Jill on Money with Jill Schlesinger

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!

Mary, a 61-year-old widow from Northern California, seeks advice on retiring in two years while financially preparing for her twin daughters' college. She shares her impressive financial portfolio, including a $740K brokerage and $2.35M in retirement accounts. They discuss practical strategies for managing monthly expenses, handling health coverage, and optimizing Social Security benefits. Jill advises potential real estate sales to enhance cash flow and emphasizes the importance of estate planning and consulting a financial advisor.

Navigating a messy divorce? This conversation dives into essential financial strategies to regain control. Discover how to assess assets and debts, deal with joint credit card responsibilities, and create an immediate financial game plan. Learn about setting income goals for re-entering the workforce and the importance of updating insurance and estate documents. With a focus on long-term rebuilding of retirement, find reassurance that financial stability can be achieved through disciplined saving and strategic planning.

Linda from Atlanta shares her financial anxieties after previous losses during the financial crisis, raising questions about her retirement savings strategy. She details her $1.2M retirement fund and two homes, revealing a heavy cash allocation. Jill evaluates her financial security, emphasizing the stability provided by Linda's conservative approach and pension. They explore estate planning, noting the completion of essential documents, including a special needs trust. It's a journey of reassurance and tailored advice for a hopeful financial future.

Fred, a caller seeking retirement and tax planning advice, shares insights about his financial situation, including his 401(k) and savings breakdown. The discussion highlights the potential tax implications of large pre-tax balances, prompting Jill to recommend shifting to a Roth 401(k) to take advantage of current tax rates. They also touch on strategies for boosting his 529 savings and reviewing life insurance and estate planning, ensuring Fred has a solid financial game plan for the future.

Lynn, a listener seeking retirement planning advice, shares her journey towards financial flexibility as she approaches her 50s. They discuss how her spouse's pension and the Windfall Elimination Provision might impact Social Security benefits. Together, they analyze Lynn's savings, debts, and income needs, calculating a gap in retirement funds. Jill emphasizes the importance of finding fulfilling work and considering job transitions to enhance financial security. It’s a thoughtful navigation through retirement options and lifestyle choices!

In this discussion, Charles, a computer programmer seeking retirement advice, explores his goal of retiring at 62. He shares details about his wife's $80,000 pension and health coverage, emphasizing their financial strengths. They dive into his income, expenses, and Social Security benefits while unpacking his retirement accounts and properties. Jill suggests a strategy for using an inherited IRA to bridge the gap before retirement. With a solid cash buildup plan in place, Jill concludes that Charles is on track to retire in just over two years!