Explore the unconventional path to success in tech and life through this keynote address delivered at All Things Open 2022. Discover how curiosity, play, and seemingly "wasted time" can lead to healthier and more successful careers. Follow Jason Lengstorf's wandering journey from college dropout living in a van to a successful career in tech, as he shares valuable lessons and concepts that shaped his outlook on life. Learn about skill transfer across industries, increased success through exploration, and building more effective teams through empathy and curiosity. Gain insights into how quitting and failure can be stepping stones rather than setbacks, how unrelated skills can create exciting new possibilities, and why not having a plan might just be the best plan of all. Challenge traditional notions of success and career development in this thought-provoking 17-minute talk that offers a fresh perspective on personal and professional growth.