Jill on Money with Jill Schlesinger
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 anyone to know. Jill takes listener phone calls and interviews informative and entertaining guests each week to uncover surprising insights and provide actionable information so you can make the most of your money. Have a question you want us to answer on the show? Head to Jillonmoney.com and click the "Contact Us" button.
Episodes
June 18, 2025 • 16 mins
With two teacher pensions on the horizon, are we on track to retire in 12 years or so?
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June 17, 2025 • 15 mins
What do you consider a safe withdrawal rate for a couple retiring at the age of 65?
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June 16, 2025 • 19 mins
My job of 30 years, with 26 of them being remote, is now requiring in office four days a week. How long, if at all, I will need to suck it up?
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June 13, 2025 • 22 mins
I am about to turn 54 and over the past few years a medical condition has slowly made it harder to work and live an active lifestyle. Can I retire?
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June 12, 2025 • 20 mins
I'm 50, changing jobs, and have to choose between a pension or a 401(k). Which should I go with?
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June 11, 2025 • 19 mins
I am looking to buy my dream retirement home and I think I'm in a strong enough position overall to take the leap. Should I do it?
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June 10, 2025 • 22 mins
We are a retired couple and own three rental properties that cover all our financial needs. Should we convert our IRAs and pay the taxes now, staying in the 24% tax bracket.
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June 9, 2025 • 15 mins
Our advisor is suggesting we look into life insurance with a long-term care rider. We are concerned about the cost/benefit of such a policy and are not huge fans of life insurance. What do you think?
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June 6, 2025 • 44 mins
Today we're joined by Barry Ritholtz, co-founder, chairman, and chief investment officer of Ritholtz Wealth Management LLC, to discuss his recently released book, How Not To Invest: The ideas, numbers, and behaviors that destroy wealth - and how to avoid them.
The goal of the book is to show you a few simple tools and models that will help you avoid the most common mistakes people make with their money.
Learn these, and you are...
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June 5, 2025 • 22 mins
I am leaving my current employer of 24 years for a new company without a pension. Should I take the lump sum or monthly payments beginning as early as 60?
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June 4, 2025 • 18 mins
With a bunch of pension options on the table, which one should we choose?
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June 3, 2025 • 16 mins
All my work comes from word of mouth and my phone never stops ringing. I'm starting to get tired and want to enjoy life. Do I have enough money to retire?
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June 2, 2025 • 17 mins
With a ton of money tied up in the business, I'm starting to worry about the overall construction of our portfolio.
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May 30, 2025 • 16 mins
Can we stop saving for retirement and basically let about $2,100,000 and our rental home values grow without contributing more?
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May 29, 2025 • 21 mins
With a new mortgage in retirement, one that has a high interest rate, are we okay to pay it off in the next year or so?
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May 28, 2025 • 16 mins
I'm 51 and preparing for retirement at the end of 2026 with a large pension on the horizon. Is there anything I'm not factoring into my decision making process?
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May 27, 2025 • 22 mins
I am currently 57 years old and considering retirement in the next one to three years. Is this doable?
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May 26, 2025 • 31 mins
In honor of the Memorial Day holiday, we're once again re-airing an interview we did back in 2017 with retired Admiral William “Bill” McRaven. If Bill’s name sounds familiar, it’s because he presided over the 2011 Navy SEAL raid that resulted in the killing of Osama bin Laden in Pakistan.
A few years later in 2014, the four-star admiral and 37-year Navy SEAL veteran delivered the commencement speech at his alma mater, the Universi...
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May 23, 2025 • 17 mins
Now that my school loans are paid off, I'm wondering what to do with my extra cash flow as well as a pretty large savings account.
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May 22, 2025 • 13 mins
From what I can see, I could pay off my mortgage and still be able to live easily on Social Security and a tiny pension. Should I do it?
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