As the nature of work has evolved, the process of career transition and job search has evolved as well. During the world’s transformation from analog to digital, the tenure of an individual’s career went from one person, one company, to one person, many companies. Today, the average person changes jobs 12 times during his or her career. In the digital age, career tools are more ubiquitous, candidates have a broader reach, and communication is instantaneous. Although technology change is generally positive for those in career transition, candidates are expected to articulate clearly what they seek in a position and prepare a polished, concise, and focused statement of the value they provide to their prospective employer. Today, more than ever, candidates are required to provide information quickly and consistently across digital media and in person. This study examines the importance of defining career direction clarity and mastering, or becoming unconsciously competent at, communicating career direction clarity, and effectively telling a cohesive ‘career story’ during the outplacement/career transition process.