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It's a one Path, not skill(s). And it has separate levels.
Each Path has its own bonuses on specific levels (Travel Posts, Black Market access, etc) while also having upgrades you can choose once you gain a level.
Best way to think about Paths is your mercenary company's progress in various fields. Fighting progresses Power and Glory path, trading and crafting progresses Trade and Craftsmanship, stealing and other crimes progress Crime and Chaos, and exploration of all kinds progresses Mysteries and Wisdom. Pretty much everything you do in the game progresses one Path or another.