Simon's initial foray into The Pit is a rude awakening, a brutal deconstruction of his Isekai fantasies. He approaches the subterranean dungeon with gamer-like confidence, expecting levels, skills, and clear objectives. Instead, he endures a series of agonizing, humiliating deaths: a fatal tumble down stairs, being eaten alive by rats, impaled on spikes, drowned in a subterranean river, and torn apart by goblins. Each respawn, a jarring return to his cabin, chips away at his composure. The mirror, his only interface, initially provides cryptic non-answers, but eventually reveals a "character sheet" that shatters his gamer logic: negative experience points, "very poor" skills, and the devastating truth that "levels" are merely floors, not earned progress. Helades, the goddess, reappears to cruelly confirm his fears, revealing the Pit as a cosmic "garbage can" for "weeds" like him, a place of endless, pointless suffering. This divine mockery ignites a fierce, spiteful determination in Simon. He begins to actively engage with the Pit's hidden mechanics, experimenting with magic and discovering that spells require not just words, but intense visualization and emotional intent, a taxing process that hurts but yields powerful results. His first successful fire spell, born of pure rage, marks a turning point, transforming him from a passive victim into an active, if still suffering, participant in Helades' twisted game, setting the stage for his desperate quest for mastery and revenge.

Simon's journey takes an unexpected emotional turn with the discovery of Freya, a barmaid trapped in the zombie-infested city of Schwarzenbruck. His burgeoning affection for her, a genuine human connection in the brutal isolation of the Pit, becomes both his greatest strength and his most profound vulnerability. He dedicates himself to protecting her, navigating the zombie hordes and the insidious threat of infection. However, the Pit's relentless reset mechanics mean their love story is doomed to repeat, with Freya dying in various horrific ways—turned into a zombie, killed by a fellow survivor, or simply lost to the chaos. Simon himself experiences the ultimate horror: forced undeath as a zombie, trapped within his own rotting corpse, compelled to devour the living, including the man who tried to save Freya. This experience, coupled with Freya's repeated loss, plunges him into despair, driving him to seek an escape from the Pit entirely. His desperate attempt to find an exit leads him to the harsh mountain wilderness, where he ultimately freezes to death. Upon his return, Helades reveals the true cost of his "immortality": the use of magic drains his life force, causing him to age rapidly with each spell, culminating in a death by old age.

Reborn and rejuvenated, but haunted by Freya's memory and the terror of undeath, Simon's purpose solidifies into a grim quest for understanding and vengeance. He dedicates himself to mastering the Pit's magic, studying a grimoire that reveals the modular nature of spells and a host of new abilities: cure, transfer, ice, protection, force, and light. His time in Rivenwood, a plague-ridden village, allows him to hone his healing and combat skills, transforming him into a formidable warrior-mage. He crafts a flaming sword and cold-resistant armor, physical manifestations of his growing power and defiance against the Pit's cruel designs. Returning to the early levels, he speedruns through them, effortlessly dispatching rats, bats, and goblins. He confronts Brenna, the barmaid who became a zombie in one timeline, and, understanding the plague's spread, makes a morally ambiguous choice to unleash a giant slime to "eat" the zombies, effectively clearing the level. This strategic, almost detached approach to the Pit marks his evolution from a reacting victim to a calculating agent, driven by a desire to conquer the system that tormented him and find a way to make Helades pay.

Simon systematically progresses through the Pit's middle levels, from the sewer's carrion crawler to the jungle's carnivorous plants, the haunted mansion's poltergeists, and the frozen village's ice mage. His encounters with the Demon in the "church" level offer cryptic insights into the Pit's cosmic purpose: a "reality knot" created by Helades for a previous hero's failed quest to "cleanse the world." Simon learns he is one of millions of "weeds" trapped in parallel iterations, a pawn in a divine game. This revelation, coupled with the escalating difficulty and the emotional toll of his journey, solidifies his resolve. He faces his most feared opponent, the Basilisk, the creature that petrified him for years, in a brutal, magic-infused battle, finally overcoming his trauma. Upon reaching level 20, Helades appears, confirming the Pit's origin and his own unexpected "promise" as a hero, but also revealing the profound cost of his magic: accelerated aging. Now old, wise, and burdened by the weight of his experiences and losses, Simon stands at a crossroads, understanding the Pit's true nature as a failed attempt at salvation, and his own unwilling role in its continuation, yet resolute to conquer its remaining 79 levels.