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
August 1, 2025 • 15 mins
I don't hate my job but I can see the end in sight and would like to know if I'm close to being able to retire and spend $10k per month.
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July 31, 2025 • 19 mins
When I look at the numbers with a life expectancy of 90, it seems like I can finally retire with a conservative withdrawal rate. Are the numbers right?
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July 30, 2025 • 21 mins
As I navigate my single life (no children) as I enter my mid-50s, should I be considering a long-term care policy?
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July 29, 2025 • 20 mins
Should we switch all of our retirement accounts to traditional from Roth to reduce income and qualify for all the tax deduction we are eligible for?
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July 28, 2025 • 16 mins
We've started working with a financial planning firm, and part of the strategy requires the use of annuities, is this the best approach?
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July 25, 2025 • 14 mins
I’m 60 years old and plan to work until 67, at which point I would like to call it quits. Am I on track to make this happen?
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July 24, 2025 • 16 mins
I just changed jobs and I'm not sure what to do with my 401(k) from my previous employer as the new employer does not offer a retirement plan.
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July 23, 2025 • 14 mins
After 34 years of working for the government I took an early retirement offer, am I good to never work again?
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July 22, 2025 • 14 mins
With the new Trump Accounts now in the mix, is a 529 plan still the best account for college expenses?
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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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