Minority groups are the fastest growing demographic in the U.S. In addition, the poverty level in the U.S. is the highest it has been in the last 50 years. We argue that the community needs more research addressing this user segment, and we present a novel study about how underserved youths react when presented with different UI designs aimed at promoting creative writing. The act of creative writing per se can become the driver of change among underserved teenagers, and researchers should strive to discover novel UI designs that can effectively increase this target group's productivity, creativity and mental well-being. Using MS Word as baseline, our contribution analyzes the influence of a Zen-like tool (designed by the authors and called Haven), a nostalgic but realistic typewriting tool (Hanx Writer), and a stress-based tool that eliminates writer's block by providing consequences for procrastination (Write or Die). Our results suggest that the Zen characteristics of our tool Haven were capable of conveying a sense of calm and concentration to the users, making them feel better and also write more. The nostalgic Hanx typewriter also fared very well with regard to mental well-being and productivity, as measured by average number of words written. Contrary to our initial expectations, the stress-based UI (Write or Die) had the lowest productivity levels.