When does a person feel most alive/healthier, and what can organizational leaders do to make work an anchor of psychological well-being? After listing the salient characteristics of a healthier individual, it is suggested that attention must be paid to the underlying forces, particularly the higher-level motivational need systems of attachment/affiliation and exploration/assertion. Leaders wanting to get the best out of their people must pay attention to these systems and engage in activities that can ensure congruence between their employees’ inner and outer realities. They must also create conditions that foster a sense of competence, encourage personal development, enable self-determination, and imbue confidence. Meaning and motivation are central to an individual’s sense of self-fulfillment. And, as it is our search for meaning that makes us truly human, an assessment tool—Meaning in Life Questionnaire—is offered that can enable the reader to self-assess how effectively they are dealing with the five pillars that comprise “meaning”—belonging, purpose, competence, control, and transcendence. The chapter ends with the challenges and aims of executive coaching based on the psychodynamic-systemic approach. Ultimately, life is about the journey not the destination. Most obstacles are human-made and often self-made. If we want, we can change them.