Hidden Retirement Planning Risks with Chris Maduri

Chris Maduri has spent nearly two decades helping people prepare for one of life’s biggest transitions: retirement—the moment when work no longer defines the structure of your days.

He began his career just before the 2008 Financial Crisis, an experience that shaped how he sees risk. Watching well-built plans unravel under pressure taught him early that markets don’t always cooperate—and assumptions don’t always hold. Since then, his focus has been clear: build plans rooted in predictability, reliable income, and the ability to hold up in real-world conditions—not just ideal ones.

Over time, Chris noticed something deeper. The people who thrive in retirement aren’t just financially prepared—they’re personally prepared. Because retirement doesn’t just change your income… it changes your identity, your routine, your sense of purpose, and how you relate to your time and the people around you.

That’s why Chris frames retirement as the “fourth quarter of life”—and, if you’ve done things right, a little overtime. In his view, the goal isn’t just to retire from something, but to step intentionally into something meaningful. A great plan answers a simple but powerful question: What are you retiring to?

He also helps people understand that risk evolves. During your working years, volatility is something you ride through. In retirement, it feels different. You’re no longer accumulating—you’re drawing down.