My policy is always to be considerate to other people, never to try to hurt someone's feelings on purpose, but beyond that, I feel like I'm generally being somewhat guarded even when it's anonymous.

It's not impossible that there could be some kind of leak, or that an algorithm could look at what you wrote, and compute some kind of signature based on what you wrote (eg: n-gram probabilities), and match it up with your other online identities. In general, you kind of have to assume that anything you write online could eventually be tied back to your public identity.

That being said, I tend to assume that if you said something your employer might disapprove of, it wouldn't be a problem unless what you said somehow gathered a lot of attention online. For that you'd have to be famous, or stir some serious shit on twitter. Even if the identities of everyone on HN were outed, I'm guessing mostly nobody would care, except if they found out Jeff Bezos was secretly posting hateful messages.

Unfortunately, it's very hard to keep a pseudonymous identify separate from your actual identify for a long period of time.

For example, in general my accounts related to video games go by one identify, while my other personal/professional accounts use my real name-ish. Problem happens when I have a discussion on a game account and want to reference something that I know because of activity in the other sphere. By linking to my real identify, the pseudonymous one has been identified. So, now I am careful what I say on those accounts, too, and I save my controversial opinions for in-person, offline discussions.

Your content isn't anonymous: who you are is distilled from what you say, creating a unique fingerprint. Doesn't matter if you your name is hnaccy or SoSoRoCoCo.

I change details, times, various things, just a little. Whenever I need to make a reference as a citiation, 20% of the facts change just slightly. Sometimes I'm a woman, sometimes I'm from a different state, sometimes it is a different company I worked for. These details don't matter to the content, but there is so much contradiction in my history that I hope to defeat the algorithms. I got the idea from how Firefox defeats browser fingerprinting (or tries to).

I also create new accounts routinely.

However, even HN knows who I am because I occasionally forget to use my randomized VPN, and HN keeps track of you.

I know this because I was banned from an IP address once and had to renew it from my ISP to come back to HN.

That will probably still cause social cooling, because you have to manage and be conscious what you are able to say on different identities. You are essentially training to be less spontaneous and more cautious about what you say in real life.

Employers get sued and sometimes they demand social media accounts during discovery. I decided a while ago that I’m not prepared to quietly defy a court order by trying to conceal an anonymous account, so instead I stifle a lot of what I really think because moral fashions always change: http://www.paulgraham.com/say.html

Many aspects of data collection, however, are not related to posting your thoughts online. As an example, think about ordering food with Uber Eats and the like. What if health insurers find a way to get their hands on that data, and start changing your rates based on what you eat? There are so many services that can't be used anonymously. Personally, I am using online services less and less because of this.

(edit: grammar)

Yet, I am seeing more sites require phone numbers to send an activation code before you can even use or make an account.

While I understand the value of anonymous public communication, I think it comes with a huge "bad-actor" problem that we haven't figured out how to offset.

Anonymity is a problem when it is used to commit crimes and law enforcement seems inadequately staffed to police cyber crimes even when the perpetrator isn't even anonymous or pseudo anonymous.

Do we need something like an Internet "drivers" license for anyone who wants to post content to the public? Analogous to needing a license to drive on public roads? Maybe that idea can be tied into Section 230 concerns? I'm sure there are obvious difficulties, just spitballing. Balancing liberty and safety isn't easy.