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 21, 2025 • 19 mins
After having a lot of fun in my 20s and 30s, then getting serious in my 40s, how far behind am I for retirement?
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July 18, 2025 • 19 mins
I’ve interviewed CFP providers but have chickened out when it came time to sign the documents and pay a fee, but retirement is closer than ever, and I need a better plan to retire in three years.
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July 17, 2025 • 11 mins
Given that my cost of living is very low, can I retire in a few years at 59?
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July 16, 2025 • 17 mins
I have a one time opportunity to use my 457 pre-tax deferred compensation funds to purchase an annuity offered by Washington State to former employees. Is there any downside?
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July 15, 2025 • 25 mins
I could really use your help, as we've been worrying ourselves sick thinking about what our options are and where we sit financially.
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July 14, 2025 • 16 mins
After being retired for a few years, I am terrified thinking about the future and can't help but worry that we'll lose everything we own.
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July 11, 2025 • 19 mins
I recently retired after working in tech for 27 years but now I'm struggling with the transition and how to think about this new phase for the next 30-40 years.
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July 10, 2025 • 17 mins
My daughter is very upset with an early inheritance she received. How should I proceed?
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July 9, 2025 • 24 mins
I am retiring in June of 2026 after 30 years in the Navy. There will be some kind of reset, but before I embark, are we on track for the next phase?
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July 8, 2025 • 23 mins
Can I retire at age 59, which is the very last day of this year, or should I keep going for another year or so?
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July 7, 2025 • 17 mins
We're in our 30s, have about $300k saved with a nice pension on the horizon, but we don't own any real estate. Is that holding us back?
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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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