I like this question as I have had an interest in design for many years, but largely hired designers to work for me, and focused on technology.<p>One thing that separates good designers from hacks (in my opinion) is their appreciation of the history of design. Say you take your text, shrink the font down, and then jam the paragraphs far away from each other in a two column layout leaving a giant gutter (is that the right word?) in the middle and no left or right margins. That's (whether you want to or not) referencing a period in design history; if my memory serves, starting with some reasonably high-concept magazines in the late 1960s.<p>Same idea, but add thin borders as if you cut the text out of a block of paper, rotate randomly and slightly, and you're referencing fanzines of nearly the same era, a little bit later.<p>Now, distress the text horribly, and make everything bigger like you photocopied on 'enlarge', and you've got '80s punk.<p>Now, sharpen filter it all, crisp the whole thing up, stylize the borders and cut-aways, choosing a font with built-in crispy distressing, add a muted dark distressed background with a large image pattern (and probably a little pink) and you've got some sort of 2010-era crispy new proto-punk / ironic nod to punk design.<p>All that to say, you still want to have some understanding of the 'rules' of design, and typography, but they will be nearly worthless to you without some experience of the mental and emotional connections people make with existing significant design movements.<p>Luckily, this experience is pretty easy to get. <a href="http://www.designhistory.org" rel="nofollow">http://www.designhistory.org</a> seems pretty cool, although I just found it for purposes of writing this response.<p>With some of that experience, you will be able to 'parse' design in a technical way alongside your own artistic sense -- and since you're a technologist, you'll be able to understand how the changing technology allows new design looks to spread as well on the web, and that will put you ahead of 95+% of 'designers' on the web. Early web 2.0 was puffy letters, reflections, and large fonts for forms -- all this enabled by browser changes, and design needs of the time.<p>Late web 2.0 looks like we're going to have a lot of rounded boxes, shadows, and browser-based gradients, since those things are getting easier to do; whether or not that's what happens, I will be able to assess the online designs when they come about with some sense of what's come before, and appreciation for what people are doing now.<p>On Typography: all this goes for typography as well, one of my pet nerdy subjects. I really love The Elements of Typographic Style by Bringhurst. Design's 'rules' are far less codified than typography's rules; despite that, there continues to be amazing work and amazing font design happening, in fact, maybe more and more high quality font design. A thorough understanding of typography is a great joy for anyone who reads, in my opinion. Check it out. <a href="http://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881792063/" rel="nofollow">http://www.amazon.com/Elements-Typographic-Style-Robert-Brin...</a><p>p.s. I was thinking about what design group HN falls into in my head while I wrote this, and I decided "neo-Greenspun". Thoughts anyone?