The 5 years before retirement are the highest-leverage planning window most people ever have.

Social Security timing, Roth conversion windows, RMD planning, and estate freeze strategies all interact in this period. Decisions made now compound for decades. Decisions deferred now cannot be undone.

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Washington state estate tax

Live in Washington or own WA property? The state's $3M exemption is five times smaller than federal — and most $3M–$10M households have real exposure.

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What changes at the $2M–$50M level

Social Security claiming age affects lifetime benefits significantly — the break-even age varies by household and should be modeled, not assumed

The Roth conversion window between retirement and your RMD start age (72, 73, or 75 by birth year) is a period when you control the timing of conversion income

Medicare enrollment at 65 has permanent penalty windows that cannot be reopened

Estate freeze planning is generally most effective before asset appreciation accelerates

Withdrawal sequencing from taxable, tax-deferred, and Roth accounts affects taxes for 30+ years

Your action plan

Ordered by urgency. Items marked "Immediate" should be addressed within 60–90 days.

⚡ Immediate priority

Model Social Security claiming scenariosImmediate

Delayed retirement credits increase your benefit for each year you wait after full retirement age, up to age 70. For couples, survivor benefit coordination adds another dimension.

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Model the Roth conversion windowImmediateWithin 90 days

After retirement and before your RMD start age, you may have more control over taxable income — a common window to evaluate Roth conversions. Converting tax-deferred assets before RMDs begin reduces the pre-tax balance subject to future RMDs.

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⏰ Within 90 days

Confirm Medicare enrollment timingWithin 90 daysWithin 180 days

The Initial Enrollment Period around your 65th birthday cannot be extended. Late enrollment causes permanent premium penalties.

Build your withdrawal sequencing strategyWithin 90 days

Which accounts you draw from first — and in what order — determines your tax burden for the next 30 years.

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📋 Within 6 months

Review estate freeze opportunities before retirementWithin 6 months

Estate freeze planning works best when assets are still appreciating. Retirement often marks the peak of earned income and asset growth. An attorney can walk through the options.

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5-Question Assessment