This book brings a character-based, virtue ethics approach into education and coaching to help practitioners, clients, and students pursue contextually flourishing lives. Positive psychology has highlighted the importance of virtues and strengths in applied practice, yet it often overlooks practical wisdom: The ability to navigate real-world complexity, where virtues can conflict or be expressed in excess. Virtues must be applied with balance, neither in excess nor deficiency, and practical wisdom is an essential tool to help navigate these competing values. This book bridges the gap between theoretical virtues and their practical application, to unpack the theory and provide empirical evidence and practical methods for addressing such tensions in everyday life and professional practice. Presenting a structured and philosophically grounded framework for flourishing, this book will appeal to coaches, coaching psychologists, counsellors, educators, therapists, mentors, and leaders seeking to integrate timeless wisdom into their work.