The traditional model of education and career transitions is linear, but a better model may be cyclical or overlapping. Learning happens both formally in schools and informally in everyday life. Success and happiness are more about balancing relationships, purpose, and self-improvement than financial achievements. To learn and grow, one must try new things, get outside their comfort zone, and experiment through potential mistakes. The future involves humanizing technology and facilitating shared global learning to develop leaders who mentor and coach others.