Is it time to retire? Two questions to ask.

On the last day of November, a friend of mine who has enjoyed a long career will reach a milestone: her last day of work. After 25 satisfying years with the same nonprofit organization, she has decided to retire.

As that day approaches, she will begin the parting rituals familiar to soon-to-retire employees everywhere. She will clean out her desk. She will enjoy lunches with co-workers and friends. There will be an exit interview with the human resources department. And there will be a farewell party, of course, with speeches and tributes, gifts, refreshments, warm handshakes and hugs, laughter, and probably more than a few misty eyes at the prospect of a department without her.

Then, after the last piece of cake has been eaten and the last goodbyes exchanged, the newly minted retiree will turn in her security badge and head home to begin a new chapter in her life.

To an outsider, the process might look easy or predictable. In truth, she says, she "agonized" over the decision, weighing the pros and cons carefully.

To leave or not to leave? It's a question more and more baby boomers will find themselves asking as they approach conventional retirement ages. But these days there is nothing conventional about retirement, either in terms of its timing or its structure.

This stage of life is undergoing a transformation – what some are even calling a revolution. But here and there, what began as a reward for a lifetime of work is beginning to get a bad rap. "Leisure? Who needs it?" some workers ask. Others add, "Who can afford it?"

The voices of financial caution are everywhere. Even some of the wealthiest Americans, we are told, worry that they won't have enough for their later years.

Has it really come to this?

Crunching the numbers to determine retirement income can be a sobering task, to be sure. No wonder the security of a steady paycheck, the satisfaction of a job well done, and sociability with colleagues all exert powerful and legitimate tugs to keep employees tethered to their work.

Other encouragement to stay comes from a report issued last week by the National Center for Policy Analysis. It notes that in just two years the first of 77 million baby boomers will become eligible for early retirement benefits from Social Security. That will begin a three-decade-long "tidal wave" that will ultimately double the ranks of retired workers and severely test the nation's economy.

"Funding boomers' retirement benefits will put a severe strain on workers," says Andrew Rettenmaier, coauthor of the report. The study suggests that the government "encourage boomers to stay in the workforce longer, or at least not encourage them to leave."

This assumes employers will gladly keep current older workers on the payroll, or be willing to hire others. That is hardly a sure assumption, considering the number of companies that appear only too happy to thin the ranks of those in their 50s and 60s during downsizings.

Still, there comes a time when other pursuits beckon. When my soon-to-be-retired friend told a colleague of hers about her indecision, he offered a suggestion. "After all the agonizing, there are only two questions to ask yourself," he said. "What do you want to do? And when do you want to do it?"

Suddenly her decision became clear. Although she will miss her colleagues and her work, she knows that no one is indispensable. Her retirement plans include a lengthy stay with relatives halfway around the world. They also include the pleasure of participating in a theatrical group that gives her new outlets for singing and dancing and connects her with new friends.

Already she finds that she is beginning to "reinvent" herself. She also looks forward to having more time for reflection.

To leave or to stay? The answer – and the timing – will vary for each individual. But at a time when paid work is too often taken as the chief measure of a person's worth, every satisfied retiree offers a reassuring reminder that unpaid activity can be fulfilling, too.