In our quest for "best practices", we often forget that what works brilliantly in a large software company might fail spectacularly in a small to medium size business or startup. Practices that literally save lives and improve quality for one team can be a waste of time for another. This talk shares at least twenty-five contextual elements (references to them online will be shared, we will only cover a few during the presentation) that can impact everything from your choice of software methodology to the amount of time a developer should spend trying to make a function run faster. Functional requirements, business regulations, security demands, deployment frequency, and architecture, are just a few of the elements that should inform our technical decisions. Should you use TDD? Should you provide estimates? Should you automate deployments? Should you hold retrospectives? All these questions and more can be answered once you identify your context. Through examples based on real-world experiences, research, and learning from others, you'll gain new perspectives for evaluating your unique development context and making decisions that work for you, rather than blindly following what worked for someone else.