Five Worlds · 21-page PDF
The 5-Year Window Checklist
The years around retirement can give you options you may not have before or after.
The decisions that show up within a few years of your last paycheck, and how your pension, Social Security, taxes, withdrawals, and health coverage fit together.
You can spend 30 years preparing for retirement and still have several of the most important decisions show up within a few years of your last paycheck.
Which decisions show up in the years around retirement?
Some are obvious, like choosing a retirement date or deciding when to start Social Security. Others are easier to miss. Your taxable income may temporarily fall. Your health insurance may change. The way you take money from your investments starts to matter differently. A pension election may become difficult or impossible to change once it's made.
The point isn't that everything has to be perfect before you retire. It doesn't. The point is that some decisions are easier to make while you still have choices.
The harder part is that the answers don't stay in their own boxes.
Why look at the decisions together?
Waiting on Social Security may create more room for Roth conversions, but it also means your investments have to fund more of your spending in the meantime. A Roth conversion may reduce future taxable retirement balances, but it can increase income for Medicare or health-insurance purposes today.
None of those tradeoffs automatically tells you what to do. They tell you why the five-year window is worth looking at as one plan rather than a series of unrelated decisions.
What this is, and is not
Ten short sections, with sourced charts, worksheets you can fill in on screen or print, and a nine-question check near the end.
It is education, not advice. It shows you what to look at and where one decision starts affecting another, not what to decide.
Inside the guide
- Your dates on one page. Retirement, Social Security, pension, and Medicare on one timeline, and the decisions that get harder to change once made.
- The pension election. Both versions of the future, and what your spouse would still have if you die first.
- Social Security timing. If you wait to claim, what funds your life in the meantime, and what it means for a surviving spouse.
- The tax window after work. Whether lower-income years open up, and what a Roth conversion would change besides the tax bracket.
- The first few years of withdrawals. Where next month's spending comes from if the market falls early in retirement.
- Health coverage until Medicare. Retiree coverage, COBRA, a spouse's plan, or the Marketplace, and whether your income changes the cost.
- Your five-year check. Nine questions: mark the ones you can answer, circle the ones that still feel fuzzy.