I'm lounging in the living room of a vacation home located in the high country of Colorado with a handful of close friends from Boulder. We each work for startups of various sizes and maturity. We've rented the home for the weekend to relax in the nearby hot springs and hike local mountain trails, as well as set aside time from our harried schedules to discuss our hopes, dreams—and startup careers. As the sun sets and the dry mountain air cools, we bundle up with blankets and take turnssharing life updates, which, especially this particular weekend, offer a snapshot into the variety and complexity of startup life.