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
July 4, 2025 • 27 mins
Since it's the 4th of July, we're re-airing an interview we did with Ken Langone, the legendary financier, who helped take a bunch of companies public before co-founding Home Depot. He joined us seven years ago to talk about his book, I Love Capitalism!: An American Story, but really it was just a fascinating conversation with a guy who grew up in a working-class family, put himself through school, and after some hard work and smar...
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July 3, 2025 • 19 mins
I'll be turning 65 in two years and would like to retire at that time, if it's financially feasible. Is it?
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July 2, 2025 • 15 mins
My financial advisor is recommending a company to manage my 401(k). He says this company will be managing it constantly and said studies show they increase returns by 2-4%. Should I jump for joy or run for the hills?
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July 1, 2025 • 22 mins
We are building a house that will be way more expensive than we thought, initially. Are we over-extending ourselves?
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June 30, 2025 • 15 mins
If my employer, a federal agency, offers an early retirement option, can I say yes and call it quits?
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June 27, 2025 • 21 mins
A financial planner is suggesting an annuity to provide guaranteed income to bridge the gap between retirement and Social Security. Is it the right product for us?
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June 26, 2025 • 22 mins
My husband hates his job, and has hated it for years. Can he get a lower paying job earning about half of what he does now, but still keep us on track for retirement at age 55.
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June 25, 2025 • 16 mins
I've been on the show before, but I'm still struggling to convince my hubby that we have enough money to retire. Can you help again?
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June 24, 2025 • 15 mins
I'm 68 and was planning on waiting until 70 for Social Security, but I am concerned about the shortfall and the potential for means testing. Should I take it now?
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June 23, 2025 • 27 mins
We're looking to increase our retirement contributions and wondering what is the best choice(s) as we would also like to help our children pay for college.
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June 20, 2025 • 20 mins
I'm 64 and hoping to retire next fall at the age of 65. Am I on track to do it?
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June 19, 2025 • 15 mins
I just turned 60 and now I'm wondering if I can retire next year?
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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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