Simplicity is one of the most important principles of design. It has been a pillar of design thinking for a very long time—long before the advent of human factors, usability, and user experience. But, realistically, simplicity isn’t always simple. Commercial software, enterprise applications, software as a service (SaaS), and other highly interactive applications often have no choice but to do a great number of things, because they support a range of real world tasks, some of which are complex. In this presentation, we will discuss what to try when removing functionality or features isn’t an option. We provide practical questions to ask when deciding whether and how to simplify an application. And we summarize proven design techniques to use when simplifying applications, illustrated with examples from real projects.