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 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

Episode 28 of Retirement Tax Matters discusses the different types of investment accounts high-net-worth retirees can use to bridge the income gap when retiring in their 50s. While technical workarounds like SEPP 72(t) exist for pre-tax funds, Garrett and Adam address the access and wisdom of using Roth IRAs and taxable brokerage accounts to fund an early lifestyle.

The conversation dives deeper regarding the specific order of operations for Roth IRA withdrawals, highlighting that while original contributions can be accessed penalty-free at any time, earnings remain restricted until retirement. Garrett explains why the taxable brokerage account is often the favored vehicle for early retirees due to its ultimate liquidity and the ability to realize income at preferred long-term capital gains rates.

For those in the $2M–$8M range, prioritizing these taxable assets first may protect the high-value growth of pre-tax IRAs and the permanent tax-free status of Roth IRAs for future legacy goals. The episode underscores that making these tactical funding decisions requires annual intra-year tax projections to monitor for Medicare IRMAA thresholds and avoid unnecessary penalties .

(00:00) – March Madness & The Start of Tax Planning Season

(01:45) – Can You Access a Roth IRA Before Age 59½?

(04:00) – Order of Operations for Roth Withdrawals

(06:20) – Why Roth May Not Be Best for Early Retirement

(08:50) – The Ultimate Early Retirement Tool: Brokerage Accounts

(11:00) – Understanding Preferred Long-Term Capital Gains Rates

(14:00) – Why Tax Return-Driven Planning is Important

(15:15) – Avoiding Traps (Like Medicare IRMAA)

(16:40) – Free Year-End Tax Checklist

Here is a 5 step tax-return driven financial planning framework for making better tax planning decisions for Retirees between $2M-$8M https://www.retirementtaxmatters.com/checklist

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

Episode 27 of Retirement Tax Matters examines a couple bridge strategies for retirees in the $2M–$8M range who have a large amount of pre-tax funds but restricted by the age 59 ½ milestone. Garrett Crawford, CFP® and Adam Reed break down Substantially Equal Periodic Payment (SEPP) method and the Rule of 55 for 401(k) plans.

(00:00) – Intro

(01:45) – Accessing Retirement Funds Before 59½

(06:15) – Why the IRS Penalizes Early Withdrawals

(08:40) – Strategy 1: SEPP for IRAs Explained

(12:20) – The Risks, Formulas, and Strict Rules of SEPPs

(16:30) – Partitioning Your IRA

(19:10) – Strategy 2: The Rule of 55 for 401(k) Accounts

(21:45) – The Danger of Rolling Your 401(k) to an IRA Too Soon

(25:00) – The Roth 401(k) Pro-Rata Landmine

(28:00) – Our Tax Return-Driven Planning Process & Free Checklist

Download a FREE Year-End Tax Planning Checklist for HNW Retirees: https://www.retirementtaxmatters.com/checklist

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

In this episode of Retirement Tax Matters, Garrett Crawford, CFP® and Adam Reed tackle one of the largest roadblocks for high-net-worth retirees considering early retirement: health insurance costs before Medicare age 65.

For retirees in the $2M–$8M range, the decision to retire early often hinges on a psychological standoff. Is it wise to pay $2,000 or more a month for private insurance after years of employer-subsidized coverage? We explore the primary paths to bridging the gap—including spousal plans, the ACA Marketplace, and sharing ministries—while reframing the premium not as an expense, but as the purchase price for your most valuable asset: your time.

Discover how tax-return driven financial planning provides the tactical clarity needed to handle high-cost prescriptions and volatile premium landscapes without delaying your best years of freedom.

Timestamps:

(00:00) – Introduction: The Healthcare Boogeyman

(02:25) – The Psychological Friction of Paying for Health Insurance

(06:45) – Option 1: The Spousal Plan Advantage

(08:40) – Option 2: Healthcare.gov, High Premiums & Expired Subsidies

(12:25) – The Value of Pre-Existing Condition Coverage

(13:50) – Option 3: Health Share Ministries (Medi-Share & CHM)

(18:25) – Math vs. Psychology: Don't Let Fear Keep You Working

(21:20) – The Power of Tax Return-Driven Financial Planning

(23:45) – Closing Thoughts & Free Year-End Tax Checklist

Resources:

Year-End Tax Planning Checklist for HNW Retirees ($2M-$8M)

Disclosures:

⁠https://www.retirementtaxmatters.com/disclosures⁠

If you are planning to stop work before age 60, your Social Security statement estimate for age 67 or 70 likely contains misleading benefit amounts. Standard benefit projections assume you will continue earning your current salary until the year you file—an assumption that is incorrect for early retirees who have gap years before filing with $0 in earnings .

In the kickoff of our Early Retirement series, Garrett Crawford, CFP® professional, explains why your statement estimate is misleading and how to fix it. We discuss how to use the online estimator tool to model $0 income years and why bridging the pre-60 gap requires a strategic focus on taxable brokerage accounts to avoid early withdrawal penalties .

Finally, we examine the survivor benefit as a critical piece of longevity insurance, emphasizing that optimizing for a higher check is often about protecting a surviving spouse from a future tax shock.

(00:00) – Intro

(01:15) – Announcing the New Early Retirement Series

(03:00) – The Big Mistake Early Retirees Make with Social Security

(05:30) – How to Calculate Your Actual Early Retirement Benefit

(07:45) – Bridging the Gap: Income Strategies Before Age 59 ½

(09:20) – The Secret Weapon for Early Retirement: Brokerage Accounts

(11:00) – Spousal & Survivor Benefits Explained

(13:30) – Math vs. Happiness: When Should the Higher Earner Claim?

(15:00) – Key Takeaways & Free Retirement Checklist

(19:54) – Outro

Free Tax Planning Framework Resource for HNW Retirees:

https://www.retirementtaxmatters.com/checklist

Disclosures:

https://www.retirementtaxmatters.com/disclosures