The Modern Retirement Playbook

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 growing gap in retirement savings, the conversation highlights the challenges many families face. Jason...

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 stress-testing retirement plans, understanding claiming strategies, and exploring ways to supplement...

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 a false sense of security, trigger unnecessary tax burdens, and even increas...

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,” AI voice scams, romance fraud, and impersonation schemes designed to t...

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 annuities, fixed, variable, and fixed‑indexed annuities, along with common misconceptions abo...

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 Social Security, 401(k) contributions, taxes, and guaranteed income planning, while also weigh...

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 health insurance and Medicare don’t work the way many expect, and how care often ha...

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. Host Jason Matthews explores common retirement roadblocks, from taxes and inflation...

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 decisions. Through real‑world examples, the conversation explores how childhood experien...

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 why emotions matter just as much as numbers. The conversation explores how life e...