questions whether or not Jesus was a "peasant." I've long been interested in this question—even in high school I wondered how a first-century carpenter might also be literate (see Luke 4:16–19, John 7:57–8:11, etc.) in a time when only the wealthiest elites had access to education and literacy. It seems that either Jesus was a tekton ("builder," often translated as "carpenter"), or Jesus was literate, but unlikely—given his historical context—that he was both.
However, I wonder about the possibility (and granted, I have no historical or scriptural evidence for this) that Jesus may have in fact been a relatively comfortable tradesman living on inherited land (see Richard Bauckham's chapter on the family of Jesus in Jesus Among Friends and Enemies), but that he divested himself when he began his public ministry as an attempt to show solidarity with the peasants. This is not an unfamiliar practice among history's most recognizable spiritual giants. For instance, Siddharta Gautama (who later became the Buddha), was said to have been an ivory-tower prince before he escaped the walls of his family's castle and experienced suffering and death in the world around him. Giovanni di Pietro di Bernardone (St. Francis), the son of a wealthy textiles merchant in Assisi, Italy, stripped himself naked in the town square in front of the Roman Catholic religious authorities as a display of his identification with the poor. More recently, a young, highly educated lawyer named Mohandas Gandhi gave up his worldly possessions to live in an ashram community with other societal outcasts.
The facts are admittedly much more complicated than the brief thoughts I have presented here, and I'm not saying that Jesus was without a doubt a person of means who eventually rid himself of all possessions to pursue his ministry. But it is curious to consider his emphasis on divestment (see Matt. 19:21 and Luke 18:22; Luke 9:3; Matt. 8:20 and Luke 9:58; etc.), and whether or not this was a direct result of personal experience.