Gone are the days where our parents and their parents would start working with a company and retire from the same organization. The Gen X & Gen Y or the Millennials want so much more from their Career today. Today’s Professionals are not only more invested in their careers but also expect to achieve results in the same proportion. Writer Annie Dillard famously said, “How we spend our days is, of course, how we spend our lives.” A large portion of our days is spent at work; in fact, on an average- 1/3rd of our life we spend at work over a lifetime. And so our Career can make a huge impact on our quality of life. This paper aims at inquiring the changing landscape of Career, it’s meaning and how it may vary from people to people. The definition & the meaning we derive from the word Career- has evolved over the years and despite various career theories it is hard to generalize how the career may be perceived differently by different individuals, fulfilling different needs, at different times in their life-span with varied & unique situations, challenges & circumstances. This paper also substantiates a few challenges faced by the working professionals today, with help of Case Study to elucidate & support the observation made. Some of the important aspects that this paper investigates is the internal & external factors that contribute to the development of one’s career and the satisfaction one derives from it. The paper offers new guidelines for creating a comprehensive definition of career and the meaning people derive from it. This work is inspired by the several career theories and career success research done in the past.