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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![Roth vs Pre-Tax 401(k) Contributions]()
Roth vs Pre-Tax 401(k) Contributions
08/01/2026 Duration: 14minMy employer recently announced that they will finally be offering a Roth 401(k) option. My plan is to start making Roth contributions. How will this impact my paycheck? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Can I Fully Retire in 2-3 Years?]()
Can I Fully Retire in 2-3 Years?
07/01/2026 Duration: 14minCan I fully retire in two or three years or do you think I'll need to find a part-time job? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonm
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![Could Operation in Venezuela Impact Gas Prices?]()
Could Operation in Venezuela Impact Gas Prices?
06/01/2026 Duration: 17minPresident Trump claims Venezuela's oil industry will make more money with the U.S. behind it. Venezuela is estimated to have 303 billion barrels of crude oil still in the ground, which is about 20% of the world's reserves. I joined CBS Mornings to explain how it could impact U.S. prices. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Pension Lump Sum or Annuity?]()
Pension Lump Sum or Annuity?
05/01/2026 Duration: 15minHave I saved enough to retire now, and if so, should I take a lump sum pension from my employer or the lifetime annuity? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![The Secrets of Perfect Timing Part Two]()
The Secrets of Perfect Timing Part Two
02/01/2026 Duration: 24minEveryone knows that timing is everything, and what better time to dissect and analyze the science behind it than the end of one year and the beginning of a new one. To help make sense of it all, we're re-running an interview we did in 2019 with Daniel H. Pink, author of When: The Scientific Secrets of Perfect Timing. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![The Secrets of Perfect Timing Part One]()
The Secrets of Perfect Timing Part One
01/01/2026 Duration: 18minEveryone knows that timing is everything, and what better time to dissect and analyze the science behind it than the end of one year and the beginning of a new one. To help make sense of it all, we're re-running an interview we did in 2019 with Daniel H. Pink, author of When: The Scientific Secrets of Perfect Timing. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Should I Be Making Financial Tweaks?]()
Should I Be Making Financial Tweaks?
31/12/2025 Duration: 15minI'm 64 and wondering if I should be making any tweaks to my financial game plan? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney
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![Feeling Stuck as I Approach Retirement]()
Feeling Stuck as I Approach Retirement
30/12/2025 Duration: 18minI'm approaching retirement, yet after getting burned in the past, I'm feeling stuck at 63. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney
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![Do I Have Enough to Slow Down?]()
Do I Have Enough to Slow Down?
29/12/2025 Duration: 13minGiven that I'm a natural worrier, I need somebody to tell me if I have enough saved to slow down. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney
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![Taking Advantage of a Unique Year]()
Taking Advantage of a Unique Year
26/12/2025 Duration: 21minGiven that I've earned very little in 2025, I’m wondering if this gives me a unique opportunity to do a Roth conversion? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Happy Holidays From Jill and Mark!]()
Happy Holidays From Jill and Mark!
25/12/2025 Duration: 06minHappy Holidays from Jill and Mark!!! Whatever it is you're doing, we hope you have a good one! Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Burned Out in Tech, Can I Retire at 49?]()
Burned Out in Tech, Can I Retire at 49?
24/12/2025 Duration: 21minI'm only 49 but I work at a high demand tech job and would like to retire. Is this a possibility? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Maximize Our Assets and Optimize Our Taxes]()
Maximize Our Assets and Optimize Our Taxes
23/12/2025 Duration: 24minWe're looking for some guidance on developing a financial plan that will help us maximize our assets and optimize our taxes as we prepare for retirement. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Am I Ready to Retire at 62?]()
Am I Ready to Retire at 62?
22/12/2025 Duration: 22minI am 60 and plan to retire at 62. With a pension and a rental part of the equation, can I make it happen? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @j
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![Roth Conversion Strategy]()
Roth Conversion Strategy
19/12/2025 Duration: 22minShould I convert my traditional IRA to a Roth by maxing out our current tax bracket, or the next bracket, prior to required minimum distributions? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![If I Retire, Does Our Plan Work?]()
If I Retire, Does Our Plan Work?
18/12/2025 Duration: 23minIf I walk away from my job at the end of June 2026, and never earn another dollar, will our long-term retirement plan be impacted? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Is Retirement in 2027 a Possibility?]()
Is Retirement in 2027 a Possibility?
17/12/2025 Duration: 16minI'm 60 years old and thinking about retirement in 2027, is it doable given my circumstances? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney
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![Too Much in Pre-Tax Retirement?]()
Too Much in Pre-Tax Retirement?
16/12/2025 Duration: 16minI've done a decent job of saving for retirement over my career, but most of my savings are in pre-tax accounts. Should I switch it up for the last couple of years? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Can I Retire in Two Years?]()
Can I Retire in Two Years?
15/12/2025 Duration: 27minI'm a widow at 61 and have twin 17 year olds heading to college next year. I would like to retire in two years, but want to make sure that I have enough saved for retirement and college for the kids. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Restarting After a Divorce]()
Restarting After a Divorce
12/12/2025 Duration: 19minI'm in the middle of a messy divorce, once the dust settles, how do I get my financial life back on track? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney
