Even successful founders can stay at their companies too long, beyond the point when giving your all means hurting yourself beyond repair -- or even damaging your company beyond reconstruction. How long is too long? Too often the founder is the last to know

It was 10 o'clock on a brisk November night. Jan Pringle, 47, cofounder of the Atlanta ad agency Pringle Dixon Pringle (PDP), was sitting at her desk, staring at the wall in front of her. Being there at such a late hour was typical. For 20 years she'd regularly clocked 12-hour days, six days a week. She had a presentation due in the morning for one of the biggest radio stations in town. The yearly budgets for two of her largest clients were due. She had 10 client meetings in the next five days.

But that night all she could do was stare at the wall. She couldn't get up. She couldn't leave her desk. She couldn't call for help. Her husband and PDP's cofounder, Jim, innocently phoned to ask when she'd be home. She mumbled, "I can't come home. . . . I can't leave." The next thing she remembers, her teenage son appeared at the door, physically pried her away, and took her to the hospital.

After exhaustive testing, doctors concluded that Pringle suffered from a stress disorder that would require her to take an extended leave from her company. Back at home, she lay down on the living-room couch and thought to herself, "I just want to die. I don't care if I ever return to my company."

But a year later she did. That was three years ago, and every day since then, Pringle has wrestled with one of the toughest questions a leader can face. Is it time for her to move on -- to leave behind the company she started building 20 years ago?

How can she tell if the company she founded, believed in, and built has had enough of her? She says it's hard to know. The company gives no clear signs. No doctor says, "Slow down." No spouse threatens a divorce. If profits slip, it can be blamed on a bad year or an errant client. "This isn't about whether the widget I make is outdated," she explains quietly. "It's about whether I am."

For Jan Pringle, it wasn't always this difficult.

Back in the 1980s PDP was one of the hottest shops in Atlanta -- "the kind of place where breakthrough work was being done," declares Dan Scarlotto, PDP's creative director of five years. The momentum and excitement of the day were perhaps best captured in a pro bono campaign against drunken driving that PDP did for the governor's safety council in 1983. It featured stark black-and-white photos of tombstones, a man in a wheelchair, and a body in a morgue. The entire city of Atlanta -- from taxicabs to police cars -- was blanketed with a campaign that blared the slogan "Drunk Driving Is Just Murder on Our Roads." The impact was irrefutable. The state's alcohol-related traffic fatalities dropped by nearly 40% that year. The campaign was recognized as one of the best public-service spots in the country and was repackaged for markets as far off as Tokyo and Moscow.

Founded in 1973, PDP had in Jan and Jim Pringle a compelling duo. With a Southern tell-it-like-it-is charm and infectious enthusiasm, Jan handled public relations and was the front person for the firm. Conversely, Jim, tall and lanky, with a Cary Grant kind of reserve, oversaw the advertising creative work and was behind the scenes to make the agency deliver on its promises. In a crowded market -- cluttered with more than 60 shops -- the Pringles offered "integrated marketing services," combining public relations, marketing, and advertising. At the time, it was an approach that gave the firm some differentiation.

What also set the agency apart was Jan's unusual commitment to the value of pro bono, or public-service, work. "Jan has always done more than almost anyone else for the city," says Greg Stone, general manager of ABC-TV's affiliate in Atlanta. "She genuinely cares and commands great respect." But public service is undeniably smart business -- especially for an ad agency. There is no client budget to confine pro bono work, since the agency typically assumes the cost, which gives it unusual ability to flex its creative muscle in a very public setting. The campaign against drunken driving for the state, for example, cost PDP $70,000 to produce, but a year later Georgia moved $400,000 worth of advertising business over to the agency. Within four years, that account alone had grown to $4 million. In later years PDP, with Jan leading the charge, spearheaded campaigns for many other civic causes, from saving the Atlanta Zoo to saving the inner cities. Says a former employee, "Jan has always been very smart about going after high-profile public-service work."

And for other clients, she has always known how to stretch the ad dollar, says Preston Ridlehuber, a onetime client of PDP's. Ridlehuber recalls his beverage-distribution company's spending around $15,000 with the agency but garnering easily a half million dollars' worth of publicity. "'Entertainment Tonight' did a feature on us," he explains.

Beyond attracting as clients well-known giants like McDonald's and Contel, then one of the largest cellular-communications companies in the country, PDP's good work also attracted smart, hardworking young employees hungry to work in a "creative shop." The staff, or "family," as Jan prefers to call employees, was growing. And for many, Jan was more cheerleader than chief executive.

In a business that demands an almost unnatural ability to hopscotch from financial services to tire sales, and to approach them both with an equal amount of creativity, knowledge, and zest, Jan was a tireless source of energy and enthusiasm. Curtis Zimmerman, former senior vice-president at PDP and once its number one rainmaker, says, "Jan's enthusiasm was unusual because it was genuine." He adds, "I called Jan 'the big sell' and brought her on as many sales calls as possible."

By the late '80s PDP was posting impressive billings of $50 million -- an annualized growth rate of 20%. And the ADDYs and Effies -- awards for creativity and marketing distinction, respectively -- were piling up. From 1980 to 1989 PDP won more than 1,000 awards.

For Pringle the recognition was undeniably appealing -- she was invited to the governor's office for an outstanding-citizen commendation, named top communications woman of the year by American Women in Radio and Television, and featured on the cover of Atlanta Woman. By the end of the '80s she was serving on 31 outside boards and committees and living next door to the likes of Arthur Blank, cofounder of Home Depot, and Russell Umphenuer, the largest franchisee of Arby's Restaurants in the world. When asked by a local reporter whether she considered herself the Mary Wells of the South -- referring to the revered founder of the New York City agency Wells Rich Greene BDDP -- Pringle smiled and replied, "No, I consider Mary Wells the Jan Pringle of the Northeast."

No one could argue that she hadn't come a long way from the housing projects of Phenix City, Ala., where she had grown up. She was seven when her father deserted her mother; young Jan started working odd jobs to help support her family. One source of income was her voice. By age nine, she was singing on local radio and doing opening acts for the likes of Jerry Lee Lewis and Elvis Presley. A gifted athlete as well as a striking blonde, she was voted most athletic in high school and a runner-up in the Miss North Carolina beauty pageant. Having grown up with a mother who had only a fifth-grade education, Pringle entered the local college with such a poor grasp of English that she says "it was like a second language." Despite that, she graduated with honors in business administration.

Pringle was 27 years old when she first opened her public-relations firm, and a year later she went into business with her husband to form PDP. She still remembers the year she opened her business as "the happiest year of my life." When she turned 50, last year, she and her husband celebrated the birthday as "the 23rd anniversary of her 27th year."

Pringle, like many owners, has always felt one with her company. Her victories are the firm's victories, her missteps PDP's failures. "How can I separate the company from me?" she asks. "Since the beginning it's been a reflection of our ideas, our beliefs, and our hard work."

Sure, there was stress. Despite the marquee value of having, for example, a McDonald's on the client roster, working with large accounts was often a tough, thankless job. "There was never any appreciation of the hard work we put in," Pringle confides. "It was always, 'What have you done for me this hour?' " She missed the partnership shared and the appreciation expressed by the small accounts in the early days.

But if that was the price of success, so be it. After all, while small agencies like PDP were being gobbled up by their larger brethren, PDP remained independent. As for the added stress, Pringle considered herself a leader able to "juggle many balls in the air at the same time." Her day typically began at 7 a.m., with breakfast with either a client or one of the many outside boards she served on. By 8:30 a.m. Pringle was at her desk, on the phone, madly scribbling notes, making her way through 40 to 60 calls, while winding her way through 10 or so meetings daily. By 6 p.m. she was either scrambling out the door for dinner with a client or ordering takeout and preparing for a late night at the office. Either way, she usually didn't roll up to her Sandy Springs home much before 10 p.m.

But as the company grew, Pringle and her husband seemed unable to share credit. Although their employees played integral parts in key campaigns, few of them felt financially compensated for their roles. Employees felt unappreciated, and many left. "The talent PDP assembled was incredible, and the talent they let go was equally incredible," says Jeane Cartwright Aydlotte, an advertising account executive who was one of those who left. "In advertising you're only as good as your people; Jan and Jim forgot this." And with employee turnover running high, at almost 50%, employees allege, clients felt a lack of continuity, and many took their business elsewhere. In the mid '80s, Aydlotte recalls, PDP's clientele was turning over at least every two years; the industry norm is seven years.

It didn't help, either, that Jim Pringle, PDP's creative genius, was being tugged deeper and deeper into administrative tasks. "Our strength had always been that we didn't do cookie-cutter work," Jan explains. "I could see that losing Jim's creative leadership was putting that in jeopardy." One industry observer says that in the mid to late '80s, as Jim stepped further and further away from creative control, PDP "seemed to lose its creative brilliance." Jan worried about the loss but also felt hesitant to tell her husband how to manage his side of the business.

By the late '80s management problems began wearing on Jan not only mentally but physically. The signs began slowly. There were the bouts with bronchitis, the chronic migraines, the wild weight fluctuations of 30 pounds, and a loss of memory. "I would start a sentence and forget what I was going to say," she explains. In the summer of 1989 she was sitting on the beach with her son when her heart rate dropped to 39 beats per minute. "I was sure I was going to die," she recalls. At the hospital the doctors found no heart disease but cautioned Pringle to slow her pace. She didn't.

She wouldn't give any more credibility to criticism of her lifestyle than she would to criticism of her company. "If I don't stop, I won't see it," she claimed. Slowing down was tantamount to leaving the company, and that just wasn't under consideration. "I have appointments to keep, employees depending on me," she proclaims. Even when on vacation, she and her husband typically got more than a dozen calls a day from the office. "Look, it's our name on the door."

By the fall of 1989 Pringle was battling a chronic case of the shakes and had no energy. Friends and colleagues urged her to slow down. Her own husband resorted to behind-the-scenes tactics: before she picked up her mail, he'd throw out invitations to evening galas he thought she could afford to miss. He didn't have much of a choice, he explains. "Jan isn't the kind of person you can tell to put on the brakes."

The only person who even stood a chance was Judy Williams, Jan's closest friend. Williams also owned a public-relations firm, and she and Jan spoke on the phone at least twice a week. Late in the summer of 1989 they slipped away for a five-day vacation in Acapulco.

There Pringle let Williams speak to her as no one else had. "I told Jan she had to stop defining herself by work and clients and start defining herself by herself," recalls Williams. "Jan always had more energy than anyone else, but it was clear she was running real low." Pringle listened to her friend's advice but didn't know what to do with it. "If I stop," she wondered, "what will I do?"

Three months later Pringle got her answer. Paralyzed at her desk, unable to even call for help, she was finally forced to leave her agency, like it or not. Doctors told her she had chronic fatigue syndrome, a disease that sends the immune system into overdrive, causing total exhaustion. Called a "stress sensitive" disease, it has no known cause or cure.

During her treatment, Pringle's doctor asked her to write down everything she did in a day. Seated in front of that list, she first viewed herself and her company separately, from a distance. It was the first time, for example, that she realized she was serving on 31 committees. She realized how wedded she'd become to recognition and bigness -- "the new Mercedes, the Cartier watch, the bigger houses" -- and she realized she wasn't having fun anymore.

But Pringle was forced to forget that introspective moment when her husband developed his own medical condition -- a chronic back problem that required surgery and a long recovery -- and she was forced to take back the reins.

So in October 1990, nine months after leaving, Jan returned to work while Jim left for surgery. She reentered the company not quite sure of what her sabbatical had taught her, not quite sure of how she could -- or would -- change.

She tried to fall into her familiar role: cheerleader. Clearly, morale needed a lift. Too much work and too few people to do it were taking their toll. Hoping to turn the tide, she staged a companywide party at a local athletic club. Employees were handed T-shirts emblazoned with the credo "PDP -- We've Got a New Attitude."

But day in, day out Pringle struggled to find her place. "People had filled in while I was gone," she declares. "There was this sense of 'Who is she, waltzing in and taking over again?' " Nowhere was that sentiment more evident than in Pringle's relationship with her second-in-command. He had helped fill the leadership vacuum in her absence, but now she was back -- more than filling the vacuum. "We argued about everything." Pringle wasn't ready to give up anything. A few weeks later he resigned.

And there was more disruption to come. Late one Sunday night the Pringles' longtime banker approached the two with some bad news. He was sure that their chief financial officer was embezzling money from the company -- $55,000 to date, some from the corporate coffers and some from the Pringles' personal savings account. With the money, the CFO had bought a new Mercedes and a computer. Both Pringles were shocked. The CFO was a seven-year veteran of the company, a hardworking member of the "family."

The next day, calm and composed, Jan approached her CFO with the evidence. He didn't deny the accusations. Instead he agreed to "a leave pending further investigation" and left his office and the building quietly. That night, though, he took a gun to his head and shot himself.

For Jan, it was the first time that she openly wondered if she had what it took to lead PDP. She spoke to her priest; she called her friend Williams; she began seeing a therapist.

Over and over she replayed the confrontation, wondering if there was anything she could have done differently -- any words she should have held back. In the end she resolved that she'd been calm, perhaps stern, but never accusatory -- and that the mental stability of an employee was out of her control.

So was much else, it seemed. By the end of 1992 PDP had lost three of its largest accounts -- McDonald's, the state of Georgia, and Contel. McDonald's apparently told its present agency that it left PDP because it didn't feel its account was getting "senior staff attention." The state of Georgia says that its departure wasn't PDP's fault, "it was just time to move on." Whatever the reasons, the loss of those three cut the agency's billings in half. A third of the employees were laid off. Morale was battered.

Pringle kept trying, though. For herself, she tried daily injections of vitamin concentrate. For her company, she tried to remain the ebullient cheerleader.

But the vitamins don't seem to be making a difference. And the cheerleading is wearing thin. Not a day goes by that she doesn't wonder if it's time to step down. "Have I used up all my energy for this business?" she asks. "On some days I say, 'Absolutely'; others I say, 'Never.' "

There are contradictory messages. This past July, after losing to another agency in a bid for a local consulting firm's account, Pringle called the client to ask why PDP lost out. "It wasn't anything said directly," he told her. "But there's the question about the financial health of your agency." And then the toughest words Pringle could hear: "And there's a rumor you might be leaving."

Just a couple of days later, though, PDP employees gathered for a celebratory piece of pie. It was the product of Pringle's latest coup, Edwards Baking, one of the largest pie-making companies in the country. Edwards expects to spend several million dollars in advertising with PDP in the coming year. Pringle herself had wined and dined the company's managers for more than six months before winning the account. The baker is among five multimillion-dollar new accounts she's courted and won in the last year.

On weeks like that, Pringle can't help wondering if she's part of the problem or part of the solution. Has she reached the end of the line, or is she helping the firm gather steam for the next ascent?

And then, of course, there are the formidable business challenges facing PDP that both Pringle and her husband discuss openly. First, they must rebuild a damaged client base while combating rumors about Jan's involvement. Second, they have to confront Jan's lessened role and groom someone to fill the void. "It's hard, though," Jim admits candidly. "Jan's a great salesperson and the proverbial cheerleader. How do you go out and hire that?" And last, PDP must find a new edge in the marketplace. Integrated marketing, once the agency's exceptional calling card, is now a widespread advertising practice.

Seated in a restaurant far from the deadlines and blinking phones of her corner office, Pringle sums up her predicament. "There's an argument that it's time for me to move on," she begins. As if she were the prosecutor arguing against her continued stewardship, she declares: "I've been sliding downhill. Often, I'm hardly involved in the company at all. And I wonder how confusing that is for employees."

It's also painful to be only half involved. "It's hard to watch others make decisions without me," she explains. Even to watch her husband and partner. "I'm willing to take more risk than he is, and there's a great argument that this is the time for risks."

Looking back, Pringle sees a couple of unfortunate detours: her quest for success and recognition in the '80s, for example. "When you're focused outside, it saps your creative juices." She wonders if her father's desertion of the family makes her crave attention too much. "Sometimes I think getting recognition became my way of proving he was wrong for leaving us." Today, in part because of hard times at PDP, Pringle reports, her limited energies are better focused. Still, she admits it's tough being out of the limelight. "I miss the calls from the press.

"I've always been one to shoot for the stars and ask questions later," she says. On the downside that meant it was hard to know if dealing with "abusive larger clients" or "losing the PDP-family feeling" flew in the face of her vision or was simply growing pains.

And then there's the Pringle 2,000, a list she and her husband have been compiling on her laptop of the 10 or so companies she'd start if she left PDP. "What about a travel guide?" she pipes up. "Jim's a great photographer. We love to travel, and I could do the copy." Carried off on a jet stream of possibilities, she goes on: "Or an ice-cream company, or what about a heart catalog? Everything would be high-end, heart-shaped gifts." Already, Pringle has procured exclusive rights to distribute a line of specialty porcelain dolls.

But is it time to leave? Without hesitation, Pringle flips to the defense of why she should stay. She has more to give PDP, for one. "My husband tells me he'd rather have one day of me than five days of some other people."

And it's true: on some days, she can buzz from meeting to meeting, munching a sandwich along the way, just as she did in the old days. But then there are the tough days. And for those days -- unlike the days of old -- it's a matter of pretending. "I just put on a little more makeup, wear a brighter outfit, and think, 'Smile, smile, smile,' " she says.

Financially, there's no doubt it would be a bad time for Pringle to walk off the scene. Hard times in the ad business, along with the agency's recent tumbles, make leaving a risky step. She claims her agency's billings are near $30 million, but the agency's observers doubt that PDP can be doing much more than $14 million, if that.

But perhaps the most compelling reason not to leave, Pringle argues, is her own history and the history of her company. "It's like walking away from a game before the end of the ninth inning."

No one can say for sure what will happen to Pringle. Come back in five years and she might have sold PDP and be happily building a travel-guide company. Or equally plausible, PDP will have risen out of the doldrums, with Pringle leading the way, and she will be a heroine for licking the odds.

You might even read about the latter scenario in the pages of Inc. Why? All the right ingredients are there: A hero who goes it alone, who, despite the odds, conquers, trampling the naysayers. The doubts. The fatigue. In this quest there is no place for a discussion of limits, of persistence gone too far, of haunting doubts unheeded. There is only the adulation for dogged determination.

In all of this, though, perhaps there is a failure to recognize the more complex story -- how easy it is to slip from determination to destruction, from persistence to possession, from conquering to crashing. Many of the milestones of success can, with the glass half empty, be indicators of a leader out of sync. The owner who builds a company by "swimming against the tide" only to later miss a critical industry shift. Or the founder who is so fully engaged in the building of his company that he fails to see that he has swerved dangerously far from his original vision.

Knowing when those indicators move from points of pride to points of peril is difficult. Often, the company builder is the last to know when the line has been crossed. That is particularly true in a privately held company, in which none of the usual checks and balances are in place to rein in the wayward founder. Who dares approach him or her with the news? A friend, a partner, a trusted employee?

Around Jan Pringle a company culture has grown, as it has around most company builders facing this question. It's a culture built on and sustained by a leader who "shoots for the stars," not one who defines the limits.

Pringle has spent years building a reputation as a hard-charging, energy-filled leader. It's allowed her to build a business she values. "I've always been the kind of person to go 90 miles per hour until I hit a brick wall," she says. But does she want to put her company in jeopardy of hitting that wall with her? "Absolutely not," she insists. "Of course not, that's my concern.

"It's a real switching of gears," she confesses. "In the beginning I plowed past my weaknesses just to get the job done; now I'm supposed to stop and wonder if my strengths have become my weaknesses?" When building PDP with Jim, she says, "I never thought about my limitations. What would have been the use?

"So how will I know when it's time to move on?" she finally asks. "I'm not sure. It's a big question mark.

"Ask me tomorrow."

For examples of people who've made a graceful exit, see "Walking Away," page 6.


A self-audit for the CEO who wonders whether or not it's time to let go

No quick and easy blood test tells a leader whether or not it's time to move on. It shouldn't take a physical breakdown like the one Jan Pringle of Pringle Dixon Pringle suffered to make a founder examine these questions. But who is there to talk to? Admitting that you're even thinking of leaving can send shudders through the company and cause customers to ask tough questions. Is it time to go? The first step toward knowing, experts agree, is to note the warning signs that betray a leader who's losing his or her grip -- the signs that put you at high risk for an unheroic farewell.

1. The Hero Complex

The hero complex stems from isolation -- isolation from colleagues, isolation from family, isolation from subordinates. In a culture bent on lionizing individuals rather than groups, the stars who build companies are often whispered about at parties and treated as a breed apart. "The risk is huge that these people will see themselves as the fuel rather than part of the engine," warns Steven Berglas, management psychologist and author of The Success Syndrome. That mentality makes it almost impossible for leaders to step back and assess their strengths and weaknesses.

2. Reward-Based Rather Than Interest-Based Motivation

The inspiration to launch a company is rarely the mounds of money that might follow. More times than not, it's the heated pursuit of an interest -- a fascination with fashion, a theory about thermodynamics -- that spurs an idea and then a company. But if all goes well, the interest yields rewards: money, recognition, and bigger, brighter things. The danger, says Berglas, is that without knowing it, a leader can easily get hooked on the rewards.

It's not just that "acquiring successes" is a transient business, Berglas insists. More important, the interest-oriented leader is usually inner directed and able to call on vast reserves of creativity, whereas the reward-driven one is externally oriented and less creative, preferring to protect all that's been acquired.

3. Industry Headed North; CEO Headed South

Where's the industry headed? Are you on the same track? Is the industry speeding up as you want to slow down? Is it maturing as you want to diversify? Beware if the industry is bearing right and you're about to go careering left: it could mean trouble.

4. A Good Thing Gone Too Far

Many successful start-ups begin with a singular vision, a vision that's the bedrock for the company's growth. At some point, however, that vision becomes dated, worn, irrelevant. It's one of the hardest things for a CEO to see: that the seed is no longer nourishing the company. "It's a bad sign when you try to freeze a company in time," says Jeffrey Sonnenfeld, author of The Hero's Farewell. "The founders who do that are scared of letting go of their vision, of their way of thinking," he says. "They ritualize the past."

5. Roads Less Traveled

Deciding whether it's time to move on can sometimes be as simple as asking yourself what you ache to do when given an ounce of spare time. Do you rush to play on your computer? Hunger to refurbish an antique? Scribble down notes for a novel? Maybe it's a hobby that fits nicely into weekend and vacation time; maybe it's an avocation demanding to be more. If so, can your current job description expand to include that interest? If your business is tires and your passion is art, you might have a problem, but if you see a closer fit, you might try bringing it into your business.

6. Whispering in the Hallway

What's the talk at the water cooler? Most founders have a hard time knowing what their employees, even the top lieutenants, really think about their leadership or the company's direction. Yet employees are often the first to know when their leader should pack the bags. Consider your employee turnover. Are you losing key people? Do conversations get muffled when you enter the room? Are you scared to know what your employees really think? If getting a clear reading from inside the ranks is impossible, ask friends and family.

7. My Self, My Company

The metamorphosis from "I am my company" to "I have a company" is a subtle rite of passage. Separating "me" from "what I do" is comparable to a child's detachment from a parent, says Harvard Business School professor Carl Sloane. But that doesn't mean it's easy. "Often a leader's best friends, social structure, and source of self-esteem are wrapped up in the company," says Sloane. Leaders who cannot separate themselves from their company are often poor judges of what's best for the company or what's best for themselves.

Is personal catastrophe a necessary precursor to making such distinctions? No, says Sloane. "But thinking about your company as separate from yourself is often a radical change, and most people dread that. Something has to happen that overwhelms the fear of change."

8. Not What I Envisioned

Close your eyes and recall the dream -- the day you dared to map out the "new" company. What did it look like? How big was it? What kind of customers did it serve? What kind of employees walked the halls? Difficult as it may be, try to remember the essence of the dream. Now, compare that dream with the company before you. Is there any likeness?

9. Is This Burnout?

"If you're not having fun, you have no ability to recharge the batteries," declares prominent management psychologist Harry Levinson. "All the hard work just becomes draining." And there's no quick fix, either. A trip to the Bahamas isn't going to do it. The question then becomes, Can I realign my work to make it fun again? If you can't, it's trouble.

10. The Limit

How do you know when you're nudging up against your personal limits? Age is no indicator. Pablo Picasso, the Spanish painter and sculptor, created artworks until his death. Alan J. Lerner, author of such Broadway hits as My Fair Lady and Camelot, did his best work in his twenties and thirties and argued that age rendered him too cautious and dampened his creativity.

Whatever your age, the best way to know your bounds is to assume you have bounds. Many founders are starters but not maintainers. Ask yourself whether employees are enthusiastic about your ideas. Are people pushing you to do new things, and are you resisting? Have you met the goals you set?


There are second acts -- and sometimes third -- in American lives, though those subsequent performances often get less airplay than the first. Here, a collection of widely known overachievers comment on why they left

Thomas P. (Tip) O'Neill:

The Sudden Decision That's a Long Time Coming

Former Speaker of the U.S. House of Representatives Tip O'Neill has never shied away from the public eye. But when it came time to decide whether or not to end his political reign, he says, the decision was intensely personal and private: "It is a discussion that can happen only in the sanctity of one's family."

After he had spent 50 years in politics, 10 of them presiding over the House, O'Neill jokes, it was his wife, Mildred, who sat him down and told him straight out that he should pack his political bags: "She told me that I was thwarting the next generation if I didn't leave." So he left. And after O'Neill had spent a few months at home, his wife was also quick to inform him, again quite bluntly, that it was time "to get out of the house and find another job." Now 81, O'Neill has written one best-seller, has starred in a string of commercials (for American Express and Quality Inn, among others), and has a second book on the market. Nevertheless, looking back, he warns that the decision to leave is never made "on one day, at one moment"; rather, it's "something you phase into slowly."

Cynthia Gregory:

Planned-for Obsolescence

Cynthia Gregory, 46, one of the American Ballet Theatre's most celebrated prima ballerinas, was 17 years old when she started planning how and when she'd leave her dance career. "I saw so many dancers continue beyond their prime," she explains. "They were artists who couldn't keep up with their artistry."

After pirouetting beside Rudolf Nureyev and almost every other international dancer of note, Gregory ended her 30-year dance career a year ago and is now busy writing children's books and coaching up-and-coming dancers. But she still misses the stage. "There's an invincibility that you feel when you're doing what you're naturally good at. You ask yourself, 'Will I ever be that good at anything else?' " And despite her years of planning and her full life today, Gregory explains that leaving dance "is like a death -- one that I'm still grieving for."

Kareem Abdul-Jabbar:

Taking Comfort in the Long View

"You have to see yourself as part of a continuum," says Kareem Abdul-Jabbar, the 46-year-old former center for the L.A. Lakers. A six-time winner of the National Basketball Association's most-valuable-player award, he sees himself as just one "in a series of players that push the envelope." Abdul-Jabbar quickly points to past players as inextricably leading to his own success. For example, he cites the 1940s and 1950s star postman George Mikan as the one who proved that "a big guy could be tough and competitive. Without Mikan I couldn't have done what I did."

In June 1989, after helping bring his team to the finals of the NBA championship series for the eighth time, Abdul-Jabbar retired. "Mentally, I see it as a long-distance race," he says. "You have to know when you're approaching the finish line." That doesn't mean leaving was easy, though. For any peak performer, "it's hard to walk away from the position that defines you," Abdul-Jabbar says. "Suddenly, you're an average citizen."

Mel Ziegler:

When Reality Collides with Your Vision

Mel Ziegler, who founded Banana Republic in 1979, knew it was time to move on when his company no longer resembled his original vision. "I started with the idea of building a small company; suddenly, I was overseeing 110 stores." When Banana Republic was sold to the Gap, the publicly traded casual-clothing empire, in 1983, Ziegler found his energy consumed by answering to thousands of shareholders and influential analysts. "I no longer owned a business. It owned me," he says. "It was the reverse of what I'd intended when I founded the company." Five years after joining the Gap, Ziegler decided the disparity between his vision and reality was too great and left his company.

Despite the twists and turns any business will take, a leader, Ziegler contends, "has to have a clear idea of what the business will be and won't be" from the start, in order to know when it's time to call it quits.

Beverly Sills:

Letting Go, Eased by a Focus on Family

Former world-famous opera singer and New York City Opera general manager, and now corporate-board mogul Beverly Sills has never had a problem saying good-bye to one career and hello to the next. Her trick? "My identity was never tied up in what I did, because I've always had an enormous family life," she explains. "What I did was the icing on the cake." Mother to two children with severe birth defects, Sills says her family had to come first.

She says it helps to move from one post to the next quickly. For example, when she left singing she reported to her position at the New York City Opera the very next morning. And as for keeping the passion alive from one career to the next, Sills never worried: "A person's nature travels with her. I knew that anything I took on I'd develop an obsession for."

Peter Lynch:

The Discovery of New Priorities

For Peter Lynch, the epiphany came at his daughter's soccer game. "I remember standing in the rain, cheering her on, and thinking, 'I want to see more of these,' " says the 46-year-old former portfolio manager of Fidelity's Magellan Fund, which grew from $20 million to more than $14 billion in his 13-year tenure.

In the time leading up to his decision to quit as portfolio manager, Lynch felt increasingly frustrated and anxious. Father to three daughters, then ages 16, 12, and 7, he was actively managing money for a number of Boston charities while running a growth fund with more than a million shareholders. "You know you're in trouble when you need a Cray computer to arrange your free time," he says about those days.

Of course, the multimillionaire admits that "financial freedom makes it easier to consider other options." Ultimately, Lynch based his decision to leave on what he calls the hot-fudge-sundae index. "For me it was all like hot-fudge sundaes: I liked my job, I loved my family, and I liked working with outside charities," he explains. "It became a matter of, How much can you handle without getting a stomachache?"