Retirement readiness is a buzzword phrase that gets thrown around a lot. But what does it actually mean? And how do you know if you’re ready to retire, or if you’re going to come up short? While there are certainly math equations involved, retirement readiness goes way beyond numbers. It also includes logistical, emotional, and even spiritual elements that must be accounted for.
Most people focus on the financial benchmarks, and that’s important. But there’s a whole other set of questions that don’t show up on a retirement calculator. The kind that can shape how fulfilling your retirement years actually turn out to be. If you want more than just a well-funded endgame, it’s time to ask yourself some deeper questions before taking the plunge.
What Will You Do With Your Time?
It sounds simple, but it’s one of the most overlooked questions. When your career disappears from your calendar, how will you fill your days? It’s not enough to say, “I’ll travel” or “I’ll relax.” That might be satisfying for a few months, but eventually, you’ll crave routine and purpose.
Think beyond the bucket list. Will you volunteer, consult, pick up a hobby, or spend more time with family? Will you work part-time just to stay mentally active? A blank calendar may feel luxurious at first, but too much unstructured time can lead to restlessness, boredom, or even depression. You need purpose in your retirement, or you’ll end up feeling useless and restless.
Have You Talked About It With Your Partner?
You might have a perfectly clear vision of what retirement looks like. But what if your spouse imagines something totally different? What if they want to move across the country while you’re envisioning more time in your current home? Or what if they plan to keep working?
Retirement changes the rhythm of your relationship. You’re suddenly spending a lot more time together – and that can either strengthen your bond or surface long-ignored issues. Talk openly and early about your priorities and day-to-day expectations. Your relationship will thank you for it.
How Will You Handle Health Care (and Its Surprises)?
It’s easy to assume Medicare will cover everything once you hit 65. But the reality is more complicated – and more expensive. You’ll likely need supplemental insurance, and long-term care isn’t typically covered. Even routine medications, dental work, or vision needs can add up fast if you’re not prepared.
If you’re retiring before 65, the gap in coverage could be a serious expense. And even after Medicare kicks in, costs don’t vanish. Have you budgeted for out-of-pocket health costs? Do you know the difference between Medicare Part A, B, and D? Have you looked into a Health Savings Account (HSA) or long-term care insurance?
One unexpected diagnosis or fall can wreak havoc on an otherwise solid retirement plan. Plan for it before it becomes an emergency.
What Will Your Taxes Look Like in Retirement?
Just because you’re retired doesn’t mean you stop paying taxes. In fact, you might end up paying more than you expect – especially if you’ve accumulated savings in pre-tax retirement accounts like traditional IRAs or 401(k)s.
Required Minimum Distributions (RMDs) can push you into a higher tax bracket. Social Security benefits can be taxed based on your income level. And if you’re planning to sell a home, cash in stock options, or convert a traditional IRA to a Roth, that could come with a hefty tax bill.
Working with the right financial planner can make a world of difference. They’ll help you map out withdrawal strategies, time your Roth conversions, and structure your income in ways that reduce tax drag – so you keep more of what you’ve earned.
Have You Stress-Tested Your Plan for Longevity?
It’s tempting to assume retirement will last 20 or 25 years. But what if you live into your 90s or beyond? That’s a good problem to have – unless you outlive your money.
Longevity risk is one of the most underestimated threats to retirement security. A plan that works beautifully at age 65 might fall apart at 85. Inflation, market downturns, unexpected expenses all add up over time.
With this in mind, have you modeled your plan against different life expectancy scenarios? Make sure you’ve factored in how your spending may change as you age. Building flexibility into your plan matters. You want to be able to adapt if life lasts longer than expected (which, thanks to medical advances, is more common than ever).
Are You Emotionally Ready to Stop Working?
This question doesn’t get asked enough. Retirement can bring tremendous freedom, but it can also surface identity issues that catch you off guard.
For decades, your work may have given you structure, validation, and a sense of purpose. Without it, you might feel a little disconnected. And that’s why it’s important to think about not just what you’re retiring from, but what you’re retiring to. Build a vision for your post-career life that excites you and helps you stay socially connected.
Putting it All Together
We often think we have an idea of what retirement will look like. However, as you get closer to clocking out of your career, you’ll probably find that you have more questions than answers. But, by asking the right ones now, you can hopefully put yourself in a better place to enjoy your golden years!
