There are so many good ideas in this thread already.
I think for me, the issue of engaging people about digital privacy (and security) is similar to engaging people about any important topic. Lots of people in my social circles are frequently talking about community. I think digital privacy is a community issue, and specifically a community safety issue. If the vast majority of people continue giving consent to governments and big tech to monitor our every move, manipulate, and control us, there’s not much the minority of people who currently choose to resist mass surveillance can do about it. So, I actually view this as an area of activism, and from some of the other viewpoints presented here already, it seems like others are also taking something like an activist approach. I believe this is warranted, but like all activism it needs to be approached skillfully. There’s no checklist you can create that will explain how to do activism well or communicate kindly and persuasively. There are thousands of books on those topics. Improving our skills in these areas comes down to trial and error, it comes down to humility, and it comes down to practice.
For me, activism at its core comes down to motivation and inspiration. People are much more likely to buy into a cause if you can inspire them to do so. If you make people feel bad about themselves, they will just think you’re a jerk and create walls between you. If you can link why digital privacy is important to values that people already have and then give them some actionable steps to take that they’re likely to have success with…then you can move people from a place of inaction to a place of action. You’re unlikely to be able to change people’s values. If someone actually doesn’t care about this stuff, it’s unlikely you’ll be able to change that. Spend your time on others who do care, but just aren’t taking action yet.
I think it’s important to remember that people who currently use big tech products don’t necessarily do so because they don’t care. Those companies spend hundreds of millions of dollars on literal brainwashing that tells society that their products are harmless, or even beneficial. They also spend hundreds of millions of dollars having PhDs in psychology make their products as addictive as possible. Brainwashing is real, and it’s incredibly powerful. Addiction also is incredibly powerful. (I say this as someone who’s deeply experienced both.) To be effective, I think we need to acknowledge that many people are using big tech products (especially social media) because they are addicted. I mean this literally. In cases of addiction, shame and pressure are usually not helpful. These situations require empathy, care, and support.
I’ll wrap this up soon. Basically, I live my life, and my privacy journey in a way that works for me. What works for others will be different, but in my privacy journey, I focus on testing and implementing solutions that might also work for others who are less tech savvy. This means I focus on stuff that might not be the 100% best choice but is a balance of efficacy and user friendliness. This means recommending people something like Proton vs. self hosting email (I know this is an extreme comparison, but I’m just trying to illustrate the point). We live in a technological world. People often discuss tech, even if they aren’t super into it. Stuff like someone asking if they can add me on Instagram is an opportunity to tell them that I don’t have Instagram and maybe like two sentences about why. These conversations happen slowly over time. Eventually people who care actually start asking me what more they can do. For that, I either direct people to this site, or I have prepared a short checklist for people, as well as like a fifteen page document that explains more rationale and nuance about some of the privacy solutions. (The longer document is obviously not for everyone and is not a first step, but people are starting to ask for it more often. About five people asked me to send it to them this week, for example.) I have other friends who are hosting like essentially small consciousness raising groups among friends where they cook a meal and give people an opportunity to ask questions.
There are all kinds of cool ways to help those in our lives move from a place of inaction to a place of action. Be creative and humble about it and just keep practicing.