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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Prepping for Retirement at 53
07/05/2026 Duration: 16minWith retirement at the age of 53 just weeks away, are there any financial adjustments I should be looking to make? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Realistic Next Steps for Living Life Now?
06/05/2026 Duration: 28minI work a far distance from my employer, but moving closer is much more expensive due to housing costs. Is it still worth considering? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Still on Track to Retire at 55?
05/05/2026 Duration: 19minWith some life changes over the last few years, are we still on track to retire in our 50s? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Should I Stay or Take the New Job Offer?
04/05/2026 Duration: 17minShould I stay at my current job, one that comes with a pension, or make a move for a higher salary? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Roth vs. Traditional
01/05/2026 Duration: 19minI'm struggling to make a decision in terms of pre-tax versus Roth. Will it matter in my situation? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Can We Afford to Help Out Our Sons?
30/04/2026 Duration: 16minWith retirement right around the corner, can we afford to give our two sons a good amount of financial assistance? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Pay Off My Mortgage Quickly?
29/04/2026 Duration: 17minI always hear you say not to make paying down the mortgage a priority, but my interest rate is 6.125%. Do I have permission? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Can I Retire at 65 Instead of 67?
28/04/2026 Duration: 14minThe original plan was to retire at 67, but now I'm wondering if I can call it quits at 65? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Have We Saved Enough for Retirement?
27/04/2026 Duration: 24minWith a bit of job uncertainty entering the mix, we're wondering if we have saved enough for retirement? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Introducing Family Lore
25/04/2026 Duration: 03minFamily Lore is a weekly narrative podcast that celebrates and investigates ancestral mystique. Each episode begins with a guest sharing a fascinating family legend, followed by a historical deep-dive to uncover the truth and meaning behind the tale. Available now: link.pscrb.fm/f0281/FLFD To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices
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Are We Ok to Be Work Optional?
24/04/2026 Duration: 21minAfter 30 years at the same company I was recently let go. Do I need to find another job? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Can I Help Kids With Student Loans?
23/04/2026 Duration: 19minWith both kids graduating with significant student loan debt, can I afford to help them out? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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I Want to Take Social Security Early
22/04/2026 Duration: 14minYou usually tell people to wait to take Social Security as long as they are in good health and have a long life expectancy, and I tend to agree if a person doesn't need the money. That said, I'm starting to feel like I need the money. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Evaluating Term Life Insurance Coverage
21/04/2026 Duration: 16minWith a military pension and early retirement on the horizon, are we adequately covered by our existing term life insurance? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Consolidating Old 401(k) Plans
20/04/2026 Duration: 14minWith three different 401(k) plans in the equation, is there an easy way to simplify and make my financial life easier? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Managing the Finances for My Mother
17/04/2026 Duration: 13minShould I be making any adjustments as I manage the finances for my 87 year old mother? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on
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Planning Around Our Pensions
16/04/2026 Duration: 18minWith two pensions in the mix, how should we be planning for our eventual retirement? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money
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Managing a Career Transition
15/04/2026 Duration: 17minWith a major career transition on the horizon, how should I be preparing financially? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money News
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Trying Not to Screw It Up
14/04/2026 Duration: 16minAfter being diligent savers for many years, we want to make sure we don't do anything to screw things up. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Ji
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What Should I Be Doing Differently?
13/04/2026 Duration: 16minAs I get closer and closer to 60, should I be doing something different with my investments? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newslet