About

Why this exists

Most retirement calculators either oversimplify to a single rule of thumb ("just withdraw 4%") or bury real methodology behind a paywall. The good free tools that do it properly — FIRECalc, cFIREsim — are trusted for exactly the right reason: they run your numbers against real market history instead of a guess. When to Retire is built the same way, with a design that doesn't look like it shipped in 2005.

What it does

Enter your savings, spending, and time horizon, and it runs your scenario two ways:

• Historical Cycles — walks the actual sequence of market returns starting from every year in 1929–2025, so you see how your plan would have survived the Depression, the 1970s, 2008, and 2022, not a hypothetical.
• Monte Carlo — runs 1,000 randomized trials built from the same real historical data (not an assumed bell curve), giving a wider stress test than history alone provides.

You can model three withdrawal strategies (fixed real dollar, percentage of portfolio, or guardrails), add Social Security, and layer in one-time expenses or windfalls — a new roof, an inheritance, whatever's specific to your plan.

What it doesn't do

It doesn't calculate taxes, Required Minimum Distributions, healthcare costs, or state-specific rules, and it doesn't know your actual Social Security benefit — you'll need your own estimate from ssa.gov for that. Full methodology, including exactly where the data comes from and what's simplified, is on the calculator page.

Nothing you enter is saved, tracked, or sent anywhere — every simulation runs in your browser. See the privacy page for specifics.

Who's behind it

When to Retire is an independently built, ad-supported tool — not a robo-advisor, not a company collecting your financial data, just a calculator that tries to give you an honest answer.