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 the Fee Worth It?]()
Is the Fee Worth It?
12/09/2025 Duration: 19minI 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: 24minI 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: 18minI 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 Twitter:
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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: 18minGiven 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: 21minMy 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: 26minI 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 Tw
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![Income Streams in Retirement]()
Income Streams in Retirement
04/09/2025 Duration: 15minWhat'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: 11minThe 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: @jillonmone
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![In-Plan Roth Conversions]()
In-Plan Roth Conversions
02/09/2025 Duration: 13minWith 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: 08minWith 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: @jillon
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![On Track as We Approach Retirement?]()
On Track as We Approach Retirement?
29/08/2025 Duration: 12minAs we approach retirement age, are the finances where they should be at this stage of our lives? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Should I Ditch the Target Date Fund?]()
Should I Ditch the Target Date Fund?
28/08/2025 Duration: 13minIs it a good move to ditch my target date fund and instead invest a bit more aggressively? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Can We Splurge a Little Bit?]()
Can We Splurge a Little Bit?
27/08/2025 Duration: 18minHow much extra money can we afford to spend on "fun" things, such as travel and hobbies? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Should I Combine Accounts?]()
Should I Combine Accounts?
26/08/2025 Duration: 16minWhen I retire next year, I'll have various retirement accounts, should I look to consolidate them? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Evaluating Pension Options]()
Evaluating Pension Options
25/08/2025 Duration: 14minWith different pension options to choose from, we're not sure which one to pick for my husband. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Can I Scale Back and Live a Bit More?]()
Can I Scale Back and Live a Bit More?
22/08/2025 Duration: 16minAm I in a good position to scale back at work and pursue my next endeavor and live a bit more? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney Twitter: @jillonmoney
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![Retirement After 25 Years, What’s Next?]()
Retirement After 25 Years, What’s Next?
21/08/2025 Duration: 12minI know I’ve saved (what for me) seems like a ton of money but I'm not sure how to transition to not having a steady paycheck. 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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![Trying to Figure Out Our Next Steps]()
Trying to Figure Out Our Next Steps
20/08/2025 Duration: 14minWe think we are on track with our savings and want to figure out how and when we decide to sell our house and move somewhere else. 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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![At an Inflection Point, Seeking Guidance]()
At an Inflection Point, Seeking Guidance
19/08/2025 Duration: 16minWhile my job is good, lamentably, the relationship with my boss is not. My position is due for renewal later this year and I'm fairly certain it will not be renewed. 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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![My Planner Is Suggesting I Buy an Annuity]()
My Planner Is Suggesting I Buy an Annuity
18/08/2025 Duration: 16minA financial planner is suggesting I purchase an annuity as a "private pension." Is this product necessary in my 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:
