Shizuo knew that this gesture was Kasuka's way of encouraging him. He himself wanted to be able to stick with one job, and with Kasuka giving him more reason to --he felt like he would actually be able to succeed. The two brothers shared a strong, silent bond. They didn't show their love with words, but with actions instead. Every time the anger would get to Shizuo's head back then, Kasuka would immediately hand him a bottle of milk to calm him down. Though nothing was said, it was highly effective.

"Thanks, I'll do my best, I guess."

And Shizuo did try his best. He did try his fucking best until he found himself being dragged out of the bar one night by a total of seven policemen. Even for the law enforcement; Shizuo is a pretty hard person to deal with. The main question was: Why?! What the hell did he do now? What did they want with him?! As Shizuo stood pinned against the fence with several policemen struggling just to keep him still, he learned the answer. It was like high school all over again. Orihara Izaya --that damned louse-- smiled at him from behind the safety of all those policemen. Apparently, he was back in town, and thought this to be a befitting greeting. Izaya had framed Shizuo once more, but at a much larger scale now. It wasn't petty classroom disputes anymore; they were adults now, after all --surely the extent of Izaya's trickery would increase proportionately as well. Izaya had framed him for a crime this time, and well, there was just no way his boss was going to take him back after that.

He gets released soon after when they finally confirm his innocence, and walks out unemployed once more. It isn't a good feeling. What about that promise he made to his brother? He's got a closet full of bartender outfits at home, and they'll just serve to remind him that he had broken it. As he walks out of the police station, it is here that he gets his final job offer: the one he actually manages to stick to. An old friend from middle school, Tanaka Tom, approaches him and invites him to work in a debt-collection agency. Shizuo doesn't like the idea of it at first. He knows that he would be the muscle behind the operation, and the last thing he would ever want to do is actually hurt people for a living. Tom reassures him, though. Because the name 'Heiwajima Shizuo' was quite a well-known and powerful one in Ikebukuro --no surprise there, considering what Shizuo did to the city from time to time-- Tom only had the intention of using him to scare the debtors into payment. There was no actual violence involved.

And so, convinced, he accepts it. Yeah, it still means breaking his promise to his brother. He does feel guilty over it; that's why he tries to honor that promise in all his ability by wearing a bartender's uniform every day, despite the fact that he isn't a bartender anymore. It's not long before that bartender outfit becomes a trademark of his, and immediately recognised by the debtors of Ikebukuro as their cue to either run away or beg for their lives. Shizuo still has this job to this day, finally coming as close as he can to actually settling down.