The study examined the barriers faced, the goals selected, and the optimization and compensation strategies of older workers in relation to career change. Thirty open-ended interviews, 12 in the United States and 18 in New Zealand, were conducted, recorded, transcribed verbatim, and analyzed for themes. Barriers to finding and maintaining work included task difficulty, problems with coworkers and management, lack of self-confidence, health/physical limitations, ageism, and stereotyping. Respondents' most frequently selected goals for a new career were the desire to help others, work satisfaction, and acquisition of learning. Seventy-five percent of respondents in paid employment had earning an income as a goal. Optimization strategies included drawing on past experience, assessing skills, seeking careers/organizations that fitted their values, and a willingness to accept lower pay or unpaid work. Attitudinal strategies included focus and persistence, optimism, and positive attitudes toward change. The compensation strategies reported were on-the-job training; help from coworkers, clients, or customers; friends and family social support; and professional networks. Management practices considered helpful were flexible work schedules, supervisors' patience, and formal recognition of the value of older workers. This qualitative study, using the SOC framework, showed that evaluating one's skills and values, being positive about change, and being part of a supportive work environment were key contributors to adaptive competence.