Young people with psychiatric disabilities are significantly overrepresented in the juvenile justice system, tend to be employed sporadically if at all, and frequently have negative connections within and to their communities. Recent research conducted in Montana with youth who have developmental and/or physical disabilities demonstrates the effectiveness of using a customized career planning model to increase linkages to resources and access to community- based employment. Side benefits include improved self-esteem and positive community connections. The customization model holds promise as a way to reduce the risk factors young people with psychiatric disabilitiesf ace and increase the resiliency factors that can assist them to achieve healthy long-term outcomes. The author describes the model as it has been applied in Montana, explores additional considerations when working with youth diagnosed with psychiatric disabilities, provides an example of the model in action, and makes recommendations for further areas of research and inquiry.