I also try to find a compromise. If we're talking pragmatic, as opposed to ideal, my suggestions in the current environment are:

1) Be offline as much as possible. I have banished the webbrowser from my phone and tablets. The main computer is completely airgapped; I keep an old laptop around to go online. But I installed an app called Self-Control and use it in whitelist mode. I keep a separate To Do list for things that require internet access and when the time I set in Self-Control has passed, I do all my "internet errands" in one go. Usually does not take more than 1-2 hours/ week all in all.

2) Since you care about privacy, you already do all this but for completeness sake: ublock, ghostery, etc. are your friend. I also use an app called Little Snitch. Very useful! Obviously, I don't approve of Facebook, Google etc. but I actually went one step further and block all their properties in Little Snitch. No beacons, "like buttons" or supercookies for me, thank you.

3) Even with (2), I avoid the web as much as possible. In fact, with the exception of HN, I'm usually not on the web anymore. For news or some light magazine reading, I download the PDF editions (or have them sent to my email). For documentation and manuals, I use an offline reader called Dash. When I want to watch a video, I use youtube-dl (on my "internet groceries day"). For ebooks, I have a dedicated reader that is completely offline (needless to say, I do not sync with "the cloud"; Marvin is an excellent alternative to iBooks for reading epubs). In general, all my media library is local: Music, movies, TV shows, magazines/newspapers,…. I don't do streaming, I don't do "cloud". Storage is cheap, why give up your privacy for nothing? Unlike fking webpages, PDFs don't track your reading/thinking behind your back, you can annotate them if you want, and overall I think they offer a better reading experience compared to a webbrowser, esp. on a bigger tablet like the iPad Pro or (haven't tried but should be the same) Surface. Since I really, really dislike ads (= being told what to think, how to feel, etc) I even paste over all the ads before I read a magazine or newspaper! After a bit of practice, I can do it now in about 1-2 minutes per PDF. It's a small price to pay to keep these mercenary memes from infiltrating your mind.

4) For email, I switched to Protonmail. I understand that the NSA can hack them if they really want, but that's okay, they are not my threat model. My goal is to keep what I write in confidence from being read by Google/Gmail, Microsoft/Hotmail etc. So I usually send "pseudo-encrypted" versions to such addresses (where the reader has to enter a simple password, just to keep it from being machine-read as per default). Alternatively, I might send an encrypted PDF if it's more formal or important.

5) For more fluid, extemporaneous communications with friends and family, I mainly use iMessages. In general, Apple is your sole remaining friend among the mainstream vendors (and like I said, I'm talking pragmatic here, not ideal). If someone is on Android, there's still the cross-platform Signal app. Facebook-owned Whatsapp is an obvious no-go. I found that people usually can understand if I explain it to them why. It's like second-hand smoking, only worse. If they insist on exposing me to their "smoke" (or, negative externalities), then I cut the contact.

One last comment: If you feel like you are getting "de-synchronized" from your environment, consider that that might actually be a sign that you are detaching from the hivemind and starting to think on your own again. It's not a guarantee that you will be more (or more often) right than the crowd but at least you have a chance of thinking an interesting thought or developing your own good taste, of not being trite. So take courage! :-) I found that with a bit of effort, it's possible to keep some measure of privacy and make it a bit harder for these people to psychologically profile and manipulate you.