9/23/26: With my cash reserves feeling a bit low, what's the best way to replenish them?

9/22/26: Did I make a mistake by purchasing two separate annuities in retirement?

9/21/26: We're recently married and already looking forward to retirement. When will we have enough money?

9/18/26: My husband and I are wondering what the best strategy is to pay for my doctorate tuition?

9/17/26: With school back in session, we're here with some advice on how to create strong financial foundations and habits for your kids.

9/16/26: I'm 66 and still working but starting feel bummed out at the tax bills we will face due to the large pre-tax dollars we have accumulated.

9/15/26: I was recently part of a layoff and now I'm wondering if I need to go back to work full-time or will a part-time gig be enough?

9/14/26: Our financial advisor is advising us to buy long-term care insurance but we're wondering if we'd be better off investing the money instead?

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?