Seven Money Conversations That Will Change Your Life with Skyler Fleming

Welcome back to Don’t Retire… Graduate! In today’s episode, we’re deep diving into the power of money conversations—why talking about your finances is crucial, and how it can serve as the foundation for a life of financial independence and fulfillment. Joining me is Skyler Fleming, financial coach and host of the “Money Talk with Skyler Fleming” podcast. With over 150 episodes under his belt and firsthand experience working his way up in a credit union, Skyler has become an enthusiastic advocate for breaking the taboo around discussing money and making finance approachable for everyone.

During our conversation, Skyler and I explored how simple, honest conversations can be the gateway to better financial habits, awareness, and ultimately, confidence. Skyler shared his journey, from fielding frustrated calls at a credit union to helping everyday people master their money both one-on-one and through podcasting. We unpacked his signature “seven money talking points,” covering everything from emergency funds and tracking your cash flow to the big philosophical questions about debt and financial goals. We compared coaching versus planning, debated the age-old question of whether or not to pay off debt early, and dove into how technology and automation can make managing your finances easier and less intimidating.

We also discussed mindset shifts through each life stage—why younger folks might want to maximize cash flow and debt leverage, while those closer to retirement may crave the security of being debt-free. Skyler and I both underscored the importance of not just focusing on retirement, but also on all the fun and meaningful goals that happen along the way: dream vacations, supporting your community, or funding your kids’ education. Ultimately, whether you’re in a partnership or on your own, we talked about building your own “money buddy” system for accountability and growth.

5 Key Takeaways:

1. Start Money Conversations Early and Often: Breaking the taboo and having simple, honest money talks—whether with a partner, friend, or coach—can demystify finances and set you up for success, no matter your starting point.
2. Master the Seven Money Talking Points: Skyler’s framework covers crucial questions: your emergency strategy, how you make, spend, and save money, your approach to debt, what you want your retirement to look like, and your big, aspirational financial goals.
3. Automation and Tracking Are Allies: Whether you love spreadsheets or apps, regularly tracking income and expenses—and leveraging automation—can take the pain out of budgeting and ensure your money goals stay on track.
4. Debt Decisions Are Personal: The question of paying off debt isn’t just about numbers; psychology and life stage play huge roles. Make debt payoff decisions based on your comfort, goals, and current opportunity costs, not just the math.
5. Design the Life You Want—Not Just a Retirement: Planning isn’t limited to the finish line of retirement. Identify and segregate funds for your “big money goals,” and build systems (and buddies!) to stay accountable and intentional every step of the way.

Join us as we explore how a little financial transparency and proactive planning can empower you to live with passion and purpose—today, in retirement, and every step in between. Don’t forget to subscribe, rate, and share this episode with anyone eager to have their own “money talks” and transform their financial future!