

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

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.

12 snips
Sep 16, 2025 • 13min
Is the Fed Ready to Cut Rates?
The discussion dives into the Federal Reserve's upcoming meeting, focusing on the potential for interest rate cuts. It weighs the likelihood of different cut sizes amid economic uncertainty and mixed job data. The podcast also tackles the challenging job market, highlighting cautious hiring practices and the significance of adaptability for job seekers. Additionally, it examines how fluctuating energy prices impact inflation, shedding light on the labor market's role in the economy's evolving landscape.

18 snips
Sep 15, 2025 • 20min
Downshift or Double Down?
Explore the impact of charitable giving as new federal policies emerge. Learn about the challenges of juggling family finances while preparing for retirement and managing childcare costs. Listen in on a couple's candid discussion about achieving financial flexibility amidst rising living expenses. Gain insights on financial planning, from savings and investments to housing decisions, all while balancing career satisfaction and family responsibilities. And don't miss essential tips for navigating mid-career financial challenges!

Sep 12, 2025 • 21min
Is the Fee Worth It?
I belatedly looked at my quarterly statements and saw that my quarterly advisement fees are in excess of $13k. Is the fee worth what I'm getting in return?
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15 snips
Sep 11, 2025 • 27min
Can I Take a Break?
Feeling burned out at 39, the discussion dives into the prospect of taking a break from work. Personal stories reveal the emotional toll of significant life events, like 9/11, and how they shape career choices. The importance of financial planning during transitions and caregiving highlights navigating burnout while juggling responsibilities. Listeners receive practical tips on retirement savings, life insurance, and engaging with community, all while exploring delightful wine selections that foster connection and gratitude.

19 snips
Sep 10, 2025 • 21min
Brokerage Over 401(k)?
Explore the intriguing debate between choosing a brokerage account and a traditional 401(k). Discover the financial pros and cons of paying off a mortgage versus investing. The hosts highlight unique wines while discussing estate planning and life insurance. Dive into retirement strategies and the advantages of Roth accounts, alongside insights on navigating debt and college savings. Tune in for tailored advice on personal finance decisions that cater to individual circumstances!

20 snips
Sep 9, 2025 • 21min
I’m 28, Can I Ever Buy a House?
The discussion dives into the tumultuous housing market and the financial anxieties surrounding homebuying. A listener grapples with her late husband's investment portfolio, demonstrating the emotional toll of financial decisions. The hosts also explore plans for a live event that could enhance community engagement and promote financial literacy for families. Plus, they highlight the importance of being financially prepared for unexpected life changes, emphasizing the need for life insurance and thoughtful estate planning.

34 snips
Sep 8, 2025 • 24min
Do We Have Enough To Retire at My Age 59.5?
The conversation dives into navigating retirement finances for those in their mid-fifties, emphasizing careful planning for healthcare and asset management. There's a thoughtful discussion about the role of inheritances in retirement plans and the uncertainties tied to them. The podcast also touches on the importance of estate planning, especially for blended families, and encourages younger listeners to secure their financial futures. A listener shares their desire to retire early and explores investment strategies like Roth conversions.

27 snips
Sep 5, 2025 • 29min
Feeling Lost, What's the Next Step?
The discussion kicks off with insights on the rise of contract talent post-Labor Day and the multifaceted services of Amazon Prime. A chaotic travel tale from China leads into the importance of estate planning. Listeners hear a family's inspiring financial journey from modest savings to significant wealth, alongside the challenges faced by their adult children. Retirement finances are unpacked, covering social security and investment strategies. Finally, there's a focus on tailored wealth management for immigrant families, including tax liabilities and aligning financial goals.


