The human drive to conquer experiences with nature is often manifested in artifacts such as paintings, photographs or digital posts. In this thesis an artist traces this vein through baroque etching, romantic landscape painting and daredevil instagram selfies to create works that question the ideas of ownership and failure. The research, process and final paintings, which depict failed mountaineering expeditions and digitized landscapes are discussed. It analyzes instagram ‘trophy photos’ in an art historical context. It also provides a detailed account of high mountaineering culture and its relationship to collecting and nostalgia.