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

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 ChecklistResources:Year-End Tax Planning Checklist for HNW Retirees ($2M-$8M)Disclosures:⁠https://www.retirementtaxmatters.com/disclosures⁠

Show Notes

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

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.