Career Sessions

Hosted by JR Lowry

Business Careers ManagementInterviews guests

Website RSS feed LinkedIn Facebook Instagram YouTube

Episodes

214

Latest episode

Aug 2026

Language

EN-US

About the show

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.

Listen to episodes

60 recent

August 17, 2026Episode 21530 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

August 10, 2026Episode 21435 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

August 3, 2026Episode 21332 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

July 27, 2026Episode 21234 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

July 20, 2026Episode 21132 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

July 13, 2026Episode 21040 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

July 6, 2026Episode 20939 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

July 1, 2026Episode 20833 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/

June 24, 2026Episode 20733 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/

June 15, 2026Episode 20633 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/