In my almost twenty years as a professional programmer I’ve tried to guide my career using two phrases: “we’re not losers, we’re choosers” and “luck is the intersection of skill and opportunity.” Armed with this mindset I’ve been able to turn what started out as a job building a web site for a small company that sold CD’s to professional DJ’s into a very rewarding career that have given me some memorable experiences. In this talk I’m going to share my journey with you and highlight the role that getting involved in open source software and community organization let me go from programming as a job to programming as a career. I’ll talk about my approach to skill building, job selection, and how being able to take advantage of what life presented me allowed me to be Grumpy and happy.