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.

----- 

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)

Disclosure: This content, which contains security-related opinions and/or information, is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances, and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment.

The commentary in this "post" (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of the Plancorp LLC employees providing such comments, and should not be regarded the views of Plancorp LLC. or its respective affiliates or as a description of advisory services provided by Plancorp LLC or performance returns of any Plancorp LLC client.

References to any securities or digital assets, or performance data, are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others.

Please see disclosures here.