Could you step back earlier than you think?

The honest answer is that it depends on what you spend, not on a multiple of income. Once annual spending is established, you can work backward through expected Social Security, any pension or deferred comp, and how long the portfolio must last. Two households with identical portfolios can land a decade apart on that date, because one spends considerably more than the other.

There is no universal order, and the sequence has real tax consequences. Common approaches use taxable accounts first while filling lower brackets with tax-deferred withdrawals or Roth conversions, leaving Roth assets for later years or for heirs. The right pattern depends on your bracket, your Medicare surcharge thresholds, and when required minimum distributions begin.

It is the stretch between when your employment income stops and when Social Security and required minimum distributions begin, a period when your taxable income may be unusually low. Converting tax-deferred dollars to Roth during those years can move money at a lower rate than you would pay later. The window is often only a handful of years, and it is easy to miss.