The dot-com boom in the late 1990s attracted vast numbers of undergraduate students into the field of Information Systems (IS) with the promise of being the next “big thing”. As the dot-com bubble deflated amidst the general slowdown in the global economy, the outlook of these batches of students had been changing dramatically over the years due to the long “gestation” period (frequently 4 years) in the tertiary educational arena. Coupled with the perennial shifts in the nature of critical IS knowledge and skills, the current situation presents a unique, valuable and close-up opportunity for studying the evolving identity of the IS professional. This research employs symbolic interactionism as the informing theoretical perspective for examining newcomer socialization processes in an ethnographic study, in which the researchers were immersed in the education environment of a university. We adopt a longitudinal form of analysis by examining three major role transitions along the road to being an IS professional, starting from his/her formative years as an (initially earnest) undergraduate student. Our findings regarding the evolving outlook of these students indicate that they initially attached certain symbols to being an IS professional. Interestingly, some of these symbols got sedimented over time while others exhibited relatively less permanence. More importantly, the evolving symbolism was enacted into various job-seeking actions towards the end of the long university education process.