Pre-retirement
The decade that matters most.
The 10 years before you stop working are where decades of compounding meet the decisions that lock it in or give it back. Social Security timing, sequence-of-returns risk, Medicare IRMAA, Roth conversion windows — in plain English, sourced, and with the math shown.
The five decisions
The math worth getting right.
1. Social Security — claim at 62, 67, or 70?
Every year you delay claiming Social Security past 62 increases your benefit by 6–8%. At 70 you've maxed it out. But break-even math and spousal coordination can flip the answer — and most households make the decision without running either calculation. A typical break-even age for claiming at 62 vs 70 is 80–82; live past that and you win by delaying, die before and the math flips. Health, marital status, and spousal earnings history all change the answer.
2. Sequence-of-returns risk
The five years on either side of retirement are when sequence-of-returns risk is highest. Two retirees can have identical long-term average returns and radically different outcomes based on when the bad years hit. The standard defense is a "bucket strategy": 2–3 years of spending held in cash and short-term bonds so you don't have to sell equities into a drawdown.
3. Medicare IRMAA — the stealth surcharge
At 65 you enroll in Medicare. Your Part B and Part D premiums are means-tested based on your income from two years earlier. Cross an IRMAA bracket by a single dollar and your monthly Medicare premium can jump by $70+/month — per spouse, for the year. Large Roth conversions, RMDs, and one-time capital gains can all push you over a bracket if you're not watching. The brackets are the single most important retirement-tax input nobody talks about.
4. Roth conversions — the window between retirement and 73
Between the year you retire and the year RMDs start (currently age 73), you have a low-income window. This is when most high-net-worth households do Roth conversions — moving dollars from Traditional to Roth while their tax bracket is temporarily low. The goal: reduce the size of future RMDs (which at $1M+ balances can push you into the top bracket involuntarily) and give yourself a tax-free bucket for heirs. The math is dense, the savings over a 10-year window can be six figures, and the right annual amount changes every year based on IRMAA thresholds and your actual income.
5. Inherited vs spousal accounts
If one spouse dies first, the survivor's tax picture changes overnight — the standard deduction halves, the married-filing-jointly brackets compress to single, and required minimum distributions can push them into a higher bracket than when both spouses were alive. Planning for this is a standard part of a retirement income plan, and it's why spousal Roth conversions in the joint years often make sense.
When it's worth a human
Talk to a fee-only fiduciary.
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