Jill on Money with Jill Schlesinger

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10 snips
Jan 16, 2026 • 19min

Burned Out and Really Want to Quit

Jennifer, a 62-year-old nurse with three decades of experience, shares her struggles with burnout and desire to retire soon. She discusses her pension options and the complexities of her financial assets, including brokerage accounts and a 403(b). The conversation delves into her monthly expenses, caregiving for her mother, and how these factors impact her retirement plans. Together with Jill, they explore various options, such as working fewer hours or delaying retirement while emphasizing the importance of planning for health insurance and estate documents.
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9 snips
Jan 15, 2026 • 21min

When Can I Downsize My Job?

In this engaging discussion, Paul from Chicago, a 57-year-old contemplating a more meaningful and less stressful second act, seeks guidance on downshifting in his career. He explores the intricacies of his savings, retirement accounts, and the potential of leveraging his home equity. Jill offers strategic advice on managing college costs, emphasizes testing a new location by renting first, and underscores the significance of engaging a financial planner for tailored insights. Their conversation is enlightening for anyone considering a mid-career pivot.
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6 snips
Jan 14, 2026 • 16min

Can Trump Cap Credit Card Rates?

President Trump's proposal to cap credit card interest rates at 10% raises intriguing legal questions. Jill discusses the necessity of congressional action for such a cap, highlighting the challenges of bipartisan cooperation. Current credit card rates hover around 20%, and a cap could save consumers significant money. She also examines the ripple effects of Federal Reserve rate cuts and the industry’s response to potential changes. Additionally, insights into the politicization of central bank decisions offer a broader view of economic implications.
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5 snips
Jan 13, 2026 • 16min

Roth Conversions Leading to Early Retirement?

Is now the right time for Roth conversions if you're close to retirement? Discover insights on whether to convert assets or defer until your income decreases. Learn about managing taxes effectively, along with the importance of liquidity. Also, find out the best ways to seek out fee-only financial planners for personalized advice. Plus, hear practical tips on making small annual conversions and considerations for estate planning and survivor benefits. Tune in for valuable financial strategies!
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8 snips
Jan 12, 2026 • 25min

Managing the Moving Parts

Navigating retirement can feel overwhelming, especially with family dynamics at play. The couple discusses their financial landscape, including pensions and retirement savings. Jill offers valuable advice on timing Social Security claims to maximize benefits. She encourages using pre-tax accounts for early income needs and shares tax strategies to stay within certain brackets. Plus, they delve into the importance of estate planning, especially for a child with special needs, and Jill's mortgage advice keeps their finances in check.
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9 snips
Jan 9, 2026 • 20min

Do You Need a Registered Investment Advisor?

Jonathan Beatty, head of Schwab Advisor Services at Charles Schwab, sheds light on the world of independent Registered Investment Advisors (RIAs). He explains the fiduciary duty of RIAs to prioritize client interests and details how they offer comprehensive services beyond just investments. The conversation delves into the collaborative culture among RIAs, emerging trends like succession planning, and the transformative role of AI, which enhances advisor workflows while maintaining crucial emotional connections. Beatty also emphasizes the importance of democratizing financial advice.
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5 snips
Jan 8, 2026 • 15min

Roth vs Pre-Tax 401(k) Contributions

The discussion dives into the implications of switching to a Roth 401(k) and how it affects paycheck amounts. Listeners learn about the importance of starting contributions at the employer match level and gradually increasing them. Jill highlights the significance of using the IRS withholding estimator for financial planning. The conversation also touches on the pros and cons of mutual funds versus ETFs, emphasizing low-cost index options. Overall, the insights are practical for anyone considering retirement contributions.
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6 snips
Jan 7, 2026 • 15min

Can I Fully Retire in 2-3 Years?

Angela, a listener seeking advice on her retirement plan, discusses her aim to retire in just two to three years. She shares insights about her household finances, including 401(k) balances and Social Security estimates. The conversation dives into options for a pension lump sum and managing appreciated company stock. Jill also highlights the importance of spending needs, flexible income sources, and the impact of taxes on retirement accounts. They wrap up by confirming Angela's estate planning is in place, setting her on a path toward financial freedom.
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8 snips
Jan 6, 2026 • 17min

Could Operation in Venezuela Impact Gas Prices?

The discussion dives into Venezuela's massive oil reserves and their potential impact on global prices. Jill highlights that despite Venezuela holding 20% of the world's crude oil, immediate price changes for U.S. consumers aren't expected. She explores the challenges of extracting this oil and the uncertainty surrounding whether U.S. companies will invest. Additionally, the hosts touch on mortgage rates and consumer behavior, emphasizing the importance of financial planning amidst market volatility.
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5 snips
Jan 5, 2026 • 15min

Pension Lump Sum or Annuity?

What should you do with your pension: take a lump sum or an annuity? Explore Amy's retirement timing and the implications of health insurance coverage before Medicare. Delve into the calculations of her income needs, Social Security, and hefty retirement assets. Jill suggests leaning towards the lump sum option due to the potential for growth and personal legacy goals. Plus, key estate planning reminders to ensure a smooth transition into retirement. Tune in for practical advice filled with financial wisdom!

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