Jill on Money with Jill Schlesinger
Audacy
Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of what’s important for anyone to know. Jill takes listener phone calls and interviews informative and entertaining guests each week to uncover surprising insights and provide actionable information so you can make the most of your money. Have a question you want us to answer on the show? Head to Jillonmoney.com and click the "Contact Us" button.
Episodes
Mentioned books
9 snips
Mar 27, 2026 • 25min
Can I Quit My Job at 57?
Anthony, a 57-year-old caller balancing retirement accounts, brokerage, HSA and cash, seeks clarity about leaving work early. He discusses renting vs buying, timing a sabbatical around bonuses, short-term cash and health insurance plans. The conversation covers using Rule of 55, withdrawal timing from 401(k)s, tax strategy, and updating estate paperwork.
8 snips
Mar 26, 2026 • 25min
Laid Off at 62, Will We Be Okay?
Cindy calls in about her husband’s surprise layoff at 62; she’s a wife navigating pensions, Social Security timing, annuities, and retirement income. They discuss pension coordination, 401(k) withdrawals and annuitization, COBRA and near-term cash needs. Practical income-bridging options and boundaries around helping adult children are highlighted.
8 snips
Mar 25, 2026 • 28min
Struggling to Even Think of Retirement
Kat, a caller juggling two mortgages and a loss-making rental, seeks clarity on retiring at 70. She discusses household income, negative cash flow from an out-of-state property, and a $50K renovation plan. The conversation covers using retirement-plan loans, repairing units to boost rent, shifting priorities toward retirement savings, and managing college funding expectations.
7 snips
Mar 24, 2026 • 15min
Is 67 Our Magic Number to Retire?
Jay, a listener from Atlanta planning retirement at 67, shares household finances and account balances. They discuss pension survivor choices and Social Security timing. Short conversations cover mortgage, health, and using traditional accounts tax-smartly. The talk highlights staggered retirement options and practical drawdown strategies.
7 snips
Mar 23, 2026 • 21min
Balancing Retirement With Tuition
Parents balancing late-in-life adoption, high school tuition, and retirement funding. Discussion of 529 account tradeoffs versus boosting retirement contributions. Review of pension, Social Security, cashflow, and mortgage impact. Practical steps on using loans, pausing 529 contributions, and completing estate and guardianship paperwork.
Mar 21, 2026 • 2min
Welcome to Becoming You with Suzy Welch
Suzy Welch, three-time NYT bestselling author, business journalist and NYU professor who teaches self-discovery. She discusses decision-making, choosing between being the author or editor of your life, and how values and aptitudes guide scary but joyful choices. Short, clear, and refreshingly honest.
8 snips
Mar 20, 2026 • 29min
Too Much in a Single Stock?
Katrina, a Long Island caller balancing family life and retirement planning, asks for a financial gut check. She discusses a $1.3M concentrated company stock position, tax worries about selling appreciated shares, and whether their savings and new job pay mix will keep them on track. The conversation covers diversification strategy, Roth vs traditional contributions, college 529 shortfalls, insurance, and estate planning.
14 snips
Mar 19, 2026 • 20min
Can I Retire in 18 Months?
CJ, a caller from Wisconsin considering a career downshift after a long career, shares his finances, property and pension. They discuss timing a move to part-time work, using a 457 and cash reserves, housing and construction loan complications, college and healthcare costs, rental and vacant land options, and contingency plans like selling property.
7 snips
Mar 18, 2026 • 16min
Are We on Track, or Way Off?
Practical money fixes for retirement and tuition planning. Strategies for handling concentrated company stock and evaluating advisory fees. A breakdown of oil futures speculation and when to keep cash in 529 plans. Real-life customer service wins and tips for reducing spending to stay on track.
4 snips
Mar 17, 2026 • 21min
Moving From Saving to Spending
Chris, a recent retiree navigating the shift from saving to spending, calls in with questions about withdrawals, Roth conversions, and asset allocation. The conversation covers tax-smart conversion timing, using savings to pay conversion taxes, pension and Social Security timing, charitable giving via donor-advised funds, and simplifying accounts and fees. Practical choices and next steps are explored in short, actionable talk.
