The 5-year retirement runway: what to do in the years before you stop working

Most of the wealth-building work happens in the decades before retirement. But most of the planning leverage happens in the five years right before you stop working.

In that window, you still have earned income to absorb taxes, you still have employer healthcare to bridge to Medicare, and you still have time to make moves that are difficult or impossible to reverse later.

The four areas we walk every pre-retiree through

• Tax-bracket management — using lower-income years to fill brackets on purpose, not by accident.
• Roth conversion sizing — coordinated with IRMAA brackets and Social Security taxation.
• Healthcare bridge planning — covering the gap between leaving an employer plan and starting Medicare at 65.
• A 90-day test drive of your retirement budget — while a paycheck is still there as a safety net.

"The point is not to optimize every dollar. It is to remove avoidable surprises — so the day you retire feels less like a leap and more like a step."

Where this fits in our process

Pre-retirement runway planning is part of our broader retirement income work, and we usually pair it with a Social Security filing review and a Medicare-at-65 walkthrough. If you want a feel for the math behind conversion sizing, the Social Security Administration estimator is a useful starting point for the income side.