Under the standard rules in The Broken Hourglass, when characters reach certain experience point thresholds, they become eligible to level up. The process is similar to the concepts of "classes" or "levels" in other systems, but with a twist reflecting the point-buy underpinnings of the system.

Advancement is managed with level "paths." These paths represent a template of study, behavior, or personal focus roughly analogous to a character "class." Paths include the Scout, the Diplomat, the Marauder, and the Soldier. Paths automatically buy traits and points in primarily attributes and secondary skills to reflect the priorities expressed by the path--for instance, characters following a Diplomat path invest heavily in social skills. The player character may employ any path the player wishes to follow (or no path at all--see below for more details).

Joinable NPCs, on the other hand, have certain preferences and opinions about the way they should manage their personal development. Halima, who has devoted most of her young life to the study and advancement of her magical talents, will not consent to follow the Soldier path--it is simply too far from her interests. Meanwhile, Nekos the gladiator has little interest in becoming a spellcaster. Some NPCs can be convinced to explore different paths as you get to know them and they see new opportunities for themselves, however.​