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| Episode | Date |
|---|---|
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Episode 80: Michelle from Glenview asks: “What happens if the market crashes right after I retire—am I in trouble?”
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Jun 01, 2026 |
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Episode 79: Karen from Arlington Heights asks: “If Illinois estate tax kicks in at $4 million, how do I avoid getting hit?”
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May 25, 2026 |
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Episode 78: Linda from Northbrook asks: “Are tax rates really going up after 2028—and what should I do now?”
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May 18, 2026 |
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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?”
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May 11, 2026 |
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Episode 76: Lisa from Glenview asks: “Are we going to get hit with Illinois estate tax even if we’re under $10 million?”
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May 04, 2026 |
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Episode 75: Mary from Park Ridge asks: “Should I convert to a Roth before the tax rates go up?”
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Apr 27, 2026 |
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Episode 74: Karen from Naperville asks: “How Do I Protect My Retirement Savings from a Market Crash?”
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Apr 20, 2026 |
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Episode 73: Angela from Lincoln Square asks: “Should I Convert My IRA to a Roth Before Taxes Go Up?”
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Apr 13, 2026 |
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Episode 72: Debbie from Park Ridge asks: “Should I Pay Off My Mortgage Before I Retire?”
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Apr 06, 2026 |
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Episode 71: Listener Question from Karen: How Much Can I Safely Withdraw in Retirement?
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Mar 30, 2026 |
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Episode 70: Listener Question from Susan: Should I Move to Cash Because the Market Feels Risky?
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Mar 23, 2026 |
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Episode 69: Listener Question from Linda: Should I Take Social Security at 62 or Wait?
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Mar 16, 2026 |
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Episode 68: Brian asks: “How do I protect my retirement income if I live longer than expected?”
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Mar 09, 2026 |
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Episode 67: Susan asks: “Should I be moving money out of my 401(k) now that I’m retired?”
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Mar 02, 2026 |
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Episode 66: Kevin asks: “Is it risky to retire in a year when the market is at or near all-time highs?”
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Feb 23, 2026 |
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Episode 65: Dave asks: “How Do I Reduce Risk Five Years Before Retirement Without Going Too Conservative?”
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Feb 16, 2026 |
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Episode 64: Linda asks: “How Do We Control Taxes When RMDs and Social Security Start?”
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Feb 09, 2026 |
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Episode 63: Mark asks: “How Bad Is the Illinois Estate Tax If You’re Just Over $4 Million?”
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Feb 02, 2026 |
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Episode 62: Dave Asks: How Do I Reduce Risk Five Years Before Retirement Without Going Too Conservative?
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Jan 26, 2026 |
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Episode 61: Linda Asks: How Do We Control Taxes When RMDs and Social Security Start?
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Jan 19, 2026 |
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Episode 60: Mark Asks: How Bad Is the Illinois Estate Tax If You’re Just Over $4 Million?
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Jan 12, 2026 |
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Episode 59: Denise asks, “What’s the smartest way to start transferring wealth to our kids?”
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Jan 05, 2026 |
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Episode 58: Mark asks, “How can I keep steady income in retirement without sitting in cash?”
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Dec 29, 2025 |
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Episode 57: Karen asks, “How do Qualified Charitable Distributions really work with RMDs?”
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Dec 22, 2025 |
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Episode 56: Karen asks how to adapt when markets or tax laws change...
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Dec 15, 2025 |
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Episode 55: Linda's question: How to enjoy retirement today without jeopardizing tomorrow...
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Dec 08, 2025 |
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Episode 54: Should you do Roth conversions now or wait for Congress?
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Dec 01, 2025 |
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Episode 53: Linda’s question: Live fully or leave more?
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Nov 24, 2025 |
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Episode 52: Michael’s question: Should I make tax moves now?
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Nov 17, 2025 |
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Episode 51: Karen asks How to Build Flexibility Into Your Retirement Income Plan
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Nov 10, 2025 |
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Episode 50: Passing Assets to Siblings—While Avoiding Courts and Lawyers
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Nov 03, 2025 |
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Episode 49: When Inheritance Isn’t Equal: Greg’s Estate Planning Question
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Oct 27, 2025 |
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Episode 48: Mary Considers Selling Stock for Health Insurance—Is It the Right Move?
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Oct 20, 2025 |
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Episode 47: Dennis’s Tax Questions: Home Cost Basis, Mortgage Interest, and More…
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Oct 13, 2025 |
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Episode 46: Should Fred cash-out his life insurance policy?
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Oct 06, 2025 |
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Episode 45: Roth IRA as a sinking fund? Laurie wants to know
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Sep 29, 2025 |
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Episode 44: Can Amy max-out her 401(k) and IRA at the same time?
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Sep 22, 2025 |
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Episode 43: Can AI build Morgan’s retirement plan?
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Sep 15, 2025 |
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Episode 42: George Inherited a Roth IRA—Now What?
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Sep 08, 2025 |
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Episode 41: Barbara Asks: Are There Coverage Caps with Obamacare?
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Sep 01, 2025 |
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Episode 40: Don't Let Your Roth Sit Idle—Barb Wants to Know Where to Start
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Aug 25, 2025 |
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Episode 39: Frank's Dilemma: Tap the 401(k) or Keep the Mortgage?
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Aug 18, 2025 |
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Episode 38: Jeff asks, “I’m Thinking About a Roth Conversion—Where Do I Begin?”
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Aug 11, 2025 |
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Episode 37: Bill asks for the smart way to consolidate his investments
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Aug 04, 2025 |
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Episode 36: Mary asks about the financial tradeoffs of paying cash for her next house
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Jul 28, 2025 |
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Episode 35: Why are Barb’s tax returns so complicated in retirement?
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Jul 21, 2025 |
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Episode 34: Why didn’t Judi’s advisor fight to win her back?
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Jul 14, 2025 |
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Episode 33: Should Tobi roll-over her 401(k) & pay 1% for investment management?
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Jul 07, 2025 |
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Episode 32: Where Should You Park Inherited Money? Margie’s Short-Term Strategy
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Jun 30, 2025 |
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Episode 31: Is It Time to Reduce Risk? Jim’s Retirement Dilemma
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Jun 23, 2025 |
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Episode 30: Should You File for Social Security Early & Invest the Money? Liz’s Big Question Decoded
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Jun 16, 2025 |
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Episode 29: RMD Rule Changes 2025: Paula’s Plan for Retirement Clarity
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Jun 09, 2025 |
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Episode 28: Funding Futures: Margaret's Question About Grandkids' Roth IRAs
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Jun 02, 2025 |
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Episode 27: Protecting Your Forever Home: Georgine’s Journey to Peace of Mind
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May 26, 2025 |
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Episode 26: Roth Conversions Explained: Mary’s 401(k) and IRA Dilemma
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May 19, 2025 |
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Episode 25: Can I Max Out My Roth IRA If My Husband Maxes Out His 457(b)?
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May 12, 2025 |
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Episode 24: Mary's Dilemma: Navigating the Traditional 403(b)
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May 05, 2025 |
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Episode 23: Exploring Retirement Income Options: Kathy's Questions Answered
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Apr 28, 2025 |
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Episode 22: Cash vs. Mortgage: Carolyn Weighs the Pros and Cons of Paying Cash for a House
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Apr 21, 2025 |
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Episode 21: Helping Mom with Her 401(k): Answering Mike's Questions on Retirement Planning
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Apr 14, 2025 |
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Episode 20: Roth Conversions Uncovered: Answering William’s Questions
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Apr 07, 2025 |
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Episode 19: Understanding Taxes on Traditional IRAs: Jim's Questions Answered
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Mar 31, 2025 |
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Episode 18: Is Market Timing Worth It? Answering Walt's Big Question
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Mar 24, 2025 |
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Episode 17: Rebalancing 101: Answering Marie's Questions on Keeping Your Portfolio in Shape
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Mar 17, 2025 |
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Episode 16: Medicare Deadlines: Ron’s Question About Signing Up His Wife
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Mar 10, 2025 |
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Episode 15: Roth Converting Real Estate: Bob’s IRA Filled with Vacant Land
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Mar 03, 2025 |
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Episode 14: Taking Social Security at 62: Victoria’s Investment Strategy
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Feb 24, 2025 |
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Episode 13: Roth Conversion Strategy and CD Ladders: Anthony's Financial Game Plan
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Feb 17, 2025 |
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Episode 12: Medishare Before Medicare: Gladys' Healthcare Strategy
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Feb 10, 2025 |
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Episode 11: Awnee's Dilemma - Traditional TSP or IRA, Then Roth Conversion - Whats the Best Move
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Feb 03, 2025 |
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Episode 10: Should Val Convert Her 401(k)?
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Jan 27, 2025 |
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Episode 9: CDs, College Breaks, and IRAs – Connie’s Financial Questions Answered
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Jan 20, 2025 |
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Episode 8: Do You Need a Financial Planner if You’re Still Working in Your 50s and 60s?
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Jan 13, 2025 |
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Episode 7: Managing Medical Expenses When Working Past Age 65
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Jan 06, 2025 |
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Episode 6: How Qualified Charitable Distributions Can Save You on Taxes
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Dec 30, 2024 |
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Episode 5: Should Linda File for Social Security Now or Wait?
|
Dec 23, 2024 |
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Episode 4: How Future Inflation Could Impact Delaying Social Security
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Dec 16, 2024 |
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Episode 3: Patricia has 70% of her retirement in a 403(b) and in a 457(b)
|
Dec 02, 2024 |
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Episode 2: Linda asks for the best way to find a fee-only financial planner.
|
Dec 02, 2024 |
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Episode 1: Mary believes her net worth is sufficient for retirement.
|
Dec 02, 2024 |