Humans presented with the same problem in the same environment commonly adopt wildly different strategies for attention and learning. Indeed, psychiatric conditions are defined by qualitative differences in behavior. However, most tasks measure an individual's deviation from a single expected strategy rather than the utilization of distinct strategies. Measuring diverse strategies is especially important for psychiatry, were conditions are defined by qualitatively distinct patterns of behavior. We paired psychiatric trait questionnaires with a context generalization task whose metrics for goal-directed attention and short-term memory identify qualitatively distinct strategies. Questionnaires assessed for traits associated with ASD, attention-deficit/hyperactivity disorder (ADHD), obsessive compulsive disorder (OCD), depression, schizotypy and psychosis. The subject population recruited online was matched for self-reported sex, and the sample was enriched with those reporting a formal diagnosis of ASD. 744 subjects completed the first session of the task, and 584 returned after four to six weeks to complete the second session. We found that a strategy dominated by goal-directed attention was associated with a profile of reduced trait scores relative to other subjects across all measures. During the second session, this strategy was particularly pronounced for those with reduced ADHD traits. In contrast, a strategy of attending to features based on frequency was associated with a profile of increased trait scores relative to other subjects, particularly traits for ASD and OCD. During the second session, this strategy was again associated with elevated traits, particularly those for ASD and ADHD traits. These results provide insight into the relationship between psychiatric traits and qualitatively distinct attention and learning strategies.