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When You Stop

Can I retire now, or should I work one more year?

Compare three stop dates against the same simulated futures, and see what each one does to the money that has to last.

Educational estimates only. Not financial advice.

Your answers

Not started · 5 short steps

Your household baseline

Entered once, reused by every retirement scenario. About four minutes.

  1. Baseline

  4. This scenario

Household

Who is deciding?

Choose "With a partner" only if both your numbers matter to the answer.

A pension or annuity for life?

Social Security does not count here.

How long must the money last?

One answer for the household.

We can simulate a range of possible lifespans, or run everything to one fixed planning age instead. A fixed age means nothing in the result is adjusted for the chance of not living that long.

People

About you

Born

Why we ask

The year sets your full retirement age and the age your required withdrawals start, both exactly. It does not set your benefit amount. You enter that two questions down.

Still working?

SSA life table

Only picks the range of lifespans we test.

Social Security at full retirement age

Today's dollars, from the SSA statement. $0 if none.

Why we ask

We do the early or late claiming math for you, so an already-adjusted number would get adjusted twice.

/ mo

Enter this in today's dollars — the amount on your statement now. We adjust it for inflation across the simulation, the same way we adjust your spending target.

Social Security claiming age

Held the same across all three dates. When to claim is The Claiming Window's question.

Why we ask

We hold this age the same across all three dates. When to claim is its own question, and this comparison is about when you stop.

years old

Plan to stop working in

The year each of you would leave full-time work. They do not have to match.

Already stopped

Counted as retired from this year on.

Your stop years and claiming ages are what you plan today. Every retirement scenario starts from them, and you can change them here whenever your plan changes.

Your answers stay in this browser tab. Nothing is sent to us until you run the numbers.

Scenario progress

Answer, run, compare, then keep what you decided.

  1. Your answers
  2. Compare the three dates
  3. Plan & save

Run the scenario to compare your paths.

Run this scenario to compare the three dates

Answer the five short steps, check your answers on the review screen, then run the numbers to unlock Compare, Breakdown and Plan.

SCENARIO GUIDE

How this retirement stop-date comparison works

By Tom Brancato

Updated

Editorial policy

Use this scenario to compare three dates for when you stop working: a sooner date, your planned date, and one more year past it. You answer four short steps — your household, what matters most to you, your savings, and your yearly spending target. The scenario then runs all three dates through the same 1,000 simulated futures. You see the odds for each date, what each one tends to leave behind, and around what age money gets tight.

Stopping this year can be the sooner date. Your planned date sits 1 to 9 years out. The later date can go out to 10 years. The scenario compares those three dates. It does not pick one for you.

What you'll learn

  • How the odds compare across three stop dates that were run against the same futures
  • What "success" means here — every year's spending target met, in that simulated lifetime
  • Why the middle future can look comfortable while the odds still read Mostly held
  • What one more year moves, and what stopping sooner moves, measured on one shared set of futures
  • Around what age money tends to come under pressure in the rougher futures

Ready to compare your own dates? Run the when you stop calculator. Your planned date goes 1 to 9 years out. Stopping this year can be the sooner date, and the later date can go out to 10 years. Dates past that are not accepted.

THE QUESTION

“Can I retire now — or should I work one more year?”

Those are two ways of asking one question: what does the date do to the money that has to last? Enter your household, your savings, what you still save each month, your Social Security benefit at full retirement age, and your yearly spending target. The scenario runs a sooner date, your planned date, and a later date through the same simulated futures. Same market years, same lifespans. The only thing that differs between them is when you stop.

You can pick the date that fits your life, and the scenario reflects the odds back to you. It never picks for you.

Why one retirement number can't answer a question about timing

A single savings target, or a flat withdrawal rule, gives one answer for a whole retirement. It has nothing to say about the date. Move the date by two years and most of the picture moves with it. Your savings grow for two more years, or two fewer. Retirement has to be paid for over a different span. Social Security starts at a different distance from your last paycheck. And the number of years you buy your own health coverage changes too.

Working longer is not automatically the safer choice, and stopping sooner is not automatically the riskier one. One more year adds a year of saving and takes away a year of spending from savings. It also takes away a year of the retirement itself. This scenario does not grade that trade. It measures it, and it shows both directions with the same detail.

There is a trap in comparing dates, and it is worth knowing about. Some simulated futures end before a stop date is reached. A future like that met every spending target without ever being tested, because there was no retirement in it. Later dates collect more of those futures than earlier ones. Comparing raw rates would tilt the answer toward working longer for a reason that has nothing to do with your money. So every number that compares one date with another is measured on the futures that reached the latest of your three dates.

10–15%

the rough chance that a 62-year-old does not live another ten years, on SSA 2022 period life tables. Futures like those never reach a later stop date, so this scenario counts each date's odds among the futures where you lived to stop working — and says that count out loud.

Social Security Administration, Actuarial Life Table

What this retirement stop-date comparison helps you see

STOP SOONER · STOP AS PLANNED · ONE MORE YEAR

Three real dates, run the same way

Every path uses the same 1,000 simulated futures, the same market years, and the same lifespans. Only the stop date changes. Each path is followed for the same number of years from today, so an earlier date means more retirement years inside the same window.

PER-PATH ODDS · A STATED COUNT

Odds with the denominator said out loud

Each card leads with one percentage and one caption: of futures paid for your spending. Open the card's details and you see the count behind it — how many futures out of how many, where "how many" is the futures in which you lived to stop working. That count is not always 1,000, and the scenario says so rather than rounding the question away.

SHARED FUTURES · POINTS, NOT PROMISES

What one more year changes

The comparison between dates uses one shared set of futures: the ones that reached the latest of your three dates. Every date has real retirement years in every one of them. That is what makes "one more year moved the odds by N points" a fair sentence instead of a denominator trick.

How to read your When You Stop result

Each date gets a card. The card leads with one number: the share of simulated futures in which that date paid for your spending, every year, for as long as the household was alive. Success here is strict. One year short anywhere in a simulated lifetime, and that future did not count as a success. The card's details disclosure states the raw count — how many futures out of the futures where you lived to stop working.

Those per-date percentages each have their own denominator, so they are not meant to be subtracted from each other. The comparison between dates is a separate figure, stated separately, and measured across the futures that reached the latest of your three dates. When fewer than half the futures reach that latest date, the result says plainly that how long you live is driving the comparison more than when you stop.

Each date also gets one of three labels. Held up means 85% of futures or more paid for your spending. Mostly held means 70% to 85%. Often short means under 70%. Those are Whatify planning bands, not an industry standard, and a date labelled Often short is shown with exactly the same detail as one that held up.

The label reads the rough futures, not the middle one. That surprises people. A date can leave a healthy balance in the middle future and still read Mostly held or Often short, because the label counts how often the spending target was missed, not how much was left over when it wasn't. If a third of the futures came up short, a comfortable median does not change that.

Two views show the rest. The fan chart plots the median balance for all three dates at once, with the full spread around the date you are focused on. Later years only include the futures where the household is still living, so the number of futures behind each year shrinks with age, and the band fades once fewer than half of them are left. The Breakdown table takes one date at a time and lists every year: balances in today's dollars, and spending, Social Security, and tax in that year's dollars. It also counts how many futures fell short that year and how many were still living.

One more figure is worth finding: the pressure window. That is roughly the age at which the rough futures start to strain — either the worst tenth of futures runs dry, or one in ten of the living futures cannot pay the full spending target. It answers a different question from the headline odds. Odds say how often the plan held. The pressure window says when it tended to bend.

Coach note

“The odds and the leftover balance answer different questions. The band only looks at the odds. Read the leftover balance next to it, not instead of it. Read the pressure window next to both.”

Try adjusting:

  • The sooner, planned, and later stop dates
  • Your yearly spending target
  • What you save each month
  • Your investment style
  • Health coverage cost before Medicare

Questions to try next

STOP EARLIER THAN PLANNED

What if the sooner date is three years before my planned date instead of one?

GIVE IT ONE MORE YEAR

What if the later date is two years past my planned date rather than one?

TRIM THE SPENDING TARGET

What if the yearly spending target comes down $6,000 and the dates stay put?

CHANGE WHAT YOU SAVE

What if the monthly amount I still save goes up, or stops, before my planned date?

“RETIRE AT 62” AS A DATE

What if age 62 is entered as one of the three dates rather than looked for as a separate mode?

A note on claiming age: this scenario holds your Social Security claiming age the same in all three paths, on purpose. Varying it here would blur the thing being measured. When to claim is its own question, and its own scenario — coming to the retirement pack. Until then, the other money scenario calculators cover the nearer-term versions of the question.

Common questions about when to stop working

This scenario does not answer yes or no. It runs three concrete dates through the same simulated futures and reports how each one did. Stopping this year is supported: it becomes the sooner date, as long as your planned date is still in the future. Setting your planned date to this year is not a supported setup — the three dates have to be in order — so you get a validation message rather than a result. The odds and the label describe how a path performed. They are not a recommendation.

A worked example, from a frozen test household rather than a made-up one. Single, born 1965, age 61 in 2026, planning to stop in 2 years, with a sooner date of this year and a later date 3 years out. Savings: $180,000 taxable (mostly growth), $520,000 tax-deferred, $60,000 Roth. Still saving $1,500 a month, mostly pre-tax. Balanced style, 60% equity and 40% bonds, rebalanced yearly. Social Security $2,600 a month at full retirement age 67, claimed at 67. Spending target $68,000 a year, plus $16,000 a year for health coverage before Medicare. Modelled with a 5.0% real equity return, 2.0% real bond return, 2.5% mean inflation, a 0.40% annual fee, and federal tax only.

Across the 954 futures that reached all three dates, stopping this year paid for the spending in 31% of them, the planned date in 59%, and one more year in 71%. So one more year moved the shared odds about 11 points above the planned date, and stopping this year moved them about 28 points below it. On its own denominator, one more year came out at 71% and was labelled Mostly held, with about $368,000 left in the middle future. The planned date came out at 60% and was labelled Often short, with about $163,000 left in the middle future — a real balance in the middle, and still four futures in ten that came up short. Pressure showed up around age 71 for stopping this year, 76 for the planned date, and 78 for one more year.

Source: the single_tight fixture, engine 0.6.0 / schema m6.0, NumPy 2.4.6, Python 3.13.3, seed 20260812, 1,000 trials over 38 years. Every figure above comes from that one frozen run. It is an educational estimate for one specific set of assumptions, not a result for any real household, and not a forecast.

Compare your own three dates: run the when you stop calculator. Your planned date goes 1 to 9 years out, stopping this year can be the sooner date, and the later date can go out to 10 years. If you have a pension or annuity, have already stopped working, or would claim Social Security before the latest date you want to compare, the scenario will tell you so instead of running a number it cannot stand behind — and the money scenario calculators cover other parts of the picture.

Educational estimates only. Not financial advice. Results are not guarantees, and they are not financial, investment, tax, accounting, or legal advice. This scenario simplifies real uncertainty, and it discloses each simplification rather than hiding it. Market returns and inflation are drawn from a simple statistical model. Lifespans come from SSA period life tables. Taxes are federal only. Your Social Security benefit is held constant across all three dates, even though working more or fewer years would move it a little. Assumptions, verdict bands, and stop-date limits may change. How calculations work.

Money decisions rarely arrive one at a time. Each of these takes a few minutes and needs no account.