People with Asperger’s Syndrome have been reported to perform significantly below average a composite measure of executive functioning. Particularly, the syndrome has been characterized by difficulties with flexible switching of attention and planning. The methods and tools designed to aid these matters have been traditionally shaped after the medical model of Asperger’s Syndrome, which has been restricted to impairment-based theories and generalizations. This thesis project uses Research through Design and Autoethnography as methodologies to find representative ways in which digital artifacts can be designed to aid planning for people with Asperger’s Syndrome. The resulting prototype of this project is a personal weather-based planning tool, which explores my relationship as a person with Asperger’s Syndrome to hyper-systematization types, hyper-sensibility to weather, and planning.