
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

May 7, 2025 • 12min
Did I Pull the Plug Too Soon?
Did I pull the retirement plug too early? And if so, should I get a part-time job?
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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

May 6, 2025 • 16min
Rocky Markets, Time for an Annuity?
Given the rocky markets we've seen the last few weeks, is this the ideal environment to consider the purchase of an annuity?
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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

May 5, 2025 • 19min
In Our Mid 50s, Can We Retire?
We're in our mid 50s and ready to call it quits, can we do it?
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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

10 snips
May 2, 2025 • 15min
Should I Use TSP to Payoff Mortgage?
A 70-year-old seeks advice on paying off their mortgage using TSP funds, sparking a discussion on retirement savings versus immediate financial relief. The episode emphasizes the importance of liquidity, especially during later stages of life, and explores the implications of interest rates on such decisions. Additionally, listeners are guided through car buying strategies and the intricacies of charitable contributions, while highlighting the vital role of realtors for homebuyers in California.

16 snips
May 1, 2025 • 18min
Should We Invest in This Climate?
With some proceeds from a real estate transaction about to come our way, should we invest in the market or wait until things settle down?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @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

12 snips
Apr 30, 2025 • 13min
I’m 47, Can I Retire Next Year?
A listener grapples with early retirement at 47, pondering financial readiness and life changes. The conversation emphasizes evaluating pension plans and investments while considering a move to a less stressful environment. Topics include the decision to sell or rent a home in New Jersey versus the costs in Panama, and the importance of understanding retirement accounts and savings. The guide touches on the value of a military pension and the significance of pausing before embarking on new journeys.

12 snips
Apr 29, 2025 • 13min
Do I Need to Work Longer?
After taking a lower paying job, I'm now worried that I might have to work longer than anticipated.Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @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

6 snips
Apr 28, 2025 • 15min
Do We Have Enough for Retirement?
I think we have enough saved for retirement, but given how crazy the world is right now, I need some reassurance. Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @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

7 snips
Apr 25, 2025 • 14min
Want to Retire but Have Concerns
Listeners voice their concerns about retirement amidst economic uncertainty, stressing the need for careful financial planning. Topics include evaluating savings portfolios like IRAs and 401ks and understanding income sources for a smooth transition. The discussion also highlights the importance of managing risks associated with mortgages and inherited properties. Additionally, the idea of adopting flexible work options and the necessity for estate planning are emphasized, ensuring a secure and adaptable approach to retirement.

11 snips
Apr 24, 2025 • 16min
Should I Go All Roth?
Listeners dive into pressing financial questions, especially regarding retirement strategies. Discussions focus on whether all contributions should be Roth, balancing investments with mortgage payments, and job options for a better retirement. The impact of relocating to expensive areas is also explored, along with the decision to rent or sell homes. The merits of converting to Roth IRAs for enhanced financial security and diversification are highlighted, making for an engaging exploration of smart financial planning.