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4 Paths to a More Fulfilling Retirement

Surefire directions from the best-seller 'Decisive' may help you make smarter decisions that will pay off down the road

By Steve Vernon, F.S.A.

“I've put in my time and now I’m outta here!” All too often, that’s the extent of the retirement decision-making process for many people – with predictable results.

Many Americans actually spend more time researching a vacation or their next car purchase than they do planning for retirement.

Why Retirement Planning Matters

That’s a big mistake. After all, you’re talking about the rest of your life! It’s a period that can easily last 20 to 25 years; for some, 30 years or more. It pays to take the time to do the job right.

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To make smart decisions about retirement, follow the advice of Chip and Dan Heath, brothers who are professors at Stanford University and Duke University and co-authors of the new bestseller, Decisive: How to Make Better Choices in Life and Work.

The WRAP Steps for Your Retirement

In Decisive, the Heaths offer a four-step process, known as WRAP, for making better decisions:

  • Widen your alternatives.
  • Reality-check your assumptions.
  • Attain distance before deciding.
  • Prepare to be wrong.

Although the book isn’t specifically about retirement, here’s how to use the WRAP process that way.

Widen Your Alternatives

You'll need to make plenty of important decisions about your retirement, both before and during that part of your life. Don’t assume they’re either/or choices. Decisive says any time you think you face an either/or decision, that’s a red flag — and you need to widen your alternatives.

Most people think retirement itself is an all-or-nothing decision – either you're still working full-time or you're completely retired.

But you should widen your alternatives and consider working part-time. During retirement, your primary goals should be happiness and fulfillment. You don’t necessarily have to stop working to achieve them.

You might enjoy the retired life more if you find part-time work that provides some income and health insurance while giving you the freedom to do what you want in your non-working hours.

As you consider your options, you may find that your current, full-time employer will let you switch to a phased retirement track, working part-time and gradually cutting back those hours until you're ready to quit altogether. Ask your employer about the possibility. You might be surprised by the answer.

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Widen your alternatives by thinking more creatively about your living situation in retirement, too.

Many people think their choices are to either stay in their home or move to a sunny location or an exotic foreign climate. Don’t overlook another option: remain in your current area, but downsize to a smaller, less expensive home.

By doing so, you'll save on housing costs and be able to stay close to long-term friends and family, which will help you avoid being lonely in retirement – a common problem for people who relocate to a new area.

Reality-Check Your Assumptions

With so many assumptions built into each retirement decision, be sure you take the time to see whether they really hold up in your situation.

Many people mistakenly assume that they’ll automatically be happier once they retire. But if you don’t have a good idea of what you’ll do when you stop going to work every day, you could quickly become bored and restless. Happiness is a far more likely outcome if you retire to activities you love rather than just retire from a job.

Another common mistake is to blithely assume your financial resources will adequately sustain you for the rest of your life. It takes a boatload of money to be fully retired for 20 years or more and most people underestimate the amount they actually need. Be smart and take the time to learn the total income you’ll receive from Social Security, your retirement plan and savings. Then you'll know what you can afford to spend — and how much more you might need to finance the retirement you want.

You can get an estimate of the size of your Social Security checks by creating a My Social Security account at the government’s website, To prepare other financial estimates, use an online retirement calculator, like Fidelity’s Retirement Income Planner. (You don’t have to be a Fidelity customer to use it).

(MORE: When You Haven’t Saved Enough for Retirement)


Or you may want to find and work with a trustworthy financial adviser who is paid to have your best interests at heart, without any conflicts of interest.

Attain Distance Before Deciding

The sooner you start planning for retirement, the higher the odds that you’ll find it fulfilling.

Once you turn 50, start thinking seriously about the who-what-when-where-why of your retirement years, which I’ve explained in more detail in another article:

  • Who will you spend time with?
  • What will you do?
  • When will you retire?
  • Where will you live?
  • Why have you chosen to make these decisions? (This is the most important question of all five.)

Answering these five questions will help you answer a sixth: How much money do you need to retire and how will your finances cover that amount?

If you’re married or in a committed relationship, start talking with your spouse or partner about these issues. You’ll be surprised how much your thinking may evolve as you kick around these questions in the years leading up to retirement.

Also, don’t react quickly to a negative situation affecting your retirement without carefully considering the consequences.

Some people hastily quit their jobs as soon as they’re eligible for retirement because a co-worker does something to upset them. But they may not be ready to retire, financially or psychologically.

Instead, if you become fed up with work, simmer down, tell yourself “This too shall pass” and wait at least a few months before pulling the trigger. You might be surprised to find that the problem has faded and you’ve regained perspective about the positive features of your job.

Prepare to Be Wrong

When it comes to retirement planning, it’s wise to have a Plan B at the ready, in case things don’t turn out the way you expect.

If you think there’s a possibility you'll get bored and restless in retirement, come up with some possible ways to re-enter the workforce.

You may have determined that you’ll have enough money for retirement as long as the stock market continues to make your portfolio grow. But a market crash after you retire can derail your best-laid plans.

To protect yourself, cover your basic living expenses with guaranteed sources of retirement income, like Social Security, a pension (if applicable) and annuities.

If these won’t do the trick, be prepared to change course with your finances by reducing your living expenses, moving to a less expensive home or going back to work.

I encourage you to use Decisive to help you WRAP up your retirement and give yourself the confidence to face your future. The book provides more details on each of the four steps, including plenty of helpful examples. You’ll probably also find Decisive useful in making other key decisions during the rest of your life.

Steve Vernon, F.S.A., is a consulting research scholar at the Stanford Center on Longevity and president of Rest-of-Life Communications, where he delivers retirement planning workshops. Vernon writes the Money for Life blog for CBS MoneyWatch and is author of Retirement Game-Changers and Money for Life: Turn Your IRA and 401(k) Into a Lifetime Retirement Paycheck. Read More
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