Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees

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

Show Notes

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



What is Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees?

An educational podcast from financial advisors Garrett Crawford, CFP® and Adam Reed, dedicated to helping retirees between $2M-$8M with tax-return driven financial planning. At this level of wealth an integrated strategy for your tax return, investments, and long-term goals is critical. We explore advanced topics like Roth conversions, RMDs, and charitable giving to help you ensure your family remains your biggest beneficiary.