Career Sessions

Jaksot

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  Why Hiring Feels Broken—and How to Get Hired Anyway, with Lorena Prego Ojeda 14.09.2026 30min

  Finding a job has never been easy, but today’s hiring process can feel particularly frustrating. Hundreds of applicants compete for a single role, AI is reshaping how candidates are screened, and qualified people often struggle to get noticed. At the same time, employers insist they can’t find the talent they need. So what’s really going on?In this episode of Career Sessions, J.R. Lowry talks with Lorena Prego, founder and CEO of Prometeo Talent, who has spent two decades in recruiting and helped companies make more than 5,000 hiring decisions.Lorena takes us behind the scenes of the hiring process to explain what recruiters and hiring managers actually look for—and what separates candidates who consistently land opportunities from those who struggle to break through.They discuss why applying to hundreds of jobs may actually hurt your search, how to take more control of an interview, what recruiters notice when comparing your resume and LinkedIn profile, and how to build productive relationships with search firms. They also explore how AI and remote work are transforming recruiting and why communication, critical thinking, adaptability, and the ability to keep learning will become even more important.Whether you’re actively looking for a job or simply want to position yourself for your next opportunity, this episode offers a practical insider’s guide to getting noticed, telling your story, and managing your career for the long term.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/lorena-prego-ojeda/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  How to Stay Valuable in the Age of AI, with Liat Ben-Zur 07.09.2026 36min

  AI can already draft, summarize, analyze data, write code, and find patterns faster than most of us. So as these capabilities become increasingly commonplace, what will make you valuable?In this episode of Career Sessions, J.R. Lowry talks with Liat Ben-Zur, former senior executive at Microsoft, Qualcomm, and Philips and author of The Bias Advantage, about how AI is changing the skills that matter most—and why some of the experiences that once made your career harder may actually have prepared you for what's coming next.Liat argues that the answer isn't trying to compete with AI at what it does best. Instead, we need to double down on capabilities machines struggle to replicate: judgment, adaptability, empathy, ethical decision-making, creativity, influence, and the ability to see what others miss.They also discuss why hard work alone isn't enough to advance your career, how to make your impact visible without becoming overly self-promotional, why nonlinear careers may become increasingly valuable, and how to use AI to strengthen your thinking rather than replace it.In this episode, you'll learn:Which human capabilities will become more valuable as AI gets betterWhy career setbacks and being an outsider can build unexpected advantagesHow to make sure your contributions are recognized—not just deliveredWhy career range may be more valuable than narrow specializationHow to use AI as a thinking partner without weakening your own judgmentWhat leaders will need to do differently as AI reshapes organizationsIf you're wondering how to remain relevant, differentiated, and valuable as AI transforms the workplace, this conversation offers a practical roadmap.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/liat-ben-zur/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  How To Stay Human In The Age Of AI, With Johan Roos 01.09.2026 36min

  AI can write, analyze, summarize, code, and create—and its capabilities are advancing at a remarkable pace. So as machines become more intelligent, what will keep humans indispensable? Johan Roos believes the answer lies in what he calls “human magic”: the distinctly human capabilities that technology can support, but never replace. Johan is an internationally recognized strategy scholar, former business school dean, co-creator of LEGO Serious Play, and author of Human Magic. In this episode of Career Sessions, Johan and J.R. explore why our advantage in an AI-powered world comes not from trying to compete with machines, but from becoming more human as AI gets smarter. They discuss the five capabilities at the heart of human magic—curiosity, creativity, critical thinking, communication, and collaboration—and why practical wisdom and sound judgment are becoming increasingly valuable. They also examine the danger of “cognitive offloading”: relying so heavily on AI that the very skills that differentiate us begin to atrophy. Johan shares what leaders should be doing differently in the AI era, including asking better questions, creating the conditions for their teams to think deeply, and focusing the AI conversation on transforming tasks rather than eliminating jobs. The conversation also revisits the origins of LEGO Serious Play and what Johan learned about creativity, collaboration, and better decision-making by getting people out of conventional meetings and thinking with their hands. Those lessons may be even more relevant as organizations figure out how humans and AI should work together. The takeaway: use AI intensely to prepare—but when the room is watching, show up as a human.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/johan-roos/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  Why Great Teams Work Differently, with Ron Friedman 24.08.2026 34min

  Why do some teams consistently outperform while others—with equally talented people—struggle with endless meetings, constant interruptions, and burnout?In this episode of Career Sessions, JR Lowry sits down with organizational psychologist and bestselling author Ron Friedman to explore what separates exceptional teams from average ones. Drawing on research involving more than 6,000 workers for his new book, Super Teams, Ron reveals that only about 8% of teams qualified as “super teams”—and that what distinguishes them often runs counter to conventional wisdom about productivity, collaboration, and where work should happen.Their conversation covers:Why how a team works matters more than where it works—and what that means for the ongoing debate over remote, hybrid, and in-office workHow excessive meetings and always-on communication undermine productivity—and why great teams establish clear meeting guidelinesWhy individual productivity hacks can actually create bottlenecks for the rest of the teamThe importance of protecting focused work and why “brainwriting” can produce better ideas than traditional brainstormingHow active recovery outside of work can improve performance—and why leaders’ recovery habits can affect their teamsThe three ingredients of workplace trust: competence, caring, and consistencyWhy shared goals, role clarity, and interdependence are essential for creating a true team mentalityPractical ways to take control of your workday by looking forward, looking backward, and staying presentWhy working longer hours eventually produces diminishing—and even negative—returnsHow high-performing teams are approaching AI differently, including openly sharing prompts and learning from one another rather than hiding their AI useThe central message is simple: great teams aren't built by assembling the smartest people or forcing more collaboration. They're built intentionally, by creating the conditions that allow talented people to do their best work—both individually and together.Whether you lead a team or work as part of one, this conversation offers practical, research-backed ideas for reducing friction, building trust, protecting people's time, and creating a team that performs at a higher level.Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly conversations on careers, leadership, and the changing world of work.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/ron-friedman/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  The Rise of Disposable Workers, with Paul Osterman 17.08.2026 30min

  For decades, a good job meant stability, career development, and a long-term relationship between employers and employees. But according to MIT Sloan professor Paul Osterman, that social contract has fundamentally changed. In this episode of Career Sessions, JR Lowry sits down with Osterman to discuss the ideas behind his new book, Disposable Workers, and why more than one-third of today's workforce now falls into employment arrangements designed for flexibility rather than long-term investment. Together, they explore what's driving this shift, why it extends well beyond the gig economy, how AI may accelerate the trend, and what individuals, leaders, and policymakers can do to build a future of work that benefits both organizations and employees. Whether you're just starting your career or leading an organization through change, this conversation will challenge the way you think about job security, career development, and the future of work. Key topics covered:Why Paul Osterman believes over one-third of workers are now "disposable workers"The difference between contractors, freelancers, marginal workers, and traditional employeesWhat's driving organizations toward more flexible—and less committed—workforcesHow AI is likely to accelerate the trend toward workforce disposabilityThe costs of disposable work for employees, organizations, and societyPractical advice for building career resilience through skills, networks, and smart career choicesWhat business leaders and policymakers can do to improve the quality of workCheck out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/paul-osterman/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  Why Smart People Get Financially Stuck (and How to Break Free), with Carrie Joy Grimes 10.08.2026 35min

  Most people were never taught how to manage money. Yet they're expected to navigate rising housing costs, student debt, investing, retirement planning, and an economy that often feels stacked against them. In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Carrie Joy Grimes, founder of WorkMoney and author of the USA Today bestselling book The Joy of Money, to explore why financial success has far more to do with psychology than spreadsheets. Carrie explains why shame and avoidance keep so many people financially stuck, how small behavioral changes compound into long-term wealth, and why the biggest obstacle to financial security often isn't a lack of knowledge—it's the stories we tell ourselves about money. They also discuss: Why "I'm just bad with money" is one of the most damaging beliefs you can haveThe surprising connection between money habits and career successWhy budgeting should create freedom—not guiltHow to overcome financial avoidance and build confidence one small step at a timeWhy chasing the next hot investment rarely beats mastering the fundamentalsHow to think about raises, retirement savings, and building wealth in today's challenging economy Whether you're just starting your career or trying to gain greater financial confidence after years in the workforce, this conversation offers practical, encouraging advice that can help you take control of both your money and your future.Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/carrie-joy-grimes/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  The Hidden Risk of a Great Career (And a Different Path to Financial Freedom), with Jon Ostenson 03.08.2026 32min

  What if the biggest financial risk in your life isn't the stock market—but your paycheck? Most professionals spend years building successful careers, yet their entire financial future depends on a single employer. In today's world of layoffs, AI disruption, and economic uncertainty, that's becoming an increasingly fragile strategy. In this episode, JR Lowry sits down with Jon Ostenson, founder of FranBridge Consulting and author of Non-Food Franchising, to explore an alternative that more professionals are beginning to consider: business ownership through franchising. Forget fast food. Jon explains why many of today's fastest-growing franchise opportunities are in service businesses—from home services and senior care to B2B consulting—and why they're attracting professionals looking for additional income, long-term wealth, and greater control over their future. Together they discuss:Why relying on one paycheck may be riskier than owning a businessThe biggest myths about franchising—and what it's really likeHow professionals can own businesses while keeping their day jobsThe difference between entrepreneurship and buying into a proven systemWhat makes some businesses more recession-resistant than othersHow business ownership fits into a broader wealth-building strategy Whether you're dreaming of leaving corporate life, looking for a second source of income, or simply thinking more strategically about your financial future, this conversation will challenge how you think about work, risk, and ownership.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/jon-ostenson/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  Why Talent Isn't Enough: The Discipline That Separates Top Performers, with Dre Baldwin 27.07.2026 34min

  Most careers stall because professionals wait for permission, confidence, or the right timing rather than taking action. In this episode, host J.R. Lowry sits down with former professional athlete and entrepreneur Dre Baldwin to dissect why professional discipline outperforms raw motivation every time. Baldwin reveals how he translated lessons from overseas sports courts into scalable business frameworks centered on mindset, strategy, systems, and execution. They explore actionable ways to build true executive presence before you get the promotion, navigate career reinvention, and develop the human judgment skills AI can't replace.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dre-baldwin.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  The Leadership Lesson I Learned By Becoming My True Self, with Katherine Dudtschak 20.07.2026 32min

  What if becoming a better leader has less to do with learning new management techniques and more to do with becoming more yourself?In this episode, former RBC executive and HomeEquity Bank CEO Katherine Dudtschak shares a deeply personal journey that transformed not only her life, but also her philosophy of leadership. After publicly affirming her gender while leading thousands of employees, Katherine discovered that vulnerability, compassion, and authenticity weren't leadership liabilities. In fact, they became her greatest strengths.In this episode, you'll learn:Why success and fulfillment aren't always the same thingHow fear-based leadership limits both people and performanceWhy vulnerability builds trust faster than authorityHow curiosity and compassion can outperform command-and-control managementWhy doing the inner work is one of the most important responsibilities of a leaderPractical ways to lead with greater authenticity without sacrificing resultsWhether you're leading a team, navigating your own career, or simply questioning whether the life you've built truly reflects who you are, this conversation will challenge the way you think about leadership and yourself.If you’re interested in the impact of capitalism on leadership and innovation, make sure you tune in.Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/katherine-dudtschak/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  Why Experience Is Becoming Your Biggest Career Advantage, With Dan Pontefract 13.07.2026 40min

  Everyone talks about AI as the future of work. But what if the bigger story is something we're overlooking?In this episode, JR speaks with leadership strategist and author Dan Pontefract about why experience—not youth—may become one of the most valuable assets in tomorrow's workplace. As workforces age and labor shortages grow, Dan argues that organizations must rethink how they hire, develop, and retain talent—or risk losing decades of knowledge and expertise.In this episode, you'll learn:Why demographic change may have a bigger impact on work than AIWhat "age debt" is—and why organizations aren't prepared for itHow ageism affects professionals at every stage of their careersWhy traditional generational labels may be doing more harm than goodDan's "Rivers, Rocks, and Rubies" framework for understanding career growthHow organizations can turn experience into a competitive advantage instead of treating it as a costWhat professionals can do to build careers that remain relevant and rewarding for decadesWhether you're just starting your career, leading a team, or thinking about what's next in your 50s, 60s, and beyond, this conversation will challenge many of the assumptions we've long held about work, careers, and retirement. You'll come away with a new perspective on why experience may be one of the greatest advantages you can build—and why the organizations that recognize its value will be the ones best positioned to succeed in the years ahead.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dan-pontefract/.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  Why You're Overwhelmed At Work (And How To Fix It), With Liane Davey 06.07.2026 39min

  Why does work feel so overwhelming, even when you're getting everything done?In this episode, leadership expert and bestselling author Liane Davey explains why the problem isn't your workload—it's your thought load: the hidden combination of cognitive demands, emotional burden, and depleted energy that makes work feel harder than it should.In this episode, you'll learn:Why working harder won't solve the problem of overwhelmThe difference between workload and thought loadHow constant context switching and emotional stress drain your performanceWhy attention is your most valuable resource—not timeA practical framework for prioritizing what matters mostSimple strategies to reduce overwhelm, regain focus, and protect your energyYou'll walk away with practical tools you can use immediately to feel less overwhelmed, improve your focus, and do your best work without burning yourself out.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/liane-davey.For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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  How to Turn Anxiety Into a Leadership Advantage, With Morra Aarons-Mele 01.07.2026 33min

  Anxiety is often treated as something to overcome. But what if it’s also one of the forces driving your success? In this episode, JR speaks with Morra Aarons-Mele, author of The Anxious Achiever and host of Harvard Business Review’s popular podcast of the same name, about the complex relationship between anxiety, achievement, leadership, and performance. Morra argues that anxiety isn’t necessarily a weakness to be fixed. For many high performers, it fuels preparation, creativity, empathy, and ambition. The challenge isn’t eliminating anxiety—it’s learning how to understand it, manage it, and work with it rather than against it. Their conversation covers:What separates anxious achievers from people who are simply stressedHow anxiety can become both a leadership asset and a liabilityWhy so many high performers are driven by fear, control, and hypervigilanceThe connection between childhood experiences and achievement-oriented behaviorHow mindfulness and self-awareness help people manage anxiety more effectivelyWhy boundaries are especially difficult—and important—for anxious achieversWhat psychologically healthy teams and workplaces look likeHow managers can better support different working styles and needsWhy today’s workplace often works against mental well-beingHow leaders can build resilience in an increasingly uncertain world If you've ever felt driven by a constant inner voice pushing you to prepare more, do more, and achieve more, this conversation offers a thoughtful framework for understanding anxiety—not as a flaw, but as something that can be harnessed with greater awareness, intention, and self-compassion.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/morra-aarons-mele.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  How To Overcome The Conversational Debt That Holds Teams Back, With Gustavo Razzetti 24.06.2026 33min

  Most teams don't fail because they lack talent. They fail because they're not having the conversations that matter.In this episode of Career Sessions, Career Lessons, I sit down with workplace culture expert, consultant, and author Gustavo Razzetti to discuss his new book, Forward Talk. Gustavo argues that the biggest threat to team performance isn't conflict—it's silence. When concerns go unspoken, tensions remain unresolved, and difficult issues are avoided, organizations accumulate what he calls "conversational debt."This conversation explores why people often stop speaking up, why agreement isn't the same as alignment, and what leaders and team members can do to create healthier, more productive conversations.In this episode, you'll learn:Why teams often struggle because of avoided conversations rather than a lack of talentWhat "conversational debt" is and how it compounds over timeWhy employees frequently stop speaking up—not because they're afraid, but because they believe nothing will changeThe difference between agreement and true alignmentHow group think, blame, and avoidance keep teams stuckWhy psychological safety alone isn't enoughPractical ways leaders and team members can foster more honest, productive conversationsHow high-performing teams create cultures that encourage participation and shared ownershipTune in every week for more episodes like this. Subscribe on Apple Podcasts, Spotify, YouTube, or follow Career Sessions wherever you're listening.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/gustavo-razzetti.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  Why Work Feels Broken (And How to Fix It), With Debbie Lovich 15.06.2026 33min

  Most people spend a huge portion of their lives at work. So why do so many of us dread it?In this episode, JR speaks with Debbie Lovich, Senior Partner Emerita at Boston Consulting Group and author of Make Work Work, about why employee engagement has remained stubbornly low for decades despite billions spent on leadership training, culture initiatives, and workplace transformation programs.Debbie argues that making work better doesn't require another grand strategy or organizational overhaul. Instead, it comes down to a handful of daily leadership behaviors that create more human, enjoyable, and productive workplaces.Their conversation covers:Why most leadership training fails to change behaviorThe connection between employee joy, performance, and retentionThe five daily practices that help leaders create better workplacesWhy employee experience should be treated like customer experienceHow co-creation can replace traditional change managementThe role of middle managers in shaping workplace cultureWhat leaders get wrong about AI and the future of workHow anyone—not just senior executives—can improve the culture around themIf you're a leader, manager, or employee who wants work to be more meaningful, productive, and enjoyable, this conversation offers practical ideas you can put into action immediately.Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/debbie-lovich-2.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  From Cleaner To CFO (and Beyond): Lessons On Reinvention And Risk, With Mohamed Isa 10.06.2026 30min

  Most people see careers as ladders to climb. Mohamed Isa sees them as mountains to explore. In this episode, Mohamed shares his remarkable journey from working as a cleaner in a bank to becoming the youngest CFO of a publicly listed company in Bahrain. Along the way, he learned that success isn't about following a predetermined path—it's about taking calculated risks, continually reinventing yourself, and creating opportunities where others see limitations.JR and Mohamed explore:How a cleaning job became the foundation for an extraordinary careerWhy taking career risks can accelerate growthThe difference between having a large network and having the right networkHow to think about reinvention through seven-year cyclesWhy careers don't need to follow a linear pathWhat "peak leadership" means and how to build a lasting legacyHow mountain climbing became a powerful metaphor for life and workThis conversation is a reminder that where you start doesn't determine where you'll finish. Whether you're feeling stuck, considering a career change, or simply looking for inspiration, Mohammed's story offers a powerful perspective on what's possible when you combine ambition with action.Tune in every week for more episodes like this. Subscribe on Apple Podcasts, Spotify, YouTube, or follow Career Sessions wherever you're listening.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/mohamed-isa.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  How To Escape Overwhelm And Redefine Success, With Corrie LoGiudice 01.06.2026 31min

  Most people think overwhelm is a productivity problem. Corrie LoGiudice argues it’s something much deeper. In this episode, JR speaks with Corrie LoGiudice, author of The Five Overwhelm Culprits, about why so many high performers feel exhausted, disconnected and stuck — even when their lives look successful on paper. Corrie explains why burnout is often misdiagnosed as a time-management issue, and why the real causes of overwhelm usually stem from deeper problems like misalignment, lack of clarity, weak support systems and chronic self-neglect.Their conversation covers:Why overwhelm is more than “having too much to do”The five root causes behind burnout and chronic stressHow work and personal life pressures compound each otherWhy high performers often confuse exhaustion with successThe difference between burnout and misalignmentHow intuition helps people recognize when something is wrongWhy women experience overwhelm differently than menThe role resilience plays in navigating major life changesHow to recognize overwhelm before reaching a breaking pointWhy meaningful change either happens by choice — or happens to youSubscribe to Career Sessions wherever you get your podcasts for weekly episodes like this.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/corrie-logiudice.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  Why Success Can Destroy A Company, With Eric Ries 26.05.2026 33min

  Most companies don’t fail because they’re outcompeted. They fail because they succeed. In this episode, JR speaks with Eric Ries, author of The Lean Startup and Incorruptible, about why successful organizations so often lose their mission, values and long-term vision. Eric explains how modern corporate systems incentivize short-term extraction over long-term value creation and that the problem isn’t necessarily bad leaders, but structures that slowly corrupt organizations over time.Their conversation covers:Why “shareholder value” became the dominant philosophyHow companies like Costco resisted short-term pressureThe hidden incentives that destroy great businessesAI governance and what OpenAI and Anthropic tell us about the futureHow founders can design companies that survive beyond themWhat employees and consumers can do to help companies stay true to their missionIf you’re interested in the impact of capitalism on leadership and innovation, make sure you tune in.Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/eric-ries.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  How Successful People Actually Think About Risk, Failure, And Opportunity, With Kyle Austin Young 18.05.2026 31min

  Most people think success comes down to talent, timing, or even luck. But Kyle Austin Young suggests it could be a numbers game. In this episode, he explains how to think about success through the lens of probability so you can actively improve your odds over time.JR and Kyle explore:Why your goals have hidden probabilities attached to themHow to reduce the likelihood of failureThe power of repeated attemptsWhen to power through to achieve your goals, and when to pauseWhy differentiation is critical in today’s marketThis conversation reframes success as something you can engineer. Whether you’re early in your career or reevaluating your next move, this will help you make smarter decisions and create better outcomes over time.Tune in every week for more episodes like this. Subscribe on YouTube and follow Career Sessions wherever you’re listening to this.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kyle-austin-young.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  The Hidden Cost Of Loneliness At Work, With Tracy Brower 11.05.2026 33min

  We often talk about burnout, quiet quitting and disengagement at work, but underneath these trends is something deeper: loneliness. In this episode of Career Sessions, Tracy Brower joins JR to unpack the growing crisis of disconnection at work and why it’s affecting everything from performance to mental health.They cover:Why loneliness is rising in the age of remote work and social mediaWhy work is still the #1 place people build friendshipsHow leaders can create belongingThe need for both strong ties and weak tiesHow to build a network that actually leads to opportunitiesSimple ways to feel more connected starting todayThis conversation breaks down the science of connection and how it shapes your career, relationships, and sense of purpose.Subscribe and follow Career Sessions on YouTube and wherever you get your podcasts so you never miss an episode.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/tracy-brower.For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
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  Why Rest Is the Original Performance Tool, With Nathalie Walton 04.05.2026 30min

  Most productivity advice skips right past the most obvious lever: sleep. In this episode, JR speaks with Nathalie Walton who leads growth at Better Sleep, the app that's become the go-to sleep tool for 65 million people around the world. Nathalie's path here wasn't linear. It started with her own experience during pregnancy where she came to realize that there was a frustrating gap in support for women's health. That led her to found Expectful, a platform for fertility, pregnancy, and early motherhood, and eventually to Better Sleep, where she's helping scale something that genuinely changes how people feel day to day. JR and Nathalie get into:Why sleep isn't something you can bank or borrow againstHow Better Sleep built real trust with its users in an era when most health apps cut cornersWhy expanding access to care (especially for women and underserved communities) is one of the most important problems anyone in healthcare can be working on right now If you’re interested in health, startups or optimizing your performance at work and in life, you don’t want to skip this episode. Find and follow Career Sessions on Apple Podcasts, Spotify, and YouTube.Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/nathalie-walton.Become a PathWise member today! Join at https://pathwise.io/join-now/