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After the Snowden revelations of 2013, we learned that the NSA's global internet surveillance program XKeyscore was flagging people that read...Linux Magazine. That's right. The NSA would place you on a special high-priority surveillance list for taking an interest in one of the only operating systems that isn't known to have a backdoor. But it didn't end there.
You can see in the XKeyscore rules people that searched for Tor and Tails OS software were being targeted. These are programs written for the express purpose of anonymity and avoiding the watchful eye of Big Brother.
There seems to be a common theme here. Big Brother programs automatically targeted people that took steps to avoid surveillance. It's a fair bet to make that people that use privacy tools are still targeted more than those who don't. There's one very good reason to suspect this: Big Brother doesn't need to take a special interest in those that don't avoid mass surveillance because mass surveillance is sufficient to build a full portrait of their lives anyway. It's logical that Big Brother would only need to pay special attention to those avoiding mass surveillance since their privacy is harder to violate.
Thus we end up with a paradox: The more you avoid mass surveillance, the more interesting you become to Big Brother. This increases the likelihood that you'll end up on one of their "extra surveillance" lists and that more targeted methods will be used on you. The less you avoid mass surveillance, the less interesting you become to Big Brother. All else being equal, this decreases the likelihood that you'll get special attention. Blending in with the surveilled masses might give you more anonymity and privacy, in practice. In other words, allowing yourself to be mass surveilled might act as a kind of protection against targeted surveillance.
If you pay for everything in cash where cash payments are uncommon, if you use internet services registered outside of the Five Eyes, if you use Tor and VPNs for accessing the internet, if you use free as in freedom software and encrypted communication apps, if you avoid social media, if you drive a privacy-friendly vehicle when you can afford a newer car, you're going to attract attention to yourself. One of these things on its own isn't a red flag, but combined together, there's really only one thing you can be doing: avoiding mass surveillance. One doesn't avoid mass surveillance in today's world by accident unless you're amish or living in a poor country.
Knowing this, what ought you to do about it? Should you try to blend in or should you avoid mass surveillance and just not care how many watchlists you end up on?
Trying to blend in with the surveilled populace is like giving a thief your money so they can't steal it. If you really want to fight mass surveillance, you should take as many steps to avoid mass surveillance as you're willing to take and don't worry about being targeted. If enough people do this, it will raise the bar on privacy so that only the more expensive targeted surveillance tools will work. Then everyone will collectively have more privacy.
If you or someone you know is doing something illegal and you don't want Big Brother's attention, especially since Big Brother has been known to do nasty things such as assisting with evidence laundering, you might think it's a good idea to avoid mass surveillance only when conducting illegal activities to avoid drawing too much attention to yourself. This strategy is ill-advised for at least two reasons:
Allowing yourself to be mass surveilled on purpose some of the time is the reason the bar on privacy remains low. If all you care about is not drawing attention to yourself and your illegal activities, then fine. But if you care about wider society, then you should raise the bar on privacy by avoiding mass surveillance at all times, not only when engaging in illegal activities.
You contribute to the stereotype that a desire for privacy indicates nefarious activity. It empowers the surveillance state in the current iteration of the crypto wars because Big Brother can say that anonymity networks are mainly used for criminal purposes. If it can be shown for instance that 90% of Tor traffic is used for legal activities then it's (theoretically) much harder for the government to make the case that it should be censored because of drug dealers, money launderers, pedophiles and terrorists.
The only long-term winning strategy for all society is to avoid mass surveillance as much as possible with the hope that others will follow suit. This is true whether you're a law-abiding citizen or a criminal mastermind. To drive this point home, I'll end with a quote by Edward Snowden from his interview with John Oliver on Last Week Tonight:
"You shouldn’t change your behavior because a government agency somewhere is doing the wrong thing. If we sacrifice our values because we’re afraid, we don’t care about those values very much."
This quote was taken from the context of taking dick pics, but it can be equally applied here: Don't accept mass surveillance as reality just because the government might target you for it.
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