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
10 snips
Feb 16, 2026 • 25min
Can I Quit My Job and Become an Artist?
Jennifer, a part-time federal worker turned aspiring full-time writer, shares her plan to quit and pursue writing seriously. The conversation covers her income, expenses, savings and mortgage. Practical topics include how much runway to save, testing writing goals before leaping, and strategies for re-entry if things don’t go as planned.
5 snips
Feb 13, 2026 • 15min
Retirement and Leaving a Legacy
Mike (Jersey Mike), a retiree with long career savings and multiple pensions, describes his family, incomes, and savings. The conversation covers pension timing, annuity choices, tax issues like RMDs and Roth conversions, and plans to downsize or protect legacy wealth. Practical decisions about investment risk and when to claim fixed income are explored in short, clear advice segments.
16 snips
Feb 12, 2026 • 23min
Time for a Financial Reset?
Jason, who sold a Hudson Valley home and launched a new career in real estate and interior design, walks through his financial crossroads. He discusses timing of the windfall, paying off debt, whether to rent or build a new house, how much to invest in a new build, and fallback plans and mortgage strategies.
9 snips
Feb 11, 2026 • 14min
I Got a Late Start, Am I Okay for Retirement?
Catherine, a 58-year-old renter who started saving later, shares her retirement savings, investments and plans for travel. She discusses balances across retirement accounts, a large brokerage position and an expected foreign property sale. The conversation covers spending goals, working a few more years, risk reduction and estate planning.
5 snips
Feb 10, 2026 • 16min
How to Handle Home Sale Proceeds
Katie, a recent home seller with $265,000 in proceeds, calls in for guidance. She and Jill talk about whether to pay down a new 6.5% mortgage or keep cash. They explore income, investments, timing for retirement, emotional comfort vs liquidity, refinancing prospects, and estate planning. Practical next steps and monitoring options are discussed.
12 snips
Feb 9, 2026 • 18min
Can I Move Up My Retirement Age?
Phil, a listener weighing an accelerated retirement after caregiving and an inheritance, shares his finances and timing. They discuss Medicare timing, pensions versus lump sums, taxable and retirement accounts, home mortgage advantages, and practical next steps like consolidation and documenting assets. Short, practical financial planning talk focused on whether he can retire sooner.
9 snips
Feb 6, 2026 • 22min
Is Investing a Pipe Dream?
A lively discussion about whether middle- and lower-income Americans can realistically save for retirement. They explore handling a divorce windfall and smart next steps for debts, emergency funds, and retirement contributions. The conversation warns against treating silver or crypto as retirement plans and explains using 529s and taxes on required minimum distributions.
7 snips
Feb 5, 2026 • 18min
Should I Pursue a Great Money Reset?
West Coast Rob, a burned-out professional weighing a sabbatical after being passed over for promotion, shares salary, savings and retirement details. He and Jill explore whether his finances support stepping back. They discuss cash runway, replacing income, rollovers and Roth timing. The conversation focuses on affordability, job options and practical steps for a money reset.
10 snips
Feb 4, 2026 • 19min
Can I Retire Before Kids Are Done With College?
A listener considers retiring at 56 while still funding three kids through college. The conversation breaks down income, pensions, business sale timing and FAFSA implications. Tradeoffs between working longer, part-time work after an exit, and healthcare and tax impacts are explored. Strategies for paying college without draining retirement are discussed.
18 snips
Feb 3, 2026 • 18min
Can Dad Retire Comfortably?
Seth calls about his 68-year-old father, whom he helps manage finances for. They talk about whether dad can retire now given modest pay, Social Security, IRA/annuity holdings, and $100K in cash. Conversations cover housing choices, liquidity and high-yield options, annuity consolidation, withdrawal strategy and RMDs, plus estate titling and easing the emotional side of retirement.
