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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![Retirement After 25 Years, What’s Next?]()
Retirement After 25 Years, What’s Next?
21/08/2025 Duration: 13minI 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: 15minWe 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 Twit
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![At an Inflection Point, Seeking Guidance]()
At an Inflection Point, Seeking Guidance
19/08/2025 Duration: 18minWhile 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: 17minA 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:
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![The Wealth Ladder With Nick Maggiulli]()
The Wealth Ladder With Nick Maggiulli
15/08/2025 Duration: 18minToday we're joined by Nick Maggiulli, Chief Operating Officer for Ritholtz Wealth Management LLC, to discuss his recently released book, The Wealth Ladder: Proven Strategies for Every Step of Your Financial Life. The book is not a get-rich-quick scheme or a one-size-fits-all solution to your money problems. It’s a new philosophy for thinking about money altogether, and it breaks wealth into six distinct levels, each demanding its own strategy. What works at Level 1 won’t cut it at Level 6, and vice versa. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to Jill on Money Newsletter YouTube: @jillonmoney Instagram: @jillonmoney 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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![Annuity Decision Headache]()
Annuity Decision Headache
14/08/2025 Duration: 18minShould I absorb the annuity surrender charges and reinvest the money into my current investment, which is earning 9% compounded quarterly? 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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![How to Invest Inheritance?]()
How to Invest Inheritance?
13/08/2025 Duration: 20minI would feel horrible losing a large portion of a recent inheritance, so I want to be careful, but I also want to maximize its earnings potential. What are my options? 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 Continue to Coast?]()
Can I Continue to Coast?
12/08/2025 Duration: 24minWhen it comes to finances, I generally take the path of least resistance. Do I need to take a more active role or can I continue to coast? 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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![Am I on the Correct Path?]()
Am I on the Correct Path?
11/08/2025 Duration: 19minI would like to get some feedback on my plan and check if I am on the right path or if I should be making some tweaks along the way. 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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![Possible Health Issues, Can I Retire?]()
Possible Health Issues, Can I Retire?
08/08/2025 Duration: 18minI am 61 and my husband is 59. We've been discussing my retiring next year and he would retire two years later when he is 62. Is this doable? 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 Retire at the End of This Year?]()
Can I Retire at the End of This Year?
07/08/2025 Duration: 25minAre we in a good spot for me to step away from my job and retire (age 58) at end of the year? 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 "Jill on Money" theme music is by Joel Goodman,
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![Husband Is Afraid to Spend]()
Husband Is Afraid to Spend
06/08/2025 Duration: 13minMy husband still worries and is afraid to spend money. What can I tell him to help him see that things are fine and we can afford to have a little fun? 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 "Jill on Mon
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![Do I Need a Financial Advisor?]()
Do I Need a Financial Advisor?
05/08/2025 Duration: 23minI have met with a third financial advisor (a fiduciary) and I'm still not convinced I need a planner. What do you think? 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 "Jill on Money" theme music is by Joel Goodman,
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![Need to Find Peace and Get Some Time Back]()
Need to Find Peace and Get Some Time Back
04/08/2025 Duration: 21minWhat I’ve earned, I’ve put towards many other expenses and am now wanting to pause and see how I am doing. Am I on track to find peace and get some time back? 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 "Jill on Money" theme music i
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![55 With the Itch to Retire]()
55 With the Itch to Retire
01/08/2025 Duration: 15minI don't hate my job but I can see the end in sight and would like to know if I'm close to being able to retire and spend $10k per month. 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 "Jill on Money" theme music is by Joel Goodman,
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![Get Out of Here and Enjoy Your Life]()
Get Out of Here and Enjoy Your Life
31/07/2025 Duration: 19minWhen I look at the numbers with a life expectancy of 90, it seems like I can finally retire with a conservative withdrawal rate. Are the numbers right? 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 "Jill on Money" theme music is by Joel Goodman,
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![Navigating Single Life in My 50s]()
Navigating Single Life in My 50s
30/07/2025 Duration: 21minAs I navigate my single life (no children) as I enter my mid-50s, should I be considering a long-term care policy? 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 "Jill on Money" theme music is by Joel Goodman, www.joe
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![High Earners, Still Do Roth?]()
High Earners, Still Do Roth?
29/07/2025 Duration: 20minShould we switch all of our retirement accounts to traditional from Roth to reduce income and qualify for all the tax deduction we are eligible for? 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 "Jill on Money" theme music is by Joel Goodman,
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![Is There an Alternative to Annuities?]()
Is There an Alternative to Annuities?
28/07/2025 Duration: 16minWe've started working with a financial planning firm, and part of the strategy requires the use of annuities, is this the best approach? 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 "Jill on Money" theme music is by Joel Goodman, www.joelgoo
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![60 and Planning for Retirement at 67]()
60 and Planning for Retirement at 67
25/07/2025 Duration: 14minI’m 60 years old and plan to work until 67, at which point I would like to call it quits. Am I on track to make this happen? 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 "Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com
