The five years before retirement are a useful time to turn a general goal into a set of decisions. For households in Lexington and the surrounding Kentucky communities, a written checklist can help organize the information needed for a retirement-planning conversation.
Five years out: define the retirement you are planning for
Write down a possible retirement date, whether either spouse expects to work part time, and any plans to move or help family members. Separate essential monthly costs from flexible spending such as travel. Include expenses that do not occur every month: home repairs, vehicle replacement, insurance premiums, and family commitments.
Gather statements for workplace plans, IRAs, taxable accounts, pensions, debts, and insurance. A list of accounts is more useful when it also records ownership, beneficiaries, fees, and any restrictions on accessing money.
Three years out: compare income with spending
Build a year-by-year outline of expected income and expenses. Identify when paychecks may stop and when pensions or Social Security might begin. A gap between those dates needs a funding plan. Compare more than one retirement date and spending assumption rather than relying on a single projection.
Ask how the plan might respond to lower investment returns, higher costs, or a longer retirement. A projection is a planning tool, not a promise. The purpose is to identify decisions you can influence, such as saving more, changing timing, or adjusting flexible spending.
Two years out: review benefits and family responsibilities
Confirm what happens to employer health and life-insurance coverage when employment ends. Review health-coverage options and enrollment deadlines with the appropriate benefits or Medicare specialist. Include potential caregiving needs in the discussion; Medicare generally does not cover ongoing custodial long-term care.
Review beneficiary designations and account ownership. Ask your attorney whether wills, powers of attorney, and other estate documents reflect your wishes. Make sure a spouse or trusted person knows where essential records are kept.
One year out: rehearse the transition
Try living on the proposed retirement spending amount while still working, if practical. Identify which accounts would fund near-term expenses and who will handle the administrative steps. Discuss investment risk, reserves, taxes, pension elections, and withdrawal timing together.
Schedule a review before making irrevocable elections or moving retirement accounts. Establish a recurring review process and a list of events that should trigger an earlier conversation, such as a major expense, family change, or health concern.
Bring a short agenda to your first meeting
- What retirement date are we testing?
- Which expenses are essential, and which can change?
- What income starts when, and where are the gaps?
- Which decisions require a tax, legal, or benefits specialist?
- What should we complete in the next 90 days?
Explore our retirement-planning services and planning for pre-retirees, or schedule a conversation with Moneyline Wealth Management.
Source: Medicare: Long-term care coverage.
Important information: This checklist is general education, not individualized investment, tax, legal, insurance, or benefits advice. All investing involves risk, including loss of principal. Projections depend on assumptions and do not guarantee results. Consult qualified professionals about your circumstances.