ANNUAL FINANCIAL PLANNING REVIEW WORKBOOK

Life status

• Current age(s)
• Employment status
• Expected retirement timing
• Health concerns that may affect finances
• Caregiving responsibilities (parents, children, others)

Family & continuity

• If one spouse died tomorrow, could the survivor manage finances independently?
• Are both spouses aware of account locations, advisors, passwords, and bill flow?

Goals

• What does “retirement” actually mean for you?
• What annual lifestyle spending feels “enough”?
• Which goals are non-negotiable?
• Which goals are optional or flexible?

Income

• List all income sources
• Are any variable or unstable?
• What happens if one source stops?

Spending

• Do you know annual spending within ±10%?
• Which categories are underestimated?
• Are one-time expenses accounted for?

Liquidity

• Months of expenses in true cash
• Separate reserves for home, auto, medical surprises
• Are emergency funds tax-efficient and penalty-free?

Debt

• Interest rates on all debts
• Adjustable or resetting rates?
• Is debt strategic or accidental?

Key questions

• What is my minimum monthly burn rate?
• Which account funds emergencies with the least tax impact?
• How long could I operate without income?

Account inventory

• Can you list every account type and location?
• Are old accounts consolidated or scattered?
• Does your spouse know all accounts exist?

Tax location

• Do you know how much is taxable vs pre-tax vs Roth?
• Are tax-inefficient assets placed poorly?

Liquidity staging

• Do you have low-volatility funds for near-term needs?
• Would you be forced to sell equities in a downturn?

Concentration

• Single stock exposure?
• Employer stock risk?
• Sector or real estate concentration?

Key questions

• If I needed $250,000 in 30 days, which account supplies it cleanly?
• Where is my highest hidden risk concentration?

Governance

• Written investment strategy or IPS?
• Rebalancing rules?
• Decision discipline during volatility?

Risk alignment

• Is the portfolio designed for accumulation or distribution?
• Have withdrawals been stress-tested in bad markets?

Fees

• Do you know total all-in costs?
• Are fees justified by outcomes?

Tax-aware investing

• Is tax-loss harvesting used where appropriate?
• Are gains realized intentionally?

Key questions

• What is each dollar’s job?
• How does this portfolio behave early in retirement?
• What breaks first in a prolonged downturn?

Visibility

• Marginal vs effective tax rate understood?
• Quarterly estimates or April surprises?

Retirement tax exposure

• Pre-tax vs Roth imbalance?
• RMD exposure modeled?
• Widow(er) tax penalty understood?

Roth strategy

• Planned conversion window?
• Defined tax bracket ceiling?
• Coordinated with retirement and Social Security timing?

Charitable planning

• Are donations tax-efficient?
• DAF, QCD, or bunching strategies evaluated?

State taxes

• Are state-specific deductions optimized?
• Have retirement relocation tax effects been modeled?

Key questions

• What is my lifetime tax strategy?
• What are my top three tax risks?
• What must happen before year-end?

Income sources

• Social Security
• Pensions
• Portfolio withdrawals
• Rentals/business income

Social Security

• Claiming age modeled?
• Survivor benefits evaluated?
• Portfolio interaction considered?

Withdrawal order

• Written withdrawal sequence?
• Tax impact modeled?
• Guardrails defined?

Spending flexibility

• Core vs discretionary spending identified?
• Adjustment plan in down markets?

Key questions

• What is my after-tax retirement income?
• How do I avoid selling assets at the wrong time?
• What changes if inflation stays elevated?

Health

• Retirement health coverage strategy?
• Medicare coordination understood?
• Long-term healthcare modeled?

Long-term care

• Exposure quantified?
• Funding strategy defined?

Life insurance

• Still needed?
• Purpose aligned with goals?

Liability

• Umbrella coverage sufficient?
• Home/auto liability aligned with net worth?

Property

• Replacement costs realistic?
• Special assets properly insured?

Key questions

• What catastrophic risks could derail the plan?
• Where am I misinsured?

Documents

• Will/trust reviewed recently?
• POA and healthcare directives current?

Beneficiaries

• Retirement accounts reviewed?
• Contingent beneficiaries listed?

Titling

• Consistent with estate plan?
• Avoiding probate unintentionally?

Legacy intent

• Inheritance structure intentional?
• Survivor tax consequences considered?

Key questions

• If I died tomorrow, does this execute cleanly?
• Does the plan reflect current intent?

Ask directly

1. What is the single biggest risk in my plan?
2. What is the most expensive mistake I’m exposed to?
3. What worsens the longer I wait?

Tax & retirement

• What is my lifetime tax strategy?
• How exposed am I to RMDs and IRMAA?
• What should be done before age-based rules force action?

Investments

• What is each account’s role?
• What happens in a poor early retirement market?

Insurance & estate

• Where am I under-protected?
• Does the survivor’s plan materially change?

Accountability

• What decisions must be made in the next 12 months?
• Who owns execution?
• How will success be measured?