A cognitive assistance application combines a wearable device such as Google Glass with cloudlet processing to provide step-by-step guidance on a complex task. In this paper, we focus on user assistance for narrow and well-defined tasks that require specialized knowledge and/or skills. We describe proof-of-concept implementations for four different tasks: assembling 2D Lego models, freehand sketching, playing ping-pong, and recommending context-relevant YouTube tutorials. We then reflect on the difficulties we faced in building these applications, and suggest future research that could simplify the creation of similar applications.