
Jill on Money with Jill Schlesinger
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.
Latest episodes

Jun 16, 2025 • 20min
Back to the Office After 26 Years Remote
A listener discusses her surprising transition back to an office after 26 years of remote work, highlighting her concerns about retirement and her husband's pension. The conversation dives into the challenges of navigating company policies on benefits and the financial implications of such a shift. With a focus on financial preparedness, they explore strategies for stability, including real estate investments and retirement planning. The importance of a solid financial plan and estate planning for unexpected changes is emphasized.

Jun 13, 2025 • 23min
Medical Condition Has Me Pondering Retirement
I am about to turn 54 and over the past few years a medical condition has slowly made it harder to work and live an active lifestyle. Can I retire?
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

10 snips
Jun 12, 2025 • 21min
New Job, New Retirement Plan Options
Changing jobs at 50 brings exciting choices! Should you opt for a pension or a 401(k)? The discussion dives into the importance of financial planning for retirement and education. Addressing rental properties and cash management, the conversation highlights smart decision-making for home ownership. Pensions versus contribution plans are unraveled with personal stories, emphasizing the need for flexibility. Essential tips and the value of support are shared, making this a must-listen for anyone navigating a career transition!

14 snips
Jun 11, 2025 • 20min
Can I Buy That Dream Retirement Home?
The discussion kicks off with practical tips on setting financial goals and earning cash back through savvy credit card use. A listener's journey towards buying her dream retirement home unveils insights into her financial readiness amidst rising housing prices. The podcast also delves into the investment strategies of a young adult, tackling job market challenges and savings options. Listeners learn about the importance of customizing cash flow strategies and exploring retirement decisions, including transitions from traditional 401ks to Roth IRAs.

12 snips
Jun 10, 2025 • 22min
Retired With Various Streams of Income
Marie, a retired small business owner from Connecticut, dives into her journey of managing retirement income and assets. She shares how her rental properties sustain her lifestyle and discusses the potential tax implications of converting her IRAs. The conversation explores the intricacies of real estate investments, including a commercial property and a vacation rental. Marie emphasizes the importance of careful budgeting, emergency funds, and estate planning as she navigates her new financial landscape while adapting to retirement.

15 snips
Jun 9, 2025 • 15min
Life Insurance With Long-Term Care Rider
Explore the world of life insurance with a long-term care rider and its pros and cons. Hear insights on retirement income strategies from a financial-savvy couple. Delve into the complexities of long-term care insurance and understand the importance of professional advice for better asset protection. Discover potential investment strategies that suit varying financial portfolios, helping you navigate your financial landscape with confidence.

Jun 6, 2025 • 44min
How Not To Invest
Today we're joined by Barry Ritholtz, co-founder, chairman, and chief investment officer of Ritholtz Wealth Management LLC, to discuss his recently released book, How Not To Invest: The ideas, numbers, and behaviors that destroy wealth - and how to avoid them.
The goal of the book is to show you a few simple tools and models that will help you avoid the most common mistakes people make with their money.
Learn these, and you are ahead of 98% of your peers. Make fewer errors, end up with more money.
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

Jun 5, 2025 • 22min
A Money Reset With Pension Options
I am leaving my current employer of 24 years for a new company without a pension. Should I take the lump sum or monthly payments beginning as early as 60?
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

Jun 4, 2025 • 18min
To PLOP or Not to PLOP?
With a bunch of pension options on the table, which one should we choose?
Have a money question? Email us here
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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

Jun 3, 2025 • 16min
I’m Getting Tired and Want to Enjoy Life
All my work comes from word of mouth and my phone never stops ringing. I'm starting to get tired and want to enjoy life. Do I have enough money to retire?
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