Darius grew up in an affluent family, who believed that everyone was equal, and those who were lucky enough to have more than they needed should do what they could to help those less fortunate. His clan were all honest, hard-working, moral people, and Darius had great respect for them, though he always disagreed with them on some points, and shared few common interests with them. So, he loved them, but worried that he didn't love them as much as he should, because he couldn't really say he exactly liked most of them. But then, he found it difficult to really get close to most people, family or otherwise. He always felt different from everyone, and suffered social anxiety and occasional bouts of depression.
Meanwhile, he did have a few friends, including his doppelganger, Dave, as well as Rob and Chris. Dave came from a relatively poor family, and Rob and Chris came from middle-class families. Darius and his friends are known to have frequented Dane's Diner. In spite of being upper-class himself, Darius felt he had more in common with these three than any of the kids in Triscot from other wealthy families. His closest friend- or frienemy- aside from these three was Benj Illustri. (It should be noted that his other friends didn't take on surnames until 904, whereas Benj's clan used the name Illustri for years prior to that.) Benj was mainly an academic rival of Darius's, the two top students among the group of rich kids whose clans paid several masters to tutor them in various subjects. Like Darius, Benj loved his own clan, but disagreed with them on certain points. However, he at least agreed with his father, Xander, that Darius's clan was wrong to think of the lower classes as their equals. (In fact, the introduction of a class system is believed to be the main reason Darius's clan opposed the Coming of the Order, and one of the main reasons Benj's clan supported it.)
In 903, the last major battle of the Coming was fought, on Adam's estate. Darius was not present at the time, as he was visiting his uncle West in Tanq. Darius had often disagreed with his father's anti-Order position during the war, though he'd recently been coming around to think he may have been wrong, particularly after having heard some of the speeches of Vallus. On 9 Aut'yet, Darius's clan was wiped out by the Order (or so he thought). He and West were the only two remaining from the clan. Darius (now 13) moved back to Triscot, and stayed with Rob's family for several months, into 904 (the year that the Second Order was officially established). When the school system was established, Darius and his friends attended. Some of the masters included those who had previously instructed rich kids, and knew Darius to be at a higher level than those in his grade at the new public school. After a few months, he requested they give him a final exam, a few years earlier than would be the norm, and he passed. So, he received his mental stamp, the final one he needed to become a legal adult. Rather than move on to one of the new universities of higher education, he chose to begin wandering, and became a professional adventurer. He would occasionally write fictionalized accounts of his adventures, which sold modestly well, though most of his income came from adventuring.
When the surname law was passed in 904, Darius chose the name "Lonewander," for the obvious reason that he liked to wander alone. His uncle West went along with Darius's choice, and took the same name, himself. In spite of Darius's inclination towards solitary adventures, he has occasionally teamed up with others. In fact, his very first real adventure, shortly after turning 14, was with Lorelei Chicory, whom he'd just met. He made a number of other friends over the years, including George Taverner, to whom he was introduced by Lorelei.
Over the years, Darius always felt he would someday start a rebellion against the Second Order. While there was much he liked about how the Order had changed the world, there was also much he felt was worse than the old ways. He never gave much detailed thought to his true motivations, though it's likely the main reason he wanted to rebel was to avenge his family. Nor did he have any real idea of how he'd go about organizing a rebellion, it was always just a vague notion, which perhaps he believed would never be more than a fantasy. He just kept telling himself, he'd start thinking of it seriously if he ever came up with a name for his rebellion; but then, he never really gave that much serious thought, either. Until one day in 912 (at age 21), when he met Tom, who unwittingly provided him with the name The Chaos, and from that point on, Darius began meeting others who joined his cause, and the rebellion got started, much sooner than he ever could have expected.
Eventually, the members of the Chaos decided against rebellion, though by then it was too late: they were considered enemies of the state, without having ever taken any action against the government. They were imprisoned without trial, in Near Port, under the supervision of Col. Charles Woodman. However, they later escaped, and subsequently allied themselves with the forces of Marshal Poss Primus against Demos Royal, in a conflict that was known as the Chaos War. In 913, a proposition known as the Secession Referendum was included in that year's election, which led to the establishment of The Land's second country, the United Villages of the Chaos, of which Darius became the first First Triumvir, a position he held until 916.