The 2026 Retirement Master Class
Four essays from Mark Wade, Chief Retirement Officer, on the tax, Medicare, and longevity decisions that shape the next 30 years of your retirement. All in one report, ready to read on your schedule.
Why this report, why now
You have spent decades building significant wealth. The next phase asks a different question: not how to grow it, but how to protect it, distribute it efficiently, and make sure it lasts as long as you do.
Today’s extended tax rates have opened a planning window that won’t stay open forever. The years between retirement and your first Required Minimum Distribution are some of the most valuable tax-planning years of your life. This report shows you how to use them with intention.
Here’s What You’ll Learn
Week 1: Roth Conversion Surgery
Why the extended tax rates may be the opportunity of the decade for households with significant pre-tax savings, and how to size conversions year by year so you fill the right bracket without triggering higher Medicare premiums or Social Security taxes.
Week 2: What IRMAA and Social Security Taxes Reveal About Your Plan
How to read your Medicare statement and Social Security tax bill as a diagnostic, spot the “Retirement Tax Spiral” before it compounds, and understand what it means if you’re already paying more than your neighbor for the same coverage.
Week 3: The 2026 Retirement Ready Roadmap
A five-pillar framework for evaluating your whole plan: income architecture, tax exposure, healthcare coverage, portfolio positioning, and legacy alignment. Plus a link to the Retirement Scorecard so you can see where you stand in about five minutes.
Week 4: The 35-Year Retirement
How longevity, inflation, healthcare costs, and sequence-of-returns risk quietly strain even well-funded plans, and the 35-Year Retirement Readiness Checklist I use to stress-test whether a plan is truly built to last.
What makes this report worth your time
Real examples, real math. Walk through illustrative scenarios, like a 64-year-old couple deciding how much to convert each year, so you can see how the strategy works in practice.
Charts you can actually use. Tax bracket breakdowns, IRMAA tiers, Social Security taxation thresholds, and inflation and healthcare cost projections, all in one place.
A checklist to bring to your next planning conversation. Seven questions that reveal whether your plan accounts for taxes, healthcare, the surviving spouse scenario, and market stress.
The whole picture, not just one piece. Most retirement content tackles taxes, Medicare, or investments in isolation. This series shows how they connect, and where the gaps tend to hide.
A note from Mark
After nearly five decades of working with successful families, I’ve learned that the households who feel most confident in retirement aren’t always the ones who earned the most. They’re the ones who planned with the most intention.
I wrote this series for executives and business owners who are retired or close to it and want a clear, honest look at the decisions that matter most right now. Read it at your own pace, share it with your spouse, and bring your questions to our next conversation.
Let’s Get Retirement Ready!
Mark Wade, Chief Retirement Officer
Here’s What You’ll Learn:
How to size Roth conversions each year to take advantage of today’s extended tax rates
What your Medicare premiums and Social Security taxes reveal about your plan
How to optimize your plan for a 35-year retirement, from inflation to healthcare costs
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This report is for educational purposes only and is not tax, legal, or investment advice. Examples are illustrative and individual results will vary.
