Shuffling the deck

How it started

Jack Marsters was born the third child of an architect and a quarry owner, both in good financial standings and with wits perfectly capable of keeping it that way. The expectation was that their children would either join one of their parents' businesses, or learn other crafts. Then as a child Jack began manifesting Tarot abilities, to great surprise of his parents, as none in the family tree had ever done so before.
The Marsters had plenty of good connections with nobles, clergy, and other merchants. They made use of those to figure out the situation, and make sure Jack was taught properly. He learned physical and mental training, underwent proper education, and turned out to be quite skilled at Tarot abilities. This gave the family a goal: To get Jack to qualify for attending The Academy.

The reason

Jack and his family had multiple motives to send him to the Academy. The first was to build connections. Not all nobles are extremely prejudiced to ignoble students, so there was plenty of business opportunity to be gained here. Second was to allow Jack to further develop his abilities, so he could become skilled enough to avoid being forcefully enlisted by his country.
And lastly was Jack's personal motives. As he grew up, he noticed how people's views on Tarot users changed. From fear of the unknown, to respect, things slowly began to grew towards fear again. He realised that as Tarot user training increased, a gap was starting to grow between the nobles and the people. Furthermore, nobles slowly stopped respecting the rules restricting Tarot usage. Eventually, he surmised, things would spiral out of control and turn into wars between Tarot users.
As such, Jack wanted to see more, figure out how bad things were, how things could be improved, and who could help with that. And he also wanted to know his enemies, figure out what nobles were the biggest threat to the fragile peace. If needed, he would have to take action against them, to help keep the peace. And that too required him to improve his skills.

Arriving at the Academy

When he turned eighteen, Jack took the Academy entrance exam and passed with a rather decent score. He said his goodbyes to his family and prepared to spend five years at the Academy, knowing that due to the large distance, he would only see his family once a year. But he was fine with this sacrifice, as long as he could learn what he needed to keep his family safe and prospering.
Jack expected to find like-minded people at the Academy, and trusted his ability to make friends and allies. But never did he expect to encounter someone like Random Chenag, who observed like Jack did, but also acted. This encounter made him change his plans. Rather than figure out who to kill if needed, he would observe Random and figure out how to support Random's plans.
It only took Jack a few weeks to realise that Random was onto him, and was perfectly fine with their mutual using of each other. So began Jack's academical years, where he learned, observed, watched the Five Knights act, and helped them change society. And with that, Jack prepared for the inevitable war, but this time with good faith that it would not need to simply be endured, but could actually be won.