Under ideal circumstances he would have "known" the article was great and really important; he would have heard it got deleted; he would have gone to wikipedia and found short simple clear advice about what is included and what isn't included. Preferably in one place. Then he would have realised that the article was not a good fit for Wikipedia, but he would have met some people who were not fucking wingnuts and who encouraged him to contribute and he would have found some other articles where he starts making gentle contributions.

Instead, that information is scattered over a few different pages (and thus there's lag between them when there's a change); there's differing standards for different things (Elected national politicians are automatically notable because they're elected, Olympic athletes are not notable.) Deletion process is incredibly bitey; I don't care that people doing deletion have floods of shitty articles to plough through, they should realise that destroying (even justifiably) someone's work is going to be hard for that person and is not going to encourage them to contribute to the process, and that this is an (a tricky) opportunity to get new editors.

Combine this with weird rules about other stuff (The software stops me creating this name (which means some things are hard coded), so I read the rules, and create another name, and get newbie-bitten by some over enthusiastic 17 year old who claims that my real name is offensive or that the pseudonym I chose instead is "confusing" or whatever. My name goes in front of how ever many different username discussions they have now, where I argue my point and am "allowed" to edit.)

There are huge differences between things like the five pillars and the rest of the obscure processes.