

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

Sep 27, 2025 • 3min
Presenting: The C-Word
Explore the fascinating lives of women dismissed as 'crazy' by society, from Lindsay Lohan to Judy Garland. The hosts dive deep into cultural narratives that label women as mad, sad, or bad. Through humor and heartbreak, they reclaim these powerful stories, challenging perceptions and stereotypes. This rich, historical perspective sheds light on the complexities of mental health and societal judgment. Engage with a new understanding of iconic figures as they break down the stigma surrounding female struggles.

27 snips
Sep 26, 2025 • 21min
Can We Cut Back Our Savings Rate?
Donnie, a part-time medical professional from Pennsylvania, joins to discuss balancing savings with enjoying family life. He shares insights on their recent home renovation and the decision to potentially reduce their savings rate. The conversation evolves to their current financial strategies, including managing a mortgage and addressing college funding for their kids. Donnie weighs the pros and cons of additional work hours while navigating retirement plans, and Jill emphasizes the importance of maintaining flexibility as financial circumstances change.

10 snips
Sep 25, 2025 • 19min
Peace of Mind With Allocations Heading Into Retirement
As retirement approaches, the discussion centers around adjusting asset allocations. A caller navigates the intricacies of pensions, spending, and account balances. Experts weigh in on the importance of health costs and Social Security in planning. Jill shares strategies for withdrawing funds to minimize taxes and recommends moving away from target-date funds for a more effective asset mix. The conversation also highlights the gradual shift from stocks to bonds for stability. Valuable advice for new teachers underscores the significance of early investing.

Sep 24, 2025 • 20min
Should I Move to a Low Cost Brokerage Firm?
Should I consider moving my accounts to a low cost brokerage like Vanguard, or at this point is it better to leave them where they are?
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

Sep 23, 2025 • 24min
Should I Convert My Traditional IRAs to Roth?
I max out my 401(k) with everything going into the Roth option. I still have some pre-tax money left in a traditional IRA, should I convert it?
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

6 snips
Sep 22, 2025 • 15min
Student Loan Payment Strategy
The discussion dives into the nuances of student loan repayment strategies, highlighting the tension between income-driven plans and the uncertain fate of the Public Service Loan Forgiveness program. Logan shares insights on managing his substantial grad-school debt and the impact of COVID-era payment pauses. Jill emphasizes the importance of building a hefty emergency fund while navigating shifting repayment rules and considering future financial flexibility. It's a practical guide for anyone grappling with loan repayment amidst evolving policies.

Sep 20, 2025 • 2min
Introducing Simpsons Declassified with Nancy Cartwright
Simpsons fans —THE VAULT IS OPEN!
I’m Nancy Cartwright, the voice of Bart Simpson for 35+ years, and I’m finally taking you inside Springfield. Simpsons Declassified is your all-access pass to the world’s most iconic, animated series.
Each week, we crack open wild predictions, eerie coincidences and fan conspiracies and stories from 36 seasons (that’s 800+ episodes!) behind-the-scenes with writers, directors, the cast and celebrity superfans, PLUS…Simpsons-themed games— play along and test your Springfield IQ.
Hear exclusive stories from our guests who were there! Perhaps some scenes that almost never aired, the jokes that died, the ones that lived and the moments that still shock me at the mic.
Produced and showrun by Monica Gil-Rodriguez. From Audacy Podcasts and CRE84U Entertainment.
Follow now to get new episodes first — and drop your wildest Simpsons’ theory in a review for a chance to be featured on our uniquely unique podcast, Simpsons Declassified.
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

8 snips
Sep 19, 2025 • 20min
Left Government for Private Sector
A young couple navigates the transition from government roles to the private sector, discussing the impact on their finances. They explore strategies for maximizing retirement contributions and how to catch up on savings. The couple reflects on their home value, mortgage, and options for relocating. They also contemplate a possible return to public service while weighing long-term plans, including life insurance and estate planning. It's a blend of practical advice and personal finance insights!

21 snips
Sep 18, 2025 • 21min
Retirement Planning Checkup at 65
As Bob approaches 65, he navigates the complexities of retirement by exploring work plans and managing an inherited IRA from his late mother. Jill dives into strategies for maximizing tax efficiency while withdrawing from the $220K inheritance, and offers financial insights on Bob's $1.16M 401(k) and cash reserves. She emphasizes the importance of timing withdrawals when income is low, ensuring Bob's transition into retirement is smooth and financially sound.

7 snips
Sep 17, 2025 • 17min
What to Do With School Pension?
A couple navigates the tricky waters of school pensions after one spouse leaves teaching. They tackle the challenge of living on a single income with kids in tow, all while planning for the future. The conversation shifts to real estate decisions, weighing the pros and cons of expanding their current home versus moving. Listeners get insights on managing savings, pension rollovers, and the importance of insurance in family financial planning. The show ends with heartwarming listener engagement and advice on personal finance.