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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![Peace of Mind With Allocations Heading Into Retirement]()
Peace of Mind With Allocations Heading Into Retirement
25/09/2025 Duration: 18minI am one year away from retirement and my husband is three years out and I want to know if we should adjust our allocations? 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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![Should I Move to a Low Cost Brokerage Firm?]()
Should I Move to a Low Cost Brokerage Firm?
24/09/2025 Duration: 19minShould I consider moving my accounts to a low cost brokerage like Vanguard, or at this point is it better to leave them where they are? 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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![Should I Convert My Traditional IRAs to Roth?]()
Should I Convert My Traditional IRAs to Roth?
23/09/2025 Duration: 23minI max out my 401(k) with everything going into the Roth option. I still have some pre-tax money left in a traditional IRA, should I convert it? 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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![Student Loan Payment Strategy]()
Student Loan Payment Strategy
22/09/2025 Duration: 15minShould I continue making income-driven repayments and hope that the Public Service Loan Forgiveness program isn't canceled, or should I pay off the full balance? 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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![Introducing Simpsons Declassified with Nancy Cartwright]()
Introducing Simpsons Declassified with Nancy Cartwright
20/09/2025 Duration: 02minSimpsons fans —THE VAULT IS OPEN! I’m Nancy Cartwright, the voice of Bart Simpson for 35+ years, and I’m finally taking you inside Springfield. Simpsons Declassified is your all-access pass to the world’s most iconic, animated series. Each week, we crack open wild predictions, eerie coincidences and fan conspiracies and stories from 36 seasons (that’s 800+ episodes!) behind-the-scenes with writers, directors, the cast and celebrity superfans, PLUS…Simpsons-themed games— play along and test your Springfield IQ. Hear exclusive stories from our guests who were there! Perhaps some scenes that almost never aired, the jokes that died, the ones that lived and the moments that still shock me at the mic. Produced and showrun by Monica Gil-Rodriguez. From Audacy Podcasts and CRE84U Entertainment. Follow now to get new episodes first — and drop your wildest Simpsons’ theory in a review for a chance to be featured on our uniquely unique podcast, Simpsons Declassified. To learn more about listener dat
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![Left Government for Private Sector]()
Left Government for Private Sector
19/09/2025 Duration: 19minMy husband and I are still young in our careers since we've both pursued higher education but we want to make sure we are on the right track to "catch-up" on retirement. 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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![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: @
