Q&A: My Mom Is 73. She Has a House — But It Doesn’t Pay the Bills. Now What?

Q&A: My Mom Is 73. She Has a House — But It Doesn’t Pay the Bills. Now What?

#708: What’s the smartest way to handle big financial transitions—when the stakes are high and the “right” answer isn’t always obvious? Anonymous “Cyndi Jr.” is helping their 73-year-old mother relocate across the country and needs to decide how to use the proceeds from a home sale to balance long-term housing security with inflation protection. Anonymous is trying to figure out how to handle quarterly estimated taxes on investment income—without relying on safe harbor rules that don’t always reflect market swings. Luz, whose previous question was featured on the show, is now navigating a major job change and wondering what to do with an old 401(k)—while also rethinking how Roth accounts, an HSA, and debt all fit into a bigger financial strategy. We’ll walk through each of these and help you think it through in today’s episode. Resources mentioned: Don’t miss the YFRP Webinar! https://affordanything.com/rental2026 Join the YFRP waitlist: https://courses.affordanything.com Listen to Luz’s previous question: https://affordanything.com/episode583 Stay in the Loop: https://affordanything.com/newsletter Share this episode with a friend, colleagues, and Cyndi Lauper: https://affordanything.com/episode708 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Is a Computer Science Degree Still Worth the Debt?, with Ron Lieber

Is a Computer Science Degree Still Worth the Debt?, with Ron Lieber

#711: A computer science degree used to feel like a sure thing. Job placement rates topped 90 percent. Starting salaries cleared $80,000. You could do the math on your student loans before you enrolle...

1 Touko 1h

Q&A: He Wants to Die With Zero – Here’s How to Spend $1M Without Running Out

Q&A: He Wants to Die With Zero – Here’s How to Spend $1M Without Running Out

#710: What does it really look like to balance financial optimization with real-life tradeoffs—whether that’s choosing meaningful work, spending down your savings, or deciding where your next dollar s...

28 Huhti 1h 12min

The Financial Reality of Developmental Disabilities, with Keith Wargo

The Financial Reality of Developmental Disabilities, with Keith Wargo

#709: Keith Wargo has spent decades navigating one of the most daunting financial planning challenges a family can face: raising a child with a developmental disability. He joins us to share what fami...

24 Huhti 1h

Q&A LIVE from Texas A&M Texarkana

Q&A LIVE from Texas A&M Texarkana

#707: Joe and I traveled to the campus of Texas A&M University-Texarkana for a very special live recording. We were joined by Jay Davis, the Executive Director of Financial and Entrepreneurship Engage...

17 Huhti 50min

Q&A: The Case for NOT Paying Off Your Student Loans

Q&A: The Case for NOT Paying Off Your Student Loans

#706: When the numbers look straightforward—but the rules, timing, and future are uncertain—how do you decide what to do next? KJ has $90,000 in student loans, a recent inheritance, and a lot of ...

14 Huhti 1h 12min

What to Fix First When Everything Feels Stuck, with former Lyft COO and Tesla President Jon McNeill

What to Fix First When Everything Feels Stuck, with former Lyft COO and Tesla President Jon McNeill

#705: Jon McNeill, former president of Tesla and COO of Lyft, starts with a simple problem: his teenage son is about to start driving, and he’s worried about texting behind the wheel. Instead of sett...

10 Huhti 1h 27min

Q&A: Should I Quit My Job to Be a Stay-at-Home Dad

Q&A: Should I Quit My Job to Be a Stay-at-Home Dad

#704: How do you make smart financial decisions when you’re balancing debt, investing, and big life changes … all at the same time? Today, Brigham and his wife, ages 25 and 23, wonder: can they buy...

7 Huhti 52min

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