I was lots sloppier, when I started going dark, in the late 90s. I even talked about it in meatspace. But gradually, I compartmentalized more and more.
Anyone can do that. Just gradually disappear as your meatspace identity. Or restrict it totally to career, and friends and family. Ideally, keeping those separate, so your friends don't hose your career.
And then create and develop an ~anonymous persona. Or a few of them, one for each ~defined set of interests. And just don't talk about it in meatspace. Or mix stuff among personas.
And because I use nested VPN chains, no individual VPN provider can correlate stuff from different personas. It's the same distribution of trust thing that Tor does. Albeit far weaker, because I'm only using several VPNs, and not thousands of Tor relays. But still, it'd take some effort to obtain logs from enough VPN providers.
If I care more about keeping personas unlinked, I make sure to use different VM OS, given the risk of WebGL fingerprinting. Because using the same virtual graphics driver and physical GPU gives the same fingerprint.
If I care even more, I use Whonix via nested VPN chains. With a different Whonix instance for each persona, or group of somewhat linked personas.
If I care lots more, I do all of that, using a different host machine, on a different LAN, with different nested VPN chains.
Apart from the privacy benefits, however, I feel that it is a net negative, because it prevents me from sharing here a lot of interesting stuff that happens in FOSS projects I am a part of, or at work.
A good social network should allow you to post under a different identity, while still tying-in some attributes of your other identity to the new one.
For instance you could easily share your real life experience under another name, while still proving you have between 1000 and 1500 karma on another account. This fixes the problems of traditional throwaway accounts (lack of credibility).
The only places I see this idea explored is in crypto(currency) projets. This is great because it will be robust and reliable, but the patterns could already easily be applied to today's centralized social networks.
Like this: https://www.ivpn.net/blog/wp-content/img/Chains.png
VPN4 is OpenVPN via Tor.