Adolescence is a transitional period in the human life span linking childhood and adulthood. It is a period that marks the departure of a child from childhood to adulthood. As a developmental period, adolescence is a “stop-gap moment” whereby the adolescents undergo changes in their physical, cognitive and social-emotional development for proper adjustment. As such they are expected to weather the stormy and stressful condition of adolescence. The 21st century Nigerian adolescents are not immured to the turbulent and conflicting nature of the adolescence period occasioned by unemployment, uncertainty and gross neglect by significant others. They are daily being assailed and influenced by activities of peer group, the mass media, internet and more recently the social media. Unfortunately, these young people are segregated from the adult society and such segregation serves as an important contribution to deviant behaviours such as cybercrimes, suicide bombing, militancy, political thuggery, school bullying, kidnapping, illegal migration and human trafficking. The process of learning new experiences, examining resources of inner strength and fathom the strength of inner ability should have career guidance input. As young stars who have recently transited from childhood, the adolescents lack the ability to bring their powers to bear most effectively on the solution of the problems meaningful to them; therefore, they need expert guidance if they are to experience a successful adolescence. To this end, proper career guidance should be embarked upon to assuage the 21st century Nigerian adolescents increased concern for the future by assisting them to determine and prepare for career and entrance into the job market. What adolescents need is access to a range of legitimate opportunities and to long-term support from career guardians that deeply care about them. This is a necessary condition that will ensure youth disengagement from illegitimate activities such as cybercrime