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
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.
8 snips
Feb 27, 2026 • 20min
Do I Need to Find Another Job?
Jane, recently laid off in 2024, is seeking practical money direction after severance. The conversation covers housing decisions with a low mortgage rate, heavy ESPP stock holdings and liquidity concerns, retirement account choices including a cash-balance pension, tax timing for selling stock, and options for part-time work to bridge expenses.
9 snips
Feb 26, 2026 • 18min
Why Not a Roth Conversion?
A rundown of when converting to a Roth may not be the right move. Warnings about commission-driven annuity pitches and better financing options for home renovations. A listener’s retirement readiness and strategies for delaying Social Security. Tips on charitable giving vehicles and fixing a bank error that hurt credit.
7 snips
Feb 25, 2026 • 20min
Reducing Retirement Savings for a House
David, a listener balancing maxed retirement plans, kids’ 529s and a $140k cash cushion, calls in about buying a pricier home. They discuss mortgage costs, tapping inheritance and savings, and short-term trade-offs like pausing retirement or 529 contributions. Practical alternatives like using brokerage funds and refinancing later are explored.
7 snips
Feb 24, 2026 • 17min
Changing Investment Firms
They discuss whether to follow a long-time planner who joined a new fiduciary firm and what to ask before moving your money. They compare big banks and independent advisors and highlight differences in process and fiduciary duty. They talk tax-aware steps for retirement, shifting contributions, and checking taxable holdings. They also review conservative portfolio choices like CDs, bonds, and modest IRA diversification.
Feb 23, 2026 • 19min
Full-Time Caregiver, Will I Be Okay?
Annie, a full-time caregiver for her parents who juggles part-time work and a disability pension. She explores pensions, Social Security timing, cash flow, paying down a loan, and whether her savings and home situation will keep her secure. Short, practical next steps are discussed along with how caregiving might factor into family estate splits.
8 snips
Feb 20, 2026 • 20min
Planning After the Death of My Wife
Gail, a recent widow from Maryland seeking financial clarity after her spouse's death. She discusses comparing her advisor's performance to Vanguard. They explore heavy single-stock concentration, how RMDs and other income affect taxes, and strategies like QCDs, Roth moves, and finding reliable support for future decisions.
12 snips
Feb 19, 2026 • 23min
Am I on Track for a 2028 Retirement?
Allison, a federal employee weighing a voluntary early retirement, calls in with clear numbers and goals. She discusses pension timing, Social Security choices, tax-aware withdrawal sequencing, and housing plans. The conversation covers using inherited IRA funds, TSP/Roth allocation, travel priorities, and whether a buyout now makes sense for her timeline.
21 snips
Feb 18, 2026 • 15min
Can We Retire Now if We Get Laid Off?
They debate whether leaving work early after a layoff is realistic when facing taxes, health costs, and $12k monthly spending. Tax treatment of retirement accounts and safe portfolio income are analyzed. They weigh paying down a 5.5% mortgage versus keeping liquidity, discuss credit card fee decisions, CDs versus stock ETFs for retirees, and handling large student loans and high advisory fees.
7 snips
Feb 17, 2026 • 18min
Are We on the Correct Path?
A caller asks for a sanity check on her retirement timeline, savings and account mix. They walk through household income, pensions, mortgage and a large cash opportunity fund. The conversation covers target retirement ages, contribution plans and how projected pensions change the outlook. The host explains why a flat-fee advisor may have overstated needs and recommends annual checkups.
