

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 …

Why Planning Beyond the Portfolio Matters
Retirement isn’t just a finish line—it’s one of the biggest life transitions most people will ever navigate. In the debut episode of The Modern Retirement Playbook: Planning Beyond the Portfolio, host Jason Matthews shares the personal experiences that shaped his approach to retirement planning and…