Data Science looks at raw numbers and informational objects created by different disciplines. The Digital Society creates information and numbers from many scientiHic disciplines. The amassment of data though makes is hard to Hind structures and requires a skill full analysis of this massive raw material. The thoughts presented here on DS2 - Data Science & Digital Society analyze these challenges and offers ways to handle the questions arising in this evolving context. We propose three levels of analysis and lay out how one can react to the challenges that come about. Concrete examples concern Credit default swaps, Dynamic Topic modeling, Crypto currencies and above all the quantitative analysis of real data in a DS2 context.