Built for households with $2M–$30M in assets.
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Act within 90 days

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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What changes at the $2M–$30M level

Social Security claiming age affects lifetime income by $100K–$300K for many households
The Roth conversion window between retirement and RMD start age (73) may never be more favorable
Medicare enrollment at 65 has permanent penalty windows that cannot be reopened
Estate freeze strategies (GRATs, SLATs) are 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
1
Model Social Security claiming scenariosImmediate

Every year of delay between 62 and 70 increases your benefit by 6–8%. For couples, survivor benefit coordination adds another dimension.

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2
Model the Roth conversion windowImmediateWithin 90 days

The gap between retirement and RMD start age is often the lowest-tax period of your life. Converting tax-deferred assets now reduces future RMD burden.

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⏰ Within 90 days
3
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.

4
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
5
Review estate freeze opportunities before retirementWithin 6 months

GRATs and other freeze strategies work best when assets are still appreciating. Retirement often marks the peak of earned income and asset growth.

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5-Question Assessment

How prepared are you for approaching retirement?

Answer 5 questions and get a personalized readiness score with specific gaps identified.

1. Have you modeled Social Security claiming scenarios for your household?
2. Have you evaluated Roth conversion opportunities before RMDs begin?
3. Are you on track for Medicare enrollment at 65?
+ 2 more questions
Take the approaching retirement assessment →

Get professional help

⚖️
Find an estate attorney

An estate attorney can execute the legal documents and trust strategies this event requires.

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🤝
Find a financial advisor

A fiduciary advisor can model the financial impact and coordinate strategy across your full picture.

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Related situations

RSU / Liquidity EventSpouse Death