Jill on Money with Jill Schlesinger

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19 snips
Jun 27, 2025 • 22min

Is the Annuity Too Good to Be True?

This discussion dives into the allure of annuities as a means to generate guaranteed income during retirement. A couple shares their initial skepticism but considers expert advice while evaluating their unique financial situation. The host critiques a financial planner's proposal, exploring the potential benefits and drawbacks of annuities versus alternative investment strategies. Misconceptions about annuities are addressed, emphasizing the importance of informed financial planning and the value of getting a second opinion from a knowledgeable advisor.
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10 snips
Jun 26, 2025 • 23min

Hubby Hates Job, Can He Quit?

Minnie Mouse from Pennsylvania shares her husband's struggles with job dissatisfaction. They delve into the possibility of him taking a lower-paying role while still aiming for a comfortable retirement by age 55. The conversation covers essential financial strategies, including investment options and the emotional impacts of career transitions. They also explore the pros and cons of lump sum pensions versus steady income, all while sprinkling in delightful Disney memories to lighten the discussion.
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10 snips
Jun 25, 2025 • 17min

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!
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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.
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12 snips
Jun 23, 2025 • 28min

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.
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11 snips
Jun 20, 2025 • 21min

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.
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4 snips
Jun 19, 2025 • 16min

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.
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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.
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18 snips
Jun 17, 2025 • 16min

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.
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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.

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