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

What if RMDs didn't exist for pre-tax 401(k)s or Traditional IRAs? In this episode we discuss why even if you don't like RMDs, even if they didn't exist, you might still not want to let your pre-tax accounts grown untouched. Garrett Crawford, CFP® discusses the benefits of reverse-engineering an RMD plan. High-net-worth retirees between $2M-$8M might be playing a different RMD game than their peers and this episode will help you think through a better game plan for getting RMDs under control during your retirement.

Download a Free Tax Planning Resource - Click Here

Timestamps

• (00:00) – Intro

• (02:25) – Reverse Engineering Financial Planning

• (05:03) – What if RMDs Didn't Exist?

• (09:59) – Somebody Will Pay Taxes

• (12:09) – Required MAXIMUM Distribution Mindset

• (17:55) – How To Estimate Your Future RMDs

• (21:45) – Free Resources

Disclosures

In many high-net-worth households, one spouse naturally takes the lead as the primary financial quarterback. While this works well during the accumulation years, it often creates a significant challenges later in retirement. On this episode of Retirement Tax Matters, Garrett Crawford, CFP® and Adam Reed discuss the psychological gap between having a multi-million dollar portfolio and having the actual confidence to spend it, especially for a surviving spouse who has been less involved in the family finances.

Click Here to get our FREE 5 step tax planning framework for High-Net-Worth Retirees between $2M-$8M

Timestamps:

(00:00) - Introduction and Guilty Spending Habits(02:55) - Helping Your Spouse Spend in Retirement(06:15) - The Scarcity Mindset in Surviving Spouses(09:10) - Addressing Annuities(13:10) - Simple vs. Complicated Financial Products(15:20) - Forced Income for Surviving Spouse(19:35) - MFJ vs Single Filer(24:10) - Finding the Right Advice(28:15) - Next Steps: Tax Planning Checklists and Projections

Disclosures Here

Episode 31 analyzes why high-net-worth retirees should consider intentionally filling the 24% tax bracket to protect against future 32% RMD spikes and surviving spouses tax rates increasing when going from Married Filing Jointly to Individual Filing. Garrett Crawford, CFP® details the math behind the 2% decision and how to identify these opportunities before the December 31st deadline.

Request a 5 step framework for annual tax planning for High-Net Worth Retirees between $2M-$8M:

https://www.retirementtaxmatters.com/checklist

(00:00) – Intro: Masters Weekend & CPA Nose to the Grindstone Season

(02:21) – The $2M-$8M Niche: Why High Net Worth Doesn't Mean High Spending

(05:10) – Understanding No Man's Land: The 22% vs. 24% Tax Brackets

(06:55) – The Psychology of Saving vs. The Reality of RMDs

(10:15) – The Six-Figure RMD: How Compound Interest Becomes a Tax Liability

(11:55) – Navigating Medicare IRMAA Surcharges and Roth Conversions

(14:15) – The Age 65 Window: Converting Without IRMAA Penalties

(16:10) – Opportunity Identification: Using the Year-End Tax Planning Checklist

(18:45) – Why Rule of Thumb Doesn't Replace Personalized Tax Planning

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

For many retirees, tax season feels like the finish line. In reality, it is the starting point for smarter retirement tax planning. In this episode, Garrett Crawford, CFP® and Adam Reed explain why reviewing your tax return in the spring can help you make better decisions for the rest of the year.They walk through their tax return driven financial planning framework, including why an early income projection matters, how Roth conversion planning can start months before execution, and what a tax return review should actually uncover. You will also hear how market downturns can create Roth conversion opportunities, why communication gaps often cause tax issues, and how retirees can use this season to prepare instead of react. Like, subscribe, and check the links below for more retirement tax planning resources.

📈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/checklist

(00:00) Starting 2026 retirement tax planning

(02:28) Why April 15 is the strategic launch pad

(06:09) - Building an early income projection

(08:25) - Roth conversion planning in the spring

(10:56) - Pre-planning during market volatility

(15:41) - What a professional tax review does

(18:19) - Tax issues vs. communication issues

(20:01) - Tax returns drive better decisions

(22:20) - DIY retirement tax planning resources

Click Here For Disclosures

Discover why working just six months longer can be a bigger retirement planning boost than most near-retirees realize. But while working longer almost always works out, for retirees in the $2M-$8M range sometimes this question comes back to defining enough and knowing when continuing to wait one more year might not be the best path to take.

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) – Welcome & Spring Allergies

(01:51) – The One More Year Syndrome

(03:27) – The Power of Working Longer Study

(06:21) – The Retirement Boost of Working Longer

(08:44) – The Role of Social Security & Portfolio Preservation

(12:47) – Tax Implications & Roth Conversion Windows

(17:34) – The Identity Crisis of a High Achiever

(21:14) – Practical Tax Planning Steps for This Year

(24:02) – Finding Peace of Mind in Retirement

Disclosures: https://www.retirementtaxmatters.com/disclosures