【Abstract】 The ever progressing technology is no doubt beneficial to mankind. However, the current inventions derived from new technology is not thorough enough to cover the needs of more focused groups. More importantly, students often find themselves hard to go beyond passively receiving information and stretch their own ability to become active drivers of positive change by channeling curriculum to real life. This is where innovation and creation of tailored applications set in. This talk, by a group of three students from Dunman High School, Singapore, serves to allow people to better understand the needs of high school students and how Python can be used to benefit them. Examples based on the authors' personal observations and experiences together with illustration of procedures and real-time demonstration will be presented to show how Python can be thoughtfully utilized as an inventive computational thinking and practical problem solving tool to enrich the lives of students. Through our sharing, we would like to inspire more ideas on developing Python applications of close relevance to students and hopefully, encourage more students to use Python to actively improve their school experience. 【Outline】 Brief description of current high school students' school life in Singapore. How technology has improved their quality of life and in what other aspects can further progression be made by using Python. Case Study 1: Observation: Global aging population due to declining fertility rates despite students' increasing open-mindedness Problem: Lack of opportunities to develop healthy relationships from young Proposed solution: Crushes (Google App Engine in Python) Case Study 2: Observation: Lectures being a norm in Singapore high schools as preparation for university Problem: Students take blurred pictures of the presentation slides as they are unable to catch up with the pace of the lecture Proposed solution: Blurred Words Recognition (OpenCV) Case Study 3: Observation: Crowded school canteen during recess time Problem: Many students, being unaware of how long they have to wait, queue up for a specific stall, causing long waiting time and inconvenience Proposed solution: Canteen real time monitoring (Raspberry Pi) Conclusion and future work