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

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

Most people see careers as ladders to climb. Mohamed Isa [https://www.linkedin.com/in/mohdisa/?originalSubdomain=bh] 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/ [http://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/

How To Escape Overwhelm And Redefine Success, With Corrie LoGiudice

Most people think overwhelm is a productivity problem. Corrie LoGiudice [https://corrielo.com/] argues it’s something much deeper.  In this episode, JR speaks with Corrie LoGiudice, author of The Five Overwhelm Culprits [https://www.amazon.com/Overwhelm-Culprits-Strategies-Without-Sacrificing/dp/0757326102], 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/ [http://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/

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 [https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898] and Incorruptible [https://www.amazon.com/Incorruptible-Good-Companies-Great-Stay/dp/B0FWZZBPZB], 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 [https://www.youtube.com/@careersessions] 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/ [http://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/

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 [https://kyleaustinyoung.com/] 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 [https://www.youtube.com/@careersessions] 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/ [http://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/

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 [https://tracybrower.com/] 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/ [http://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/