The 6 most important retirement planning questions

Mid adult businesswoman holding glasses and looking sidewards. Mateusz Zagorski

(MoneyWatch) Welcome back to week two of my series, "16 weeks to plan the rest of your life." Last week we estimated how long you might live and thought about the financial and lifestyle implications of your expected lifespan. This week we'll think more about the lifestyle you want by answering five important questions: the who-what-when-where-why of retirement. Developing thoughtful answers to these questions will help you answer the sixth retirement question -- how -- which is the goal of this entire series.

In addressing the five questions, let's start with the last.

Why

What are the reasons for the life you want? One way to answer this question is to think about and answer two insightful, provocative questions.

1. What would you do if you had one year to live? When I pose this question at retirement planning workshops, many people focus on the things that have the most meaning to them and let everything else just fall away.

2. What would your retirement look like if you could live forever? In this case, most people focus on renewal -- trying new things, learning new skills, making new friends. And once again, the most undesirable features of their lives fall away, when they realize they don't want to be doing those things forever.

Of course, the truth most likely lies somewhere in between: Most of us will live longer than a year, and we certainly won't live forever. But framing our life this way offers valuable insights to help us design the life we really want. I like to sum it up this way: Do more of what you like and what you're good at, and do less of what you don't like.

Now let's go back to the first question.

Who

Who do you want to spend time with? Which people -- spouse, partner, family, old friends, co-workers, new friends -- give you the most pleasure and meaning in life?

What

What will you be doing after you retire? Will you continue to work? Do you want to travel? Are there hobbies you'd like to pursue now that you have more time? What about volunteering? Or do you want to spend more time with family and friends? What gives you the most joy, meaning and purpose in life?

When

When will you stop working? Will it be when you're tired of your current job? Or when you no longer need the money? Or maybe you'll keep working until you're no longer physically able to work? Will you stop working abruptly or phase down? The answers for each person will depend on how much money you need for living expenses, whether you enjoy your work and whether you have a "bucket list" of other things you want to do.

Where

Will you live in your current house? Or will you downsize to something that's in the same general location? Maybe you'd like to move far away or be close to children and grandchildren. Or do you plan to go where your work takes you?

Why is it important to ask yourself these questions? The answers will dictate how much money you'll spend on living expenses, which in turn tells you how much retirement income you need.

For some people, one of these questions is the most important, and your answer to it may dictate or influence your answers to all the other questions. For others, you'll need to consider all these questions at the same time, because they all influence one another.

But don't go it alone. Instead, discuss these questions with your spouse, partner, family and close friends -- people who care about you and are in the same boat. Be open to their points of view without judgment -- you might be surprised at the insights you'll gain. The discussions will also bring you closer together to your family and friends. It's a great use of your time!

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    Steve Vernon helped large employers design and manage their retirement programs for more than 35 years as a consulting actuary. Now he's a research scholar for the Stanford Center on Longevity, where he helps collect, direct and disseminate research that will improve the financial security of seniors. He's also president of Rest-of-Life Communications, delivers retirement planning workshops and authored Money for Life: Turn Your IRA and 401(k) Into a Lifetime Retirement Paycheck and Recession-Proof Your Retirement Years.

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