In today’s increasingly technological society, human activity cannot be properly understood without referencing computing artifacts. Today people access their healthcare and government services online, engage with politicians and celebrities directly through social media, and face a near-term future where self-driving vehicles and artificial intelligence will likely eliminate millions of jobs. Technical systems intentionally and unintentionally affect people's emotions and sensibilities, their thinking and decisions, how they act individually and collectively, and their expectations and desires for culture and society. Designers of artifacts, on reflection, inevitably take part in shaping the sociopolitical fabric our society. In this talk, I will reflect on what it means to engage in designing sociotechnical systems. To do so, I will draw from theory development and design research methods in value sensitive design (VSD). In particular, I will focus on the issues of multi-stakeholders and multi-lifespan design.