At the age of eleven, when his father died, he began a roving life.

He ran away from a couple of ecclesiastics who had undertaken to teach him to read and write (after having acquired the rudiments of those arts), and made numerous ineffectual attempts to obtain instruction in painting from various wretched daubers of holy pictures, having been addicted, from his earliest childhood, to scrawling over the walls of the house and the fences with charcoal drawings.

He was obliged to turn shepherd.

In 1827 he was taken on as one of his master's household servants, and sent to Vilna, where at first he served as scullion.

Later on, it was decided that he "was fitted to become the household painter." But he served at first as personal attendant on his master and handed him a light for his pipe, until his master caught him one night drawing a likeness of Kazak Platoff, whereupon he pulled Shevtchenko's ears, cuffed him, ordered him to be flogged, but simultaneously acquired the conviction that the lad might be converted into a painter to the establishment.