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Career Sessions

JR Lowry

How do you build a successful career, become a better leader, navigate career changes, and find fulfillment in your work?

On Career Sessions, host J.R. Lowry explores these questions through candid conversations with accomplished leaders, entrepreneurs, authors, academics, and professionals who have navigated the ups and downs of working life. They share not just their successes, but the difficult decisions, career setbacks, unexpected opportunities, and hard-won lessons that helped shape their journeys.

Every episode delivers real-world stories and practical career advice to help you tackle the challenges that matter most: advancing your career, changing jobs, developing leadership skills, managing workplace relationships, overcoming setbacks, and adapting to a rapidly changing world of work.

What makes Career Sessions different? We go beyond conventional career advice and polished success stories to uncover what actually works, what doesn't, and what people wish they'd known earlier. The goal is to both inspire you and give you ideas and strategies you can put to work in your own career.

Your host, J.R. Lowry, brings a unique perspective shaped by a career spanning the U.S. Air Force, McKinsey, senior executive roles in financial services, and entrepreneurship. Drawing on decades of leadership experience and hundreds of conversations with fascinating people, J.R. connects the lessons of others to the career decisions and challenges we all face.

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#227
Monday · 36 min
When Your Strengths Become Weaknesses: How To Reinvent Yourself As A Leader with Andrea Petrone
What happens when the strengths that made you successful become the very things holding you back? You've worked hard, built your career, and earned greater responsibility. But now something isn't working. Your team isn't responding the way you'd hoped. Your leadership style feels less effective. Or perhaps you've hit a career plateau despite doing everything that made you successful in the past. The problem may not be your skills or experience. It may be that the leadership habits and behaviors that got you here are no longer what you need to move forward. In this episode of Career Sessions, host J.R. Lowry talks with Andrea Petrone, executive coach, leadership advisor, and author of Reinvention at the Top: The Playbook for CEOs to Lead Under Pressure, about why successful professionals get stuck—and how to reinvent yourself as a leader without losing your authenticity. Drawing on his own experience as a young CEO and his work coaching senior executives, Andrea explains how our greatest strengths can become liabilities, why we revert to ineffective leadership behaviors under pressure, and how to recognize when it's time to change. Andrea's lessons are relevant well beyond the C-suite. You'll learn: Why success can become a trap: How the strengths and leadership habits that helped you advance can eventually limit your effectiveness. How to recognize when your leadership style isn't working: The subtle warning signs that your team may be disengaging, withholding feedback, or losing confidence. Why your past influences how you lead: How childhood experiences, former bosses, and early career lessons shape your leadership instincts—especially under pressure. How to lead with greater authenticity: Why trying to project confidence and authority can undermine your effectiveness, and how quiet leadership can build trust and influence. How to reinvent yourself without putting your career on hold: Practical steps to question old assumptions, change ingrained behaviors, and develop a leadership approach that fits your current responsibilities. Whether you're a new manager, an experienced executive, or a professional preparing for your next career move, this conversation offers a practical approach to leadership development, career growth, self-awareness, and personal reinvention.Because sometimes the biggest obstacle to becoming a better leader isn't what you don't know. It's what you need to unlearn. About the guest: Andrea Petrone is an executive coach, leadership advisor, and author of Reinvention at the Top. He works with CEOs and senior leaders to help them navigate change, lead under pressure, and develop more authentic and effective leadership approaches. Learn more about Andrea's work and access his leadership assessment at reinventionatthetop.com. And be sure to check out my forthcoming book, written with Daniela De Luca, Be the Boss You Wish You'd Had: A Preople-First Guide to Management, available for pre-order wherever you buy your books. For more info, visit, https://pathwise.io/be-the-boss/ 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/andrea-petrone/. Enjoying Career Sessions? Here are more ways to put these ideas into practice: Become a better manager. Explore Be the Boss You Wish You Had: A People-First Guide to Management, J.R.'s forthcoming book with organizational researcher Daniela De Luca. Packed with practical advice and real-world examples, it's designed to help you lead people more effectively and confidently. Learn more and pre-order at https://pathwise.io/be-the-boss/. Take charge of your career. Discover PathWise's career development resources, courses, and community to help you navigate career decisions, build new skills, and achieve your professional goals. Visit https://pathwise.io/for-individuals/. Develop your people and te Hosted on Acast. See acast.com/privacy for more information.
#226
November 2 · 33 min
Are Managers Too Nice? The Case for Tougher Leadership, with Matt Hunter
Are today's managers too nice? In our efforts to create more compassionate workplaces, have we gone too far in avoiding difficult conversations, lowering expectations, and letting poor performance slide? In this episode of Career Sessions, J.R. Lowry sits down with Matt Hunter, executive coach and co-author of Tough Enough: How to Lead a Team to Greatness Without Being a Jerk, to explore why great leadership requires more than kindness. It also demands candor, accountability, high standards, and the willingness to make uncomfortable decisions. Matt argues that many organizations have fallen into what he calls the "Mirage of Compassion"—creating the appearance of caring for employees while failing to challenge them to grow and perform at their best. But there's a fine line between being appropriately tough and becoming the kind of boss nobody wants to work for. Together, J.R. and Matt discuss how to find that balance, including: Why managers often confuse compassion with avoiding discomfort How to establish clear expectations and hold people accountable without being unfair Why psychological safety should encourage honest disagreement, not suppress it How leaders can become more comfortable giving—and receiving—difficult feedback Why the right level of toughness depends on your ambitions, circumstances, and stage of life They also explore the risks of taking toughness too far, drawing lessons from high-profile business leaders and Matt's own experiences as an entrepreneur and executive coach. Whether you're managing a team, aspiring to leadership, or simply trying to navigate a demanding workplace, this conversation offers a thought-provoking perspective on what it really takes to achieve high performance without sacrificing humanity. The takeaway: Being a people-first leader doesn't mean making everyone comfortable. It means caring enough to tell the truth, set meaningful expectations, and help people become their best. 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-hunter. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#225
October 26 · 33 min
When Putting People First Results In Putting Yourself Last, with Kristen Hadeed
What happens when your commitment to putting others first comes at the expense of your own well-being? Kristen Hadeed built Student Made into a successful business known for its people-first culture. But after years of prioritizing her team and company above herself, she reached a breaking point. She had lost her passion, felt disconnected from herself, and realized that the leadership philosophy she believed in had become a source of burnout and resentment. In this episode of Career Sessions, host J.R. Lowry sits down with Kristen, author of Permission to Screw Up and Human Leadership, to explore her journey from people-pleasing entrepreneur to a leader who understands that caring for others shouldn't mean abandoning yourself. Kristen shares why she made the difficult decision to close the business she'd spent years building, how deeply held beliefs from childhood shaped her leadership style, and why avoiding uncomfortable conversations can actually damage the relationships we're trying to protect. They also discuss practical ways to become a more effective and authentic leader, including how to recognize the beliefs holding you back, make time for self-reflection, give meaningful feedback, and have difficult conversations with courage and compassion. Whether you're leading a team, navigating burnout, or questioning whether you've outgrown your current role, this conversation offers a powerful reminder: great leadership isn't about being perfect or keeping everyone happy. It's about having the self-awareness and courage to lead yourself as well as others. 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/kristen-hadeed/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#224
October 19 · 37 min
You’re Always in the Job Market: How to Manage Your Career Before You Need To, with Kelly Kay
A lot of people spend plenty of time thinking about how to succeed in their jobs, but far less time thinking about how to choose the right jobs in the first place. In this episode of Career Sessions, J.R. Lowry sits down with Kelly O. Kay, managing partner at executive search firm Heidrick & Struggles and co-author of Show Up to Win: How to Land the Leadership Role You Want. Drawing on decades of experience advising executives and companies, Kelly shares an insider’s perspective on how to manage your career more deliberately. He explains why you should take the recruiter call even when you’re happy where you are, how to test your value in the market, what makes a candidate’s story compelling, and how to evaluate whether an opportunity is actually right for you. J.R. and Kelly also discuss why internal candidates sometimes struggle against outsiders, how to recover professionally after being fired, the subtle ways candidates sabotage themselves during the hiring process, and why your reputation can follow you for decades. Whether you’re actively considering a move or perfectly happy in your current role, the message is simple: the best time to manage your career is before you need to. Check out the full series of “Career Sessions” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kelly-kay/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#223
October 12 · 27 min
Stop Following Someone Else’s Career Playbook, with Andy Paul
You may not think of yourself as a salesperson, but every day at work, you’re selling something—an idea, a proposal, your capabilities, or even yourself. In this episode of Career Sessions, J.R. Lowry sits down with sales expert, author, and longtime podcast host Andy Paul to explore what the rest of us can learn from great salespeople about influence, curiosity, and human connection. Andy explains why the best way to persuade someone isn’t to push harder, but to understand what matters to them. He shares how asking better questions and truly listening can strengthen relationships, why curiosity is often trained out of us as we move through school and work, and how to avoid making conversations about ourselves. The conversation also moves beyond sales to a bigger career question: Are you building the career you actually want—or simply following someone else’s playbook? Andy discusses why success is situational, how to find environments where you can be yourself, the importance of choosing the right boss, and why it’s sometimes better to leave a bad fit rather than keep trying to make it work. Along the way, Andy shares lessons from nearly five decades in business—and a reminder that there’s no age limit on taking on new challenges. In this episode, you’ll learn: Why everyone is selling, whether they realize it or not How curiosity can make you more influential The difference between listening to understand and listening to respond Why great questions create stronger relationships How to find work environments that fit your strengths and values Why you should define success on your own terms 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/andy-paul/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#222
October 5 · 33 min
Success Isn’t Enough: Building a Work Life Worth Living, with Jeff Westphal
What if you achieve everything you thought you wanted in your career, and still find yourself wondering if that's really all there is? Former Vertex CEO Jeff Westphal joins host J.R. Lowry to discuss how you can build a Work Life Worth Living when traditional status isn't enough. Jeff Westphal spent two decades as CEO of Vertex, helping grow the company from roughly 75 employees to more than 1,000 and increasing its value fortyfold. Along the way, he started asking deeper questions about purpose and why listening can be far more powerful than having all the answers. He shares how an intense focus on reflection transformed his leadership and helped him create an environment where employees felt truly invested. They also examine how rapid changes in AI mean distinctly human qualities like empathy, judgment, and connection will define our professional future. Whether you're rethinking your path or leading a team, this conversation will help you reflect on what truly makes your career meaningful. 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/jeff-westphal/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#221
September 28 · 41 min
Why You? How to Stand Out in a Crowded Market, with April Dunford
Most professionals assume great work speaks for itself, but solid Product Positioning proves that value never communicates automatically. When competitors offer flashy feature checklists or when crowded markets blur real differentiation, buyers and hiring managers get confused quickly. Host JR Lowry sits down with April Dunford, leading positioning expert and bestselling author of Obviously Awesome and Sales Pitch, to unpack why building something valuable is only half the battle. They walk through actionable frameworks to move past surface features, clarify unique value themes, and align internal teams before ever pitching external buyers. Together, they break down how individuals can treat their career journeys like high-stakes B2B products by narrowing focus, embracing natural strengths, and knowing exactly when to walk away from poor-fit opportunities. Finally, they tackle the rise of artificial intelligence, outlining why automated tools raise the bar for genuine business strategy rather than replacing it. 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/april-dunford/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#220
September 21 · 31 min
The Real Job Of A Leader, With Dave Ulrich
What's the real job of a leader? According to Dave Ulrich, it isn’t having all the answers, building your own reputation, or even telling a compelling story about where you’re going. Great leaders help the people around them build their stories—and create value for others. In this episode of Career Sessions, J.R. Lowry sits down with Dave, one of the world’s most influential thinkers on leadership, talent, and organizational effectiveness, for a wide-ranging conversation about what great leadership looks like in a rapidly changing world. They explore why many of the fundamentals of leadership are timeless, even as technology and workplace expectations change dramatically. Dave explains the critical distinction between values—what matters to you—and value—what your actions create for someone else. He also shares a simple question leaders can use to rethink how they spend their time: What will happen in someone else's life because of what I do today? Dave and J.R. also discuss the choices and trade-offs that come with ambition, why our definition of success should change at different stages of life, and what Dave learned from deliberately stepping back from his own career while raising his children. And, inevitably, they tackle AI. Dave argues that AI makes distinctly human capabilities more important, not less. As information becomes ubiquitous, leaders will increasingly differentiate themselves through vision, innovation, emotion, judgment, and wisdom. The conversation also explores learning agility, navigating uncertainty, admitting when you don’t know the answer, and becoming comfortable figuring things out alongside the people you lead. Whether you’re a first-time manager or an experienced executive, this episode is a reminder that leadership ultimately isn’t about you. It’s about what becomes possible for other people because you were there. 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/dave-ulrich/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#219
September 14 · 30 min
Why Hiring Feels Broken—and How to Get Hired Anyway, with Lorena Prego Ojeda
Finding a job has never been easy, but today’s hiring process can feel particularly frustrating. Hundreds of applicants compete for a single role, AI is reshaping how candidates are screened, and qualified people often struggle to get noticed. At the same time, employers insist they can’t find the talent they need. So what’s really going on? In this episode of Career Sessions, J.R. Lowry talks with Lorena Prego, founder and CEO of Prometeo Talent, who has spent two decades in recruiting and helped companies make more than 5,000 hiring decisions. Lorena takes us behind the scenes of the hiring process to explain what recruiters and hiring managers actually look for—and what separates candidates who consistently land opportunities from those who struggle to break through. They discuss why applying to hundreds of jobs may actually hurt your search, how to take more control of an interview, what recruiters notice when comparing your resume and LinkedIn profile, and how to build productive relationships with search firms. They also explore how AI and remote work are transforming recruiting and why communication, critical thinking, adaptability, and the ability to keep learning will become even more important. Whether you’re actively looking for a job or simply want to position yourself for your next opportunity, this episode offers a practical insider’s guide to getting noticed, telling your story, and managing your career for the long term. 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/lorena-prego-ojeda/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#218
September 7 · 36 min
How to Stay Valuable in the Age of AI, with Liat Ben-Zur
AI can already draft, summarize, analyze data, write code, and find patterns faster than most of us. So as these capabilities become increasingly commonplace, what will make you valuable? In this episode of Career Sessions, J.R. Lowry talks with Liat Ben-Zur, former senior executive at Microsoft, Qualcomm, and Philips and author of The Bias Advantage, about how AI is changing the skills that matter most—and why some of the experiences that once made your career harder may actually have prepared you for what's coming next. Liat argues that the answer isn't trying to compete with AI at what it does best. Instead, we need to double down on capabilities machines struggle to replicate: judgment, adaptability, empathy, ethical decision-making, creativity, influence, and the ability to see what others miss. They also discuss why hard work alone isn't enough to advance your career, how to make your impact visible without becoming overly self-promotional, why nonlinear careers may become increasingly valuable, and how to use AI to strengthen your thinking rather than replace it. In this episode, you'll learn: Which human capabilities will become more valuable as AI gets better Why career setbacks and being an outsider can build unexpected advantages How to make sure your contributions are recognized—not just delivered Why career range may be more valuable than narrow specialization How to use AI as a thinking partner without weakening your own judgment What leaders will need to do differently as AI reshapes organizations If you're wondering how to remain relevant, differentiated, and valuable as AI transforms the workplace, this conversation offers a practical roadmap. 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/liat-ben-zur/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#217
September 1 · 36 min
How To Stay Human In The Age Of AI, With Johan Roos
AI can write, analyze, summarize, code, and create—and its capabilities are advancing at a remarkable pace. So as machines become more intelligent, what will keep humans indispensable? Johan Roos believes the answer lies in what he calls “human magic”: the distinctly human capabilities that technology can support, but never replace. Johan is an internationally recognized strategy scholar, former business school dean, co-creator of LEGO Serious Play, and author of Human Magic. In this episode of Career Sessions, Johan and J.R. explore why our advantage in an AI-powered world comes not from trying to compete with machines, but from becoming more human as AI gets smarter. They discuss the five capabilities at the heart of human magic—curiosity, creativity, critical thinking, communication, and collaboration—and why practical wisdom and sound judgment are becoming increasingly valuable. They also examine the danger of “cognitive offloading”: relying so heavily on AI that the very skills that differentiate us begin to atrophy. Johan shares what leaders should be doing differently in the AI era, including asking better questions, creating the conditions for their teams to think deeply, and focusing the AI conversation on transforming tasks rather than eliminating jobs. The conversation also revisits the origins of LEGO Serious Play and what Johan learned about creativity, collaboration, and better decision-making by getting people out of conventional meetings and thinking with their hands. Those lessons may be even more relevant as organizations figure out how humans and AI should work together. The takeaway: use AI intensely to prepare—but when the room is watching, show up as a human. 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/johan-roos/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#216
August 24 · 34 min
Why Great Teams Work Differently, with Ron Friedman
Why do some teams consistently outperform while others—with equally talented people—struggle with endless meetings, constant interruptions, and burnout? In this episode of Career Sessions, JR Lowry sits down with organizational psychologist and bestselling author Ron Friedman to explore what separates exceptional teams from average ones. Drawing on research involving more than 6,000 workers for his new book, Super Teams, Ron reveals that only about 8% of teams qualified as “super teams”—and that what distinguishes them often runs counter to conventional wisdom about productivity, collaboration, and where work should happen. Their conversation covers: Why how a team works matters more than where it works—and what that means for the ongoing debate over remote, hybrid, and in-office work How excessive meetings and always-on communication undermine productivity—and why great teams establish clear meeting guidelines Why individual productivity hacks can actually create bottlenecks for the rest of the team The importance of protecting focused work and why “brainwriting” can produce better ideas than traditional brainstorming How active recovery outside of work can improve performance—and why leaders’ recovery habits can affect their teams The three ingredients of workplace trust: competence, caring, and consistency Why shared goals, role clarity, and interdependence are essential for creating a true team mentality Practical ways to take control of your workday by looking forward, looking backward, and staying present Why working longer hours eventually produces diminishing—and even negative—returns How high-performing teams are approaching AI differently, including openly sharing prompts and learning from one another rather than hiding their AI use The central message is simple: great teams aren't built by assembling the smartest people or forcing more collaboration. They're built intentionally, by creating the conditions that allow talented people to do their best work—both individually and together. Whether you lead a team or work as part of one, this conversation offers practical, research-backed ideas for reducing friction, building trust, protecting people's time, and creating a team that performs at a higher level. Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly conversations on careers, leadership, and the changing world 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/ron-friedman/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io Hosted on Acast. See acast.com/privacy for more information.
#215
August 17 · 30 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 Hosted on Acast. See acast.com/privacy for more information.
#214
August 10 · 35 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 Hosted on Acast. See acast.com/privacy for more information.
#213
August 3 · 32 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 Hosted on Acast. See acast.com/privacy for more information.
#212
July 27 · 34 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 Hosted on Acast. See acast.com/privacy for more information.
#211
July 20 · 32 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 Hosted on Acast. See acast.com/privacy for more information.
#210
July 13 · 40 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 Hosted on Acast. See acast.com/privacy for more information.
#209
July 6 · 39 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 Hosted on Acast. See acast.com/privacy for more information.
#208
July 1 · 32 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/ Hosted on Acast. See acast.com/privacy for more information.

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