Although there is a substantial literature on the institutional and administrative history of the Ottoman madrasas as well as the intellectual achievements of certain “big” scholars, we know very little about the basic social realities of life around madrasas from different levels and still lack nuanced studies on the personal reflections of individuals from various ranks of Ottoman ilmiyye as regards to the promotion and patronage system they engaged in. The aim of this presentation is to explore the autobiographical writings of a sixteenth century petty ‘alim, Zaifi (d. 964/1557), as a window into the personal lives, anxieties, and reflections of hapless and ill-fated scholars during the so-called golden age of the Ottoman enterprise. Zaifi’s career, which - as a student of the shaykh al-islam and a graduate of the leading educational institution of the time - had started quite promisingly soon turned non-thriving. Often he struggled to find a decent teaching position and was exhausted by the financial difficulties that exacerbated during especially the longer waiting periods for appointments (mülazamet). Throughout his career he could only held posts in low to mid-range madrasas and had to get involved, for his livelihood, in other activities that range from translating Persian works to Turkish, copying manuscripts, and even participating in military campaigns. We are very lucky indeed to have significant amount of autobiographical portions in Zaifi’s oeuvre that include original and translated poetry as well as treatises as to ethics and politics. Based especially upon his autobiographical narrative (sergüzeştname) and the private letters that he sent during his ill-starred career to the sultan Süleyman (r. 1520-1566), the leading statesmen, and fellow scholars/littérateurs, this paper intends to bring in a personal perspective for a more accurate understanding of the actual workings of the madrasa-mülazemet system and the patronage culture in the Ottoman world during the first half of the sixteenth century.