Real careers are not perfect. Professional success is not absolute. People shape careers and then over time, careers shape people. Feb 1999. The batch of 1999 steps out from one of India’s leading business schools—Indian Institute of Management, Kolkata—into the real world of careers, not unlike many other professionals before and after. Eighteen years later—in the middle of their working lives—32 of these professionals pause and take stock. They look back on their careers, on the choices they made, their successes and their failures, their highs and their lows. They reflect on what they assumed when they graduated from B-school and what the world has taught them since. There are Real Lessons in Their Reflections; There are Common Themes in Their Career Arcs. This is the story of real careers taking shape in the rapidly evolving post-liberalisation India of the last two decades. Of conventional careers and not-so-conventional careers and something in between. Of people who took the corporate path, who became entrepreneurs, who became academics, who went abroad, who became specialists and even those who let their careers go with the flow, unplanned. Step in as they take stock of their journeys. As relevant for mid-career professionals, to peek over their shoulders at peers, as for those starting their professional careers, curious about the careers choices ahead and the road signs on the way.