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Career Sessions

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.

Latest Episodes:

How Courage And Purpose Can Help You Find Your True Path, With Christopher Williams Mar 19, 2026

Show notes

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.

From 1,000 Rejections To Millions Hired: How Andrei Kurtuy Built Novorésumé & What Actually Makes A Resume Work Mar 12, 2026

Show notes

What does it take to go from sending 1,000 unanswered resumes to building a platform used by millions of job seekers worldwide?

In this episode of Career Sessions, Career Lessons, J.R. Lowry sits down with Andrei Kurtuy, co-founder of Novorésumé, to unpack the hard lessons he learned navigating rejection, building a global resume platform from scratch, and studying what actually gets candidates hired.

After moving to Denmark for school, Andrei struggled to land a job until one key insight changed everything: it wasn’t about luck. It was about positioning. That realization ultimately led to the founding of Novorésumé, now one of the world’s most widely used resume builders.

In this conversation, J.R. and Andrei discuss:

Why Andrei sent 1,000 resumes with no traction
The “aha moment” that changed his job search strategy
What recruiters look at first when scanning resumes
Why tailoring matters more than ever
The biggest resume mistakes even executives make
How to handle career pivots and resume gaps
What applicant tracking systems (ATS) really parse
One-page vs. two-page resumes
How AI is transforming both resume writing and candidate screening
The skills that will matter most in an AI-driven job market

If you’re actively job searching, considering a career pivot, or simply want to future-proof your professional story, this episode delivers practical research-backed advice.

Follow Career Sessions, Career Lessons for weekly episodes you’ll never want to miss.

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/andrei-kurtuy.

How Bold Questions Drive Leadership, Engagement & Performance With Dr. Debra Clary Mar 06, 2026

Show notes

Curiosity isn’t a soft skill. It’s a strategic advantage.

In this episode of Career Sessions, Career Lessons, JR chats with Dr. Debra Clary, author of The Curiosity Curve: A Leader’s Guide to Growth and Transformation Through Bold Questions, and explores why curiosity is the missing link in leadership, engagement, and high performance.

Drawing on four decades of corporate leadership experience, Dr. Clary explains how curiosity directly impacts employee engagement, innovation, decision-making, and organizational culture.

Together, they discuss:

The research-backed link between curiosity and performance
Why 65% of millennials report being disengaged at work
How leaders unintentionally kill curiosity
The difference between exploration and execution
The four components of the “Curiosity Curve”
Why “I don’t know” may be the most powerful thing a leader can say
Whether AI enhances or diminishes critical thinking
How to build a culture of curiosity during transformation or change
Practical questions leaders can ask to assess curiosity in candidates and teams

Dr. Clary also shares how organizations can measure curiosity through diagnostics, activate “curiosity ambassadors,” and create alignment from the executive team down.

If you care about leadership development, culture transformation, employee engagement, innovation, or becoming the kind of leader people actually want to work for, this conversation is for you.

Follow the podcast for weekly leadership and career insights.

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/dr-debra-clary.

Navigating A Multi-Generational Workforce & Getting Your Career In Shape With Dr. Candace Steele Flippin Feb 26, 2026

Show notes

What do Gen Z, Millennials, Gen X, and Baby Boomers really want from work, and how can leaders navigate a multi-generational workforce without falling into stereotypes?

In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Dr. Candace Steele Flippin to explore generational differences in the workplace, evolving leadership expectations, and how employees can future-proof their careers in an era shaped by technology, layoffs, and social change.

Dr. Flippin unpacks how value systems are shaped by world events, why compensation transparency matters more than ever, and how purpose has become central to career decisions post-COVID.

You’ll learn:

How generational theory shapes workplace expectations
Why Gen Z and Millennials prioritize purpose, empathy, and fair pay
The leadership skills that cut across generations: active listening, collaboration, and empathy
How the social contract between employers and employees has changed
The rise of the gig economy and career self-management
Why pay transparency is reshaping employee expectations
How to avoid generational stereotyping at work
The 5-step SHAPE framework from Dr. Flippin’s book Get Your Career in Shape

If you want to manage your career more proactively, this conversation is for you.

Subscribe for more conversations on career growth, leadership development, and navigating today’s workplace.

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/dr-candace-steele-flippin.

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

Why OKRs Fail: Radhika Dutt on Puzzle-Driven Product Strategy, AI, and Building Better Products Feb 16, 2026

Show notes

If you’re a product manager, founder, executive, or even an individual contributor navigating OKRs, AI, and innovation pressure, this episode of Career Sessions, Career Lessons offers a practical reframing of how great products and meaningful work actually get built.

Host JR Lowry sits down with Radhika Dutt, author of Radical Product Thinking, to unpack why traditional goals, OKRs, and performance targets often do more harm than good in modern product organizations.

Drawing from her experience as an MIT-trained engineer, startup founder, and product leader across industries, Radhika introduces an alternative: puzzle setting and puzzle solving. Rather than optimizing for short-term metrics, she says that the most successful teams spend more time in the problem space asking better questions, learning faster, and adapting intelligently.

Together, JR and Radhika explore:

Why OKRs and targets could kill curiosity and innovation
The difference between optimizing numbers and solving the right problem
How “puzzle-driven” teams outperform “goal-driven” teams
The dangers of AI-driven “product slop” and what humans must do better than machines
Leadership lessons on delegation, critical thinking, and psychological safety
AI’s impact on recruiting and culture

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/radhika-dutt/.

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

How Curiosity Shaped My Career Journey, With Ryan Hawk Feb 09, 2026

Show notes

The journey from individual contributor to effective manager is often called the most significant transition of a career—a shift not just in responsibilities, but in identity. Yet, the foundations of great leadership often start with a more personal, foundational practice: curiosity and continuous self-improvement. In this deep-dive interview, we sit down with leadership expert and podcast host, Ryan Hawk of The Learning Leader Show, to unpack his best-selling book, Welcome to Management, and the surprising lessons he's gathered from interviewing hundreds of the world’s most successful leaders. Ryan shares the critical mindset shifts every new manager needs to make, why leading yourself is the necessary first step, and how embracing a learning leader mindset—fueled by relentless curiosity—was the unexpected catalyst that propelled his own professional journey from cold-calling sales rep to full-time entrepreneur and author.

If you're looking to master the art of management, cultivate psychological safety in your team, or simply unlock the compounding power of daily personal growth, you won't want to miss these powerful insights on how curiosity shapes success.

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/ryan-hawk.

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

How To Boost Your Executive Presence And Visibility, With Katy McFee Feb 02, 2026

Show notes

The term executive presence shows up constantly in professional feedback—but what does it actually mean? For many ambitious professionals, especially women, this vague phrase becomes a frustrating barrier that leaves them overlooked and unsure how to advance. Today, we unpack executive presence with former tech executive and executive coach Katy McFee. She shares how she bridged the gap from director to VP—and how she now helps women do it faster. Inside, you’ll learn why “head-down hard work” stops paying off at senior levels, how to push back on vague feedback and get clarity, and Katy’s practical advice for building authentic visibility through mindset, skills, and habits. If you’re ready to stop feeling stuck and start showing up as a confident, influential leader, keep reading.

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/katy-mcfee.

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

How To Go From Surviving To Thriving, With Jon Rosemberg Jan 26, 2026

Show notes

If we are forever in survival mode, unlocking and unleashing our full potential would be impossible. Jon Rosemberg, Co-Founder Of Anther, reveals what it takes to achieve your thriving mode. He joins J.R. Lowry to talk about his newest book A Guide To Thriving, as well as what it takes to feel a greater sense of control over the things happening in your life. Jon delves into the idea of giving yourself agency to make the most of your human experience and experience profound self-transformation. Find out how to escape the constant struggle of survival mode and get into thriving mode that leads to fulfillment.

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-rosemberg.

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

How To Master Your Intentions And Lead With Purpose And Power, With Bianca D'Alessio Jan 20, 2026

Show notes

If you learn how to live with intention, you can lead with purpose and manifest all of your goals in life. This is exactly what Bianca D'Alessio did, which led to her becoming the number one real estate broker in New York City. She joins J.R. Lowry to share all about her journey centered on authenticity, leading with lasting impact, and discovering gratitude even in her biggest failures. Bianca also talks about her new book, Mastering Intentions, wherein she breaks down daily practices to amplify your own power. Discover how to manage your narrative, be comfortable with vulnerability, and unlock resilience both in business and in life.

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/bianca-dalessio.

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

How To Steer Your Small Business Through The Stages Of Growth, With Matt Pohl Jan 13, 2026

Show notes

Every entrepreneur dreams of scaling their business, but what happens when business growth stalls? You've hit a revenue ceiling, your team is expanding, and suddenly, the systems that once brought success seem to be working against you. Matt Pohl, founder and CEO of The ReWild Group, faced this exact challenge—taking his own plateaued business from $1 million to $4 million in three years after discovering a framework that fundamentally changed how he viewed organizational complexity.

In this deep-dive interview, Matt shares the revolutionary concept of organizational rewilding, explaining why employee count, not revenue, is the true driver of complexity and growth stages. Discover the hidden barriers most business owners overlook, the critical difference between being owner-centric and enterprise-centric, and the "missing gray wolves" you need to reintroduce into your company's ecosystem to thrive through chaos and competition. If you're struggling to sustain momentum, or just want to make growth easier, Matt's roadmap is the essential guide to lightening your entrepreneurial backpack.

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/matt-pohl/.

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

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