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 13, 2026 • 20min
Options After Losing Retirement Match
Elizabeth, a caller who works where the company cut its retirement match, seeks practical next steps. They talk about whether to keep contributing to the 403(b). They discuss shifting to Roth contributions, emergency funds, mortgage and insurance checks. They also cover exploring job options and how to prioritize savings after the match disappeared.
8 snips
Mar 12, 2026 • 19min
Is Early Retirement a Possibility?
Dave, a listener planning to downshift from high-stress work with his partner, seeks clarity on retiring at about $3 million. They discuss timelines, part-time pay options, spending versus saving, housing choices, and portfolio mix. The conversation focuses on whether to work a few more years, how much part-time income would help, and strategies for spending down savings.
5 snips
Mar 11, 2026 • 15min
Can We Stop Saving for College?
A lively money Q and A covering whether to ease up on 529 college contributions and when to shift that money to safer investments. Practical talk about pensions and keeping retiree portfolios low risk. Discussion on when someone might skip a financial advisor. Guidance on timing Roth conversions for high earners and handling quarterly taxes for remote PayPal income.
7 snips
Mar 10, 2026 • 21min
Are We Really Ready to Retire Early?
Sonia, a caller seeking retirement planning clarity, explains her household finances and conflicting goals. They discuss timing retirement at 55, tapping brokerage and RSU funds, healthcare costs, and whether to sell a rental for liquidity. Short-term work reduction, phased retirement, or part-time income are explored to bridge the gap and align finances and emotions.
9 snips
Mar 9, 2026 • 9min
Impact of Iran War on Economy
Discussion of how the Iran war is pushing oil above $90 and lifting gas and diesel prices. Exploration of higher energy costs rippling into food and fertilizer shortages. Contextual look at a weak jobs report and its implications for consumer confidence. Notes on stock resilience and practical tips for protecting money needed within a year.
9 snips
Mar 6, 2026 • 35min
Career Transitions With the Help of AI
Chieh Huang, entrepreneur and former CEO of Boxed who co-founded Pelgo, an AI-driven career transition platform. He discusses creating Pelgo to help workers navigate AI-driven job shifts. Short takes on practical upskilling, using AI to automate workflows, and how AI changes hiring and job roles. Tips on learning-by-doing with AI and tools to prepare for career transitions.
6 snips
Mar 5, 2026 • 25min
Financially Supporting a Parent
Kristen, a listener supporting her 65-year-old mother after she sold her home, seeks clarity on retirement and cashflow. They discuss juggling two mortgages, side-business income, liquidity needs, and whether mom should tap her retirement. Short, practical conversations about balancing parental costs with preserving the couple's future savings.
6 snips
Mar 4, 2026 • 18min
How to Handle My Pension Options
Listeners hear lively takes on prenup alternatives and keeping money separate. High-earner retirement timing and withdrawal sequencing get practical attention. Tax-smart use of pre-tax 403(b) funds between retirement and age 70 is explored. Advice on whether to move retirement accounts and consult a CFP is discussed. The pension annuity versus lump-sum tradeoffs are weighed.
7 snips
Mar 3, 2026 • 20min
On Track for FINE?
Dean, a caller seeking retirement clarity, shares detailed finances to get annuity and spending advice. They discuss whether annuities are needed, draining tax-deferred accounts to bridge income gaps, and practical ways to create steady cashflow without annuitizing. Conversation also covers working less, health insurance planning, and emotional hurdles to spending in early retirement.
6 snips
Mar 2, 2026 • 14min
Should I Convert My TSP?
Joe, a retired prior military service member with a pension and a $600k TSP, calls in about retirement planning. He outlines his income mix and low living costs. Conversation centers on whether to convert TSP to Roth, tax-bracket timing, converting gradually, and practical ways to pay conversion taxes while planning estate and simple investing steps.
