It's certainly useful to know how things got to where they are, but it's not always necessary. Even in history circles people debate how important history is if

It's certainly useful to know how things got to where they are, but it's not always necessary. Even in history circles people debate how important history is if the lessons can be handed down via knowledge of good-practices. If you want to know how good you've got it now, I'd start with building a site that uses entirely static content. After you've got a few pages, make a change that affects all of these pages. You'll see how static pages lead to redundancy and a lesson will be learned. Then setup a cgi based commenting system in either c or perl, which would arguably represent the start of interactive web sites. From here, you'll see that there are things you'd like to store, like a username, and you'll understand how frameworks make following a user easy. Once you've done these two things, add some database support for the comments and a way to search the comments. I'd say, after these three things, you'll have a pretty good understanding of how slick things like rails are and you can go back to being as productive as possible with respect for the problems it's solving. There's definitely more to learn on this topic, but it might border on distraction at this point.