Numerous studies have concluded that people do claim to care about their privacy, yet we are surrounded by people who opt for outdated devices, default settings, invasive social media, and targeted advertising. Why is that? Many of us struggle with conveying the value of privacy to those around us, and sometimes even struggle with getting them to use basic tools like a better browser or a different messenger. This talk aims to explore some of the obstacles people struggle with when confronted with privacy, and some of the "dos and don'ts" for those of us trying to spread the message. From the people who argue “I have nothing to hide” to those who claim to care yet simply don’t act, we will explore a variety of psychological phenomenon that explain this behavior and some of the roadblocks – real or imagined – that make people hesitant to make the switch to more privacy-friendly behaviors. We will also explore some commonly suggested tactics to sway these people and explain why they do (or more often, don’t) work, what does work, and why it works. Audience members will hopefully leave with a better understanding of how to engage with non-privacy people in meaningful and effective ways that leave the person more open to adopting privacy-friendly changes in the future.