Why Smart People Get Financially Stuck (and How to Break Free), with Carrie Joy Grimes
Career SessionsShow Notes
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
More from Career Sessions
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.
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.
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.
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.