Jill on Money with Jill Schlesinger

David, a listener who inherited an IRA and brokerage account, walks through plans to reshape work and lifestyle after receiving the assets. He discusses tax timing, a 10-year IRA withdrawal strategy, housing and mortgage considerations, and plans to shift to part-time work while keeping travel and hobbies like curling on the calendar.

Brad Stulberg, author focusing on performance, wellbeing, and habits, shares ideas from his book The Way of Excellence. He talks about reclaiming meaning over burnout. He contrasts true excellence with hustle culture and explains embodied attention, consistency, rest-plus-recovery, smart quitting, and the power of supportive communities.

Conversations revolve around whether paying off a mortgage or keeping liquidity is smarter for a young family expecting twins. Strategies for parking house-sale proceeds are explored, including CD ladders and short-term cash vehicles. The value of a 1.25% adviser fee gets debated. A retirement bridge plan and steps for staging investments are also discussed.

Alex, a listener facing his wife’s cancer diagnosis, calls in about finishing their mountain cabin and reworking retirement plans. They discuss income, cash flow, a $1.2M nest egg with heavy Roth holdings, pension timing, paid-off condos and HELOC options. The conversation focuses on ways to fund the cabin, protect retirement assets, and simplify finances amid uncertain health realities.

Marie, a 61-year-old caller planning to retire at 67, seeks clarity on income, assets, and housing. Conversation covers her salary, retirement accounts and annuities. They discuss her California home and mortgage, projected income versus expenses, cash allocation and investment strategy. The segment ends with practical next steps like rollovers, consolidation and working with a CFP.

Tax season officially opens with a flurry of new tax-code changes that could affect refunds and filings. The show covers new credits, deductions and a new child retirement deposit program. There is explanation of new forms like Schedule 1A and big shifts such as senior deductions, tip and overtime tax rules, and auto loan interest treatment.

Caller Manny shares his financial journey as a single guy debating between renting and homeownership in a high-cost area. He reveals his impressive savings and a recent $36,000 windfall from a student-loan class action. Jill breaks down the pros and cons of renting versus buying, emphasizing the costs, taxes, and liquidity issues involved in real estate. Ultimately, she advises Manny to maintain flexibility, keep building his retirement savings, and continue contributing to his Roth accounts—setting him on a solid path for the future!

In this conversation, Erin, a 42-year-old from Colorado, seeks financial advice on managing a $200,000 trust distribution. They dive into her family’s financial landscape, including a $700K home burdened by a $590K mortgage and $80K in student loans. Erin discusses her retirement accounts and modest 529 plans for her kids. Jill recommends clearing student debt, building cash reserves, and diversifying investments with a DIY indexing approach. Listeners gain insights into managing inheritances and creating a robust investment strategy.

A listener grapples with retiring in an expensive city, prompting a deep dive into household finances and retirement strategies. They discuss managing a $10-12k monthly budget, including high rent and college costs for children. Jill provides insights on maximizing retirement contributions and recommends targeting age 67 for retirement, with strategies for delaying Social Security. The conversation also touches on the complexities of financial advisor fees and the trade-offs between selling RSUs and investing in real estate. All this while clarifying the differences between pensions and annuities.

Dan, a caller in his early 50s, grapples with the daunting prospect of early retirement after a successful career. He discusses his financial landscape, including a substantial brokerage account and pension options. Concerns about healthcare coverage until 65 are tackled, with insights on COBRA and state exchanges. Jill cleverly navigates Dan's situation, offering ideas on spending, wealth allocation, and investment risks, ultimately revealing that with careful planning, he might just be able to live a little more freely.