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4 Questions Everyone Should Ask Before Retirement

Finding the answers can make all the difference.


For most retirees, happiness doesn’t just happen. It’s something they need to plan for. But how do you actually begin planning to have more joy and satisfaction in retirement? By asking yourself these four key questions—and finding the answers. 

1. How do I want to spend my time?
That’s a big question, but it’s an important one to ask first. If you don’t know where to start, write down all of the things you’ve had on your bucket list—even if you don’t think they’re financially possible. “Don’t view it from a budgetary standpoint,” says Melody Juge, founder and managing director of Life Income Management, a firm specializing in retirement income planning and education. “By taking money out of the equation, you can focus on what will bring you emotional satisfaction in retirement.” Is that adventure and travel? Spending more time with your grandchildren? Maybe starting a second-act career or pursuing a personal passion?

2. Where do I want to live? 
That’s almost as big a question as the first, because it will guide what you’re going to do with your time. If you want to garden year round, the Northeast might not be your ideal retirement location, for example. Also, consider how much home maintenance you want to do. Maybe you’re not interested in going to a retirement community just yet, but you may want to downsize from the big family home and move into a townhouse that’s easier on your budget and better fits your ideal retirement lifestyle. For a lot of people, a major factor in the answer to the question of housing is family: How close do you want to be to them? And if you’re looking at finances and considering moving to a state with lower taxes, consider what that will mean in terms of spending time with your family and whether you might wind up spending your tax savings on driving or airline tickets.  

3. Who will I be sharing my retirement with?
If you’re married and retiring together, the answer to that question is an easy one, but it’s important to make a plan together. Also, realize that your lives and time together are going to change, especially if one of you has retired first or spent significantly more time at home while the other was in an office all day.

If you’re not partnered up, do you see yourself sharing your retirement years with someone else? Or have you always wanted a Golden Girls–esque life of living with your best friends? This is a big part of your retirement vision, and asking these hard personal questions now—whether you’re asking them solo or with someone else—can help secure your plan.

4. Where’s your money?
This is where your dreams get a dose of reality. “You will be surprised to find that more often than not you can afford some version of your dream,” says Juge. It’s an important question to ask so that you can match your retirement goals to what you can afford—and make adjustments if need be, whether that means working longer or part-time, changing the way you spend and save now, or scaling down what you hope to do. Getting a clear financial picture means figuring out what you’re spending now and separating that spending into your necessities expenses (housing, health care) and cost-of-living expenses (dinners out, club memberships, sports fees). Then review all of your assets, like 401Ks, personal savings, and annuities, which will pay for the time when you’re no longer working. You’ll also want to get an estimate of what your Social Security benefit will be—and how much more you’ll get if you can hold off on collecting. You can find a benefit calculator at ssa.gov