“Dad snapped his fingers. ‘These folks zigged when the rest of the world zagged. And once you cross that line, there’s no coming back. Mark my words.’” 

Gantos recalls his father saying this to him when Gantos is a child; the pair would drive through town, and his father would point out the men and women that made bad decisions, decisions that irrevocably changed them from regular people to criminals. This echoes in Gantos’ mind: there is a point of no return, when a person allows themselves to be defined by their bad decisions, and then their life is defined by criminality.

“Someone once said anyone can be great under rosy circumstances, but the true test of character is measured by how well a person makes decisions during difficult times.” 

This signifies a sense of foreboding in the story; it alludes to Gantos’ mistakes as a young man, first in Puerto Rico, then Ft. Lauderdale, and then his fateful decision to engage in drug smuggling in St. Croix. His decisions foreshadow the many “zigs” (as his father would call them) that Gantos makes. It also foreshadows his resilience once arrested. Prison tests Gantos in many ways, but he manages to redeem himself in the darkest months of his life.

“I’d go to the casinos at the El San Juan and Americana. I’d imagine I was James Bond meeting beautiful older women at the roulette tables and walking arm in arm up to their rooms where something dangerously exotic might happen. But the only arm I managed to warm up was on the slot machines.” 

Throughout his youth, Gantos is obsessed with adventure. He is also obsessed with posturing himself after great writers or fictional characters he deems courageous or sexy. In his many efforts to be more interesting, he actually finds himself sinking deeper into a mindset of shirking accountability, which will be his undoing.

“Even I knew enough to understand what Buddha meant when he said, ‘[a]lways walk the road of happiness to prosperity.’ They seemed miserable and loveless. Nothing gave them pleasure because they were unable to receive it. And there I was, full of promise and hope and desire for real love and real events to shape and change my life.” 

Gantos often draws a line between himself and those he deems less romantic: the Bacon family he lives with after returning from Puerto Rico offend him, much like Hamilton does later, on the boat, via a lack of imagination and eagerness for adventure. This helps Gantos justify his poor decision making; he rationalizes that his quest for adventure and meaning is an excuse for breaking laws and personal irresponsibility.

“I had lost control. Temporarily. But I’d get it back, I figured. I always did. My family had highs and lows, made money and lost what money can buy, had good days and days that were ground out like cigarette butts. So I was used to hitting the bottom. Now I was waiting for the bounce.” 

Before his arrest, Gantos primarily adopts an attitude of positivity, even in his darkest moments. With each poor decision and its consequence, he finds a way to imagine that his future is brighter around the corner, which allows him to shrug off his guilt and go onto make another poor decision. It is his constant quest of the easy “bounce,” to recover day by day or feel instantly more optimistically about a bad decision, which causes him to ignore any consequence these transgressions might have on his long-term goals.

“Day and night I wrote down these ideas in my frantic, spastic penmanship. But that is all they ever amounted to—ideas [….] I just didn’t have the confidence and determination to sit still and nurture them properly.” 

A recurring theme in the narrative is the divide between Gantos wanting to be a great writer and his lack of dedication to the craft. It is an analogy for how little he nurtures himself and his future; by not taking the time to dedicate himself to writing, he increasingly risks his welfare in the same neglectful manner. 

“It seemed to me that no amount of forgiveness would even wash away his need to be forgiven every day.”

Here, in another example of foreshadowing in the earlier chapters, Gantos is watching a school assembly with mocking indifference; he hears the narratives of men that have been incarcerated in the local prison but draws a major line between himself and these men, whose fates will mirror Gantos’ fate more than Gantos, at this juncture, is aware of. 

“Yet I went to the apartment. Why? For the same deadhead reason people climb mountains—it was there and I wanted to try it.”

Gantos uses this reasoning to justify his entrance into drug culture: at first hesitant and thoughtful about starting drug use, the seed in his mind grows as he thinks about the offer of weed all day. He succumbs to the temptation, and that is the first active step he takes into his criminal future. This is echoed later in the story, when he sublimates his lack of dedication to writing with drug and alcohol use. Immediate gratification becomes more important to Gantos than anything else: respect for others, his family’s safety, and his own future.

“And I was especially itchy to feel new things, to shed my skin and grow […] I had a strong sense that I needed to snap off my past in order to have a future.” 

The concept of change and its possibility permeates the memoir. From the yellow, decaying interiors he inhabits, he yearns for romantic, unfamiliar landscapes. Gantos shows his unhappiness with himself and his desire to be something else. Early in the text, he is able to justify each poor decision he makes, shrugging each bad decision off and believing himself free of any guilt. He also employs change as he shifts his mindset in prison, shedding the skin of immaturity and achieving some level of self-awareness.

“From the first week I landed in St. Croix I became part of a drug culture.” 

This defines the setting Gantos steps into as a young man rejoining his family in the U.S. Virgin Islands. Already a drug user, Gantos immerses himself in smoking hash amid a culture defined by drugs and their trade. He lives and works in an area teeming with drug use and smugglers.

“Hamilton had read my mind—I’m not doing anything wrong. I’m just afraid of the punishment.” 

These are words Gantos records in the ship’s log, later to be found and read back to him during his sentencing. It is this damning conclusion that leads to Gantos’ maximized sentence; while recording this, however, Gantos knows that this is truly how he feels about smuggling drugs: he wants to do it, and just doesn’t want to get caught.

“Being scared together created a great bond among boys, and being scared of each other created a great bond in prison.” 

Among the other prison inmates, Gantos compares his own story with stories of the other men’s capture. He likens this to sitting around a campfire as a Boy Scout, sharing stories to excite and illicit envy from childhood friends. In this setting, the twist is that the men share the horrific details of their crimes to illicit fear from their fellow inmates, as each man aims to be intimating enough to not be hurt or killed, while at the same time feeling intimidated by their surroundings.

“‘Then we have photos of you at the boat loading hash into a shopping cart—look at the smile on your face. Would you like a mirror to see how you look now?’” 

This shows the juxtaposition of the adventure Gantos signed on for versus the sense of dread he feels after his capture. As DA Tepper shares the photographic evidence of Gantos’ crimes, Gantos feels beaten down, which is in contrast to his carefree attitude only weeks before.

“I figured my face was the landscape of my attitude.” 

Gantos, from the time of his arrest through months into his prison sentence, continues to pick at his skin as a form of control. When he is confronted with a lack of control over his fate, he begins to manipulate his face.This fixation suggests that what is happening to him on the inside is externalizing; Gantos marks himself for others to see the internal torment over his loss of free will.

“‘You like to sell it, but did you ever consider what it could do to the people who bought it?’” 

This is spoken by Lucas’s wife (Lucas is one of the customers Gantos sold hash to, who is also incarcerated and to be sentenced on the same day as Gantos); her words strike Gantos dumb because this is something he has never considered to this point. Lucas goes onto suffer immense brutality in prison. 

“One after the other the men in prison clothes were escorted into court, then returned to the cell. Not one of them was released.” 

During his sentencing, the ramifications of Gantos’ actions fully sink in. He expects a lighter sentence because of his youth and lesser involvement in the hash bust, but as he watches different men come back and relive their respective sentences, he notes that the shortest sentence, a couple of years, is more than he expects, or is prepared, to do.  

“It was the fear of being a victim, and that I would be next in line.”

After being gang-raped, Lucas, asks Gantos for help to clean himself up because his wife and child are coming to visit. Gantos, however, struck by the brutality of Lucas’s rape, wishes to distance himself from the man, rather than help him. He feels that associating with Lucaswill mark him as weak in the eyes of the other inmates. This highlights the lack of humanity and altruism some men adopt to survive in a brutal environment.

“‘Count me in.’ Those were three words I’d take back if I could. Those were my words to Rick and Hamilton. ‘Count me in.’” 

Each day, in prison, the inmates are counted; this act makes Gantos recall the exact words he said to Rik and Hamilton when offered the job smuggling drugs. It is a strong reminder of the cost of his desire for adventure; he is now ‘counted in’ among criminals as a result.

“When life was funny in prison it was hysterically funny. And when it was scary it was menacing.” 

In the manner of many texts seeking to depict the dangerous and brutal with both honestly and irony, Gantos notes some of the ridiculous events he sees in prison. One such darkly humorous thing is that he is arrested for drug smuggling and put into prison, a place rife with drug use, and a place where access to drugs is as common as it was when Gantos was on the outside selling. The brutal component of drug use comes into play when Gantos discusses why prisoners use drugs: he notes they have no desire for books or writing instruments—things to help them remember their time inside. They seek only the release of drugs to forget each day spent locked up.

“I felt insane from having no control over my fate.”

Gantos manages to obtain his case file while in prison; therein, the parole board remarks that he is a potential sociopath, completely without remorse for his actions. Seeing this in writing, the permanence of his situation weighs on him, and he feels he is not in control of his life upon reading the file.

“The memory of my youth was [so distant] from all the hatred and despair, blood and drugs that surrounded me.”

At night, Gantos often looks outside the prison to homes on the outside. He imagines the holidays celebrated therein and decides that life is what happens outside of prison. During one particular reverie, he remembers a Halloween growing up, where the festivities are canceled because two escaped convicts are on the loose. He gains solace in this memory, a reminder that his life is one rich with memories that are very different from his time inside prison. 

“I poured myself into that book, and it poured itself back into me. It was like pouring one glass of water back and forth between two glasses.” 

During his time in prison, Gantos hides a contraband journal in a copy of The Brothers Karamazov. In this journal, he records his reflections on prison life around him. This isin sharp contrast to the journal he keeps before prison, where he mostly comments on things great writers already said. 

“In prison I got a second chance to realize I did have something to write about.” 

One common question people ask of a criminal is what they will do if given a second chance to reenter society. Gantos finds his own answer to this question during his incarceration; he develops the confidence and nurturing spirit he needs to turn his past ideas—those scribblings in his high school journal—into real writing. He uses his time to develop his writing and come to terms with the fact the he merely used lack of experience as an excuse to go looking for trouble.

“But in the dozen or so attempts I saw or heard about, not one man made it over the first fence.” 

Nearing the end of his time in prison, Gantos reflects on the futility of trying to escape. Describing the security in prison, he states there is a first fence, then two more that stand between inmates and their freedom. His practical observation of past prisoners’ failed attempts to escape andhis own refusal to attempt to do this show Gantos’ transition into a wiser man, aware that he can’t simply run from the consequences of his bad decisions.