Can I retire? Start with these seven questions.

1. What will your retirement life actually cost?

Begin with spending, not an account balance. Estimate a normal month in today's dollars and include the categories that tend to disappear from optimistic budgets: health premiums, taxes, home repairs, car replacement, travel, gifts, and support for family.

Separate essential spending from flexible spending. Groceries and housing are different from a large vacation. That distinction gives you options when markets are weak without pretending every expense can be cut overnight.

• Essential: housing, food, utilities, insurance, health care, and taxes.
• Flexible: travel, hobbies, dining, gifts, and major purchases.
• Irregular: roofs, vehicles, dental work, family help, and long-term care planning.

2. Which income arrives without selling investments?

List Social Security, pensions, annuity income, and durable net rental income separately from portfolio withdrawals. These sources can cover part of your monthly life before your investments need to do any work.

Use conservative, after-expense figures. For a rental property, for example, gross rent is not retirement income. Maintenance, vacancies, management, debt service, insurance, and taxes come first.

3. How much must your portfolio provide?

Subtract dependable monthly income from planned monthly spending. The remainder is the job assigned to your investments. A starting withdrawal guideline can translate that income gap into a rough target, but it is a planning shortcut—not a guarantee.

A real plan also tests poor early returns, inflation, taxes, fees, longevity, and spending changes. The first estimate should help you identify the problem worth analyzing next, not declare your future solved.

4. Is health coverage solved from your last workday forward?

If you retire before Medicare eligibility, map the months between employer coverage and Medicare. Compare COBRA, a spouse's plan, retiree coverage, and Marketplace coverage. Premiums alone are not enough; include deductibles and expected out-of-pocket costs.

Losing job-based coverage can create a Marketplace Special Enrollment Period. Medicare enrollment timing also matters because late enrollment can create gaps or penalties in some situations.

5. Have you compared Social Security dates as a household?

The earliest claiming date is not automatically the best date. Claiming earlier generally produces a smaller monthly benefit; delaying beyond full retirement age can increase the benefit until age 70. Couples should also consider the larger earner's benefit as potential survivor income.

Compare at least three timelines: claim early, claim near full retirement age, and delay. Then ask how each choice changes the amount your portfolio must provide in the bridge years.

6. What happens when the first five years go badly?

A market decline shortly after retirement can be more damaging than the same decline later because withdrawals lock in losses. Your response plan might include a cash reserve, flexible discretionary spending, temporary work, a later retirement date, or a different withdrawal sequence.

Write the response down before a stressful year arrives. A backup plan is valuable only if you know when and how you would use it.

7. Can both people explain the plan?

A retirement plan is fragile when only one partner understands the accounts, income sources, passwords, professionals, and decisions. Create a one-page household map and review it together at least annually.

You are ready to move from estimating to execution when the spending target, income timeline, health coverage, tax questions, and bad-market response are understandable—not merely stored inside a thick report.