Taxes DeskIssue #7 · Jun 30
Bracket-filling: the quietest tax strategy in your 50s and 60s.
The multi-year plan that turns a few low-income years into a permanent reduction in lifetime tax.
Tax planning in a single year is a rounding error. Tax planning across five to fifteen years is where real money moves. Bracket-filling is the discipline of intentionally realizing income — through Roth conversions, capital-gains harvesting, or accelerated distributions — up to the top of your current bracket, but not one dollar into the next.
The people who do this well don't do anything dramatic in any given year. They just refuse to let a low-income year go to waste.