BusinessCareersEntrepreneurshipManagement

Career Sessions

JR Lowry

Career paths rarely unfold in a straight line. Some careers accelerate quickly, while others take unexpected turns, requiring us to adapt, reinvent ourselves, and seize new opportunities along the way.

On Career Sessions, host J.R. Lowry sits down with accomplished leaders, entrepreneurs, academics, coaches, veterans, and professionals from all walks of life to explore the stories behind their careers. Through candid conversations, guests share the decisions, challenges, successes, setbacks, and lessons that shaped their professional journeys.

Whether you're early in your career, navigating a transition, pursuing leadership opportunities, or simply looking for inspiration and practical advice, Career Sessions offers insights you can apply to your own path. Each episode goes beyond résumés and job titles to uncover how people build meaningful careers and thrive through change.

J.R. Lowry has built a career across military service, management consulting, financial services, executive leadership, and entrepreneurship. Drawing on his own experiences and conversations with hundreds of guests, he helps listeners better understand the realities of career growth and the choices that can make the biggest difference over time.

Play

Open in

26 episodes
weekly
Avg 33 min
English

Episodes 26

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

#219
Monday · 30 min
Why Hiring Feels Broken—and How to Get Hired Anyway, with Lorena Prego Ojeda
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
#218
September 7 · 36 min
How to Stay Valuable in the Age of AI, with Liat Ben-Zur
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 better Why career setbacks and being an outsider can build unexpected advantages How to make sure your contributions are recognized—not just delivered Why career range may be more valuable than narrow specialization How to use AI as a thinking partner without weakening your own judgment What leaders will need to do differently as AI reshapes organizations If 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
#217
September 1 · 36 min
How To Stay Human In The Age Of AI, With Johan Roos
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
#216
August 24 · 34 min
Why Great Teams Work Differently, with Ron Friedman
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 work How excessive meetings and always-on communication undermine productivity—and why great teams establish clear meeting guidelines Why individual productivity hacks can actually create bottlenecks for the rest of the team The importance of protecting focused work and why “brainwriting” can produce better ideas than traditional brainstorming How active recovery outside of work can improve performance—and why leaders’ recovery habits can affect their teams The three ingredients of workplace trust: competence, caring, and consistency Why shared goals, role clarity, and interdependence are essential for creating a true team mentality Practical ways to take control of your workday by looking forward, looking backward, and staying present Why working longer hours eventually produces diminishing—and even negative—returns How high-performing teams are approaching AI differently, including openly sharing prompts and learning from one another rather than hiding their AI use The 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
#215
August 17 · 30 min
The Rise of Disposable Workers, with Paul Osterman
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 employees What's driving organizations toward more flexible—and less committed—workforces How AI is likely to accelerate the trend toward workforce disposability The costs of disposable work for employees, organizations, and society Practical advice for building career resilience through skills, networks, and smart career choices What business leaders and policymakers can do to improve the quality 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/paul-osterman/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
#214
August 10 · 35 min
Why Smart People Get Financially Stuck (and How to Break Free), with Carrie Joy Grimes
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 have The surprising connection between money habits and career success Why budgeting should create freedom—not guilt How to overcome financial avoidance and build confidence one small step at a time Why chasing the next hot investment rarely beats mastering the fundamentals How 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
#213
August 3 · 32 min
The Hidden Risk of a Great Career (And a Different Path to Financial Freedom), with Jon Ostenson
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 business The biggest myths about franchising—and what it's really like How professionals can own businesses while keeping their day jobs The difference between entrepreneurship and buying into a proven system What makes some businesses more recession-resistant than others How 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
#212
July 27 · 34 min
Why Talent Isn't Enough: The Discipline That Separates Top Performers, with Dre Baldwin
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
#211
July 20 · 32 min
The Leadership Lesson I Learned By Becoming My True Self, with Katherine Dudtschak
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 thing How fear-based leadership limits both people and performance Why vulnerability builds trust faster than authority How curiosity and compassion can outperform command-and-control management Why doing the inner work is one of the most important responsibilities of a leader Practical ways to lead with greater authenticity without sacrificing results Whether 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
#210
July 13 · 40 min
Why Experience Is Becoming Your Biggest Career Advantage, With Dan Pontefract
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 AI What "age debt" is—and why organizations aren't prepared for it How ageism affects professionals at every stage of their careers Why traditional generational labels may be doing more harm than good Dan's "Rivers, Rocks, and Rubies" framework for understanding career growth How organizations can turn experience into a competitive advantage instead of treating it as a cost What professionals can do to build careers that remain relevant and rewarding for decades Whether 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
#209
July 6 · 39 min
Why You're Overwhelmed At Work (And How To Fix It), With Liane Davey
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 overwhelm The difference between workload and thought load How constant context switching and emotional stress drain your performance Why attention is your most valuable resource—not time A practical framework for prioritizing what matters most Simple strategies to reduce overwhelm, regain focus, and protect your energy You'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
#208
July 1 · 33 min
How to Turn Anxiety Into a Leadership Advantage, With Morra Aarons-Mele
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 stressed How anxiety can become both a leadership asset and a liability Why so many high performers are driven by fear, control, and hypervigilance The connection between childhood experiences and achievement-oriented behavior How mindfulness and self-awareness help people manage anxiety more effectively Why boundaries are especially difficult—and important—for anxious achievers What psychologically healthy teams and workplaces look like How managers can better support different working styles and needs Why today’s workplace often works against mental well-being How 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/
#207
June 24 · 33 min
How To Overcome The Conversational Debt That Holds Teams Back, With Gustavo Razzetti
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 talent What "conversational debt" is and how it compounds over time Why employees frequently stop speaking up—not because they're afraid, but because they believe nothing will change The difference between agreement and true alignment How group think, blame, and avoidance keep teams stuck Why psychological safety alone isn't enough Practical ways leaders and team members can foster more honest, productive conversations How high-performing teams create cultures that encourage participation and shared ownership 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/gustavo-razzetti. For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
#206
June 15 · 33 min
Why Work Feels Broken (And How to Fix It), With Debbie Lovich
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 behavior The connection between employee joy, performance, and retention The five daily practices that help leaders create better workplaces Why employee experience should be treated like customer experience How co-creation can replace traditional change management The role of middle managers in shaping workplace culture What leaders get wrong about AI and the future of work How anyone—not just senior executives—can improve the culture around them If 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/
#205
June 10 · 30 min
From Cleaner To CFO (and Beyond): Lessons On Reinvention And Risk, With Mohamed Isa
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 career Why taking career risks can accelerate growth The difference between having a large network and having the right network How to think about reinvention through seven-year cycles Why careers don't need to follow a linear path What "peak leadership" means and how to build a lasting legacy How mountain climbing became a powerful metaphor for life and work This 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/
#204
June 1 · 31 min
How To Escape Overwhelm And Redefine Success, With Corrie LoGiudice
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 stress How work and personal life pressures compound each other Why high performers often confuse exhaustion with success The difference between burnout and misalignment How intuition helps people recognize when something is wrong Why women experience overwhelm differently than men The role resilience plays in navigating major life changes How to recognize overwhelm before reaching a breaking point Why meaningful change either happens by choice — or happens to you Subscribe 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/
#203
May 26 · 33 min
Why Success Can Destroy A Company, With Eric Ries
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 philosophy How companies like Costco resisted short-term pressure The hidden incentives that destroy great businesses AI governance and what OpenAI and Anthropic tell us about the future How founders can design companies that survive beyond them What employees and consumers can do to help companies stay true to their mission 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/eric-ries. For more career guidance and resources, subscribe to my member community at https://pathwise.io/join-now/
#202
May 18 · 31 min
How Successful People Actually Think About Risk, Failure, And Opportunity, With Kyle Austin Young
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 them How to reduce the likelihood of failure The power of repeated attempts When to power through to achieve your goals, and when to pause Why differentiation is critical in today’s market This 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/
#201
May 11 · 33 min
The Hidden Cost Of Loneliness At Work, With Tracy Brower
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 media Why work is still the #1 place people build friendships How leaders can create belonging The need for both strong ties and weak ties How to build a network that actually leads to opportunities Simple ways to feel more connected starting today This 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/
#200
May 4 · 30 min
Why Rest Is the Original Performance Tool, With Nathalie Walton
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 against How Better Sleep built real trust with its users in an era when most health apps cut corners Why 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/

Showing 1–20 of 26 episodes