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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Tips for Retirement Planning
23/07/2026 Duration: 11minWorking and retired Americans are much less confident in their financial ability to maintain a comfortable retirement compared to a year ago, according to a new survey from the Employee Benefit Research Institute. Have a money question? Email us hereSubscribe to Jill on Money LIVE
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How to Calculate the Monthly Spend?
22/07/2026 Duration: 21minI've been tempted to contact the show to do a "how am I doing" check-in, but have one thing holding me back. I'm having trouble figuring out our monthly spend.Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe
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Priorities as I Prepare for Retirement
21/07/2026 Duration: 19minWith three more years left in the workforce, how should I be preparing as I start to think about retirement?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Second Guessing My Financial Decisions
20/07/2026 Duration: 18minAfter making some recent financial money moves, I'm starting to wonder if I made the right decision or if I made a mistake?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Mid-Year Financial Check-In
17/07/2026 Duration: 10minI recently joined CBS Mornings with financial tips that will help you save money, from cutting bills and streaming services to savings accounts.Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Funding a Condo Purchase
16/07/2026 Duration: 12minWould it be wise to use money in one of my brokerage accounts to buy a condo in a place that aligns better with my way of life?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Does My Plan Work, or Should I Be Worried?
15/07/2026 Duration: 22minEven though my husband says we're fine, I still find myself worrying about the markets and whether or not we have enough saved to last us for the long haul. Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Physical Job, Can I Retire at 57?
14/07/2026 Duration: 12minI'm 55, work a physically demanding job, and would like to retire in two years. Do I have enough saved to make it happen?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Age Gap Couple With High Paying Jobs
13/07/2026 Duration: 23minWith a significant age gap between us, what steps should we be taking as we plan for two very different retirements?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Social Security Mailbag With Heather Schreiber
10/07/2026 Duration: 51minBecause our recent Social Security webinar was such a hit, and we couldn't get to all the questions, today we're doing a mailbag episode with the Social Security Queen, Heather Schreiber. Have a money question? Email us hereSubscribe to Jill on Money LIVE
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Finalizing My Exit Plan at 65
09/07/2026 Duration: 20minMy industry is tech, and we've had tons of changes lately, so at 65 I'm wondering if my exit plan is a solid one?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Would Like to Retire in Nine Months
08/07/2026 Duration: 15minI'm currently 58, retired at 49 with a pension, returned to full-time employment at 50 and now plan to retire again in nine months. Is our plan solid?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Ensuring My Wife Will Be Taken Care Of
07/07/2026 Duration: 18minWith a strong Alzheimer's history in the family, how can I ensure that my wife will be taken care of should it become necessary?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Pension Options and Roth Conversions
06/07/2026 Duration: 25minWith two big pensions in the mix, and a big pot of pre-tax money, should Roth conversions be the priority?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Fee-Only vs Fee-Based
03/07/2026 Duration: 15minWith retirement on the horizon, should I be looking for a fee-only or a fee-based advisor?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Freedom vs Liquidity
02/07/2026 Duration: 14minI say pay off the mortgage, my wife says no. Can you be the judge?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Am I Worrying Too Much About Taxes?
01/07/2026 Duration: 16minWe are in good shape, but I don't want to do anything stupid. Am I worrying too much about taxes? Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Am I Ready for Retirement?
30/06/2026 Duration: 15minI'm officially retiring at the end of this week. Am I ready?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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I’m Fried, Can I Retire Next Year at 55?
29/06/2026 Duration: 19minMy goal is to retire in 2027 at the age of 55 from my 24-year corporate career due to burn out. Can I do it?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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How to Spend What We’ve Saved?
26/06/2026 Duration: 16minEven though we have more money than we'll probably ever need, I'm still having a hard time spending down some of the accounts. Can you help?!Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to