The life and career of Theodore Chyrtakinos span the long and tumultuous reign of Andronicus II (1282-1328). He taught as a private tutor, and among his former students are Basil the Sweet, Nicholas Metochites, and Alexius Apokaukos, the future grand duke. He claimed that the remuneration he received was never sufficient to sustain him.

He conversed with men of power and wealth, yet had no share in it. His correspondence, preserved in the Parisian codex gr. 1209, a unique 14th-century manuscript, offers a type of autobiography intended to be read and published. His letters project the image of a poor intellectual, which he consciously cultivated in hopes of winning the sympathy of the emperor and powerful men.

His constant engagement with money and other worldly goods, his appeals seem to underscore a permanent financial insecurity. However, flattery of the rich and the display of knowledge were the typical means through which aspiring intellectuals sought to attain high positions in the state bureaucracy and the ecclesiastical hierarchy.