

Jill on Money with Jill Schlesinger
Audacy
Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of what’s 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 you want us to answer on the show? Head to Jillonmoney.com and click the "Contact Us" button.
Episodes
Mentioned books

20 snips
Aug 22, 2025 • 19min
Can I Scale Back and Live a Bit More?
This discussion dives into the challenges of achieving work-life balance while managing financial goals. It highlights strategies for funding children's education using 529 plans and Health Savings Accounts. The hosts also tackle the importance of financial transparency in relationships, especially for couples planning to marry. Listeners are encouraged to assess their spending habits as they pursue a fulfilling lifestyle. Additionally, the conversation touches on the significance of estate planning, ensuring that financial responsibilities align with personal happiness.

16 snips
Aug 21, 2025 • 14min
Retirement After 25 Years, What’s Next?
A listener shares their emotional journey of leaving a 25-year career, highlighting the need for careful planning. The discussion dives into early retirement readiness, examining savings and investments without a pension. Health insurance costs and spending habits are tackled, illustrating their significant role in retirement finance. The importance of rental income and social security benefits is emphasized, aiming to create a balanced retirement lifestyle. The conversation also reflects on the emotional aspects of moving on from a long-standing career.

16 snips
Aug 20, 2025 • 16min
Trying to Figure Out Our Next Steps
Dive into a financial journey as a couple navigates their retirement plans and explores real estate options. They discuss aligning savings with their future aspirations and tackle the complexities of possible relocation. Valuable insights into Roth contributions and flexible job options also emerge, showcasing the need for a balanced approach to financial planning. Plus, the emotional side of money management takes center stage, making it relatable and engaging for listeners.

18 snips
Aug 19, 2025 • 19min
At an Inflection Point, Seeking Guidance
Navigating career changes and financial decisions takes center stage. The hosts dissect the implications of unused vacation payouts and retirement strategies. They delve into the risks associated with Continuing Care Retirement Communities and share stories about exit strategies. A highlight includes an inspiring listener's success story, emphasizing the value of communication in care planning. Plus, there's insightful advice for anyone contemplating a sabbatical or evaluating in-home care options.

Aug 18, 2025 • 18min
My Planner Is Suggesting I Buy an Annuity
A 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
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. 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

Aug 15, 2025 • 19min
The Wealth Ladder With Nick Maggiulli
Today 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
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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

Aug 14, 2025 • 19min
Annuity Decision Headache
Should 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
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YouTube: @jillonmoney
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Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. 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

Aug 13, 2025 • 21min
How to Invest Inheritance?
I 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
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YouTube: @jillonmoney
Instagram: @jillonmoney
Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. 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

Aug 12, 2025 • 25min
Can I Continue to Coast?
When 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
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YouTube: @jillonmoney
Instagram: @jillonmoney
Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. 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

Aug 11, 2025 • 20min
Am I on the Correct Path?
I 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
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. 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


