All Episodes

Episode 77: Sarah from Arlington Heights asks: “How do I make sure I don’t run out of money if the market crashes right after I retire?”

Episode 76: Lisa from Glenview asks: “Are we going to get hit with Illinois estate tax even if we’re under $10 million?”

Episode 75: Mary from Park Ridge asks: “Should I convert to a Roth before the tax rates go up?”

Episode 74: Karen from Naperville asks: “How Do I Protect My Retirement Savings from a Market Crash?”

Episode 73: Angela from Lincoln Square asks: “Should I Convert My IRA to a Roth Before Taxes Go Up?”

Episode 72: Debbie from Park Ridge asks: “Should I Pay Off My Mortgage Before I Retire?”

Episode 71: Listener Question from Karen: How Much Can I Safely Withdraw in Retirement?

Episode 70: Listener Question from Susan: Should I Move to Cash Because the Market Feels Risky?

Episode 69: Listener Question from Linda: Should I Take Social Security at 62 or Wait?

Episode 68: Brian asks: “How do I protect my retirement income if I live longer than expected?”

Episode 67: Susan asks: “Should I be moving money out of my 401(k) now that I’m retired?”

Episode 66: Kevin asks: “Is it risky to retire in a year when the market is at or near all-time highs?”

Episode 65: Dave asks: “How Do I Reduce Risk Five Years Before Retirement Without Going Too Conservative?”

Episode 64: Linda asks: “How Do We Control Taxes When RMDs and Social Security Start?”

Episode 63: Mark asks: “How Bad Is the Illinois Estate Tax If You’re Just Over $4 Million?”

Episode 62: Dave Asks: How Do I Reduce Risk Five Years Before Retirement Without Going Too Conservative?

Episode 61: Linda Asks: How Do We Control Taxes When RMDs and Social Security Start?

Episode 60: Mark Asks: How Bad Is the Illinois Estate Tax If You’re Just Over $4 Million?

Episode 59: Denise asks, “What’s the smartest way to start transferring wealth to our kids?”

Episode 58: Mark asks, “How can I keep steady income in retirement without sitting in cash?”

Episode 57: Karen asks, “How do Qualified Charitable Distributions really work with RMDs?”

Episode 56: Karen asks how to adapt when markets or tax laws change...

Episode 55: Linda's question: How to enjoy retirement today without jeopardizing tomorrow...

Episode 54: Should you do Roth conversions now or wait for Congress?

Episode 53: Linda’s question: Live fully or leave more?

Episode 52: Michael’s question: Should I make tax moves now?

Episode 51: Karen asks How to Build Flexibility Into Your Retirement Income Plan

Episode 50: Passing Assets to Siblings—While Avoiding Courts and Lawyers

Episode 49: When Inheritance Isn’t Equal: Greg’s Estate Planning Question

Episode 48: Mary Considers Selling Stock for Health Insurance—Is It the Right Move?

Episode 47: Dennis’s Tax Questions: Home Cost Basis, Mortgage Interest, and More…

Episode 46: Should Fred cash-out his life insurance policy?

Episode 45: Roth IRA as a sinking fund? Laurie wants to know

Episode 44: Can Amy max-out her 401(k) and IRA at the same time?

Episode 43: Can AI build Morgan’s retirement plan?

Episode 42: George Inherited a Roth IRA—Now What?

Episode 41: Barbara Asks: Are There Coverage Caps with Obamacare?

Episode 40: Don't Let Your Roth Sit Idle—Barb Wants to Know Where to Start

Episode 39: Frank's Dilemma: Tap the 401(k) or Keep the Mortgage?

Episode 38: Jeff asks, “I’m Thinking About a Roth Conversion—Where Do I Begin?”

Episode 37: Bill asks for the smart way to consolidate his investments

Episode 36: Mary asks about the financial tradeoffs of paying cash for her next house

Episode 35: Why are Barb’s tax returns so complicated in retirement?

Episode 34: Why didn’t Judi’s advisor fight to win her back?

Episode 33: Should Tobi roll-over her 401(k) & pay 1% for investment management?

Episode 32: Where Should You Park Inherited Money? Margie’s Short-Term Strategy

Episode 31: Is It Time to Reduce Risk? Jim’s Retirement Dilemma

Episode 30: Should You File for Social Security Early & Invest the Money? Liz’s Big Question Decoded

Episode 29: RMD Rule Changes 2025: Paula’s Plan for Retirement Clarity

Episode 28: Funding Futures: Margaret's Question About Grandkids' Roth IRAs

Episode 27: Protecting Your Forever Home: Georgine’s Journey to Peace of Mind

Episode 26: Roth Conversions Explained: Mary’s 401(k) and IRA Dilemma

Episode 25: Can I Max Out My Roth IRA If My Husband Maxes Out His 457(b)?

Episode 24: Mary's Dilemma: Navigating the Traditional 403(b)

Episode 23: Exploring Retirement Income Options: Kathy's Questions Answered

Episode 22: Cash vs. Mortgage: Carolyn Weighs the Pros and Cons of Paying Cash for a House

Episode 21: Helping Mom with Her 401(k): Answering Mike's Questions on Retirement Planning

Episode 20: Roth Conversions Uncovered: Answering William’s Questions

Episode 19: Understanding Taxes on Traditional IRAs: Jim's Questions Answered

Episode 18: Is Market Timing Worth It? Answering Walt's Big Question

Episode 17: Rebalancing 101: Answering Marie's Questions on Keeping Your Portfolio in Shape

Episode 16: Medicare Deadlines: Ron’s Question About Signing Up His Wife

Episode 15: Roth Converting Real Estate: Bob’s IRA Filled with Vacant Land

Episode 14: Taking Social Security at 62: Victoria’s Investment Strategy

Episode 13: Roth Conversion Strategy and CD Ladders: Anthony's Financial Game Plan

Episode 12: Medishare Before Medicare: Gladys' Healthcare Strategy

Episode 11: Awnee's Dilemma - Traditional TSP or IRA, Then Roth Conversion - Whats the Best Move

Episode 10: Should Val Convert Her 401(k)?

Episode 9: CDs, College Breaks, and IRAs – Connie’s Financial Questions Answered

Episode 8: Do You Need a Financial Planner if You’re Still Working in Your 50s and 60s?

Episode 7: Managing Medical Expenses When Working Past Age 65

Episode 6: How Qualified Charitable Distributions Can Save You on Taxes

Episode 5: Should Linda File for Social Security Now or Wait?

Episode 4: How Future Inflation Could Impact Delaying Social Security

Episode 3: Patricia has 70% of her retirement in a 403(b) and in a 457(b)

Episode 2: Linda asks for the best way to find a fee-only financial planner.

Episode 1: Mary believes her net worth is sufficient for retirement.