The Pre-Retirement Financial Planning Checklist: Six Areas to Settle Before Your Last Paycheck

If you are looking for a financial plan for retirement and want to know what has to be in place before the date, this is the list. In the second half, money becomes more complicated at exactly the time you want life to become less complicated, and the complication is not any one of the six areas below. It is that they interact, and most people settle them one at a time with different professionals who never see each other's work.

Before the plan: what to gather

• Recent statements for every retirement, brokerage, bank, and annuity account, with how each is titled
• Your Social Security earnings record and benefit estimates for each spouse
• Pension plan documents and the election options, if any
• The last two years of tax returns
• Every insurance policy: life, long-term care, disability, umbrella
• Existing estate documents: will, trusts, powers of attorney, healthcare directive, and the beneficiary form on every account
• Employer benefit summaries: matching, stock plans, health savings account, retiree medical, and the rules for keeping any of it after separation

These are the raw material. A plan built without them is a conversation.

The six areas

1. A written retirement income plan

Where each year's spending comes from, in what order, and what adjusts if the first years are poor. Income is built in segments so each dollar has a job and a timeline. Our article on why the answer is a plan, not a percentage explains what the document contains.

2. An allocation built for distribution

The portfolio that grew the savings has a different assignment now: produce income, survive a bad start, stay tax-aware. Near-term spending sits in stable assets; later years stay in growth. The shift is planned in the years before the date, not on it.

3. A multi-year tax and withdrawal strategy

Which account each year's spending comes from, when and how much to convert to Roth in the low-income years before required minimum distributions, how to keep the income that drives Social Security taxation and Medicare surcharges under the thresholds that matter. Our article on the seven tax mitigation strategies covers each lever, and West Virginia residents should read about the 2026 state exemption.

4. Social Security and pension decisions

Claiming age for each spouse, modeled against RMDs, survivor income, and taxes. Pension election, single life or joint, with the survivor's income planned either way. Neither is chosen by default.

5. Healthcare, Medicare, and long-term care

A healthcare line in the cash flow projection with its own inflation assumption, a bridge plan if retirement comes before Medicare eligibility, and a long-term care decision, insure, self-fund, or hybrid, made while coverage is still underwritable. Our article on long-term care insurance in a retirement plan goes deeper.

6. Estate and beneficiary alignment

Documents current, beneficiary forms matching them, trust funded if there is one, titling checked. The most valuable hour in estate planning is the one spent comparing every beneficiary form against the will. Our article on legacy and estate planning for retirees walks through the seven documents.

The mistakes that derail the transition

• Starting too late. Conversions, the care decision, and benefit elections all need runway. Three to five years is the practical window.
• Treating each area as a separate decision. A conversion changes Medicare premiums and the inheritance. A claiming date changes survivor income. Decide them together.
• Overlooking the Medicare surcharge. Premiums are set by income from two years earlier. A large withdrawal or conversion at 63 raises premiums at 65.
• Skipping the non-financial side. What the days will hold, where you will live, who you will see. The plan funds a life; it helps to know which one.

How Beacon builds the plan

At Beacon Wealth Management, every client follows the same four-step Guided Journey, Understanding, Identification, Recommendation, and Actions, which produces a written Financial Summit Map coordinating six areas: wealth planning, retirement income, investment management, tax mitigation, long-term care and life insurance, and legacy and estate planning. The checklist above is the Identification step made visible. Business owners bring the exit question into the same room; professional practitioners bring the practice and its benefits; lifetime savers bring accounts accumulated over decades at several employers. Advisory services are offered through Cambridge Investment Research Advisors, Inc., a Registered Investment Adviser, and securities through Cambridge Investment Research, Inc., a broker-dealer.

Close to home: Morgantown

Morgantown, forty minutes north of our Bridgeport office up Interstate 79, is Monongalia County's seat and home to West Virginia University and WVU Medicine, two of the largest employers in the state. Faculty, physicians, and health-system staff approaching retirement typically carry a mix of 403(b) balances, state retirement plan benefits, and sometimes an older pension, each with its own distribution rules, which is why item three on this checklist, the multi-year tax and withdrawal strategy, usually takes the longest for Morgantown households. We meet with families there in person and throughout north-central West Virginia.

How to confirm the plan is ready

• All six areas are in one written document, not six conversations.
• The plan has been stress-tested against a poor first three to five years, and you have seen what adjusts.
• Every beneficiary form has been compared against the documents in the last twelve months.
• The Social Security and pension decisions were modeled, not defaulted.
• The long-term care question has an answer, whether or not that answer is a policy.
• There is a review schedule, and a stated trigger for reviewing outside it.

If you would like the six areas settled together, in one plan, let's have a conversation. A short discovery call is where the Guided Journey begins.