Pre-retiree planning: income spikes and Roth windows

Your finances have layers—investments, taxes, planning for the future. If you want a second set of eyes, Peter opened up a few spots for a quick, no-obligation call. Grab yours now.

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Tax law shifts can change the best time to recognize income, give to charity, and make big business decisions. This episode unpacks how the “One Big Beautiful Bill Act (OBBBA)” reshapes year-end planning for pre-retirees, equity-comp executives, and business owners—and what still works vs. what to rethink. Listen now and learn: ► How the new charitable-deduction mechanics affect bunching and donor-advised funds ► What the updated SALT landscape means—and when a PTET election may still be worth it ► Where pre-retirees can find Roth-conversion “windows” and how NIIT thresholds influence capital-gain timing ► The big moves for owners and executives—from RSU withholding gaps and ISO/AMT credits to QBI and bonus-depreciation options

Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.

(03:08) OBBBA: What Actually Changed in 2025 (Rates, Estate & Gift) (05:29) Charitable Giving After OBBBA: 2% AGI Floor + Pease-Style Haircut (What It Means for DAF Timing) (7:42) SALT Deduction: $40k Cap With a Phase-Down for Higher Incomes (Plus PTET Strategy) (9:14) Social Security Isn’t Tax-Free; New Senior Deduction Helps at Lower Incomes (10:11) Timing Still Wins: Why November Is the Last Best Window (and Why 2025 vs. 2026 Is Odd) 

(12:33) Pre-Retirees: NQDC Spikes, Roth-Conversion Windows, and Capital-Gains/NIIT Coordination (17:31) Equity Compensation: RSU Withholding Gaps, Concentration Risk, and ISO/AMT Credits (21:34) Business Owners: QBI Permanence, 100% Bonus Depreciation, and Smoother Elections

(24:15) PTET: Powerful, But Don’t Miss the Payment Deadline (26:05) Often Missed: SEP IRA for Self-Employed Income and Director Fees (27:00) How a Tax-Led Engagement Works (and Why Advisory + Tax Prep Reduces Errors)

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