Models of offender motivation to change exist, however there is a lack of theory-driven psychometric tools that measure motivational constructs to support offenders in positive life goal pursuits. This research extends the Personal Concerns Inventory (Offender Adaptation), presenting a Goals and Plans tool that supports users to: identify and prioritize goals in life domains of importance to them; detail how a goal can be attained; and consider obstacles to attainment. Literature informed the benchmark for the tool, which was evaluated through implementation in Prisons (n = 62) and Approved Premises (n = 105) across Wales, UK. Results indicate that goals in the life domains of Home & Future Living, Relationships, Physical & Mental Health and Learning & Working were prioritized. Goal attainment/restrictions were influenced by perceived control over a goal. Goals that relied upon external factors (i.e., services) reflected a more maladaptive motivational structure, whereas those that relied upon internal (self-focused) barriers to participation reflected an adaptive structure. This research offers practitioners a tool to assist users to ‘plan for the future’ and monitor progress by capturing motivations and assessing factors that might impact the likelihood of a goal being pursued.