Jill on Money with Jill Schlesinger

Mary, a 60-year-old realtor, calls in seeking advice on whether she can afford to slow down her work life. With $1.6M in brokerage accounts and a mortgage-free condo, she discusses her solid financial foundation. They explore spending needs, part-time work options, and the timing for her Social Security benefits. Jill recommends strategic Roth conversions to optimize her tax situation while ensuring Mary's lifestyle goals, including her dream trips to Italy and Sardinia, remain within reach.

Jennifer, a former high earner, took a planned year off work, creating an opportunity for strategic financial planning. She explores whether her unique low-income year allows for a Roth conversion to minimize taxes. Jill advises her to roll over her 457 account to Vanguard and consolidate her investments while discussing ongoing conversion strategies. They also touch on charity planning and ensuring her estate documents are updated, all while navigating the complexities of retirement planning in this transition year.

Jill and Mark send heartfelt holiday greetings while encouraging listeners to focus on loved ones during tough times. The discussion highlights the importance of life experiences over finances, urging compassion and grace for oneself. They share cherished holiday traditions, including favorite films to watch with family. The duo emphasizes the importance of kindness and community support, inviting listeners to connect for assistance and celebrate the season with gratitude and generosity.

In this engaging discussion, John, a senior tech professional who’s spent 29 years in the industry, shares his experiences with burnout and his dream to retire at just 49. He details his impressive financial setup, including multimillion-dollar stock grants and various asset breakdowns. They delve into John's living expenses and plans for part-time work post-retirement. Jill offers practical advice on managing mortgage payments and cash reserves while reflecting on the privilege of such financial freedom. Tune in for valuable insights!

Dave, a listener from North Carolina, seeks advice on retirement timing and tax strategies. He discusses household income, plans to retire soon, and a significant concentration in company stock. Jill dives into his 401(k) and after-tax conversion strategies while emphasizing the importance of diversification. They explore his real estate holdings, healthcare options, and the potential of 529 funds for his son. Jill encourages simplifying investments and reassures Dave he's on track for an early retirement.

Lee, a 60-year-old planning to retire at 62, delves into her financial landscape, including a $195k salary and nearly $1M in her TSP account. She discusses her $65k pension and Social Security benefits alongside monthly expenses of $6,500. Lee considers a move to a smaller home and the complexities of her rental properties, while Jill advises on a smart withdrawal strategy. They also discuss the pros and cons of keeping or selling investments, all as Lee prepares for a purposeful retirement full of new adventures.

Rich, a retired caller, dives into the world of Roth conversions and retirement planning. He discusses his current financial situation, including pensions and Social Security. Jill helps him navigate the tricky waters of converting traditional IRAs before RMDs, emphasizing the importance of timing and tax brackets. They explore the strategy of maxing out current brackets and using brokerage funds for tax payments. Rich gains insights on partial conversions and the importance of coordinating with financial advisers to optimize his retirement income.

Joy, a public-sector employee with 25 years of service, explores her early retirement plans with Jill. They dive into the nitty-gritty of pensions, rental properties, and savings strategies. Jill reassures Joy that her financial footing is secure, discussing the impact of mortgage decisions and health insurance changes. They strategize on cash flow from rentals and outline a withdrawal plan to bridge the gap before Social Security kicks in. With a smile, they conclude that Joy's retirement plan is not just a dream, but a reachable goal!

In this discussion, guest Bradley, a 60-year-old New Yorker with plans to retire in 2027, seeks crucial retirement advice. He details his financial landscape, including a significant TIAA balance and various debts. Jill emphasizes the importance of paying off high-interest loans and managing his duplex renovation for potential rental income. They also explore the roadmap Bradley needs to follow before taking the retirement plunge, ensuring he’s well-prepared for the transition ahead.

This time around, Bill, a 58-year-old saver's financial journey takes center stage as he grapples with his pre-tax retirement savings. Jill and the team dive into Bill's income and generous employer match, recommending a shift towards brokerage accounts for better liquidity. With insights from Mark, they also discuss the advantages of Roth contributions, emphasizing long-term tax benefits as Bill nears retirement. A lively conversation ensues about balancing immediate needs with future planning, making financial decisions that truly impact Bill's golden years!