Five Financial Decisions to Make Before You Retire
By Andrew Joski, NSSA®
Founder of Joski Financial
Published September 14, 2026
Retirement is not one financial decision. It is a series of connected decisions involving Social Security, income, investments, taxes, and healthcare.
A decision in one area often affects several others. Claiming Social Security changes how much you may need from your investments. IRA withdrawals affect your taxes and could increase future Medicare premiums. Retiring before age 65 creates a healthcare gap that must be funded.
Before choosing your retirement date, work through these five questions.
1. When Should You Claim Social Security?
You can generally begin receiving retirement benefits at age 62, claim at your full retirement age, or delay as late as age 70.
Starting early provides income sooner but permanently reduces your monthly benefit. Waiting increases the benefit, but you must fund the years before Social Security begins.
Consider:
Your health and family longevity
Whether you will continue working
Other income and savings available
Your spouse’s benefit
The income available to a surviving spouse
One of the biggest mistakes I see is evaluating Social Security as an individual decision when it is often a household decision.
When one spouse dies, the surviving spouse generally does not continue receiving both checks. The survivor will typically receive the larger applicable benefit and lose the smaller one. For married couples, the higher earner’s claiming decision may therefore affect income for both lifetimes.
The goal is not simply to identify the age that produces the most money on paper. It is to choose a strategy that supports your income needs and protects against the possibility of living longer than expected.
2. How Will You Replace Your Paycheck?
Throughout your working years, income usually arrives from an employer or business. In retirement, that paycheck may need to be recreated from several sources:
Social Security
Pensions
Traditional retirement accounts
Roth accounts
Brokerage accounts
Savings
Annuities or other income sources
Begin by estimating your monthly spending. Then subtract income that does not depend directly on investment withdrawals.
For example:
Desired monthly spending: $6,000
Social Security and pension income: $3,500
Remaining monthly need: $2,500
The investments and savings would need to provide approximately $30,000 per year, plus any applicable taxes and occasional large expenses.
That leads to three important questions:
How much will you need to withdraw?
Which accounts should provide the money?
Can the strategy continue throughout retirement?
Having money saved is important. Retirement confidence comes from understanding how those savings will become usable income.
3. Do Your Investments Need to Change?
A portfolio built primarily to accumulate money may need to evolve as retirement approaches.
That does not mean moving everything into cash. Retirement may last 20 or 30 years, so long-term growth may still be important. The challenge is balancing future growth with the need for current income and protection from poorly timed market declines.
Consider:
How much you expect to withdraw
How much should remain readily accessible
How much volatility you can tolerate
Whether the portfolio is overly concentrated
What will fund withdrawals during a market decline
How the portfolio will be monitored and rebalanced
The investment strategy and withdrawal strategy should be built together.
A portfolio is not successful simply because it produces a competitive return. It must support your spending, taxes, timeline, and ability to remain invested when markets become uncomfortable.
4. How Will Your Retirement Income Be Taxed?
Not every retirement dollar is taxed the same way.
Traditional IRA and 401(k) withdrawals are generally taxable as ordinary income. Qualified Roth withdrawals may be tax-free. Brokerage accounts can generate dividends and capital gains. Depending on your total income, a portion of your Social Security may also become taxable.
This creates both planning opportunities and potential surprises.
A large IRA withdrawal or Roth conversion could:
Increase taxable income
Move part of your income into a higher tax bracket
Cause more Social Security to become taxable
Affect future Medicare premiums
Reduce future required minimum distributions
The years after retirement but before required minimum distributions begin may provide an important planning window. Depending on your circumstances, those years could create opportunities for deliberate IRA withdrawals or partial Roth conversions.
The objective is not necessarily to pay the least possible tax this year. It is to make informed decisions about when and where taxes may be paid throughout retirement.
Tax strategies should be coordinated with a qualified tax professional.
5. How Will You Pay for Healthcare?
Healthcare planning changes significantly around age 65.
If you retire before becoming eligible for Medicare, you may need coverage through a spouse’s employer, COBRA, the individual marketplace, retiree benefits, or another private option.
The cost of marketplace coverage may be affected by household income. That means IRA withdrawals, Roth conversions, and capital gains could influence healthcare costs before Medicare begins.
After age 65, Medicare provides valuable coverage, but Medicare is not free.
Retirees may still pay for:
Medicare Part B
Prescription-drug coverage
Medicare Advantage or supplemental coverage
Deductibles and copays
Dental, vision, and hearing care
Long-term-care expenses
Higher income may also trigger Income-Related Monthly Adjustment Amounts, commonly called IRMAA, which increase Medicare Part B and Part D costs.
Because Medicare generally examines income from two years earlier, a large withdrawal or Roth conversion today could affect premiums later.
Bring the Decisions Together
These five decisions should not be made independently.
Your retirement date affects healthcare. Social Security affects portfolio withdrawals. Withdrawals affect taxes. Taxes can affect Medicare premiums. All of those decisions influence how your investments should be managed.
That is the value of coordinated retirement planning: seeing how the pieces interact before making decisions that may be difficult to reverse.
You do not need every answer before beginning. Start by understanding where you are, what matters to you, and which decisions need to be made next.
Questions to Consider
As retirement approaches, ask yourself:
What will retirement realistically cost each month?
Which income sources will cover those expenses?
When should each spouse claim Social Security?
How much will need to come from investments?
Which accounts should be used first?
How would a market decline affect the plan?
What healthcare coverage will be available?
Could withdrawals affect taxes or Medicare premiums?
What happens financially after the first spouse dies?
If those answers are not yet clear, that does not mean you are unprepared to begin. It means you have identified the work that needs to be done.
About Andrew Joski
Andrew Joski, NSSA®, is the founder of Joski Financial, an Idaho-registered investment adviser serving individuals and families in Boise, Meridian, Star, and throughout Idaho. He helps clients coordinate retirement income, investments, Social Security, taxes, Medicare, and insurance decisions.
Ready to bring your retirement decisions together?
Schedule an introductory conversation with Joski Financial.
This material is provided for educational and informational purposes only and should not be considered individualized investment, tax, legal, insurance, Medicare, or Social Security advice. Individual circumstances differ, and applicable rules may change. Consult the appropriate qualified professionals before implementing a strategy. Investing involves risk, including the possible loss of principal.
