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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![Is Early Retirement a Possibility?]()
Is Early Retirement a Possibility?
12/03/2026 Duration: 19minGiven our fairly low expenses, is it reasonable to “retire” once we reach three million in assets? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Can We Stop Saving for College?]()
Can We Stop Saving for College?
11/03/2026 Duration: 14minWith two young kids, and with a lot of money already saved in 529 plans, is it wrong to think we can stop saving for college? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Are We Really Ready to Retire Early?]()
Are We Really Ready to Retire Early?
10/03/2026 Duration: 21minMy husband wants to retire in a year when he turns 55, but I don't feel comfortable with our numbers. Am I wrong? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Impact of Iran War on Economy]()
Impact of Iran War on Economy
09/03/2026 Duration: 08minI joined CBS Saturday Morning to discuss how the war against Iran is impacting the overall economy. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Career Transitions With the Help of AI]()
Career Transitions With the Help of AI
06/03/2026 Duration: 35minFrom the CEO of Boxed to the artificial intelligence landscape, Chieh Huang is back on the show to discuss his latest creation, Pelgo, an AI generated personal career transition agent, whether you're starting out, leveling up, or reinventing what’s next. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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![Financially Supporting a Parent]()
Financially Supporting a Parent
05/03/2026 Duration: 25minFive years ago, my mom sold her house and moved in with us, and we're covering all her expenses. Are we jeopardizing our own retirement? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![How to Handle My Pension Options]()
How to Handle My Pension Options
04/03/2026 Duration: 18minWith various pension options to choose from, analysis paralysis is starting to set in. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![On Track for FINE?]()
On Track for FINE?
03/03/2026 Duration: 19minAs we pursue financial independence, could an annuity act as a pension and give us a floor so we feel comfortable spending a set amount? 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 Convert My TSP?]()
Should I Convert My TSP?
02/03/2026 Duration: 13minWith no need to tap my pre-tax retirement accounts, should I consider converting to a Roth? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Do I Need to Find Another Job?]()
Do I Need to Find Another Job?
27/02/2026 Duration: 20minAfter being laid off in 2024, I'm starting to wonder if I really need to keep looking for another job? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Why Not a Roth Conversion?]()
Why Not a Roth Conversion?
26/02/2026 Duration: 18minUnder which scenario would a Roth conversion not make the most sense? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Reducing Retirement Savings for a House]()
Reducing Retirement Savings for a House
25/02/2026 Duration: 19minWould it be a mistake to reduce our retirement savings in order to float the purchase of a more expensive house? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Changing Investment Firms]()
Changing Investment Firms
24/02/2026 Duration: 16minMy planner of 20 plus years has struck out on his own with a large fiduciary firm and would like me to move my money to his new company. Should I? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Full-Time Caregiver, Will I Be Okay?]()
Full-Time Caregiver, Will I Be Okay?
23/02/2026 Duration: 19minI'm a full-time caregiver for my parents and now I'm starting to wonder if my own finances are okay for the long haul? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Planning After the Death of My Wife]()
Planning After the Death of My Wife
20/02/2026 Duration: 20minAfter the death of my wife I'm looking to make some changes with my finances. Am I making a mistake? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Am I on Track for a 2028 Retirement?]()
Am I on Track for a 2028 Retirement?
19/02/2026 Duration: 23minThere is a pretty good chance I am going to be offered a voluntary early retirement at some point in the near future. Am I in good shape to call it quits? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Can We Retire Now if We Get Laid Off?]()
Can We Retire Now if We Get Laid Off?
18/02/2026 Duration: 14minIf we wind up jobless next year, can we retire early and focus on our health? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
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![Are We on the Correct Path?]()
Are We on the Correct Path?
17/02/2026 Duration: 17minWe’re DIY investors and are really just looking for a sanity check in terms of what’s a realistic retirement timeline and nest-egg target for a household like ours? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Can I Quit My Job and Become an Artist?]()
Can I Quit My Job and Become an Artist?
16/02/2026 Duration: 24minI want to quit my job and take the leap and try to write full-time, but the idea is terrifying. Should I do it? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter
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![Retirement and Leaving a Legacy]()
Retirement and Leaving a Legacy
13/02/2026 Duration: 15minWith two sizable pensions in the picture, can I retire and focus on leaving a legacy for my kids? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube:
