



Are You Doing the Right Financial Moves at Every Stage of Life?
What should your finances look like at every decade of your life? In this episode, Jason Matthews walks through a decade-by-decade approach to building financial health, from your twenties to your seventies and beyond. The conversation highlights how early habits like saving and automation can shap…

Can You Still Afford the American Dream in Today’s Economy?
Is the American Dream still within reach or just getting more expensive? In this episode, Jason Matthews explores how rising costs, longer lifespans, and shifting financial responsibilities are reshaping what retirement looks like today. From the realities of multi-generational households to the gr…

A 2032 Countdown: What Happens If Social Security Falls Short?
Could a future cut to Social Security reshape your retirement income? With projections pointing to a 2032 shortfall and potential benefit reductions, this episode breaks down what it could mean for retirees and those planning ahead. Jason Matthews discusses how to prepare for uncertainty, including…

Is Your Money Working—or Just Sitting There?
Is your money quietly losing value even while it feels safe in the bank? In this episode of The Modern Retirement Playbook, Jason Matthews unpacks the concept of “dead money”—cash that isn’t working hard enough to keep up with inflation or taxes. Jason explores how too much idle savings can create …

Think You’re Scam-Proof? Think Again
Think it can’t happen to you? Today’s scammers are counting on that assumption. In this episode of The Modern Retirement Playbook, Jason Matthews breaks down how fraud targeting retirees has become more sophisticated—and more costly than ever. He discusses common tactics like urgent “bank alerts,” …

Annuities: Fact, Fiction, and the Fine Print
Few retirement topics spark as much debate—or confusion—as annuities. In this episode of The Modern Retirement Playbook, Jason Matthews breaks down what annuities are, why opinions about them vary so widely, and how different types work in real retirement plans. The conversation covers income annui…

Should You Work One More Year?
Is working one more year the smartest move—or the wrong tradeoff? In this episode of The Modern Retirement Playbook, Jason Matthews breaks down the financial, tax, healthcare, and emotional considerations behind delaying retirement. The conversation explores how one extra year of income can affect …

The Retirement Risk Most People Don’t Want to Talk About
What if the biggest retirement risk isn’t market volatility, but what happens when health changes? In this episode of The Modern Retirement Playbook, Jason Matthews unpacks what long-term care really means and why it’s often misunderstood. He explores how long-term care shows up in real life, why h…

Why Big Paychecks Still Lead to Broke Retirements
Sixty percent of NBA players go broke within five years of retiring—so what does that reveal about everyday retirement planning? Using a Shaquille O’Neal quote as a jumping-off point, this conversation unpacks why retirement success isn’t about how much money you have, but how you plan around it. H…

How Childhood Money Beliefs Follow You Into Retirement
Your relationship with money didn’t start with your first paycheck—it started long before that. In this episode of The Modern Retirement Playbook: Planning Beyond the Portfolio, Jason Matthews dives into the emotional baggage people carry around money and how those beliefs quietly shape retirement …