The 36-Month Retirement Decision Calendar
Moss Wealth Management
A practical guide to the decisions that can matter before your final paycheck, organized from 36 months out through the first years of retirement. Very little about the retirement transition is urgent on any given day, which is exactly why it tends to arrive all at once. Not every item applies to every household. This is a map of the terrain, not a set of instructions.
36–24 months out — Establish the picture
Far enough out that almost everything is still adjustable. This is the window where questions cost nothing to ask.
Retirement income picture
What might income look like if you stopped on the date you have in mind? Understanding the expected income sources, the spending they need to cover, and the timing of each is what makes the remaining 36 months useful rather than reactive.
Spending clarity
Not a budget exercise so much as an honest estimate: what does your life cost now, and which parts of that change when you stop working — commuting, healthcare, travel, supporting family.
Debt and cash reserves
Debt, liquidity, taxes, and timing can interact with one another, which is why this is worth reviewing while there is still earned income. What makes sense varies by household.
Employer benefits inventory
Deferred compensation, company stock, unused HSA balances, and retiree health coverage each have their own rules and their own deadlines.
Pension elections, if applicable
Lump sum versus annuity, and the survivor options that accompany them. Some elections may be difficult or impossible to change after they are made, which is why they are worth understanding long before the election form arrives.
24–12 months out — Coordinate the moving parts
The year where decisions start to interact with one another, and where sequence begins to matter more than any single choice.
Social Security timing
Claiming age can affect the monthly amount, the taxation of other income, Medicare premium tiers, and what a surviving spouse receives. It is rarely a standalone decision.
Potential tax-planning windows
The years between the last paycheck and required distributions can look different from the years on either side. Roth conversions or other tax strategies may or may not be appropriate depending on the individual situation, and are topics to discuss with qualified tax professionals.
Withdrawal sequencing
Different account types — taxable, tax-deferred, tax-free — may create different tax and cash-flow effects over time. Understanding those differences is part of the picture.
Investment positioning
No single approach applies to everyone. Investment strategy may need to be reviewed in light of near-term spending needs, time horizon, risk tolerance, and individual circumstances.
Charitable giving
For those who give regularly, the method and the timing are worth considering alongside the amount, particularly in years when income changes.
The final 12 months — Deadlines and paperwork
Much of what remains here is date-driven, and the dates tend to arrive whether or not the paperwork is ready.
Medicare enrollment and IRMAA
Enrollment windows are tied to specific dates, and premium tiers are based on income reported two years prior — which means earlier decisions can show up here.
Health coverage bridge
If retirement precedes Medicare eligibility, the gap needs attention: COBRA, a marketplace policy, or spousal coverage each carry different costs and timelines.
Final-year compensation
Bonus timing, unused paid leave, deferred comp start dates, and final 401(k) contributions all land in a year that may be among your highest-income years.
Estate documents and beneficiaries
Beneficiary designations override wills. Reviewing them alongside titling and powers of attorney is routine work that tends to go undone for years.
Spouse preparedness
Both people knowing where accounts are, who to call, and how income arrives — this is the item most often postponed and most consequential when it's needed.
The first years of retirement — Run the system
The plan stops being a document and starts being a monthly routine, reviewed as circumstances change.
Establishing the retirement paycheck
Setting up the actual transfers so money arrives on a schedule, from the accounts the plan intended, without a decision required each month.
Annual tax review
Income in retirement often comes from several sources with different tax treatment, which is part of why an annual review is a planning conversation rather than only a reporting one.
Rebalancing and withdrawal review
Markets move in ways no one controls. Reviewing how spending and investment decisions may interact during periods of volatility is part of the ongoing work, not something settled once.
Required distributions on the horizon
They arrive eventually. Looking at them earlier may provide more time to understand how required distributions could affect future income and taxes.
Legacy and family conversations
What you want the money to do beyond your lifetime, and who needs to know about it before it matters.
Important disclosures
Information and interactive calculators are made available to you as self-help tools for your independent use and are not intended to provide investment, tax, or legal advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Securities and Advisory Services offered through LPL Financial, a registered investment advisor. Member FINRA / SIPC.
The LPL Financial registered representative(s) associated with this website may discuss and/or transact business only with residents of the states in which they are properly registered or licensed. No offers may be made or accepted from any resident of any other state.
This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor. Moss Wealth Management / Main Street Advisors and LPL Financial do not offer tax advice or services.
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