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
Apr 9, 2026 • 15min
Reset Dilemma Advice
A listener wrestles with a seven-figure inheritance and whether to reshape life and finances. Legal safeguards and the danger of commingling assets get careful attention. Debt and mortgage choices come up for homeowners deciding between cash or carrying a loan. Questions about national debt, potential tax impacts, and long-term care insurance versus self-insuring are also explored.
7 snips
Apr 8, 2026 • 19min
Has My Roth Conversion Ship Sailed?
Carol, a 69-year-old retiree calling in about a $900k rollover IRA. She discusses whether Roth conversions make sense and details her income, pension, Social Security, and savings. They explore using withdrawals to build taxable savings, managing tax brackets before RMDs, timing and withholding tactics, and tax-free charitable distribution options.
7 snips
Apr 7, 2026 • 16min
Should I Tap a CD or My Roth?
They debate whether to break a CD or tap a Roth IRA to buy a car. They cover pros and cons of selling or holding a fully depreciated rental property. They weigh pension lump sum versus rolling it over to avoid big tax hits. They question early Social Security claiming and urge a retirement spending plan first.
7 snips
Apr 6, 2026 • 28min
Concerned About Running Out of Money
Renee, a retired listener planning a move from California to Arizona, calls in about retirement finances and housing choices. They discuss annuity and Social Security income, weighing buy versus rent after a home sale. Conversation covers monthly cash-flow concerns, comparing costs between states, and why keeping proceeds liquid may be safer than buying right away.
8 snips
Apr 3, 2026 • 16min
A Holistic Giving Solution for Donors and Advisors
Julie Sunwoo, President of DAF Giving 360 and former financial services pro, explains donor-advised funds and why they simplify giving. She covers contributing appreciated assets, tax-smart strategies like bunching, recent tax law impacts, recordkeeping benefits, and planning for successors. Short, practical talk on making philanthropy easier and more strategic.
5 snips
Apr 2, 2026 • 16min
Encore Career at Age 50?
Jay, a 50-year-old corporate worker planning a bold shift into law enforcement, shares his family, finances, and timeline. Conversation covers burnout and desire for public service. They discuss income change, hiring steps like fitness tests and academy timelines, retirement planning and contingencies, and practical pre-transition steps such as maximizing contributions and getting fit.
7 snips
Apr 1, 2026 • 15min
Retirement in Three Months?
They run retirement numbers for people wondering if they can stop working soon and stress the hidden costs like healthcare and spending clarity. They discuss safe withdrawal rates and timing work for Medicare. They cover inheritance planning and tax traps with annuities. They offer practical tips on what paperwork to keep, where to park large cash balances, and why credit scores can dip after paying off a mortgage.
8 snips
Mar 31, 2026 • 14min
10 Years Until Retirement, Can I Do It?
Kay, a 55-year-old marketing professional planning retirement at 65 while supporting an aging parent. They cover her income, savings, IRA and Roth balances, mortgage with a low rate, Social Security timing, and realistic projections. Conversation also explores lifestyle choices, side income options like thrifting and reselling, and care considerations for her 92-year-old mother.
16 snips
Mar 30, 2026 • 22min
Life Has Changed, Are We Okay?
Michael, a listener from the Northeast balancing two teens, a pension, and mixed retirement accounts, checks whether retiring in his 60s is still realistic. He talks about household income shifts, a spouse’s lower-paid role, college savings questions, account consolidation, and plans for selling a condo to boost retirement cash.
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.
