This thesis explores tentative hypotheses relating to four conceptually related factors of potential importance in young :eeople's lives; factors which it argues are little acknowledged in the mainstream British literature of psychology and psychiatry. These factors are: 1) young people's 'Relationship with Reality' ( - this is a new concept proposed by this thesis - ) which is characterised by the content, intention and effect of an individual's accumulated cognitive and behavioural traits and to what extent these traits invest in real-life or distort or avoid it. 2) young people's sense of having an 'Occupational Identity'. 3) young people's experience of Careers Education and Careers Guidance. 4) young people's experience of being 'mentored'. The thesis explores whether these factors are self-reported as potentially important in the lives of some young people, and whether such self-reports differ significantly between individuals. A cross-sectional, retrospective comparative study of 18 to 22 year olds is presented, in which non-randomly sampled participants were assigned to three groups according to their apparent levels of measurable achievement (academic, professional and extra-curricular): High-Achievement, ModerateAchievement, and Under-Achievement (Imprisonment). As part of an initial exploration, 50 HAs and 18 UAs were each interviewed for two hours; a 75 minute self-completion questionnaire was then administered to a new set of participants: 68 UA individuals (Imprisoned Young Offenders) 75 MA individuals (Undergraduates) 94 HA individuals (Undergraduates) The Eysenck Personality Questionnaire and also the Short Imaginal Processes Inventory (a well-established measure of daydreaming) were administered among 50 UAs and 50 HAs to gauge the possible overlap of these established scales with the proposed concept of a 'Relationship with Reality' personality dimension and its component factors. Only moderately low correlations were found. It is acknowledged that adequate levels of validity and reliability are difficult to achieve when investigating the self-report of sensitive and complex issues, and that generalisations cannot be made from a non-random sample. With these caveats, the findings support the concept of a Relationship with Reality personality dimension, and suggest that all 4 factors studied in this thesis may be amenable to scientific research, are conceptually related, and were self-reported as potentially important in at least a substantial minority of the participants' lives. The thesis is inspired by and is integrated into a body of existing literature that includes psychoanalytic, humanistic, cognitive and behaviourist perspectives on 'forensic', 'normal', and in particular 'high-achievement' psychology and psychiatry from Britain and the United States. exploration, 50 HAs and 18 UAs were each interviewed for two hours; a 75 minute self-completion questionnaire was then administered to a new set of participants: 68 UA individuals (Imprisoned Young Offenders) 75 MA individuals (Undergraduates) 94 HA individuals (Undergraduates) The Eysenck Personality Questionnaire and also the Short Imaginal Processes Inventory (a well-established measure of daydreaming) were administered among 50 UAs and 50 HAs to gauge the possible overlap of these established scales with the proposed concept of a 'Relationship with Reality' personality dimension and its component factors. Only moderately low correlations were found. It is acknowledged that adequate levels of validity and reliability are difficult to achieve when investigating the self-report of sensitive and complex issues, and that generalisations cannot be made from a non-random sample. With these caveats, the findings support the concept of a Relationship with Reality personality dimension, and suggest that all 4 factors studied in this thesis may be amenable to scientific research, are conceptually related, and were self-reported as potentially important in at least a substantial minority of the participants' lives. The thesis is inspired by and is integrated into a body of existing literature that includes psychoanalytic, humanistic, cognitive and behaviourist perspectives on 'forensic', 'normal', and in particular 'high-achievement' psychology and psychiatry from Britain and the United States.