Bill Flagg spent 20 years building 5 incredibly successful tech businesses, then unexpectedly sold them all. To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life. Two years ago, Bill moved with his family from Colorado to Portugal with no plans of returning anytime soon. Today we discuss this transformation, his craving for inspiration, creativity, simplicity, and soul-nourishing experiences. Bill Flagg - Linkedin: https://www.linkedin.com/in/bflagg/ _____________________________________________________ TIME STAMPS: 00:00:00 - 00:03:36 - Introduction and Background 00:03:36 - 00:04:31 - Transition to Sabbatical 00:04:31 - 00:06:24 - Loss of Passion and Creativity 00:06:24 - 00:07:45 - Embracing a Pause for Creativity 00:07:45 - 00:11:11 - Living with Uncertainty 00:11:11 - 00:16:16 - Rediscovering Life in Europe 00:16:16 - 00:19:33 - Letting Go of Past Identities 00:19:33 - 00:26:18 - Challenges with Possessions and Ownership 00:26:18 - 00:29:03 - The Root Cause of Post-Exit Struggles 00:29:03 - 00:31:13 - Embracing Retired Life 00:31:13 - 00:31:38 - Family Perspective and Legacy 00:31:38 - 00:33:22 - Final Thoughts