Objective: Develop a program providing education and skill development to increase employability for success in the 21st century work force. Background: Families face many sources of risk and barriers to long-term success. Poverty and low economic status can be the most significant barrier. One way to address these obstacles is through a two generation approach. This approach aims to address challenges in an inter-generational concept to achieve greater success. Method: A pilot study was conducted with staff members of a mental health organization. A pilot program was completed due to barriers in participant recruitment for the program. The program is titled R.E.A.C.H and has four educational topics: mindset, self-efficacy, work competency skills, and launching a career. Conclusion: The program successfully met its goal of developing employment skills for the 21st century workforce. The program did not reach a two generation implementation due to recruitment challenges. The program can be successfully implemented in the future with improvement in recruitment and marketing efforts. Implication: This program is the first two generation program to develop the skills for increased employability in parents and children simultaneously. This program increases individuals’ autonomy and fulfillment in the occupation of work. R.E.A.C.H addresses sources of risk to break down barriers for long-term success. Key words: two-generation approach, risk, skill development, parents’, employability, life-long outcomes