LePage made his "life on the streets" a major part of his campaign story, retelling it in his stump speech and in numerous interviews. According to his account, he slept in cellars, in hallways, and at friends' houses. He shined the shoes of businessmen and Brunswick Naval Air Station personnel visiting Hotel Holly, a strip joint on Main Street. Sometimes the women who worked there would let him sleep in a bedroom that was not in use. He has admitted to hiding in a Lincoln Street alley on Halloween, 1960, and mugging younger children for their candy, a story he recounted with a roguish smile. (His morally ambiguous punchline to this anecdote — "And now I'm governor of Maine, and there's nothing left to steal" — made headlines last year.) He cleaned stables out at the harness-racing track, where the caretaker told him to remember this phrase: "If it is to be, it is up to me." He met and tagged along with Myrick, who drove a delivery truck for Seltzer & Rydholm, helping the older man load and unload cases of Pepsi. He eventually started washing dishes for Eddie Collins, who had just purchased Theriault's Café, a diner at 209 Lincoln Street, in the shadow of LePage's parents' home. He has said he passed on some of his earnings to his younger siblings, so they didn't go hungry.
LePage apparently managed to conceal his semi-homeless status from many of his classmates, from the priests at St. Mary's grammar school, and even from Myrick. Moreau, who was Paul's classmate, says he was unaware of his friend's circumstances at the time. "Maybe I was very naïve or not perceptive enough to notice," he says. He recalls no interruption in Paul's studies at St. Mary's (which charged modest tuition), but that at some point he stopped playing and running around with the neighborhood kids. "Some of the kids in the neighborhood were envious of Paul because he had met up with this Pepsi delivery man, and at the end of the day he would give him a full case of Pepsi Cola," says Moreau, who also remembers often seeing Paul at work when he and other kids would drop in to Theriault's to share a big (fifteen-cent) order of french fries. "A lot of kids had little part-time jobs, but Paul was always working, always hustling and pretty serious in what he did."
LePage was especially proud of his association with Myrick. He has recalled that in seventh grade — a year into his semi-homeless period — his teacher asked each student what they wanted to be when they grew up. "Everybody gets up and wants to be a doctor, a lawyer, an astronaut," he recalled." I wanted to be a Pepsi Cola truck driver! And they thought I was a real clown and comedian and I had everybody laughing, but I was serious. I had no idea of any other level of aspiration. That's what I knew of life at the time."