Printable checklist for your desk
Print this checklist and walk through it one pressure at a time. Bring it to our meeting.
Download the PDF (large print)The short version. Retirement income rarely fails for one reason. It tends to fall short from several quiet pressures acting together. Naming each pressure, and checking it against rules you can verify, is the most useful first step.
Six pressures on retirement income
| Pressure | The question to ask | Where the rules sit |
|---|---|---|
| Living longer than planned | If I live to 95, does the income still cover my costs? | Social Security rises 8% for each year you delay past full retirement age, up to 70. |
| Markets falling early in retirement | What happens if my accounts drop sharply in my first years of withdrawals? | Where the money comes from in a down year is a choice you make in advance. |
| Rising costs | What will my spending look like if prices keep rising? | Social Security's 2026 cost-of-living adjustment was 2.8%. Check how much of your income adjusts for inflation. |
| Taxes | Which dollars are taxed, and how much, when I take them? | Required withdrawals, Roth rules, and the tax on Social Security all shape this. |
| Healthcare | What will Medicare and supplemental coverage cost, including income-related amounts? | Medicare premiums can rise with income from two years earlier. |
| Surprises and legacy | What if one of us needs long-term care, or dies sooner than planned? | Beneficiary choices and survivor benefits work differently than many people expect. |
Step 1: Add up what is guaranteed
List the income that arrives no matter what the market does: Social Security, any pension, and any other income with a fixed payment. Compare it with the expenses you cannot skip: housing, food, utilities, insurance, healthcare, and taxes. How much of the gap is covered by sources that do not depend on the market is the single most informative number in a retirement plan.
Step 2: Understand the claiming decision
Social Security is the one source of retirement income that is adjusted for inflation and paid for life. Waiting raises it, and for a couple, the larger benefit becomes the survivor benefit. See our Social Security guide. [2, 5]
Step 3: Map the taxes on each source
| Source | How it is generally taxed |
|---|---|
| Social Security | Up to 85% can be taxable, depending on your other income. |
| Traditional IRA and 401(k) | Withdrawals are taxed as ordinary income, and required withdrawals start at 73 or 75. |
| Roth IRA | Qualified withdrawals are tax-free, and the original owner has no required withdrawals. |
| Taxable brokerage account | Gains and dividends are taxed, often at different rates than ordinary income. Ask your tax professional. |
Step 4: Plan the order of withdrawals
There is no single best order. The right one depends on your tax bracket today and later, your required withdrawals, your Medicare income thresholds, and what you want to leave behind. A useful exercise is to build a year-by-year tax projection and test it against a bad early market, a long life, and higher prices.
Step 5: Look at the healthcare bill
Medicare is not free, and higher income can raise your premiums two years later. Retiring before 65 can mean paying for coverage until Medicare starts. See our Medicare guide. [4]
Step 6: Protect against the unexpected
Review what would happen if one spouse died or needed long-term care sooner than expected. Check beneficiaries on every account. See our beneficiary guide.
Questions worth asking
- How much of my essential spending is covered by income that does not depend on the market?
- What is my plan if my accounts fall in my first three years of retirement?
- Which accounts will I draw from first, and why?
- How would the answer change if I lived to 95, or my spouse did?
- How will I know if the plan is drifting off course?
This is where strategies that reduce risk, manage taxes, and create income you cannot outlive come into the conversation. They are tools that fit some situations and not others, which is why the first step is understanding what you already have.
Frequently asked questions
What makes retirement income fall short?
Usually several quiet pressures at once: living longer than planned, early market drops, rising costs, taxes, healthcare, and surprises.
How much does delaying Social Security raise the benefit?
8% for each year you delay past full retirement age, up to age 70.
Where should I start?
Name each pressure and check it against rules you can verify. This guide lists the question to ask for each one.
Sources and review notes
General education, not individualized investment, tax, or legal advice. Discuss tax decisions with your tax professional, and recheck annual limits before using this page for another tax year.