You've been working for decades and are eagerly anticipating your retirement years, when you'll finally be free to do whatever you want — whether that's travel, golfing, hiking or volunteering.
But while you may be looking forward to ending your worklife, you may not have yet created a strong enough plan. A 2026 study from the Employee Benefit Research Institute, for instance, found that only half of retirees rated their household financial well-being as at least very good, while two in five said healthcare costs have been higher than they expected. Two in five also said their overall spending in retirement was more than they expected.
Must Read
Jeff Bezos backs a platform that lets anyone invest in rental homes for as little as $100 — 6 ways to build wealth like a landlord without actually being one
Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake. Here's what it is and 3 simple steps to fix it ASAP
The tax breaks in Trump's 'big beautiful bill' expire after 2028. Here are 4 moves to make before the window closes
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.
Story Continues