By RICHARD BOUDREAUX

MOSCOW—At the start of his second term as Russia's president, Vladimir Putin gathered some leading free-market policy wonks for brainstorming at his dacha. One of them, José Piñera, had been a cabinet minister in Chile during the 16-year dictatorship of Gen. Augusto Pinochet.

Mr. Piñera's advice went beyond economics and included a warning against holding "too much power for too long." Quoting the Russian poet Alexander Pushkin, he bluntly urged Mr. Putin, in a Moscow newspaper essay after the meeting, to retire after two terms: "Oh, kings, you owe your crown and writ/To Law, not nature's dispensation."

Mr. Putin has dominated Russia ever since, as president or as prime minister. Having weathered a winter of large anti-Kremlin protests, the 59-year-old leader won a tightly controlled election in March and will start a third presidential term on Monday. He hasn't ruled out re-election in 2018 to stretch his tenure to 24 years, longer than any other Kremlin leader since Josef Stalin, but says he would step down if he lost public support.

Masters of Longevity

The careers of Fidel Castro, below , and other embattled autocrats hold lessons for Vladimir Putin as he starts a new presidential term in Russia.

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Associated Press

But rulers in Mr. Putin's shoes are loath to give up power, not least because of fear their successors will turn on them. Monarchs aside, recent history offers relatively few examples of embattled autocrats who manage to die peacefully in office or step down gracefully. Consider the misfortunes of Egypt's Hosni Mubarak(now on trial) and Libya's Moammar Gadhafi (dead) in last year's Arab Spring, and the way other strongmen, from Angola to Syria, took note and dug in.

Since the last decade of the Cold War, I've chronicled the decline of autocrats in Latin America, Eastern Europe and Northern Africa, and know the early-warning signs. Russia's winter of civic awakening felt much like the first widespread pot-banging protests against Gen. Pinochet in 1983—a noisy, unmistakable signal that Chileans had lost their fear and were turning against him, although he would hang on for another seven years.

Foes of Mr. Putin say he, too, embodies a regime built on corruption and intimidation. Some supporters doubt that its pillars—manipulated elections, subservient courts, loyal security forces—could withstand a rising clamor for democracy.

So what's his likely exit strategy? Whenever he contemplates one, he'll find limited options. Nowhere in the accumulated wisdom about building democracy is there a sure-fire retirement plan for autocrats, a guaranteed safe landing if they agree to step down.

Here, though, is a short list of options and autocratic role models who could offer Mr. Putin some guidance:

Option 1. Lead your people to democracy. Flight Lt. Jerry John Rawlings abruptly changed course in Ghana after his military dictatorship failed at socialist governance and ran out of money. He revived the economy by liberalizing, then allowed open political competition and was freely elected president twice. By embracing democracy before there was much demand for it from citizens, he gained popularity and lowered the risk of payback for prior violent excesses. He slid securely into retirement in 2001, abiding by term limits after 20 years at the helm.

Option 2. Fireproof your exit route. Weakened by a U.S.-armed insurgency against his decade-old Sandinista regime, Daniel Ortega agreed to hold Nicaragua's first free election, in 1990, and lost. Before stepping down, he cut a deal obliging all parties to refrain from post-war retribution. The deal also kept his brother in command of the armed forces. For good measure, the outgoing ruler authorized the hurried distribution of state property worth hundreds of millions of dollars, enriching his Sandinista cohorts. (This so-called piñata included several sprawling homes on the block where I lived at the time.) Thus fortified as an opposition party, the Sandinistas remained powerful and loyal to Mr. Ortega, helping him return to the presidency in elections in 2006 and 2011.

Option 3. Hang tough. Despite economic ruin and stiff political opposition, President Robert Mugabe seems bent on ruling Zimbabwe for life. He's been at it for 32 years, mixing limited openness with populism and, when necessary, brutal police crackdowns. His exit strategy, it appears, is not to exit. Deflecting international pressure, he accepted a power-sharing arrangement with his chief rival in 2008 but continued to harass and jail the rival's supporters. In February Mr. Mugabe celebrated his 88th birthday by stumping for re-election. One secret for staying the course: Diamond profits help cement the loyalty of his security forces and a narrow circle of cronies.

Option 4. Build a dynasty, or a one-party state. Monarchies are one way to perpetuate iron-fisted rule; uncrowned autocrats find other means. Fidel Castro turned over dictatorial power in Cuba to his brother. Haydar Aliyev of Azerbaijan handed it off to his son. China's Communists have mastered the art of one-party rule and leadership turnover that worked smoothly for decades in Mexico and the Soviet Union. Leaders from such parties accept curbs on their personal power—China's presidents have term limits—but are less likely than personalist dictators to be overthrown, disgraced or betrayed by a successor.

Mr. Putin's day of reckoning, his choice of an end game, may be years away, considering his many strengths. He has reasserted state control over much of Russia's oil wealth and has a loyal power base in the security services. The Kremlin controls television and portrays him as a Slavic stud, in contrast to the ailing Mr. Mubarak or the disgraced Slobodan Milošević, who lost his grip on Serbia after defeat in the Kosovo war.

Russia's opposition is far weaker and less unified than the peaceful movements that took down Mr. Milošević in 2000 and entrenched regimes in Georgia and Ukraine a few years later, overturning rigged elections. There's no Russian counterpart yet to Velimir Ilić , a gutsy small-city mayor I met in Serbia, a man whose connections and plotting with dissident officers sparked mass police defections and undermined the regime.

The upheavals so close to home spooked Mr. Putin into mobilizing pro-Kremlin youth gangs to counter the Russian opposition and restricting its Western funding .

"Nobody has studied the dynamics of these revolutions in order to pre-empt them more intensively and obsessively than Putin," said Larry Diamond, a senior fellow at Stanford University's Hoover Institution and a leading scholar of democratic transitions. "He strikes me as a skilled and adaptable autocrat."

Would he adapt to renewed popular pressure by leading Russia to democracy (option 1) or hanging tough (option 3)? A former senior Kremlin official said Mr. Putin favors "an evolutionary approach" and would liberalize politics to the extent that people demand it.

But Bruce Bueno de Mesquita, a New York University professor who co-authored "The Dictator's Handbook," said Mr. Putin would have little incentive to ease up as long as Russia's oil revenue remained high enough to keep rewarding a narrow circle.

"He doesn't need massive support," said Mr. Bueno de Mesquita, who is known academically for his international research on political survival. "But he'd be in trouble if he stopped paying the army and security forces."

In other words, the professor concluded, he'd more likely take his cue from Zimbabwe's durable Mr. Mugabe. "That would be the lesson: You can cling to power an extraordinarily long time."

That sounds improbable to Gleb Pavlovsky, an image-making consultant retained by the Kremlin for years. Sooner or later, he predicted, Mr. Putin will opt for a typically Russian exit—pick two loyalists willing to shield him from prosecution and engineer an election one of them is likely to win. Mr. Putin himself rose to power that way, as President Boris Yeltsin's anointed one, and pardoned his ailing patron's wrongdoings.

But pitfalls abound. Mr. Putin has chosen not to build a Chinese-style ruling party capable of assuring such a transition. And as Gen. Pinochet found out, even the best laid retirement plan can go awry.

The Chilean strongman gave up the presidency in 1990 after voters rejected him in a yes-or-no plebiscite, but he held on to his post of army commander for another eight years and after that became an unelected senator for life. With that power base, he wielded influence over elected governments and sought to remain above the law.

He didn't count on the tenacity of jurists abroad. In 1998 he was arrested in Britain on a Spanish judge's warrant for genocide, torture and kidnapping. Sent home to Chile instead, he spent his final years fighting hundreds of lawsuits related to human rights abuse and personal enrichment.

Gen. Pinochet, who died in 2006, all but predicted his comeuppance in a magazine interview shortly before his arrest.

"I read a lot, especially history," he said. "And history teaches you that dictators never end up well."

Write to Richard Boudreaux at richard.boudreaux@wsj.com