a “bad grade” launched a multi-thousand-bottle business—all started to prove a point, and powered by Drew’s mission to support people with disabilities.

If you’ve ever wondered how to break free from a so-called “crappy job” or doubted what’s possible for yourself, Drew...

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In today's Friday Focus episode, Ken dives into one of the biggest barriers holding professionals back: the comfort of playing it safe. As the landscape of jobs and industries shifts—thanks to changing economies, new technologies, and unexpected policy changes—the old promise of security from a steady job no longer holds true. Ken shares personal insights and real conversations to highlight that true security doesn’t come from your job, your industry, or even the government—it comes from you. If you’ve ever thought, “Something has got to change,” this episode is for you. Ge...

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This week, we get real about money mindsets with returning guest Karen Thomas, the Surefire Income Guru, whose motto—“a better life is a choice”—guides this candid conversation. We crack open the hidden limiting beliefs around money that so many of us carry without recognizing how they quietly shape our earning, spending, and sense of possibility. Karen shares her personal story of hustling from a young age, and together we dig into how deeply ingrained money stories from childhood—like growing up hearing “we can’t afford that”—can drive our adult financial decision...

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Have you ever found yourself stuck in a job you know isn’t right, but can’t seem to leave? You’re not alone. In this episode, Ken dives deep into the surprising reasons why smart, capable professionals often stay in roles they dislike. From the traps of overthinking and the drive for safety, to seeking approval or drifting without commitment, we'll unpack some behavioral patterns that keep people stuck—and discuss practical steps for breaking free. If you’re ready to understand what’s holding you back and how to move forward, this episode...

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This week on Unstuck Career, I sit down with Corey Holzer, who’s right in the thick of a huge career pivot: taking the leap from a long military career into the private sector. We dig into his personal journey and the real, raw emotions that come with leaving behind the familiar—even when you know it’s time. Corey shares what first drew him to military service in the wake of 9/11, and he gets open about the identity shifts and doubts that bubble up as retirement approaches.

You’ll hear the hard...

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Welcome back to Unstuck Career! In this episode, Ken dives into that nagging question so many professionals face: What do you do when you aren't sure what you want from your career? Are you stuck settling for a life you never chose, repeating the same old patterns, or feeling frustrated that your career ladder seems to be leaning against the wrong wall? You're not alone.

We'll explore why so many of us ignore our true desires, talk ourselves out of reaching for more, and ultimately settle for "good enough." Today, we'll...

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This week, we welcome Connor Laurent to the show for a conversation about carving your own path when the traditional rules of career advancement just don’t fit. From day one in finance, Connor has been guided not by a rigid ladder, but by a mindset of treating every job like a subway stop. Sometimes it’s uncomfortable, sometimes surprising, and there’s always an opportunity for learning. We talk honestly about how the “expected” route of just keeping your head down and waiting for the next promotion, which often leads to a feeling of...

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Have you ever looked up from the daily grind and realized your career ladder is leaning against the wrong wall? In this episode of Unstuck Career, Ken dives into what happens when the career you have isn’t the one you truly chose—or wanted. If the phrase “something has got to change” keeps echoing in your mind, this episode will resonate. We'll explore how to recognize when your career path isn’t aligning with your strengths and passions, why it’s not your boss’s job to build your dream career, and actionable ste...

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This week on Unstuck Career, I sit down with the remarkable Sarah Ausby for a raw and inspiring conversation about what it really takes to rebuild, reinvent, and get “unstuck”—even when life pushes you out of your comfort zone. Sarah doesn’t just talk about career pivots; she’s lived them. From being involuntarily released from her job after a series of personal losses, to experiencing homelessness, Sarah shares the real-life turning points that ignited her journey into entrepreneurship and authorship.

We dive into how Sarah transformed a season of hardship i...