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“The phenomenon of delayed retirement is well documented. Average retirement ages are climbing, and nearly half of baby boomers say they expect to work until age 66 or beyond, according to Gallup Inc. polls.”  — Anne Tergesen (Wall Street Journal)

For many of these potential retirees, they have no choice–they need the money. That’s why they continue to work even into their 70s and 80s. However, a large and growing number say they do it simply because they enjoy–even love–their careers. And if that’s the case, why not just keep on keeping on?

In her recent piece called “The Case for Quitting Your Job–Even if You Still Love It,” Tergesen gives two reasons to think about: first, is your job creating a sense of complacency? And second, since every job ends eventually, do you want to be caught unaware when others decide it’s time to make a change?

These are tough questions, certainly. And, there’s no magic age that dictates when one must confront questions such as these. But if there’s a silver lining, it’s that many who tackle these issues report there is much to gain on the other side.

Let’s start with the issue of complacency. For most people, it takes years of experience and practice to master their professions. Reaching the top gives them a sense of satisfaction and of course financial rewards as well. But for those who have been doing the same thing for years, it can become like a 747 on autopilot — impressive and effective, but not particularly challenging.

“‘Especially if you have been successful at what you have been doing, you start repeating yourself,’ says Sherry Lansing, age 70, who walked away from a job she loved as chief executive of Paramount Pictures’ Motion Picture Group and now runs a foundation. ‘You have done it and you know how to do it, and that’s comforting. But if you repeat yourself, the highs aren’t as high and the lows aren’t as low, and you start to lose that passion’ … [Ms. Lansing’s] first three decades in the movie industry ‘had gone way beyond any of my dreams.’ But soon after her 50th birthday, with hundreds of movies under her belt, she began to feel she was no longer learning and growing as she had been.

‘I watched the changes in myself,’ says Ms. Lansing. After her mother was diagnosed with cancer, for example, she became engrossed in ‘learning about scientific advances.’ A former teacher, she also wanted to devote more time to her responsibilities as a member of the board of regents of the University of California.

‘If your priorities shift, that’s normal and healthy,’ she says. ‘If your priorities don’t shift, then I don’t know if you are paying attention.’

But even if job complacency is not an issue, we all know that even the most rewarding jobs must eventually come to an end. For many, it is important that they have a voice in the transition.

“Philip Pizzo took the initiative at age 68 to step down as dean of Stanford University’s School of Medicine. ‘I knew that even if I wanted to stay in that role, at some point there would come a time when others would believe—even if I was doing a good job or a great job—that it’s time for a transition,’ Dr. Pizzo says. ‘The question is, to what degree do you want to influence that change? To me, it was important to have an influence.’”

Tergesen goes on to discuss how a good long “look in the mirror” can help.

“A good evaluation of your situation, career counselors suggest, includes two parts: internal, in which you appraise yourself and your performance; and external, in which you examine signals from others in the office.

Bill Winn, a psychologist with career-development firm New Directions Inc. in Boston, advises clients to start with a list of what they like and dislike about their jobs, keeping in mind such questions as: When I’m ‘in the zone’ and am so absorbed I fail to notice the passage of time, what am I doing? What am I not getting from my job? What have I set aside to do this job that I no longer want to delay?

Jacquelyn James, co-director of research at Boston College’s Sloan Center on Aging and Work, puts it more bluntly. ‘Are [you] embracing the next challenge—or coasting?'”

Of course, this internal checklist is just one part of the evaluation. In addition, a look at the external clues from those around you in the office (bosses, colleagues, and clients), is also important.

“Some are obvious, such as being passed over for a promotion. But other, less obvious clues can be equally telling. Dr. Pizzo, now 69, the former Stanford dean, recalls watching three leaders in their fields toward the end of their careers.

Two practiced medicine into their 70s, when one experienced deterioration of his technical skills as a surgeon and the other grew rigid in his thinking. Eventually, both were forced to resign from a prestigious medical institution, a denouement each could have avoided by heeding warning signals from colleagues, who had stopped asking for the doctors’ advice and voted them out of leadership positions in their specialties.

In contrast, a colleague who has become a mentor of Dr. Pizzo’s voluntarily closed his laboratory at Stanford when he stopped attracting top graduate students. Reputation intact, he segued into an advisory role at the medical school and the university at large.

‘Unless you look at the road signs around you and make alterations in your career trajectory, you run the risk of missing the flashing yellow lights and being forced to transition,’ says Dr. Pizzo, who is now the head of Stanford’s Distinguished Careers Institute, a new program for midcareer professionals transitioning to new acts.”

The article goes on to relate examples of career-changers, new entreprenuers, and volunteers who took the plunge to quit successfully. Click here to read the full article.

From a financial perspective, as “Personal CFOs” for our clients, we find the concept of “financial independence” to be the most helpful framework for these types of decisions. At the end of the day, we want to help clients get to the place where they can choose to work, or not work, based on factors other than money.