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
December 8, 2025 • 15 mins
Am I on track to have a bit more flexibility, or even retire, in just over two years at the age of 62?
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December 5, 2025 • 13 mins
After playing with a bunch of retirement calculators, and seeing really positive results, are the numbers too good to be true?
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December 4, 2025 • 15 mins
After doing my best to keep our financial house in order, is it time to enlist the help of a financial planner?
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December 3, 2025 • 13 mins
How should we be managing our finances after learning that we'll need to care for a family member?
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December 2, 2025 • 12 mins
With a toddler in the mix, can we afford to cut back at work and spend more time with our child?
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December 1, 2025 • 13 mins
I think we have enough money but need some help convincing my wife that we're in solid shape.
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November 28, 2025 • 34 mins
With the year coming to a close, and with all the uncertainty given the tariffs and the recent government shutdown, Black Friday seems like a good time for a heat check on where things stand in the economy.
To help explain it all, we're joined by Diane Swonk, the Chief Economist at KPMG, who has always been a go-to source to make sense of short, and long-term, trends.
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November 27, 2025 • 44 mins
The sluggish employment landscape explains why workers are now “job hugging,” rather than job hopping. The challenge is to fight the urge to hunker down and instead try to be proactive and focus on what you can control.
That means raise your hand for any new opportunity at your company, update your LinkedIn profile/fire up your network, and consider pursuing any side hustle that might help your cash flow and spark creativity.
Fo...
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November 26, 2025 • 25 mins
Our current asset allocation is 65% equities, 7% bonds, 28% cash/CDs, etc. My wife is concerned that we are taking on too much risk given our ages. Is she correct?
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November 25, 2025 • 16 mins
I have a 10 year ARM and I'm wondering if I should refinance or ride it out a bit longer and hope that rates continue to come down?
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November 24, 2025 • 22 mins
I made a big move in 2023 and am considering doing it again and I need your input because I don't want to blow up our retirement plans.
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November 21, 2025 • 27 mins
With Thanksgiving around the corner, the charitable giving season is upon us and changes are afoot. Of course, most people give because they want to do good, but the tax rules around philanthropy have always been an added sweetener.
To break it all down, we're joined by Fred Kaynor from DAFgiving360. The mission of DAFgiving360 is to increase charitable giving in the U.S. by providing a tax-smart and simple giving solution of a do...
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November 20, 2025 • 18 mins
With hopes of calling it quits in just a few years, when should I pull money from my different "buckets" once I get into retirement?
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November 19, 2025 • 24 mins
With a large inheritance sitting in cash, should I leave it as is and take the peace of mind it provides, or invest it?
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November 18, 2025 • 16 mins
I find myself at a fork in the road, and I'm hoping you can help me choose the right financial path.
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November 17, 2025 • 19 mins
Is it foolish if I spend $300k on a renovation project during retirement?
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November 14, 2025 • 24 mins
Retirement and college expenses are on a collision course, how should we handle both?
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November 13, 2025 • 14 mins
Should we run screaming from a potential financial planner or am I overreacting?
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November 12, 2025 • 23 mins
Will we blow up our financial plan if we tap the TSP to fund a renovation project?
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November 11, 2025 • 14 mins
With a large inheritance sitting in CDs, should we leave the money as is or start investing it?
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