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This is a fundamentally important questions because it greatly impacts the defences you apply.The measures you take to hide your identity from, say, a significant other or general member of the community may not be sufficient to hide from government oversight.I'd also like to encourage those who do give online anonymity a lot of thought to leave their suggestions in the comments section, keeping in mind the target audience being your normal, everyday people.Let's start somewhere extremely practical yet often not acknowledged in discussions on privacy and anonymity.If you don't want your participation in certain sites going public, then this will be useful.If you're a budding Edward Snowden then you'll need to go much, much further.
Gmail (or equivalent - there are many other free online mail providers) gives you a full blown email address and obviously requests a lot of info in the process.
Let's jump into it, and we'll start somewhere simple.
The easiest personal identifier that will match you to a site is your email address.
It's a well-known identity attribute, it's unique to you and there are multiple ways of discovering if it exists on a given website. Also consider how you fill out the following form when you create the account: These attributes won't show up on other sites where the address is used, but they can start to surface in other places.
One of those ways is obviously when data is breached from a system and all the email addresses are on easy display: address. It's not always that explicit either, for example Ashley Madison returned slightly different responses which could still be observed. For example, when doing a password reset: If you authenticate to another site using your Gmail account (social logins are increasingly common), then you may be prompted to share data attributes such as your name with that site.