Synopsis
Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of whats 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? Email us at askjill at jillonmoney dot com.
Episodes
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![Retirement Planning Checkup at 65]()
Retirement Planning Checkup at 65
18/09/2025 Duration: 20minI'll soon be 65 and am looking for a retirement planning checkup as I contemplate a possible new job and/or career change for the next few years. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillon
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![What to Do With School Pension?]()
What to Do With School Pension?
17/09/2025 Duration: 16minMy wife is not returning to teaching this year so we're trying to figure out what to do with the money in her pension plan. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney
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![Is the Fed Ready to Cut Rates?]()
Is the Fed Ready to Cut Rates?
16/09/2025 Duration: 12minI joined "Face the Nation with Margaret Brennan" to preview the Federal Reserve's September meeting amid the Trump administration's push for the agency to lower interest rates. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram:
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![Downshift or Double Down?]()
Downshift or Double Down?
15/09/2025 Duration: 19minWith potential big changes on the horizon, I'm looking for a gut check on where we are and if/where we could/should go next. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney
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![Is the Fee Worth It?]()
Is the Fee Worth It?
12/09/2025 Duration: 20minI belatedly looked at my quarterly statements and saw that my quarterly advisement fees are in excess of $13k. Is the fee worth what I'm getting in return? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney
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![Can I Take a Break?]()
Can I Take a Break?
11/09/2025 Duration: 26minI just turned 39, and I know it sounds crazy, but I'm feeling burned out and want to know if I can take a break from work. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney
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![Brokerage Over 401(k)?]()
Brokerage Over 401(k)?
10/09/2025 Duration: 20minI am in the Roth camp for sure, but is there ever a reason to choose a brokerage account over a pre-tax 401(k)? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twi
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![I’m 28, Can I Ever Buy a House?]()
I’m 28, Can I Ever Buy a House?
09/09/2025 Duration: 20minGiven the crazy housing market, will I ever be able to afford a piece of real estate? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter:
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![Do We Have Enough To Retire at My Age 59.5?]()
Do We Have Enough To Retire at My Age 59.5?
08/09/2025 Duration: 23minMy calculations tell me we're okay, but now I'm wondering if we can retire even earlier than originally planned? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter:
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![Feeling Lost, Whats the Next Step?]()
Feeling Lost, What's the Next Step?
05/09/2025 Duration: 28minI hate feeling stupid and don't want to be the dope that is too lazy to take an interest in how my money is managed. What's our next step? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney
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![Income Streams in Retirement]()
Income Streams in Retirement
04/09/2025 Duration: 17minWhat's the best way to manage four different annuities, plus Social Security, during my retirement years? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter:
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![59 and Considering Retirement]()
59 and Considering Retirement
03/09/2025 Duration: 12minThe calculators tell me I'm okay for retirement, are they correct? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jill
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![In-Plan Roth Conversions]()
In-Plan Roth Conversions
02/09/2025 Duration: 15minWith Roth conversions permitted within my workplace retirement plan, what's the best way to handle the taxes? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter:
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![Lump Sum or Monthly Payments?]()
Lump Sum or Monthly Payments?
01/09/2025 Duration: 09minWith two pension choices to choose from, which one makes the most sense given our situation? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @
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![On Track as We Approach Retirement?]()
On Track as We Approach Retirement?
29/08/2025 Duration: 14minAs we approach retirement age, are the finances where they should be at this stage of our lives? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonm
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![Should I Ditch the Target Date Fund?]()
Should I Ditch the Target Date Fund?
28/08/2025 Duration: 14minIs it a good move to ditch my target date fund and instead invest a bit more aggressively? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Can We Splurge a Little Bit?]()
Can We Splurge a Little Bit?
27/08/2025 Duration: 20minHow much extra money can we afford to spend on "fun" things, such as travel and hobbies? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Should I Combine Accounts?]()
Should I Combine Accounts?
26/08/2025 Duration: 17minWhen I retire next year, I'll have various retirement accounts, should I look to consolidate them? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Evaluating Pension Options]()
Evaluating Pension Options
25/08/2025 Duration: 15minWith different pension options to choose from, we're not sure which one to pick for my husband. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Can I Scale Back and Live a Bit More?]()
Can I Scale Back and Live a Bit More?
22/08/2025 Duration: 18minAm I in a good position to scale back at work and pursue my next endeavor and live a bit more? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
