The 90-Day Retirement Roadmap
The 90-Day Retirement Roadmap is Phase 1 of working with me. Over the first three months we answer your most pressing retirement questions and build the plan we then carry out together in Phase 2, Implementation & Ongoing Wealth Management. It is billed as a one-time planning fee, quoted after our initial conversation.
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. The Roadmap is designed as Phase 1 of one relationship. Nearly every client continues into Phase 2, Implementation & Ongoing Wealth Management, where the plan is carried out and kept current. Clients who begin with ongoing management directly receive the same planning work, and 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 Roadmap answers whether Roth conversions make sense for you, which years form your conversion window, and the tax bracket to target. It does not size the specific dollar amount for a given year — that depends on income that hasn't happened yet and is set annually in ongoing wealth management. The Roadmap does not include tax-return preparation; recommendations should be 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?
In the Roadmap we set your target allocation, the principles for structuring investments across your account types, and flag anything that needs fixing: concentrated positions, overlapping funds, excess cash. The Roadmap stops at the plan. Choosing, trading, rebalancing, and monitoring the investments is Phase 2, once I begin managing your accounts.
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 Roadmap 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's Included — and What Isn't
Every plan is built around your situation, but the first 90 days always include:
- A complete review of the planning areas that matter to your situation, so we both know exactly where you stand
- The decisions I’ll recommend and why, prioritized by how much each one improves your retirement
- Retirement projections showing the outcomes and tradeoffs behind each decision
- A set schedule of planning meetings across the 90 days: discovery, analysis, strategy, and the handoff into Phase 2
- Your target allocation and the principles your portfolio will follow once I begin managing it
- A written plan, sequenced and ready to be carried out in Phase 2
The goal of the first 90 days is that we both understand where you stand, agree on the decisions that matter most, and know exactly what I’ll be responsible for carrying out next.
After the First 90 Days
By the end of the Roadmap we have a clear picture of where you stand and a prioritized set of decisions, and the work shifts from planning to doing.
A small number of clients take the plan and carry it out on their own. That’s available, but it isn’t how I’m set up to do my best work, and I take on only a limited number of Roadmap-only clients each year.
For everyone else, the Roadmap hands off directly into Step 4 (Implement the Plan) and Step 5 (Continue Adapting), delivered through Implementation & Ongoing Wealth Management: I take responsibility for consolidating accounts, implementing investments, coordinating withdrawals and taxes, and adapting the plan as life changes.
Is the Retirement Roadmap Right for You?
The Roadmap is the first 90 days for clients who intend to have me manage their investments but have a good reason not to start today. That usually means one of three things: your money can’t move yet (a current 401(k) or TSP, a pension election still pending, a home sale or inheritance that hasn’t closed), you want to see the plan and how I work before consolidating a lifetime of savings, or there’s a decision to settle first, like when to retire or whether to convert to Roth, that should be made before anything moves.
If any of those describe you, the Roadmap is where we start, and the planning fee reflects the work of building the plan before I begin managing it.
The Roadmap isn’t a second opinion on a portfolio you’ll keep managing yourself, a one-time checkup, or planning added on top of an advisor you’re keeping. If that’s what you’re looking for, I’m not the right fit, and I’ll tell you so in our first call.
Take the Next Step
Schedule a complimentary introductory conversation to discuss the questions you are facing and whether working together, starting with the Retirement Roadmap, is the right fit for your needs.
Schedule a Free Initial Consultation
Want to see what happens after the Roadmap? Learn about Phase 2, Implementation & Ongoing Wealth Management.
