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Retiring Early in 2027? Make Sure You Have a Plan for These 2 Things.

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Key Points

  • You can’t apply for Medicare until you are 65.

  • You’ll generally pay an early withdrawal penalty for taking money from retirement accounts if you’re under 59 1/2.

  • Make sure you have a strategy for how you’ll get healthcare coverage and money for expenses before you retire early.

Retiring early has its perks — more years to spend on things you enjoy, less time tied to a 9-to-5 — but it also comes with challenges that are easy to underestimate until you’re in the middle of them.

The government sets rules for retirement account withdrawals and other benefits that can make life difficult for early retirees without a strategy in place. Here are two things you need to plan for before leaving the workforce if you’re retiring early in 2027.

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1. Healthcare

Medicare forms the backbone for most retirees’ healthcare plans, but you’re not able to apply for it until you’re 65. If you plan to retire earlier, you’ll need to get health insurance coverage another way until then.

You might be able to hang on to coverage through your former employer for a few years, but this is often much more expensive than it was when you were an active employee. You can also purchase individual health insurance through a health insurance marketplace. But make sure you price this out in advance so you know if your budget can accommodate it. Married people may be able to join a spouse’s health insurance plan if the spouse is still working.

Whatever you do, don’t skip health insurance coverage, even if you’re a pretty healthy person. All it takes is a single accident to wipe out tens or hundreds of thousands of dollars from your savings.

2. Early retirement account withdrawals

The government typically requires you to wait until you’re at least 59 1/2 to withdraw money from your retirement savings without paying the 10% early withdrawal penalty. There are ways around this, though.

If you have Roth savings, you can withdraw your personal contributions to these accounts tax- and penalty-free at any age. You can also withdraw Roth IRA conversions penalty-free after five years. Earnings, however, must remain in the account until you’re 59 1/2 to avoid the penalty.

You could also take Substantially Equal Periodic Payments (SEPPs). These are annual withdrawals that you take for the longer of five years or until you turn 59 1/2. There are different ways to calculate your SEPPs, but once you start taking them, you must complete them all as scheduled. Failure to do so can cause you to owe early withdrawal penalties retroactively.

Tapping savings stashed in a taxable brokerage account is another great option. There are no limits on when you can withdraw these funds, so they’re a great fallback to get you to 59 1/2 when you can access the rest of your retirement savings penalty-free.

You can also use more than one of the strategies above. Just make sure you have a plan that will cover all of your expenses until you’re 59 1/2.

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