Retirement Timing Is the Most Sensitive Variable in Your Plan

Why 'how much do I need' is the wrong first question

The right first question is 'when do I want to stop, and on what terms?' Retiring at 55 with healthcare costs out of pocket is a different financial problem than retiring at 65 onto Medicare. Once you know the timing, the 'how much' resolves itself.

• Pre-65 retirement = self-funded healthcare bridge
• Sequence-of-returns risk dominates the first decade
• Roth conversion windows often live in early retirement

Social Security claiming changes the math

Claiming at 62 vs 67 vs 70 isn't just a personal preference — it's a major lever in any retirement plan. For most healthy single earners, delaying to 70 wins by a wide margin; for couples with a large age gap, the strategy gets more nuanced.

The 'one more year' trap

Many high earners hit FI but keep working 'one more year' indefinitely — usually because they don't trust their number. A real plan with stress-tested scenarios fixes that, and most users discover they could have stopped 1–3 years earlier than they thought.

How PeakWorth models your retirement timing

Retiring at 55 vs 62 vs 67 is run as separate scenarios — each with its own healthcare bridge, Social Security claim, and withdrawal sequence — and reported as your FI Age (the year your portfolio reaches ~25× the expenses it must cover after Social Security — roughly 20× your total annual expenses) and PeakWorth (highest projected lifetime net worth), so 'when can I actually stop?' becomes a dated answer instead of a 'one more year' guess.