Retiring in the Next Five Years: What to Review Now
Start with decisions, not a single savings number
Five years before retirement is a useful time to turn an idea into a set of practical questions. How much might you spend? What income will be available? Which decisions depend on your employer, your household or the timing of benefits? A retirement account balance matters, but it cannot answer those questions by itself.
This checklist can help you organize a conversation. It does not determine whether you can retire or replace a plan based on your circumstances.
1. Sketch the life you expect to fund
Write down the expenses that would continue if work stopped, then add the changes you anticipate. Consider housing, insurance, food, transportation, healthcare, family support and the activities you want to enjoy. Include irregular costs such as home repairs and replacing a vehicle. Use a range when a number is uncertain and distinguish essential expenses from flexible choices.
For example, a household that plans to travel heavily at first may need to discuss a different spending pattern from one expecting part-time work. Neither example establishes the right budget for you; the point is to make assumptions visible.
2. Map income by starting date
List potential Social Security benefits, pensions, employment income and withdrawals from savings. Note when each could begin and whether its amount or timing is uncertain. For eligible workers, claiming your own Social Security retirement benefit before full retirement age reduces the monthly amount; delaying after full retirement age can increase it up to age 70. Household and survivor considerations also deserve review.
Explore Social Security claiming ages.
3. Check the healthcare bridge
If you expect to leave work before Medicare eligibility, identify what coverage may be available and what you would need to pay. Ask about premiums, out-of-pocket costs, provider access and enrollment deadlines. Do not assume a spouse's employer coverage or another option will be available without confirming the details.
Review healthcare before Medicare.
4. Review investments and account choices
Consider how your investments relate to the timing of future spending and your ability to tolerate losses. Review costs, account features and withdrawal rules before making changes to workplace retirement savings. A rollover or account consolidation should follow a comparison of the relevant options, not an assumption that moving an account is always preferable.
5. Decide what needs attention this year
Some tasks can wait; benefit elections, debt decisions or a planned work transition may have deadlines. Identify the next decision, who needs to be involved and what information is missing. Coordinate tax and legal questions with the appropriate professionals.
Your first conversation checklist
- A retirement date you would like to explore, plus alternatives.
- A general spending estimate and known larger expenses.
- A list of income sources and retirement accounts.
- The question that would make the biggest difference to your next step.
You do not need perfect figures to begin. A productive review can identify what to clarify, what to compare and which assumptions to revisit as retirement approaches.
Further reading: Social Security Administration: Plan for retirement.
Start with a free discovery meeting
Your first conversation lasts approximately 30–60 minutes. We get to know you, your goals and your current financial picture; no recommendations are made yet. James responds to conversation requests within one business day to arrange a time. Submitting the form does not reserve an appointment.
Request Your Free Discovery Meeting
Prefer to call? (219) 400-0485. Do not include account numbers, Social Security numbers or financial documents in an online request.
This material is for general educational purposes and is not individualized investment, tax or legal advice. Investing involves risk, including possible loss of principal. No strategy guarantees a profit or protects against loss. Consult your tax and legal professionals about your individual circumstances.