You’ve decided to retire. Who do you tell and when?

Preparation and timing can be key to making a graceful exit from the workplace.

  • By Matthew Kassel,
  • The Wall Street Journal
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The decision to retire can be a daunting one. But announcing your retirement may be even harder.

It’s a process that’s filled with uncertainty. How will your friends and family react? When is the right time to tell your boss and your co-workers? And how do you make clear that this isn’t the end of the line but an exciting new chapter?

Being financially prepared to retire

A few simple calculations can help you determine if your money will last throughout retirement.

There are no hard and fast rules, but there are approaches that can help people get through the process as smoothly as possible—in the workplace, on the home front and in their social life.

Here are some tips from experts as well as those who’ve made the leap.

Send up a trial balloon

The first thing you’ll want to do is talk with your spouse or partner to gauge their comfort level—and yours. That’s according to Larry Swedroe, research director at Buckingham Strategic Wealth and the co-author of “Your Complete Guide to a Successful and Secure Retirement.” Most people achieve a sense of accomplishment from their work, he says, so you should be prepared to explain how you will replace that feeling without burdening those close to you.

“There’s that old joke, ‘I married you for better or worse, but not for lunch,’ ” Mr. Swedroe says. “You need to show your spouse that you’ll be spending your time well.”

Be careful who you tell

When David Sheslow decided to retire after more than 30 years as a practicing psychologist at a pediatric hospital in Delaware, he found that the process of revealing his plans to his many co-workers was draining. His colleagues began asking difficult questions about his thought process. Why was he retiring now? How would he spend his time? So to shield himself from uncomfortable conversations, he began to watch his mouth at work. “Be careful who you tell,” says Dr. Sheslow, “unless you’re prepared to answer the hard questions.”

Hone your message

If you want to answer the hard questions, try to anticipate what questions people will ask most and have convincing and polite answers ready. This isn’t always easy. After all, how do you answer a question (such as, “How will you stay productive?”) if you haven't figured out the answer yet?

For those to whom answers don’t come easily, a public-relations specialist can help construct a convincing narrative, says Teresa Ghilarducci, an expert on retirement and a professor of economics at the New School for Social Research. Or, just ask close friends and family members to help you practice before the onslaught begins.

The reason this is important, says Dr. Ghilarducci, is there is a stigma attached to retirement, particularly among white-collar workers, and you may need to defend yourself against the notion that you are being phased out. Having a well-oiled story at your disposal will help you maintain your dignity and assuage any doubts about your worth.

Protect your time

A good story can also help fend off those who view your pending retirement as an invitation for them to ask for favors now that you have the time, says Rick Rodgers, a retirement specialist in Lancaster, Pa. Your children, for instance, may now look at you as a full-time babysitter, while your friends may ask you to volunteer for their pet causes.

“A lot of people find out that after they’ve retired, they’re busier than when they were working,” says Mr. Rodgers, “because they don’t know how to say no.” With that in mind, he says, you should make clear when you tell people about your retirement that you will have a full schedule, even if you haven’t decided what you’ll be doing.

Don’t jump the gun

The question of when to tell your superiors that you’re ready to retire can be tricky. Essentially, you want to figure out when you’ll be ready to go, and then give them just enough time to manage the transition.

Tell them too early, and you risk being pushed to the side before you’re ready. Too late, and you may inconvenience your colleagues. A couple of months’ notice is usually a reasonable buffer, says Jamie Hopkins, the director of retirement research at Carson Group, an investment-advisory firm.

Be firm

Decide for yourself how much involvement, if any, you’ll continue to have with your employer, and stick to your plan, says Ted Kurlowicz, a professor at the American College of Financial Services who recently announced his retirement.

Mr. Kurlowicz, who is in his mid-60s and is an expert on retirement planning, says that some people have asked him to continue full time, even though he is scheduled to leave his job at the end of April. Having anticipated such reactions, he laid out his terms, making it clear that his plans were firm but that if he were needed in a pinch, he could still come on board temporarily as a consultant.

Don’t burn any bridges

When Keith Correira, 54, left his job as the chief financial officer of a small energy company in southwest Colorado and moved to Las Vegas with his wife not long ago, he wanted to make sure that his employers were aware that he was happy he had gotten to work for them as long as he had and that his decision to leave for an early retirement was a personal one.

It was important to him to prevent any ill will, by making it clear his departure wasn’t about any issues he had with the company.

That’s the right move, says Robin Ryan, a retirement specialist in Seattle. It’s important to leave your job on good terms, because you don’t want any lingering animosities to carry over into retired life. “People remember you not from the great work you did all along,” she says. “They remember how you leave.”

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