Early Retirement Checklist: Are You Ready to Retire Early?

Nine things to settle before you quit, built around the three ages that set the rules: 59 and a half, 62 and 65.

The short answer

You’re ready to retire early when four things are settled: savings of 25 to 33 times your yearly spending, money you can reach before age 59 and a half, health coverage priced for every year until 65, and a plan that works without Social Security before 62.

Age 59 and a halfPenalty endson most 401(k) and IRA withdrawals
Age 62Social Security opens30% smaller if your full age is 67
Age 65Medicare eligibility startsyou buy your own coverage until then
Your target25 to 33 timesyour yearly spending

Rules and dollar figures on this page are for tax year 2026 unless a line says otherwise.

Early Retirement Calculator: How Many Years You Have to Bridge

Leaving work early opens three gaps: years before you can touch retirement accounts freely, years before Social Security and years before you’re eligible for Medicare.

Enter the age you want to stop and what you spend in a year. The math runs in your browser. Nothing you type is sent or stored.

Half years are fine, like 59.5
Include health insurance, taxes and travel

Example shown. Change either number to see yours

Before age 59 and a half4.5 years$225,000 of spending to cover from money you can reach without the 10% additional tax

In today’s dollars. No investment growth, inflation or tax is included.

Before Medicare eligibility at 6510 yearsof health coverage you buy yourself. Social Security cannot start for 7 years
Savings target$1,450,00029 times $50,000 a year, this page’s guide for stopping in your 50s

The savings target is the total you need, with the bridge money inside it. It assumes growth. The bridge figure above does not, so read that one as a ceiling.

Your way across

At 55 the rule of 55 may apply, if your plan allows withdrawals: leave your job in or after the year you turn 55 and that employer’s 401(k) or 403(b) can be reached without the 10% additional tax.

The table under this calculator lists every source of money and when you can reach it. See when each account opens

The savings target follows one simple guide: 25 times your yearly spending if you stop at 60 or later, 29 times if you stop in your 50s and 33 times if you stop before 50.

Twenty-five times comes from research on retirements that last about 30 years. Leave work at 45 and your money may need to last 50. That’s why the multiple rises. The guide is our reading of that research, not a rule from it.

The financial freedom calculator shows where both figures come from and how long it takes to get there.

The Early Retirement Checklist

Work through these nine items in order. The first four decide whether you can leave. The rest decide whether it lasts.

CheckWhat to settleYou are ready when
1. Your numberWhat you spend in a year, times 25 to 33Your investments reach the multiple for your age
2. AccessWhich accounts you can reach before 59 and a halfReachable money covers every year until then
3. Health coverageA plan and a price for each year before 65The premium is in your budget, in writing
4. Social SecurityWhat claiming at 62 would cost youYour plan works without it before 62
5. TaxesHow much of each withdrawal you keepYour spending figure includes the tax
6. DebtBalances that would follow you into retirementHigh-interest debt is gone
7. A bad first yearWhat you do if markets drop right after you leaveOne to two years of spending sits in cash
8. A trial runLiving on the retirement budget while still workingYou have done it for six months
9. Your daysWhat you will do with the timeYou can describe a normal Tuesday

1. Know Your Number

Start with what you spend in a year, not what you earn. Multiply it by 25. That’s the usual starting target before you stop.

Where does the 25 come from? The 4% guideline. A 1994 study by planner William Bengen found that taking out 4% in the first year, then raising it with inflation, never drained a half-stock, half-bond portfolio in less than 33 years.

Good odds if you’re leaving work at 62. Thin if you’re leaving at 45.

In the same study, only withdrawals of 3% to about 3.5% lasted 50 years in every case. That’s roughly 29 to 33 times your spending. So this page uses 25 times if you stop at 60 or later, 29 times in your 50s and 33 times before 50.

If you spend $50,000 a year, the gap between the two ends is $400,000: $1.25 million at 25 times and $1.65 million at 33.

2. Check Which Money You Can Reach Before 59 and a Half

Take money from a 401(k) or traditional IRA before age 59 and a half and you generally owe a 10% additional tax on top of regular income tax.

On a $40,000 withdrawal, that’s $4,000 gone before the income tax bill.

Early retirees get around it by lining up money that isn’t locked. Here’s each source and when it opens, under the current IRS rules.

Where the money isWhen you can take it without the 10%The catch
Bank and brokerage accountsAny timeInterest, dividends and gains are taxed as usual
Roth IRA contributionsAny timeOnly what you put in. Earnings wait until 59 and a half and five years in
401(k) or 403(b) at the job you are leavingIf you leave in or after the year you turn 55That employer’s plan only, and only in the ways the plan allows. IRAs and old 401(k)s do not qualify
Governmental 457(b) planAny age, after you leave that employerMoney rolled in from a 401(k) or IRA keeps the 10% rule
IRA or old 401(k), taken as equal paymentsAny agePayments must run 5 years or until 59 and a half, whichever is later
Money you converted to a Roth IRA5 tax years, counted from January 1 of the year you convertYou pay income tax in the year you convert
Everything else in a 401(k) or IRAAge 59 and a halfIncome tax still applies to pre-tax money

The Rule of 55

If you leave your job during or after the calendar year you turn 55, you can take money from that employer’s 401(k) or 403(b) without the 10% additional tax. For public safety employees in a governmental plan, the age is 50, or 25 years of service if that comes earlier.

Two limits trip people up. It only covers the plan at the job you just left, so an old 401(k) from a past employer doesn’t count. And it doesn’t cover IRAs at all, so rolling that 401(k) into an IRA before 59 and a half throws the exception away.

The rule removes the 10%. It doesn’t decide how your plan pays you. Each plan sets its own terms, and some only pay a lump sum. A lump sum paid to you has 20% withheld for federal income tax, even if you meant to roll part of it over.

Ask the plan administrator what withdrawals are allowed after you leave, before you count on this money.

Equal Payments Under Rule 72(t)

At any age, you can avoid the 10% by taking a series of substantially equal payments from an IRA, or from a workplace plan after you’ve left that employer. The IRS allows three ways to work out the yearly amount.

What do you give up? Flexibility. Once you start, you can’t add money to that account or take anything extra, and you have to keep going until five years have passed or you reach 59 and a half, whichever comes later. Break the schedule and the IRS charges the 10% on everything you took in earlier years, plus interest.

Start at 52 and you’re locked in for seven and a half years.

Roth IRA Money

This part is about Roth IRAs. The IRS treats Roth IRA withdrawals as coming out in a set order: your regular contributions first, then converted money, then earnings. Contributions come out tax-free and penalty-free at any age, because you already paid tax on them.

Converted money has its own clock. Each conversion from a traditional IRA or 401(k) starts a five-year period, and pulling that money out sooner can trigger the 10%. That’s why people planning to retire early often convert a slice every year, starting five years before they need it.

And each conversion is taxable income in the year you do it.

A Roth 401(k) works differently. An early withdrawal from one is treated as part contributions and part earnings, and the earnings part is taxable. Don’t assume the contributions come out first.

More: The types of IRAs and how each one is taxed

3. Line Up Health Coverage Until 65

Medicare is health insurance for people 65 or older, so eligibility starts at 65. Retire at 55 and you have 10 years to cover on your own.

That coverage is the easiest cost to underestimate, so price it before you give notice.

You’ve got three main routes.

  • COBRA. If your employer has 20 or more employees, you can keep its plan for a limited time, but you can be charged the entire premium, up to 102% of what the plan costs. It buys time and keeps your doctors, at the full price your employer used to share.
  • A Marketplace plan. Losing job-based coverage when you retire qualifies you for a Special Enrollment Period. You can apply from 60 days before to 60 days after the day you leave. Open Enrollment for 2027 plans starts November 1 on HealthCare.gov. A state-run exchange can set its own dates.
  • A spouse’s plan or retiree coverage. If either is on offer, compare it first. One warning from HealthCare.gov: if you’re enrolled in retiree coverage, you can’t get premium tax credits on a Marketplace plan.

The Income Line That Decides Your Premium

On a Marketplace plan, a premium tax credit can cut your monthly cost. For 2026, you can get it only if your household income is at least 100% and no more than 400% of the federal poverty level. From 2021 through 2025 there was no upper limit. That expansion has ended.

This is the law as of October 2026. Bills to bring the expansion back have been introduced in Congress, and the rule could change again.

Before you plan a year of income around the line, check HealthCare.gov or your state exchange for the rule in force.

Household size400% line for 2026 coverage400% line for 2027 coverage, under the law as of October 2026
1 person$62,600$63,840
2 people$84,600$86,560

The amounts are higher in Alaska and Hawaii. Each year’s credit uses the poverty figures in place when Open Enrollment opens, which is why 2027 coverage uses the 2026 figures.

This matters more to early retirees than to anyone else. Why? Because you choose your income.

Most 401(k) and traditional IRA withdrawals count toward it. So do interest, dividends and capital gains from selling investments. Social Security counts too, including the part that isn’t taxed. Roth IRA contributions you take back out aren’t taxable income, and neither is spending down cash you already have.

Two traps sit on either side of the range. Go $1 over the top line and the credit is gone, and starting with tax year 2026 there’s no cap on how much of the advance credit you have to pay back at tax time. Come in under 100% and you probably won’t qualify for the credit either. In states that expanded Medicaid, income under 138% of the poverty level may qualify you for Medicaid.

One more timing rule: you can’t drop COBRA in the middle of the year and switch to a Marketplace plan just because it costs less. Outside Open Enrollment, the switch is only allowed when COBRA runs out.

So decide between them in the first 60 days.

Sign Up for Medicare on Time

Medicare doesn’t always start on its own. You’re signed up automatically only if you’re already getting Social Security at least four months before you turn 65.

If you’re waiting to claim, you have to sign up yourself.

Your first chance is a seven-month window: the three months before the month you turn 65, that month and the three months after. Miss it and Medicare says you may have to wait to sign up, which can leave a gap in coverage, and pay a late penalty on Part B. The penalty is 10% for each full year you could have signed up and didn’t, and it lasts for as long as you have Part B.

Having COBRA doesn’t give you more time. A Marketplace plan doesn’t replace the sign-up either: once you’re eligible for Medicare Part A, you can no longer get premium tax credits on a Marketplace plan and would pay its full price.

More: How to get health insurance when you do not have an employer

4. Decide What to Do About Social Security

You can’t collect Social Security retirement benefits before 62, so if you leave work at 50 or 55, don’t put it in the first years of the plan.

At 62 you can start, at a price. If you were born in 1960 or later, your full retirement age is 67, and starting at 62 cuts your monthly benefit by 30%. A $1,000 benefit becomes $700. A spouse’s benefit is cut by 35%. Waiting past 67 raises it, up to age 70.

Your benefit is figured from up to 35 years of earnings, using your highest-paid years. A shorter career means fewer of those years, so don’t assume the figure on an old statement. Check your current estimate with Social Security before you build it into the plan.

One more rule matters if you plan to claim early and keep earning. Until you reach full retirement age, Social Security withholds $1 of benefits for every $2 you earn above a yearly limit.

For 2026 that limit is $24,480.

5. Plan the Tax Bill for the Gap Years

Every dollar you take from a pre-tax 401(k) or traditional IRA is taxable income. If you need $50,000 to live on and all of it comes from those accounts, you’ll have to withdraw more than $50,000.

The standard deduction softens it. For tax year 2026 it’s $16,100 for a single filer and $32,200 for a married couple filing jointly, so that much income isn’t taxed at the federal level.

And your state may tax withdrawals too.

A low-income year is also the cheapest time to convert traditional IRA money to Roth. Watch the health coverage line from step 3 while you do it, because a conversion counts as income there too.

6. Clear the Debt That Would Follow You

A monthly payment in retirement raises your number. Every $500 a month you owe adds $150,000 to a 25 times target, because your savings have to produce that $6,000 a year for as long as the debt lasts.

High-interest debt goes first. Credit cards that charge interest average about 22%, according to the Federal Reserve. That’s far more than a retirement portfolio can be counted on to earn. Here’s how to pay off debt in the right order.

What about a low-rate mortgage? That’s a different decision, and it doesn’t have to be gone before you leave.

7. Protect Yourself From a Bad First Year

The worst time for a market drop is right after you stop earning. You’re selling investments to live on, so a fall in the first few years does more damage than the same fall later.

A common defense is cash. Keep one to two years of spending in savings, outside your investments, so you’re never forced to sell in a bad year. Your emergency fund can be the start of it.

The second defense is a spending plan with give in it: know in advance what you’d cut for a year if you had to.

8. Live on the Budget Before You Quit

A retirement budget on paper is a guess. Test it. For six months, live on exactly what you plan to spend in retirement and send the rest of your pay to savings. Add the health premium you priced in step 3 and take out work costs like commuting.

If it holds, you’ve got proof and a bigger cushion. If it doesn’t, you found out while you still had a paycheck.

9. Decide What You Are Retiring To

Money is the part you can calculate. The harder question: what fills 40 or more hours a week for the next 30 or 40 years? Answer it before you leave, not after.

Part-time work helps on both counts, the money and the days. Earning $1,000 a month covers what $300,000 of savings would at a 4% withdrawal, and it keeps your withdrawals low in the years your portfolio is most exposed. If you’ve also claimed Social Security early, remember the earnings limit in step 4. If that appeals, look at ways to earn side income on your own schedule.

Signs You Are Not Ready Yet

  • Your plan needs more than 4% of your savings in the first year.
  • Nearly all of your money is in a 401(k) or traditional IRA, and you have no bridge to 59 and a half.
  • You haven’t seen an actual premium for health coverage after you leave.
  • The plan only works if Social Security starts the day you turn 62.
  • You’re still carrying credit card balances.
  • You’ve never lived on the retirement budget for more than a month.

None of these means never. Each one is a specific problem with a specific fix, and working a little longer fixes most of them.

That’s a much smaller price than running short at 70.

Early Retirement FAQ

How much money do I need to retire early?

Plan on 25 to 33 times what you spend in a year. Twenty-five times is built on retirements of about 30 years and fits stopping at 60 or later. Use 29 times if you stop in your 50s and 33 times if you stop before 50, because the money has to last longer. On $50,000 a year of spending, that’s $1.25 million to $1.65 million. The financial freedom calculator works out your own figure and how long it takes to reach it.

How do I get health insurance if I retire before 65?

Most early retirees use a Marketplace plan from HealthCare.gov or their state exchange. Losing your job-based coverage gives you a Special Enrollment Period that runs from 60 days before to 60 days after you leave. COBRA is the other common option, at up to 102% of the full cost of your old plan. Medicare eligibility starts at 65, and unless you already get Social Security you have to sign up yourself.

What is the rule of 55?

It’s an IRS exception to the 10% additional tax on early withdrawals. If you leave your job in or after the calendar year you turn 55, you can take money from that employer’s 401(k) or 403(b) without the 10%, if the plan allows the withdrawal. It doesn’t apply to IRAs or to plans at earlier employers, and you still owe regular income tax.

Can I take money out of my IRA before 59 and a half without a penalty?

Yes, in a few ways. You can take back your own Roth IRA contributions at any time. You can set up a series of substantially equal payments under rule 72(t), which must continue for five years or until 59 and a half, whichever is later. The IRS also lists narrower exceptions, including disability and certain medical costs.

What happens to my Social Security if I retire early?

Nothing is paid until you claim, and the earliest you can claim is 62. Claiming at 62 cuts the monthly benefit by 30% if your full retirement age is 67. Your benefit is based on up to 35 years of earnings, so stopping work early can also leave you with a smaller benefit than a full career would.

What age is considered early retirement?

It depends who you ask. Social Security treats any claim before your full retirement age as early, starting at 62. In everyday use it means leaving full-time work before 65, when Medicare eligibility starts. The ages that carry rules are 55 for the rule of 55, 59 and a half for penalty-free retirement account withdrawals, 62 for the earliest Social Security and 67 for full Social Security benefits if you were born in 1960 or later.

Is it better to retire at 55 or 62?

It depends on what you can cover. At 55 you need seven more years of spending and 10 years of your own health coverage, and Social Security isn’t available. At 62 you’re past the 10% additional tax, you can claim Social Security at a reduced amount, and you have three years to cover before Medicare eligibility.

Early retirement comes down to a checklist with nine lines on it. Run your ages through the calculator and find the line you can’t tick yet. Fix that one first.

Next stepTest your plan with a retirement planning toolModel your withdrawals, taxes and health costs year by year before you give notice

Related in Retirement: the best retirement planning tools, how to choose a retirement plan and the types of IRAs.

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Brian Meiggs
Brian Meiggs founded My Millennial Guide and has spent over a decade writing about money. He tries every app and product before it goes on the site. No fluff, no guesswork. Named to the Northern Virginia 40 Under 40 earlier this year, and featured in WSJ, Business Insider, and Entrepreneur. Off the clock: chess, the gym, a quiet night in.