Career Sessions

JR Lowry
  • 5.0 (147)
  • Careers
  • Updated Weekly

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.

  1. Why Work Feels Broken (And How to Fix It), With Debbie Lovich

    Jun 15

    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 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 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/

    34 min
  2. From Cleaner To CFO (and Beyond): Lessons On Reinvention And Risk, With Mohamed Isa

    Jun 10

    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 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 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/

    30 min
  3. How To Escape Overwhelm And Redefine Success, With Corrie LoGiudice

    Jun 1

    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 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 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/

    32 min
  4. Why Success Can Destroy A Company, With Eric Ries

    May 26

    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 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 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/

    33 min
  5. How Successful People Actually Think About Risk, Failure, And Opportunity, With Kyle Austin Young

    May 18

    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 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 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/

    32 min
  6. The Hidden Cost Of Loneliness At Work, With Tracy Brower

    May 11

    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 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 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/

    34 min
  7. Why Rest Is the Original Performance Tool, With Nathalie Walton

    May 4

    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 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/

    31 min
  8. How To Explore Careers Without Guesswork, With Gabe DeSanti & Alex Dworsky

    Apr 27

    How To Explore Careers Without Guesswork, With Gabe DeSanti & Alex Dworsky

    In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Gabriel DeSanti and Alex Dworsky, co-founders of Staj, a platform built around a simple but powerful idea: What if you could experience a career before committing to it? They explore why traditional career decision-making is often based on limited information and how that leads many people to feel misaligned years into their careers. Drawing on Gabe’s experience trying nearly 200 different jobs and Alex’s background in corporate America, they discuss how career exploration can shift from guesswork to intentional experimentation. They cover: Why most people choose careers without truly understanding themHow short-term “career experiments” can provide clarityPractical ways to explore new industries without prior experienceWhy curiosity and initiative matter more than a perfect resumeHow to build credibility quickly when pivoting careersThe role of networking and real-world exposure in unlocking opportunities They also share insights from building Staj and what they’re learning about how people test and transition into new paths.  If you’re early in your career or considering a pivot, this conversation is for you. Follow Career Sessions for weekly insightful episodes just 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/gabe-desanti-alex-dworsky/. Become a PathWise member today! Join at https://pathwise.io/join-now/

    32 min
See All (206)

5
out of 5
147 Ratings

About

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.

Information

  • Creator
    JR Lowry
  • Years Active
    2022 - 2026
  • Episodes
    206
  • Rating
    Clean
  • Copyright
    © Copyright 2026 | PathWise LLC. All Rights Reserved.
  • Show Website
    Career Sessions

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