Career Sessions

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

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

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

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

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