Encouraging and assisting homeless people to become self-employed provides a way for some of them to increase their incomes, and may help close the gap between the cost of housing and labor market earnings. A survey of operators of homeless shelters was conducted to determine the types of work activities that adult homeless men participate in. Self-employment was found to be a common activity for a substantial proportion of adult homeless men; and a preferred mode of employment for many. Advantages and disadvantages of such an approach are discussed. Several program models are described which can be used to enhance and initiate self-employment activity for adult homeless men.