At 53, Jessica found herself no longer fulfilled by the medical practice that she had built over the prior 20 years. She possessed an appetite for new activities, new venues, and new horizons. The health care industry was changing but her identity was wrapped up in the enterprise she had created. She longed to move on as her interest had waned but didn’t know where to start. She wanted to work on her terms, impact a broader audience as a speaker and educator, and travel the world with less stress and more free time.