In the fall of 1887, Johnny enrolls in Cole Grammar School in West Oakland and becomes friends with Frank Atherton. He continues to be a newsboy and do other odd jobs (load ice wagons, set up pins in a bowling alley, sweep out saloons). It is during this time that he changes his first name from “Johnny” to “Jack”.

The next few years sees Jack become a competent sailor and  graduate from 8th grade. He borrows $300 from Jennie Prentiss to purchase a sloop, Razzle Dazzle. With his own sloop, Jack becomes known as the "Prince of the Oyster Pirates"  and "Frisco Kid", as he raids oyster beds in the San Francisco Bay.
 

But he soon realized that the profession of oyster thief did not offer much in the way of career opportunities, so he got himself hired as a cabin-boy on the seal schooner, Sophie Sutherland. Still this way of life also offered it's share of terrors and humdrum and so the young lad Jack started thinking of settling down with his family again. He started working in a factory producing  under conditions even worse than the ones he'd known before. Late at night after work he tried to get some education into himself, an undertaking doomed to failure due to the harsh working conditions. Again he tried to escape from it all, this time as a tramp traveling the freight trains across America. His experiences, which eventually led him to a county jail and thus to the foundations of his socialist beliefs, he later on described thoroughly in his autobiographical novel, The Road.

By 1896, Jack is already known as the “Boy Socialist” of Oakland. He joins the Socialist Labor Party while at the same time cramming for university entrance examinations. He attends the University of California at Berkeley for the fall semester; but disillusioned, he drops out after only one semester.