8/26/26: With private school and college tuition now part of the equation, should I be looking to make some financial adjustments?

8/25/26: After receiving a huge raise, please tell me the money moves I should be making to secure my financial future.

8/24/26: Does the annuity pitch we've received make sense given our overall financial situation?

8/21/26: Today we're sharing a recent chat with ⁠⁠Joseph Moore, author of How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t).

In richly told stories and wild self-experiments, Joseph tests history’s best and worst financial advice to find what worked, what didn’t, and why everyday people can still get ahead, including you.

8/20/26: With retirement upon us, and with no kids in the picture, should we be looking to convert our hefty pre-tax accounts?

8/19/26: Some older Americans find themselves at a loss when it comes to managing healthcare expenses after retirement starts. Today we're discussing how to navigate this financial headache.

8/18/26: I recently started a new job, and with my old 401(k) still with the old employer, should I be looking to consolidate accounts?

8/17/26: I'm in a new city, still own my house in the old city, and now I'm wondering if I should try to buy another piece of real estate.

8/14/26: Today we're sharing a recent chat with ⁠⁠David Booth, founder and Chairman of Dimensional Fund Advisors. A trailblazer in the financial world, David helped create one of the world’s first index funds in the 1970s and launched the first passively managed small company strategy in the early ’80s.

David joined us to discuss his soon-to-be released book ⁠Stay Calm: Learn to Embrace Uncertainty in Investing and Life, a practical guide to long-term investing and a philosophy for living with clarity and confidence. Whether you’re just starting out, rethinking your financial plan, or guiding others, this book will change the way you think about markets, risk, and what really matters.

8/13/26: Last year, the cost of damage from natural disasters in the U.S. was $115 billion. Today we're discussing what you need to know about insurance for your home, whether you own or rent.

8/12/26: I recently joined Jeremy Hobson on his show, The Follow Up, to discuss how Americans are navigating rising prices, the financial pressures facing households across the country, and the tough choices many families are making to balance their budgets in today's challenging economy.

8/11/26: Even though I don’t need Social Security benefits to meet my monthly expenses, I still took them early at 67. Did I make a mistake?

8/10/26: With two pensions in the mix, and retirement on the horizon, are we in good shape or do we need to shape up?

8/7/26: With my asset allocation out of whack, should I bite the bullet and fix it all at once, or slowly over time?

8/6/26: We're looking to do a major renovation project, will it jeopardize our long-term financial outlook?

8/6/26: Jill and Mark discuss the spectacular collapse of the Situational Awareness hedge fund and what it reveals about today's AI-fueled investing boom.

They help a caller fighting back tears figure out how to balance three competing priorities: saving for retirement, paying for her children's college, and preparing to care for her mother following the diagnosis of a degenerative illness.

Plus: a reaction to billionaire Jeremy Grantham's outrageous advice that investors should ditch U.S. stocks altogether.

8/5/26: We're looking for the most tax efficient savings vehicle for retirement contributions in a new job.

8/4/26: I want to retire at the end of this year, can we do this without spreading ourselves too thin, or blowing up our savings?

8/3/26: Do you need travel insurance? What about foreign currency? Maybe skip it all and do a staycation! We're discussing it all on this episode.

7/31/26: With the Trump Accounts now available, is the 529 plan still the best way to save for college?