Building Your Financial Planning Checklist | What it Should Include

What Belongs on Your Retirement Planning Checklist?

Retirement planning can feel like one enormous decision.

In reality, it is a series of smaller, interconnected decisions. When will you retire? How much income will you need? When should you claim Social Security? Which accounts should you draw from first? How will healthcare costs and taxes affect your plan?

A retirement planning checklist can help you organize those questions, identify areas that need attention and prepare for a more productive conversation with your financial professional.

The goal is not simply to check every box. It is to understand how each decision may affect the others—and create a coordinated strategy around the retirement you want.

1. Define Your Retirement Vision

Before focusing on account balances and income projections, think about what you want retirement to look like.

Your ideal retirement may include travel, time with family, volunteering, hobbies, part-time work or a move to a new community. Those choices will influence how much income you may need and how your financial plan should be structured.

Questions to consider:

• At what age would you like to retire?
• Will you retire completely or continue working in some capacity?
• Where do you plan to live?
• Do you expect to travel frequently?
• Will you provide financial support to children, grandchildren or aging parents?
• What would make retirement feel meaningful and fulfilling?
• Are you and your spouse envisioning the same kind of retirement?

The clearer the vision, the more intentionally you can build a plan to support it.

2. Estimate Your Retirement Expenses

Many people assume their expenses will decline substantially after retirement. Some costs may decrease, but others—such as travel, healthcare or home improvements—could increase.

Begin by separating your anticipated expenses into categories.

Essential expenses may include:

• Housing
• Utilities
• Groceries
• Transportation
• Insurance
• Healthcare
• Taxes
• Debt payments

Lifestyle expenses may include:

• Travel
• Dining and entertainment
• Hobbies
• Gifts
• Charitable giving
• Second-home expenses
• Memberships and activities

It can also be helpful to identify larger, less frequent expenses, such as replacing a vehicle, renovating a home, helping with a grandchild’s education or paying for a family celebration.

Rather than assuming you will spend the same amount throughout retirement, consider how your spending could change during its different phases.

3. Inventory Your Retirement Income Sources

Once you have an idea of what retirement may cost, identify the resources available to support it.

Your income sources may include:

• Social Security
• Employer pensions
• 401(k), 403(b) or other workplace plans
• Traditional and Roth IRAs
• Taxable investment accounts
• Annuity income
• Rental or business income
• Part-time employment
• Cash savings
• Health savings accounts

For each source, document its estimated value, tax treatment, withdrawal restrictions and the age at which it becomes available.

This exercise can help reveal the difference between income that is predictable and income that depends on market performance or ongoing withdrawals.

4. Review Your Social Security Strategy

Deciding when to claim Social Security can affect your income for the rest of your life.

Although benefits may generally be claimed beginning at age 62, claiming before full retirement age can permanently reduce the monthly amount. Waiting beyond full retirement age may increase the benefit until age 70.

The right decision may depend on:

• Your health and anticipated longevity
• Your spouse’s benefit
• Your need for immediate income
• Whether you plan to continue working
• Your available retirement savings
• The tax implications of your other income
• Survivor benefits for a spouse

For married couples, the decision should usually be considered as a household strategy rather than two separate claiming choices.

5. Prepare for Medicare and Healthcare Costs

Medicare eligibility generally begins at age 65, but enrollment rules, premiums and coverage decisions require advance preparation.

Your checklist should include:

• Understanding your Medicare enrollment window
• Comparing Original Medicare and Medicare Advantage
• Evaluating prescription-drug coverage
• Considering supplemental insurance
• Reviewing Health Savings Account rules before enrolling
• Planning for premiums, deductibles and out-of-pocket expenses
• Determining how you will obtain coverage if you retire before age 65

Medicare does not cover every healthcare expense. Dental care, vision care, hearing services and many long-term care needs may require separate planning.

6. Create an Investment Strategy for Retirement

The investment strategy that helped you accumulate wealth may need to evolve as you begin relying on your portfolio for income.

That does not necessarily mean eliminating investment risk. A retirement that could last several decades may still require growth to help offset inflation. The challenge is finding an appropriate balance between near-term income needs, stability and long-term growth.

Consider reviewing:

• Your current asset allocation
• The amount held in cash or short-term investments
• Your comfort with market fluctuations
• When portfolio withdrawals will begin
• How a market decline early in retirement could affect your plan
• Whether your accounts are overly concentrated
• How often the portfolio will be monitored and rebalanced

Your investment strategy should reflect the job each portion of your portfolio needs to perform.

7. Develop a Retirement Withdrawal Strategy

Accumulating retirement assets is only the first half of the process. You also need a strategy for turning those assets into income.

That includes deciding how much to withdraw, which accounts to use and when withdrawals should occur.

Your withdrawal strategy may need to coordinate:

• Taxable investment accounts
• Traditional retirement accounts
• Roth accounts
• Required minimum distributions
• Social Security income
• Pension or annuity payments
• Cash reserves
• Charitable giving

A simple rule that always withdraws from one account type first may overlook tax-planning opportunities. The appropriate order can change from year to year based on income needs, tax brackets and market conditions.

8. Look for Tax-Planning Opportunities

Retirement does not end tax planning. In many cases, it creates new opportunities—and new complications.

Several decisions can affect your taxable income:

• When you claim Social Security
• How much you withdraw from traditional retirement accounts
• Whether you complete Roth conversions
• How investment gains and losses are managed
• When required minimum distributions begin
• How charitable contributions are made
• Whether withdrawals affect Medicare premiums
• Which assets you use to fund larger purchases

The years between retirement and the beginning of required distributions may create a valuable planning window for some households. Decisions made during that period could influence taxes for many years.

Tax strategies should be evaluated with your financial professional and tax adviser based on your specific situation.

9. Plan for Long-Term Care Possibilities

Long-term care is difficult to predict, but avoiding the subject does not eliminate the possibility.

Planning can begin by considering:

• Where you would prefer to receive care
• Whether family members could realistically assist
• What care may cost in your community
• Which assets could be used to pay for care
• Whether insurance should be evaluated
• How one spouse’s care needs could affect the other spouse
• What legal documents would allow someone to act on your behalf

There is no single solution for every family. The goal is to understand your options before a health event forces decisions to be made quickly.

10. Review Beneficiaries and Estate Documents

Your retirement plan should also address what happens if you become unable to make decisions or when your assets eventually pass to others.

Review your:

• Retirement-account beneficiaries
• Life-insurance beneficiaries
• Transfer-on-death or payable-on-death designations
• Will
• Trust documents, if applicable
• Financial power of attorney
• Healthcare power of attorney
• Advance healthcare directive
• Digital accounts and access instructions

Beneficiary designations on retirement accounts and insurance policies generally control who receives those assets, even if your will says something different. Review them following marriages, divorces, births, deaths or other significant family changes.

Your attorney should help you evaluate and prepare your legal documents.

11. Prepare for the Unexpected

A retirement strategy should support the future you want while allowing room for the future you cannot predict.

Ask how your plan might respond if:

• You retire earlier than expected
• You or your spouse experiences a health issue
• The market declines near your retirement date
• Inflation remains elevated
• A family member needs financial assistance
• One spouse dies much earlier than the other
• Your home requires a major repair
• Your retirement priorities change

Planning for uncertainty does not mean trying to predict every possible event. It means building enough flexibility to adjust when life changes.

Questions to Ask a Bradford Financial Advisor

A checklist can help you prepare, but retirement decisions rarely exist in isolation. Consider bringing these questions to your next planning conversation:

1. Is my current savings trajectory aligned with the retirement I envision?
2. How much income could my resources reasonably support?
3. What assumptions are we making about inflation, longevity, and investment returns?
4. When should I consider claiming Social Security?
5. How should my investment strategy change as retirement approaches?
6. Which accounts should I draw from first?
7. Are there tax-planning opportunities I should consider before retirement?
8. How should I prepare for healthcare and long-term care costs?
9. What happens to my plan if I retire earlier than expected?
10. How often should we review and update the strategy?