Imagine that you could spend the second half of your life doing whatever you want (within reason), that you no longer were confronted with the traditional financial constraints of needing to earn a living, that you could explore choices and opportunities that might have appeared unrealistic to an earlier generation.

A growing number of Americans don't have to daydream about achieving financial independence. They are already there. But for the vast majority of individuals, freedom from financial constraints remains elusive. It's the stuff of fantasies. Still, many working stiffs face more choices in their careers and their larger lives than they would have thought a decade ago, even after the stock market bubble of the late 1990s burst.

For financial advisors who work with affluent clients, helping them sort through these newfound choices is becoming an increasingly important part of their practices. Indeed, what has been labeled "life planning" has emerged as one of the hottest areas of specialization and topics of conversation among practitioners.

Advisors are discovering that helping clients navigate the maze of opportunities they suddenly face is a very different task from what they have been trained to do. And many individuals who find themselves in this envious predicament are finding that liberation from the daily grind is downright frightening. People who are able to retire at age 50 are sometimes deciding there are other things they'd rather do.

Instead of planning to stay with the same company until they are 65 and then quitting cold turkey, many Americans in their fifties are switching careers and moving into more rewarding, less stressful positions in which they can remain vital well into their seventies.

To understand how American society got to his point, it's instructive to look where we came from in the last 50 years. After all, the institution of retirement is largely a modern, post-World War II phenomenon.

The world in which our notion of retirement was conceived was, in many ways, a complete opposite of today's socioeconomic environment. In the 1950s, the Cold War loomed large in the nation's collective conscience, and business and government collaborated in many endeavors to ensure social harmony. Insulated from global economic competition, America was a far more socialistic nation than it is today. When the Eisenhower administration came into power, its top economic advisors wanted to cut the highest marginal tax rate on personal income from a punitive 94% to a more acceptable level, so they reduced it to 90%, reasoning that anything more might be inflationary.

The nation's culture was decidedly conformist, and the book that encapsulated the work environment of that era was William Whyte's The Organization Man, published in 1956. Big corporations were far more paternalistic than they are today. If you gave them 30 or 40 years of your life, they promised financial security.

Organization men were, to use a contemporary term, role models and, as Whyte wrote, "their values set the national temper." Their influence became pervasive, not only in large corporations, but also in government, universities and other nonprofit institutions. Although many organization men preached the virtues of free markets and individualism, their actions belied a far more cautious approach to work as they embraced their companies with reverence and traded career fulfillment, innovation and self-expression for good pay and a generous pension.

Fast forward 40 years and the world of work and retirement has come full circle. One can argue for hours about whether it was government, business, global competition or the citizenry who broke the social contract created in the New Deal and cemented in the 1950s, but everyone agrees it's toast. Few books have depicted exactly how work and life have been transformed more accurately than Daniel Pink's Free Agent Nation, published earlier this year.

Today's work environment may be short on security, but it's long on choice and opportunity. Ironically, Pink explains it was the decline of the organization man in the late 1980s, coupled with the advent of PC technology, that spawned the explosion of independent workers in the 1990s. This diverse group of 33 million people encompasses high-end software consultants, independent financial advisors and immigrant day laborers.

At the same time, giant corporations no longer can be counted on for job security. More than a few of today's free agents became independent contractors after they were victims of downsizing. Yet as Pink points out, more than 80% of independent workers prefer to work for themselves (even 66% of those forced into independent-contractor status favor that arrangement).

So why is any of this relevant to financial advisors helping clients wrestle with issues of retirement planning and life planning? Because what clients really want, aside from financial independence, is control over their own destiny.

The bull market of the 1990s has brought many clients closer to financial independence than they could have imagined a decade ago. But once they reach their wealth goal, figuring out what to do isn't so easy. And for many, remaining on the corporate treadmill is a lot safer default option than jumping into the unknown. A random survey of financial advisors around the nation reveals that individuals are considering the option of becoming more independent but often are taking the safe route.

Eleanor Szymanski, head of EKS Associates in Princeton, N.J., sees her clients grappling with this dilemma all the time. "My objective is to show them that they can afford to risk following their bliss," she says. "What many of them say is that 'I'm good at this job, but it's taking its toll on my health and my relationships.'"

However, more than a few of her clients who are executives in their late forties and fifties indicate, either explicitly or implicitly, that they "are scared of what's out there." Big corporations rarely have had to worry about losing senior executives earning six figures, but smarter corporations know that is changing. "I've seen a lot of high-powered executives who are able to do something else, but the company gives them golden handcuffs," Szymanski notes.

Making a major life change can be a daunting challenge, and it requires planning. For folks working 60 hours a week and struggling to find an afternoon or evening to spend with their families, it's easy to procrastinate and postpone a decision. Szymanski can spell out the options, but ultimately it's the client's choice. "It's the world against the individual. To me, the biggest risk is staying there," she says. People who have reached financial independence "are better off risking yourself instead of going along with the crowd. But our culture is short-term oriented, and we don't have a longer-term view. Taking small steps towards certain goals in this culture requires discipline."

Attitudes toward independence vary by age, profession and cultural orientation. To some degree, clients like Szymanski's who have successfully climbed far up the corporate ladder are well aware they could enter a new independent world. It may look enticing, but they are still bound by habit and financial incentive to their old worlds.

At Utley & Associates in Eugene, Ore., Ben Utley works with many professionals, including physicians and business owners, who do not work in large organizations and have been willing to make the leap. "Nobody I work with is employed by someone else," he says.

Some of his physician clients prefer scaling back their workload rather than quitting altogether and moving on to something else. But Utley cautions that can be a risky move for these professionals because their income may decline, but their potential liabilities don't.

What all his independent clients have in common is the need to remain vital. This is what the advisory profession has come to call life planning, for lack of a better word. "I haven't had anybody who was able to just retire. Some volunteer. They are not able to sit home, or they just get depressed," Utley continues. "But they are ready to move on, to leave the thing that made them all the money."

Although these individuals don't have to fight the trauma of cutting the proverbial umbilical cord with a giant employer dangling golden handcuffs and the appearance of security, stepping into the unknown isn't easy, even for the brave. "The reality is people don't know what they want to do, or they do, but they can't express it in words," Utley says. What he tries to do is provide "creative encouragement."

For example, his clients who are business owners often are happy to become consultants, stay active, use their brains and give up the headaches. "It's like the joy of parenting without children," he jokes. "We call it grandparents."

Gender often plays as important a role in a client's attitude toward a second, scaled-back career as age, profession and cultural orientation. Cicily Maton of Aequus Wealth Management Resources in Chicago spends more time than most advisors addressing issues of life planning and often engages in in-depth discussions with clients about doing something more fulfilling. One of the questions she asks is, "How do you see yourself?"

Typically, there is a noticeable divergence that runs along lines of gender. "Men typically say I'm a president or an executive vice president of their company," Maton says. While women may hold the same titles, their perception of themselves is far less likely to be dominated by their careers.

What Maton is seeing among many of her clients who have been successful is a lot of re-evaluation of what's important in life. "Just encouraging them to think realistically about doing what they were dreaming of doing is the first step," she says. After they think all the issues through, "we're inclined to say, 'Go for it-within reason.'"

It's not surprising that clients who have achieved a high degree of success become increasingly concerned about their legacy. "People who are financially well-off are looking for second jobs that give them an opportunity to give something back," Maton explains. She cites the example of a high-powered lawyer specializing in trusts and estates who became a development officer for a nonprofit organization.

The surge of interest in life planning is being driven by such factors as increased longevity and the desire of most people to spend the second half of their lives engaged in activities that are more meaningful and fulfilling than the conventional retirement the old organization men enjoyed. The overriding factor creating the current buzz is the rising wealth levels among Americans. Yet some practitioners are discovering that clients don't need to have a seven-figure net worth to enjoy more choices in their sixties than which early bird dinner special to line up for in Florida.

Tom Rogers of the Portland Financial Planning Group in Portland, Maine, goes out of his way to take on middle-class clients and reports that some are embracing an expanded perspective on retirement and coming up with creative solutions. One couple in their early sixties plan to join the Peace Corps for two years. Not only will their expenses be negligible, but they also can bank their Social Security checks during that time.

Part-time work also can help clients who failed to save sufficiently from dipping deep into their capital in their sixties. "Even someone who can earn $15,000 a year for five to seven years will find that their shortfall shrinks significantly," Rogers says.

Some innovative solutions middle-class clients are experimenting with play off the wealth of others. One client of Rogers' who decided to retire from his regular job at 60 with $400,000 saved decided to become a butler. "He's heading to Amsterdam to attend a leading school for butlers, and his life partner is retiring from her job at 50 and plans to become a massage therapist," Rogers says.

Clients often require guidance when they leave a traditional job- in which much of their career path is prescribed-for the uncharted waters of a second career that is far less conventional. Judy Martindale of Martindale & Associates in San Luis Obispo, Calif., often provides coaching advice on career transitioning. Many of her clients are nurses and other medical professionals weary of the increasing workloads and decreasing benefits. She also advises a large number of teachers.

Much of her advice involves acclimating clients to a different environment. "Eighty percent of coaching is developing accounting or checking in on progress," Martindale says. "You need to create systems that the client can eventually make self-generating." In other words, a major part of her job is to help clients who initially require lots of handholding as they move to a second career and become more self-reliant.

For all the recent interest in life planning and helping clients improve their quality of life, not all advisors are buying into this latest stage of evolution in what still is a young profession. One prominent advisor who requested anonymity sees several flaws behind all the recent noise. "The whole life-planning thing is something we've been doing all along," she says. "I'm not a big fan of retirement in general. People live too long. They need to stretch their minds, and the workplace is uniquely suited to that. It has more moving parts."

The current obsession many clients have about retiring in their fifties could prove dangerous, she fears. "It's certainly not for everybody, and if you are long-lived and there is an extended period of single-digit returns, clients will trade the stress of the workplace for the stress of not outliving their money," she warns. "What will 75 million baby boomers do for second-career, part-time jobs because most don't have the money to retire?"

While she understands the desire of folks to scale back, the potential loss for society and the economy could be staggering if we were to become a nation of butlers and volunteers. "People in their fifties and sixties have a lot of knowledge that business and society need," she continues. "Most people don't retire because they want to. They retire because they feel they are not wanted."

Nonetheless, she acknowledges that for many people, money is not their most important goal. Advisors can be facilitators in helping some clients make a transition, but she thinks it's a big mistake for them to try to become the driving force in clients' lives. It's one thing to be a client's personal CFO and an entirely different-and inappropriate- thing to attempt to be a client's personal CEO. "I'd certainly like to know a good second-career counselor in my area because it's an area where I have a little common sense but no real expertise. But a hybrid money management/fulfill-all-your-fantasies practice is unrealistic for many people," she quips. "This could trivialize what we do."

Right now, however, she is in the minority. Even after a severe 15-month bear market, most advisors are reporting that clients are just as concerned about quality-of-life issues as they are about whether they will have enough money. So the life-planning movement appears destined to remain the most intriguing new sub-discipline to watch within the advisory profession.