With the use of case examples, seven major life themes emerging during executive coaching are highlighted: loss, interpersonal conflict, boredom, addictions, developmental imbalance, life balance, and the primacy of meaning. It is important to recognize these themes for formulating frames of understanding and interpretation. Loss, and its depressive consequences, be it past, present, or impending, can be long-lasting and can encompass the business environment via job loss, community loss, demotion, retirement, and disappointment. Interpersonal conflict can occur within intimate relationships or between work colleagues. Boredom can have underestimated implications for those who find their job satisfaction progressively diminishing. Addictions cover a vast area, with many triggered by frightening experiences that have been forgotten. Developmental imbalance is when life expectations remain unfulfilled or failing to cope when changing social roles. The final two themes inevitably reoccur among the most senior executives: life balance—including how to rearrange their priorities—and the primacy of meaning. What can you do to give your life meaning? Here, the stealth motivator—death, and our anxiety about it—comes into play. To create a full and interesting life, it is essential to create meaning. Fundamentally, the only impossible journey maybe the one we never went on.