Career Sessions

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.

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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/

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/

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 them
• How short-term “career experiments” can provide clarity
• Practical ways to explore new industries without prior experience
• Why curiosity and initiative matter more than a perfect resume
• How to build credibility quickly when pivoting careers
• The 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/

In this episode of Career Sessions, J.R. Lowry sits down with author, speaker, and culture expert Greg Hawks to tackle one of the biggest challenges facing organizations today:

Why are so many people disengaged at work—and what actually changes that?

Greg introduces the concept of the “ownership mindset,” a powerful shift in how individuals approach their work and how leaders build environments where people feel invested, accountable, and motivated.

Drawing on decades of experience working with organizations, Greg explains why most employees start with energy and intention—but often lose it over time—and what both individuals and leaders can do to bring it back.

They discuss:

• What it really means to “act like an owner” (and why it has nothing to do with your title)
• The difference between owners, renters, and vandals in the workplace
• Why engagement breaks down—and how culture often unintentionally discourages initiative
• The five “unlocks” that help individuals and teams build ownership and accountability
• How leaders can re-engage employees who’ve stopped investing their energy
• Why values only matter when they are consistently lived—not just stated
• How to think about ownership not just in your role, but across your entire career

Greg also shares practical tools—from identifying where you’re placing blame to making small, consistent changes that compound over time—to help you take greater ownership of your work and your future.

If you’ve ever felt stuck, disengaged, or frustrated by your work environment, this conversation offers a clear and actionable framework for reclaiming control, finding meaning, and building a more fulfilling career.

Follow Career Sessions 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/greg-hawks/.

Become a PathWise member today! Join at https://pathwise.io/join-now/

In this episode of Career Sessions, JR Lowry sits down with coach, speaker, and bestselling author Mary Olson Menzel to explore a question many professionals wrestle with: What does it really mean to build a career that lights you up and is it realistic to do so?

Mary challenges the conventional wisdom that playing it safe is the responsible path. Drawing from both personal experience and her work with clients, she argues that ignoring what energizes you can come at a much higher cost over time.

They discuss:

• What Mary calls your “light” and why it’s a real competitive advantage
• Why employers often choose energy and authenticity over credentials
• How to balance passion with financial responsibility using the concept of Ikigai
• Practical strategies for navigating job searches in a difficult market
• How to know when it’s time to pivot and how to do it thoughtfully
• The role of storytelling and networking in standing out

Mary also shares actionable tools from building a targeted job search strategy to tracking your own “light” through daily reflection.

 If you’re feeling stuck, burned out, or unsure what’s next, this conversation offers a practical and grounded path forward – one that doesn’t force you to choose between purpose and stability.

Follow Career Sessions 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/mary-olson-menzel/.

Become a PathWise member today! Join at https://pathwise.io/join-now/

In this episode of Career Sessions, JR Lowry speaks with behavioral scientist Jon Levy to explore what actually makes teams effective and why the answer isn’t what most people think.

Drawing on research across psychology, business, and even sports, Jon breaks down the hidden dynamics behind high-performing teams, including the overlooked role of “glue people” – those who quietly elevate everyone around them.

They discuss:

• Why emotional intelligence matters more than IQ on teams
• The surprising reason too much talent can hurt performance
• What “glue players” do differently and how to spot them
• How influence really works (and why it’s not about power)
• The role of trust, belonging, and feedback in team success

Jon also shares insights from his unconventional work building communities and designing experiences that foster deep human connection.

If you’re leading a team or want to become more effective within one, this conversation will challenge how you think about performance, influence, and success.

Follow Career Sessions with JR Lowry 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/jon-levy/.

Become a PathWise member today! Join at https://pathwise.io/join-now/

Why do so many successful leaders feel burned out, misaligned, or unfulfilled? According to Raj Sisodia and Nilima Bhat, the issue isn’t a lack of skill or intelligence, but rather a lack of healing. In this episode of Career Sessions, JR Lowry sits down with Raj Sisodia, co-founder of the Conscious Capitalism movement, and Nilima Bhatt, leadership coach and author, to explore the deeper emotional and psychological dimensions of leadership. Drawing from their new book Healing Leaders, they argue that many leadership challenges stem from unprocessed trauma, unconscious patterns, and a disconnect from purpose.

In this episode, JR, Raj, and Nilima discuss:

• Why leadership today is facing a “healing crisis”
• The hidden cost of success: burnout, misalignment, and “hollow achievement”
• Why traditional leadership training often fails to create lasting change
• How unhealed wounds shape leadership behavior
• Why many leaders resist doing inner work
• The seven steps to healing as a leader
• How trauma, if processed, can become a source of growth
• Why leadership starts with self-awareness

If you’re feeling stuck, burned out, or questioning your path, this episode offers a deeper lens on what it really takes to grow.

Follow Career Sessions with JR Lowry for weekly conversations on leadership, career growth, and navigating the future 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/raj-sisodia-and-nilima-bhat.

Become a PathWise member today! Join at https://pathwise.io/join-now/

What’s really holding leaders back? According to executive coach Muriel Wilkins, it’s often not skills, strategy, or experience -- it’s hidden beliefs. In this episode of Career Sessions, JR Lowry sits down with Muriel Wilkins, executive coach to senior leaders, host of Harvard Business Review’s Coaching Real Leaders, and author of Leadership Unblocked. Drawing from more than 20 years of coaching C-suite executives and analyzing hundreds of leadership cases, Muriel explains how deeply and often unconscious beliefs can quietly limit how leaders show up, make decisions, and work with others.

In this conversation, JR and Muriel unpack:

• The seven “hidden blockers” that often derail leadership effectiveness
• Why beliefs matter more than leadership tactics
• The difference between behavior and the belief driving it
• Why high-performing leaders often struggle with perfectionism
• How the belief “I know I’m right” can undermine collaboration
• How uncertainty and layoffs are amplifying leadership pressure today
• The mindset shift that unlocks leadership growth
• The framework for responding to challenges

If you want to become a more effective leader and experience leadership with greater clarity and ease, this conversation offers a powerful place to start.

Follow Career Sessions for weekly conversations on leadership, career growth, and navigating the future 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/muriel-wilkins/.

What does it take to walk away from a successful global executive career to pursue a deeper purpose?

In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Christopher Williams, former global executive and author of the new book C.O.U.R.A.GE., to explore how courage shapes our careers, leadership decisions, and personal growth.

Born in Sierra Leone and educated at Morehouse College, Christopher built an international career spanning four continents, multiple industries, and senior leadership roles. Yet despite professional success, he reached a turning point that forced him to ask a difficult question: What is the real purpose of my work?

That reflection led Christopher to rethink his career, step away from the corporate track, and dedicate his work to leadership, governance, and helping organizations balance business success with societal impact.

In this conversation, JR and Christopher discuss:

• Christopher’s journey from Sierra Leone to Morehouse College and a global executive career
• The moment he felt successful but unfulfilled—and what he did about it
• Why courage is essential for meaningful leadership and career growth
• The seven-part COURAGE framework for making bold decisions
• Why rejecting distracting voices is often the hardest part of change
• What living and leading across multiple cultures and continents taught him about people
• The courageous decision to leave the corporate ladder and redefine success
• How corporate boards and leaders can create greater societal impact
• Why individuals must reclaim their personal agency in a rapidly changing world

If you're questioning your career path, navigating a leadership transition, or seeking a clearer sense of purpose in your work, this episode offers powerful insights on how courage can reshape both your career and your life.

Follow Career Sessions, Career Lessons for weekly conversations with leaders, authors, and innovators sharing the lessons that shape meaningful careers.

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/christopher-williams.