The demands of daily work offer few opportunities for workers to take stock of their own progress, big or small, which can lead to lower motivation, engagement, and higher risk of burnout. We present Highlight Matome, a personal online tool that encourages workers to quickly record and rank a single work highlight each day, helping them gain awareness of their own successes. We describe results from a field experiment investigating our tool’s effectiveness for improving workers’ engagement, perceptions, and affect. Thirty-three knowledge workers in Japan and the U.S. used Highlight Matome for six weeks. Our results show that using our tool for less than one minute each day significantly increased measures of work engagement, dedication, and positivity. A qualitative analysis of the highlights offers a window into participants’ emotions and perceptions. We discuss implications for theories of inner work life and worker well-being.