The narrative—the very nature—of what we have known as work, jobs, careers is changing amid accelerated innovation and uncertainty. To remain relevant, let alone thrive, we must reconsider our structures, styles, skills, values, behaviors, and the external conditions that define them. We must ultimately rethink our relationships with work today, and what it will mean tomorrow, when what we do on an individual plane ripples within an increasingly asynchronous workforce. This capstone assembles a dialogue of eras, of approaches, of methodologies, of priorities, of productivity, and success. At designforwork.org, the online document will evolve, capturing a fluid portrait of our individual and collective futures in a workplace that spans generations, geographies, and technologies. It is my goal to encourage a deeper understanding of work, for the goal of better understanding ourselves, one another, and the coming challenges, opportunities, and disruptions.