For many high-net-worth retiree between $2M-$8M, a successful financial life isn't just about how much you grow; it’s about how much you actually get to keep. Yet, many retirees find themselves blindsided on April 15th by an unwelcomed tax surprise. It's not the fact that paying owed tax is bad, but having to pay significantly more than planned can bother anyone. Tax return-driven financial planning is a proactive financial planning throughout the year to help minimize lifetime taxes, but it also helps decrease the amount of tax surprises you experience on April 15th each year.

This week, Adam and Garrett dive into three common tax landmines: the Social Security withholding trap, the complexities of reporting Roth conversion estimated payments, and the invisible income generated by large brokerage accounts. When your tax preparer and financial planner work together, they transform a reactive tax bill into a proactive wealth strategy that protects your hard-earned nest egg from unnecessary IRS erosion.

Time Stamps:

(00:00) - Tax Surprises in Retirement

(01:45) - The Value of Tax Return Driven Financial Planning

(03:15) - Social Security Tax Withholding

(07:00) - Roth Conversions Estimated Taxes

(11:15) - Invisible Income of Brokerage Accounts

(14:30) - Why 1099-Bs are so long

(17:45) - How to Use the Year-End Tax Planning Checklist

(19:15) - Communicating with Your Advisor about Capital Gains

📈Do you want to be more tax efficient? Do you want a guide to making sure you are on track and on schedule?

Check out our free Tax Planning Checklist:

https://www.retirementtaxmatters.com/free

Disclosure Statement: https://www.retirementtaxmatters.com/disclosures

Episode 35 analyzes the limitations of artificial intelligence in high-net-worth retirement planning and why retirees must distinguish between raw data processing and fiduciary human judgment. We explore the specific risks of AI hallucinations regarding 2026 tax law and the critical steps needed to protect your resources from sophisticated AI-driven financial scams.

We have developed a 5 step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients.

Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

(00:00) – The AI Era

(02:15) – WSJ: Can AI Manage Your Portfolio?

(04:00) – Windows 95 to ChatGPT

(07:30) – Is AI Going To Replace the Financial Advisor?

(09:45) – The Tax Planning Software Paradox

(11:15) – When AI Gets the Law Wrong

(13:30) – Elder Abuse Rising with AI

(16:45) – Why Fiduciary Advice is Being Valued More

(19:00) – Free Year-End Checklist Request

Disclosure Statement: https://www.retirementtaxmatters.com/disclosures

Single filers often feel overlooked when discussing Roth Conversions. Most content is geared towards Married households, yet Single Retirees face pretty tight tax brackets, especially for the $2M-$8M single Retiree. In this episode, Garrett and Adam dive into why the income range between $200,000 and $250,000 represents a challenging income range for individual retirees considering a Roth Conversion in 2026. Between the 32% federal bracket jump, the 3.8% Net Investment Income Tax (NIIT), and the Tier 4 Medicare IRMAA surcharge....there's a lot of ditches to watch out for! Whether you are single by choice, divorce, or the loss of a spouse, this episode provides a better path forward to navigate retirement taxes.

We have developed a 5 step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

(00:00) – The Single Filer Dilemma

(08:30) – Navigating $200k & the 32% Bracket

(11:28) – Net Investment Income Tax & IRMAA Surcharges

(15:47) – The RMD Threat & Roth Conversions

(18:14) – Beneficiary Considerations

(24:30) – Adapting After the Loss of a Spouse

(29:20) – Tax Return Driven Financial Planning for Singles

View our full disclosures here: https://www.retirementtaxmatters.com/disclosures