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Better Off 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 2,611 episodes

Scared of Losing My Money

With about $300k in various accounts, I'm worried about the market and possibly losing this money. What should I do? Have a money question?...

17:37Oct 26, 2026

Should We Stick With Our Advisor?

We have a financial advisor who is okay, but now we're wondering if we should stick with him or make a change? Have a money question? Email...

14:27Oct 23, 2026

The Alphabet Soup of Medicare

Some people believe the murkiness of health care costs and lack of transparency is designed on purpose. Do you agree? Have a money question?...

15:16Oct 22, 2026

Making Sense of Life Insurance

Nearly 47% of American households say they feel financial hardship after a primary wage earner dies, according to a recent survey, which is...

11:55Oct 21, 2026

Financing Our Dream Home

Given that we're already retired, what's the best way to finance the purchase and construction of our dream home? Have a money question? Ema...

18:58Oct 20, 2026

Giving Myself Permission to Spend at 60

With plenty saved, and fairly low expenses, I'm having a hard time giving myself permission to spend some of my money. Have a money question...

19:05Oct 19, 2026

Debt vs Investing in Pre-retirement Years

With a plan to retire in about six years, should I keep contributing to my workplace retirement plan or instead focus on some outstanding de...

16:49Oct 16, 2026

Is the Retirement Readiness Meter Accurate?

I have always managed my own retirement planning, but I would appreciate a second opinion to ensure my retirement readiness assessment is ac...

11:55Oct 15, 2026

I’m Fried, Can I Retire in a Few Months?

I'm fried, can I quit my job in six months at the age of 65? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

15:24Oct 14, 2026

Financial Decisions Ahead of Divorce

With my divorce set to be finalized in 2027, how should I be preparing for my new financial reality? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

18:58Oct 13, 2026

Needing Direction in Retirement

I’m retired and was the caregiver for my mom who recently passed, and now I’m not exactly sure how to move forward with my financial life. H...

20:41Oct 12, 2026

Paula Pant and What It Takes to Build Wealth

Today we're sharing a recent chat with Paula Pant , host of the Afford Anything podcast. Each week on her show, Paula brings in economists,...

39:10Oct 9, 2026

Should We Update the House or Sell as Is?

We are getting ready to sell a house that has not been updated for 36 plus years. Should we update/renovate or sell as is at a discount? Hav...

14:00Oct 8, 2026

Buying a New House in Retirement

Can we afford to buy a more expensive home in retirement? If yes, how should be pay for it? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

15:42Oct 7, 2026

Planning to Retire in Another Country

With plans to retire overseas, what should I be thinking about as I prepare to make the move down the road? Have a money question? Email us...

21:51Oct 6, 2026

Should We Buy a Deferred Fixed LTC Annuity?

Our advisor is suggesting we swap one annuity for another, one that comes with long-term care coverage. Should we do it? Have a money questi...

22:35Oct 5, 2026

Handling an Upcoming Inheritance

With a large inheritance coming our way in a matter of months, we're unsure of what to do with the money. Have a money question? Email us ⁠⁠...

16:07Oct 2, 2026

Does My Retirement Plan Work?

We are looking for your opinions as to whether our plan is financially stable to get us through the early retirement years. Have a money que...

14:15Oct 1, 2026

Is There a Benefit to Switching Jobs?

In the right circumstances, job hopping can actually be beneficial for your career and bank account. Today we're discussing how and why. Hav...

13:38Sep 30, 2026

Taxes and Why I Love Them

We should celebrate our ability to come together, to pool our money, and build something great. If you are successful in America, it's becau...

14:58Sep 29, 2026