Think you're ready to retire? Don't bite the bullet until you've hit these 6 key milestones

Instead of waiting until you’re actually retired, consider hitting these six milestones before you press the “no more work” button for good.

1. Create a comprehensive income and expense plan

One of the biggest concerns for retirees is whether they’ll have enough money to survive for years to come without a steady paycheck.

Financial advisors often cite the 25X rule, which states that you can expect to retire comfortably if your assets are worth at least 25 times your annual expenses. However, this rule of thumb doesn’t guarantee how much you can spend each year, or how much income your assets will realistically generate every year in retirement. You should also be clear about when you want to claim Social Security benefits and what your monthly payment will be.

You may want to consider consulting a professional financial advisor who can help you create a customized plan that accounts for your income, investments and expenses. After all, a plan is never one size fits all — some people dream of expensive vacations and yacht life after retirement, while others are happy to live in a low-cost-of-living area and spend very little.

An advisor can help you create the best plan for you, and also assist in changing or modifying your plan if needed after you retire.

2. Make sure you’ve handled your debt

Carrying debt without employment income doesn’t often make for a fun retirement, but unfortunately, many retirees live with this unpleasant burden. As the New York Fed’s credit and debt report for Q2 2026 finds, credit card debt increased by $21 billion, up nearly 2% from the first quarter. High-interest credit card debt can be the most damaging to your wallet.

Before retirement, you should come up with a plan to eliminate or at least minimize your non-mortgage debt. You might even consider paying off your mortgage, as getting rid of this monthly expense, along with the interest payments, can help boost your financial security when you are no longer receiving regular paychecks. Do keep in mind that real estate taxes never go away, although some loopholes do exist.

3. Ensure you have a robust healthcare plan

One of the reasons many seniors have debt is because of unexpected medical expenses. A National Debt Relief survey found that roughly 17% of older people carry an average of $9,144 in debt due to outstanding medical bills.

There can also be confusion about Medicare, how to enroll and which plan you want to sign up for. For example, you’ll want to consider whether or not a Medicare Advantage plan is right for you.

Don’t wait until the last minute to make these plans, or you could find yourself in a difficult situation.

4. Create a strong estate plan

If you have enough assets to retire, you may have something to leave behind for your heirs after you’re gone.

You could always wait until you stop working to plan your estate. However, managing your estate and retirement plans simultaneously can help you maximize potential tax advantages and other benefits.