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Jill on Money with Jill Schlesinger

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Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of what’s important for anyo...

Episodes

20 of 2,586 episodes

Did I Make a Mistake With Two Annuities?

Did I make a mistake by purchasing two separate annuities in retirement? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

12:16Sep 22, 2026

Just Married, When Can We Retire?

We're recently married and already looking forward to retirement. When will we have enough money? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

19:13Sep 21, 2026

How to Pay for My Doctorate?

My husband and I are wondering what the best strategy is to pay for my doctorate tuition? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

22:07Sep 18, 2026

Key Money Habits to Teach Your Kids

With school back in session, we're here with some advice on how to create strong financial foundations and habits for your kids. Have a mone...

11:44Sep 17, 2026

Disliking My Business “Partners” Uncle Gavin and Uncle Don

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. Ha...

17:57Sep 16, 2026

Do I Need to Go Back to Work Full-Time?

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? Have a money...

18:44Sep 15, 2026

Being Advised to Buy Long-Term Care Insurance

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?...

25:26Sep 14, 2026

Do I Have Too Many Funds?

I am considering changing advisors but not sure what questions to ask of my current advisor regarding the large number of funds he has us in...

21:28Sep 11, 2026

AI and Your Money

Should you let artificial intelligence manage your money? While AI might be able to help you come up with a budget, experts say there are ri...

9:56Sep 10, 2026

Impending Unexpected Surgery

With an unexpected surgery on the horizon, how should I be preparing for the worst case scenario? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

21:27Sep 9, 2026

Giving Myself Permission to Spend

With plenty of assets at my disposal, I still can't seem to give myself permission to spend. Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

26:57Sep 8, 2026

Happy Retirement to Our Auto Guru!

After 34 years with Consumer Reports, Mike Quincy is calling it a career, and on this Labor Day holiday, he joins us for his final appearanc...

47:31Sep 7, 2026

Am I Going in the Right Financial Direction?

After recently turning 50, I'm wondering if I'm going in the right financial direction? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

14:49Sep 4, 2026

Stuck in Financial Survival Mode

After working in non-profits for years and years, it feels like I'm always stuck in financial survival mode. Have a money question? Email us...

13:17Sep 3, 2026

On Track for Retirement at 56?

I'm only 51, but with a pension part of the equation, is retirement at 56 a possibility? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

14:15Sep 2, 2026

I’m 68, Is It Time to Stop Working?

I love my job, but at the age of 68, is it time to consider a life beyond work? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

10:58Sep 1, 2026

Turning 60 and Looking to Retire Very Soon

With a big birthday on the horizon, and a nice pension at work, am I in a position to call it quits? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

9:44Aug 31, 2026

The Forever Paycheck With Jean Chatzky

Today we're sharing a recent chat with ⁠⁠ Jean Chatzky , an award-winning personal finance journalist, AARP's personal finance ambassador, a...

30:20Aug 28, 2026

Second Guessing a Financial Decision

I purchased a financial product a while back and have been second-guessing myself ever since. Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

11:24Aug 27, 2026

Juggling Education and Retirement

With private school and college tuition now part of the equation, should I be looking to make some financial adjustments? Have a money quest...

13:09Aug 26, 2026