The 90-Day Retirement Roadmap

The 90-Day Retirement Roadmap is my flat-fee financial planning engagement, designed for people who want clear answers to their most pressing retirement questions through a defined, three-month process.

The Roadmap covers the first three steps of my five-step retirement planning process: Step 1, Understand Where You Stand: a complete review of your income, spending, taxes, investments, insurance, and estate picture. Step 2, Identify Opportunities: pinpointing the moves most likely to improve your retirement. Step 3, Build Your Retirement Strategy: one integrated plan, stress-tested against thousands of market scenarios.

It does not include Steps 4 and 5: implementation, investment management, or ongoing monitoring after the engagement concludes. Some clients begin here before deciding whether ongoing support is needed. Others begin directly with Implementation & Ongoing Wealth Management, where the separate planning fee can be waived.

Questions We May Address

Retirement Timing & Income

Retirement often begins with two fundamental questions: When can I retire, and how much can I afford to spend?

We may address questions such as:

When can I afford to retire, reduce my hours, or leave work earlier than planned?
How much can I sustainably spend each month in retirement?
Will my investments and other income sources support me throughout my lifetime?
How would an extended market downturn affect my retirement?
What adjustments could improve the strength and flexibility of my plan?

Tax and Roth Conversion Strategies

The years surrounding retirement can create valuable tax-planning opportunities, particularly when your income changes.

We may address questions such as:

Should I complete a Roth conversion, and how much should I convert?
How can I manage my tax brackets over the course of retirement?
Should I realize capital gains now or defer them?
Which accounts should I draw from first?
How could my income affect future Medicare premiums?
Are there opportunities to reduce lifetime taxes rather than simply this year’s tax bill?

The engagement provides planning recommendations, but it does not include tax-return preparation. When appropriate, recommendations should be reviewed and coordinated with your tax professional before implementation.

Social Security and Pension Decisions

Social Security and pension elections can have lasting effects on your retirement income.

We may address questions such as:

When should I begin receiving Social Security?
How do spousal or survivor benefits affect the decision?
Would delaying benefits strengthen my long-term plan?
Should I elect a pension lump sum or monthly benefit?
Which survivor option may be appropriate for my household?
How should these income sources coordinate with portfolio withdrawals?

Healthcare and Insurance

Healthcare costs and insurance decisions can materially affect retirement, particularly before Medicare eligibility.

We may address questions such as:

How should I obtain health insurance before age 65?
What might Medicare premiums and supplemental coverage cost?
How could my income affect Medicare IRMAA surcharges?
Do I still need my current life insurance?
Should I retain, modify, or replace an existing policy?
How should I prepare for the possibility of long-term care expenses?

Real Estate and Debt

Housing decisions often involve more than comparing an interest rate with an expected investment return. They can also affect your lifestyle, liquidity, taxes, and retirement flexibility.

We may address questions such as:

Should I pay off my mortgage or continue investing?
Should I keep, rent, or sell a property?
How would purchasing a new home affect my retirement plan?
Could I comfortably afford to downsize, relocate, or purchase a second home?
How much debt is reasonable to carry into retirement?
How would a real estate decision affect my other financial goals?

Investment Strategy and Risk

Your investments should support your retirement plan, income needs, and ability to tolerate market fluctuations.

We may address questions such as:

Is my current portfolio appropriately positioned for retirement?
Am I taking more—or less—investment risk than my plan requires?
How might different market conditions affect my retirement?
How should investments be structured across taxable, tax-deferred, and Roth accounts?
How should I prepare for future withdrawals?
Are concentrated positions or overlapping investments creating unnecessary risk?

You will receive high-level recommendations regarding your portfolio’s overall allocation and structure. You will retain control of your accounts and responsibility for selecting, trading, and monitoring investments after the engagement concludes.

Estate and Legacy Considerations

Your financial plan should reflect both how you want to live and what you hope to leave behind.

We may address questions such as:

What might my beneficiaries inherit under my current plan?
How can I balance leaving a legacy with enjoying retirement?
What is an efficient way to make gifts to family or charity?
Are my account registrations and beneficiary designations aligned with my intentions?
How could inherited retirement accounts affect my beneficiaries?
Are there estate-planning matters I should discuss with an attorney?

The engagement may identify estate-planning considerations, but it does not include legal advice or the preparation of estate documents.

Cash Flow and Personal Goals

A retirement plan should account for more than essential expenses. It should also help you understand what is possible.

We may address questions such as:

Am I saving enough to reach my goals?
How much cash should I maintain?
Can I help children or other family members without jeopardizing my retirement?
How much can I comfortably spend on travel?
Can I afford a major purchase, renovation, or second home?
Which goals should take priority when resources are limited?
Where do I have flexibility if my circumstances change?

What You’ll Receive

Although every engagement is customized, the 90-Day Retirement Roadmap generally includes:

A comprehensive analysis of the planning areas relevant to your situation
Personalized recommendations addressing your most important decisions
Retirement projections illustrating potential outcomes and tradeoffs
Meetings over a three-month period to review the analysis, answer questions, and refine the plan
High-level recommendations regarding your investment strategy
A prioritized course of action outlining the steps to consider after the engagement

The goal is to help you understand where you stand, make informed decisions, and leave with a clear sense of your next steps.

What Happens After 90 Days?

After the 90-day engagement, you will have a clear plan and prioritized recommendations to consider.

If you're comfortable implementing the recommendations yourself, the Roadmap may be all the clarity you need.

If you want someone responsible for carrying the strategy out, consolidating accounts, implementing investments, coordinating withdrawals and taxes, and adapting the plan as life changes, that's Step 4 (Implement the Plan) and Step 5 (Continue Adapting), delivered through Implementation & Ongoing Wealth Management. Because it includes the same planning work, the separate planning fee can be waived when you begin there.

Is the 90-Day Retirement Roadmap Right for You?

The 90-Day Retirement Roadmap may be a good fit if you:

Have important retirement decisions you would like to evaluate
Want a comprehensive review of your financial situation
Prefer a defined planning engagement rather than an ongoing advisory relationship
Are comfortable retaining control of your investment accounts
Are prepared to implement and monitor the recommendations after the engagement concludes

Take the Next Step

Schedule a complimentary introductory conversation to discuss the questions you are facing and whether the 90-Day Retirement Roadmap is the right fit for your needs.

Schedule a Free Initial Consultation

Looking for ongoing financial planning, implementation, and investment management? Learn more about Implementation & Ongoing Wealth Management.