The more Shikajin listened to the other man speak the less he believed that Yusuke knew exactly how businesses ran. He didn't charge shinobi, a great favor, but that probably meant that word of mouth spread quickly and more non-paying customers flocked to his establishment. How was he paying for all the food and drink the restaurant went through? How was he paying his staff? Donations were great and all but that relied solely on the goodness of others. Granted, non-shinobi did have to pay so that helped a little and without knowing the ratio of non-shinobi to shinobi customers then the Nara could not know for sure if the place was doomed to fail, but he wouldn't be too surprised to hear if it shuttered sooner rather than later; not that the chunin wanted to see it fail but it just wasn't making sense.
Then, to the medical stuff. Where Shikajin didn't really agree with the man's business plan he could agree that studying to be a medic was perhaps one of the most arduous things in the world. Many long nights of staring into books and scrolls learning the ins and outs of the body, the chakra circulatory system, how to fix it --and by association how to damage it-- and that wasn't counting the practical stuff. First on dummies, then onto fish simply trying to resuscitate them and after months of that finally getting able to see human patients.
"I can agree there, I've probably spent more time studying medicine than actually using it. Truth be told I still have much to learn and I don't think the studying ever stops." Shikajin replied as he took another bite of his gifted apple. Though he had done well in being able to combine his medical acumen with the Nara hijutsu there was still a lot the chunin could improve upon. He was proud of his skills but not dumb enough to think he had reached anywhere near the top of his profession.
Hearing the next question caused the chunin to drop his apple, the fruit rolling slowly across the ground before coming to a stop near his feet. The man looked to be in a daze of sorts, his eyes sunken and hidden beneath the low light of the early dawn. He could feel his breathing shortening and his palms beginning to clam up. No no no no, why did he have to bring that up? He could keep the memories at bay during the day by keeping himself occupied unless someone brought them to light.
"I... uh..." Shikajin stammered as he felt a pain begin to well in his chest.
"... lost a teammate some years ago. Didn't want that to happen again so I took the path that would let me achieve that goal." He finished before taking a deep breath. It wasn't Yusuke's fault, he would have never known, but the pain hurt all the same.
In reality the trio were more than teammates, they're families bonded together for generations upon generations. Shikajin and known Inoyami and Chouza for as long as he could remember, they were basically siblings to him, and perhaps that was what made the loss hurt so much, even after all this time.
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