Jill on Money with Jill Schlesinger

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10 snips
Dec 5, 2025 • 14min

Are the Numbers Too Good to Be True?

In this insightful discussion, Brian—a tech-savvy IT professional in his early 50s—shares his surprise at retirement calculators suggesting he could retire soon. With a solid income of $140k, low monthly expenses, and over $1.7M in savings, he’s positioned for a career shift. Jill guides him through options, emphasizing part-time work for health coverage and the importance of emotional readiness. They explore strategies to manage the transition smoothly, ensuring he stays financially secure while seeking fulfilling new opportunities.
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7 snips
Dec 4, 2025 • 16min

Keeping All the Balls in the Air

John, a caller juggling family life and finances, shares his concerns about retirement readiness while seeking guidance on budgeting. He reveals his income, family dynamics, and the stress of trading investments, coupled with a desire to downsize his home. Jill tackles his questions on retirement balances and projected expenses, including Social Security implications. They explore the option of part-time work in retirement as John weighs his financial security. Jill reassures him of his strong position and encourages enlisting a financial planner to ease his burden.
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6 snips
Dec 3, 2025 • 14min

Planning Around a Diagnosis

Wes shares his pressing concerns about financially planning for his mother-in-law's Alzheimer's diagnosis. They delve into the costs of long-term care, timing for potential moves to assisted living, and navigating Medicaid options. Wes discusses family contributions to cover expenses while managing their household finances. Jill offers strategies for cash-flowing care without jeopardizing retirement savings and emphasizes the importance of finalizing estate documents and insurance. It’s a heartfelt and practical conversation about family and financial responsibilities.
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6 snips
Dec 2, 2025 • 13min

Can We Cut Back on Work?

Caller James from North Carolina, a dedicated father in his early 50s, seeks financial guidance on cutting back work to spend more time with his young son. He shares details about his $2M retirement investments and minimal cash reserves, sparking a discussion on maintaining liquidity. Jill advises reducing retirement contributions for a cash cushion while balancing current income and future plans. They explore self-employment options and essential insurance coverage, ensuring James is prepared for his family’s financial future.
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6 snips
Dec 1, 2025 • 13min

Is One Million Enough?

JP, a semi-retired theater artist from Milwaukee, seeks assurance about his financial readiness for retirement. He discusses his household income, expenses, and concerns about convincing his wife they are financially secure. Jill emphasizes that 'enough' depends on lifestyle choices and reviews their projected incomes and savings. They evaluate a desired spending target of $70K, affirm JP's strong liquidity, and ultimately conclude that their financial situation is solid. Jill reassures JP, highlighting their disciplined saving habits.
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13 snips
Nov 28, 2025 • 34min

State of the Economy With Diane Swonk

Diane Swonk, Chief Economist at KPMG, shares her insights on the U.S. economy amidst fluctuating trends. She explains how AI investments and wealth effects sustain growth despite a K-shaped recovery where affluence skews benefits. Diane highlights that childcare costs push skilled women out of the workforce and discusses the challenges posed by recent government shutdowns. With a forecast of 3.2% CPI, she warns that wage growth isn't keeping up with inflation, complicating consumer budgets during the holiday season.
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Nov 27, 2025 • 44min

The Stages of Job Loss

Dr. Sharon Melnick, a business psychologist and executive coach, dives deep into the emotional landscape of job loss, explaining how it affects identity and purpose. She outlines the five stages of grief that accompany layoffs and offers strategies for coping, like reframing negative thoughts and using calming techniques to manage anxiety. Sharon emphasizes the importance of viewing job loss as an opportunity for growth and encourages young workers to embrace new experiences. Her insights provide a roadmap for navigating these challenging transitions.
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8 snips
Nov 26, 2025 • 25min

Wife Questioning Asset Allocation

Peter and Donna, a retired couple from the Bay Area, delve into their retirement planning concerns. They discuss a hefty asset allocation of 65% equities, with Donna feeling uneasy about the risk. The couple reviews their income needs, Social Security plans, and housing situation while Jill highlights the emotional toll of market downturns. With solid advice on keeping a cash buffer and tax planning strategies in place, they create a practical retirement plan that both partners can feel confident about.
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7 snips
Nov 25, 2025 • 16min

Should I Refinance to Fixed Rate?

Jill dives into the pros and cons of refinancing a 10-year ARM, advising against jumping to a fixed rate given current market conditions. She also weighs the benefits of Roth conversions against IRA withdrawals, discussing tax implications and inheritance strategies. Listeners learn smart saving tips for future home purchases and the risks of using retirement funds to tackle credit card debt. Each segment is packed with practical financial advice and insights!
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8 snips
Nov 24, 2025 • 22min

Major Move Before Retirement

Listener Vicki shares her adventurous cross-country move and the financial worries that come with it. She’s at a crossroads, wondering if her recent relocation could jeopardize her retirement plans. Jill dives into Vicki's house sale options, investment balances, and the risks linked to healthcare costs. They discuss balancing lifestyle with financial stability, recommending a cautious approach: sell, rent, and reassess. The conversation highlights the importance of thorough planning, especially as Vicki considers returning to the Southeast.

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