1. Osama bin Laden
Before he started fighting for his own violent version of Islam, terrorist Osama bin Laden led the life of a playboy. Born around 1957 to a wealthy Yemeni father and Syrian mother, bin Laden was heir to part of the massive fortune his billionaire father had accumulated in the Saudi construction business. As such, he squandered his days, acquiring a reputation for drinking too much and womanizing in his teens and early 20s in Beirut, which was then a cosmopolitan tourist hot spot. In fact, he didn’t become a firmly committed, full-time Islamic radical until he went to fight the Soviet invasion of Afghanistan in 1979. That’s where Osama began his improbable transformation from a rakish ladies’ man to a mass-murdering zealot, never having worked a day before then.
2. Socrates
Aside from a possible brief stint as a sculptor, Socrates seems to have spent most of his hours ambling around the agora—the gymnasia where Athenians exercised, which was also Athens’s central public meeting place and marketplace. When he wasn’t milling about the town, the old philosopher could be spotted going to parties and loitering in taverns where citizens and foreign guests gathered. All this isn’t to say the poor guy enjoyed the lush life. Socrates lived and dressed simply, wore neither shoes nor shirt, and owned only one coat. He also ate poorly, lived hand to mouth, relied heavily on the charity of his friends, and refused gifts when they were offered. Like, for instance, the time his friend Charmides offered to give him slaves who could have made money to support him. He also refused to accept presents from powerful leaders of Greek cities, not wanting to ever compromise his integrity. When the great philosopher was put on trial for allegedly teaching sacrilege, Socrates tweaked the Athenian assembly by suggesting that far from being a criminal, he deserved free room and board at their expense. Unamused, they condemned him to death.
3. Oscar Wilde
“Cultivated leisure is the aim of man,” Oscar Wilde once famously said, and he certainly lived his life by that dictum. Wilde was brilliant, winning a gold medal in Classics at Trinity College in Dublin in 1874 before earning a scholarship to Oxford. When his father died, however, Wilde left the family’s finances to his older brother Henry, and worked only once in his life, a brief two-year stint as the editor of a women’s magazine called The Woman’s World, from 1887 to 1889. Wilde spent the rest of his time writing, giving lectures on aesthetics, coining pithy epigrams, and generally being a wit. Sadly, Wilde was forced to do hard labor near the end of his life after he was found guilty of immoral conduct for homosexual activities. A broken man, he died shortly thereafter, in 1900.
4. Buddha
Buddha, like Socrates, was a full-time thinker whose schedule of meditation, contemplation, and conversation didn’t leave any time for work. Born around 563 BC, Siddhartha, as he was called when young, was the son of a king who ruled a small kingdom in the northern floodplains of the Ganges River in India. The young prince led a life of leisure in his early years before growing disgusted with the materialism of the royal palace. Instead of sticking around, Siddhartha wandered off into nature at the age of 28, and after seven years of travel, meditation, and conversation with Hindu mystics, he attained enlightenment under a Bodhi tree. Receiving visitors and teaching students from under the tree, he spread the message of moderation and separation from material want that became Buddhism—and never did get a job.
