Imagine you could go back in time. What advice would you give your younger self about how to do Java Web Development in a simpler and more effective way? What did you learn? What would you do differently? What would you like to forget? In this talk we will go back in time and give my younger self some advice on building a crazy web stack that I’d find shocking back then. A plethora of web frameworks, DI containers, template engines, build/deployment tools, dependency managers, web servers and testing strategies. Modern developers have more choice than ever before. I’ll share my thinking process and explain how my decision making has changed over time. With a little help from behavioural scientists, psychologists, hot dog eating contestants and my programming mentors we’ll learn how to think like a freak.