

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

10 snips
Jun 25, 2025 • 16min
Convincing Hubby We're Okay
The emotional journey of buying a home in California highlights the crucial role of realtors for first-time buyers. Dive into the couple's contrasting views on financial security as they navigate complex retirement plans. Explore the math behind savings and the importance of having a cash cushion. The discussion also covers sustainable income strategies, social security benefits, and how aligned financial goals can strengthen relationships. Tune in for valuable insights on achieving peace of mind in your financial future!

15 snips
Jun 24, 2025 • 16min
Should I Collect Social Security Early?
This discussion tackles the dilemma of when to collect Social Security, weighing the pros and cons of early versus delayed benefits. Listeners share personal experiences that highlight financial shortfalls and concerns over means testing. The conversation also shifts to homeownership, exploring whether it's a worthwhile investment compared to renting, and delves into effective strategies for balancing savings and investments. The importance of informed decision-making in navigating retirement and housing options is emphasized throughout.

12 snips
Jun 23, 2025 • 27min
Saving for Retirement vs College Funding
This discussion tackles the delicate balance between saving for retirement and funding a child's college education. They explore strategies for boosting retirement contributions while managing family expenses, highlighting the importance of 529 plans for education funding. Humor adds levity as they navigate the complexities of financial aid and debt management. Additionally, there's a focus on effective estate planning and ensuring families are prepared for future financial changes, making the often daunting tasks of saving feel more manageable.

11 snips
Jun 20, 2025 • 20min
Am I in Good Shape to Retire Next Year?
A listener questions if she's ready to retire at 65, leading to a deep dive into her financial situation after becoming a widow. The discussion highlights retirement income, Social Security eligibility, and strategic planning. They explore the importance of early financial planning, savings, and estate management. Asset allocation gets attention as they discuss index funds, stock-bond ratios, and long-term care planning. Finally, the episode emphasizes assessing personal financial skills and seeking professional advice if needed.

4 snips
Jun 19, 2025 • 15min
When Can I Safely Retire?
The podcast dives into the challenges of contemplating retirement at 60, focusing on a listener's job dissatisfaction and emotional hurdles. It highlights the importance of a solid financial foundation, discussing savings, investment portfolios, and living preferences. Strategies for retirement planning are explored, including the significance of social security, tax-advantaged accounts, and the benefits of potentially delaying retirement for financial security. An insightful look at career transitions also addresses feelings of being trapped and the exploration of new opportunities.

10 snips
Jun 18, 2025 • 17min
On Track for Retirement in 12 Years?
Explore the journey of educators navigating their retirement plans amid New York's pension system. Delve into financial strategies for balancing expenses with enjoyable living while planning for the future. Discover smart savings tactics for funding college education through 529 plans, and learn the intricacies of utilizing dual retirement accounts, especially Roth options. The conversation also touches on the emotional challenges faced by the 'sandwich generation' when making financial decisions, providing valuable insights for anyone eyeing a secure retirement.

18 snips
Jun 17, 2025 • 15min
What Is a Safe Withdrawal Rate?
Explore the nuanced world of safe withdrawal rates for retirees, challenging the traditional 4% rule. Discover how personal circumstances can impact financial decisions. Gain insights into managing 457 plans and addressing uncertainties in a changing job market. Hear a heartfelt listener message that highlights the podcast's impact on financial advising. Finally, dive into the uplifting power of community and the important role realtors play in the home-buying experience.

8 snips
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?
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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!