In this article, the author talks about labored learning under the auspices of the "outing program" of Sherman Institute, an Indian boarding school in Riverside, California. The outing system functioned as a vital part of a larger federal Indian boarding school system that sought, in the words of historian Matthew Sakiestewa Gilbert, to make Indian students "think, behave, work, and look less like Native people, and more like white Protestant Americans." A deep look at the outing program at Sherman Institute reveals a complicated story, one that saw limited expectations and the significant risks of isolated, menial labor set against the lures of money, adventure, and for some, significant work experience. Much like the Indian School system, the outing system arose from the early Progressive Era conviction that Native American peoples could be "uplifted," that "savage" ways of thinking and acting could be completely abandoned in favor of the fruits of non-Indian civilization. (Contains 1 table and 86 notes.)