Purpose: The study examined the barriers faced, the goals selected, and the optimization and compensation strategies of older workers in relation to career change. Method: Thirty open-ended interviews, 12 in the United States and 18 in New Zealand, were conducted, recorded, transcribed verbatim, and analyzed for themes. Results: 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. Conclusion: 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.