Should I Trust AI With Money Advice? An Expert’s Honest Answer

What does it actually take to build a good life? Dr. Robert Waldinger has spent decades studying that question—and he has 85 years of data to back up his answer. As director of one of the longest-running studies of human life ever conducted, the esteemed Harvard professor joins host Jennifer Borget to unpack what actually makes people thrive: why relationships matter more than your résumé, how chronic stress—including financial stress—does real damage to the body, and why it's never too late to change course. This is the season finale of A Better Way to Money, and it's the conversation we've been building toward all season.

We spend a lot of time on this show talking about how to grow, protect, and plan with your money. But today’s guest has spent most of his career asking a different question: Once you have money, can the way you spend it actually change how happy you are? Harvard Business School Professor Michael Norton’s research points to something most of us have backward—it’s not how much money you have; it’s how you use it to help and connect with the people around you.

Everyone tells you childcare is expensive. But knowing that and actually living it are two very different things. Host Jennifer Borget sits down with author and childcare expert Christina Eaglin—author of Who's Watching My Baby? and expert on navigating the childcare maze —to talk through the stuff nobody prepares you for: what childcare really costs beyond the monthly invoice, how to vet a provider before you're already attached, why you need a backup plan before you ever need to use it, and how to have the money conversations with your partner before the pressure is on. Think of it as the conversation you'd want to have with a friend who's already been through it, so the chaos of childcare doesn't hold back your finances—or your future.

Thinking about a career pause to take care of your growing family? Host Jennifer Borget sits down with Neha Ruch–Stanford MBA, founder of The Power Pause, and USA Today bestselling author—to talk through the benefits of a pause when you plan it out with purpose. We cover the budgeting conversations, the identity shift, and how to come back stronger on your own terms.

Most people picture a financial advisor behind a mahogany desk, running spreadsheets for people with serious money. Jonathon Gais grew up thinking the same thing—until he became one. Now, as VP of Client Experience and Personalized Planning at Northwestern Mutual, Jonathon shapes how NM advisors across the country think about financial planning. His core message: You don’t need to have it all figured out before you talk to an advisor. The right one helps you make smarter choices—and becomes the reason you finally start.