A) At what point? From the beginning. You said it yourself, you go through notebook pages with UI before even writing code. You need to have a structure in plac

A) At what point? From the beginning. You said it yourself, you go through notebook pages with UI before even writing code. You need to have a structure in place before you begin anything. Sure you can morph it as you go, but you need a direct connection to what you are trying to achieve. At the same time you're coding some functionality, you should be thinking about how this is going to be displayed. It's of course not necessary to do any of the graphics or styling at this point, but it works better if you give it some thought and try to form some type of layout and broad design ideas as you go. It's worth doing photoshop mockups when you reach a point where the application development can benefit from being graphically beautiful (which can vary immensely... every project is an island). You draw the line at the first moment you can. If and when you reach a minimum point where your application could be used by the masses, freaking ship it. You can fix and add features later, but the moment you have enough to ship that thing out the door - do it. Software is never "finished" anyways, so you'll need to keep going at it anyways. B) Almost all the information regarding UI usability and user experience holds up regardless of age. The concepts are the same now and when it was written. There are also a LOT of resources written in the last few years, so I'd disagree that all the information is old. In any case, it really doesn't matter, you're still going to need to come up with your own conclusions for your specific case. No amount of UI/XI reading is going to allow you to skip having to do you're own testing and to draw your own conclusions on what works for you. C) In the web industry the designer/artist is generally also the guy that codes your Html/Css/Jquery. A front end developer is generally the person that designs interaction and pretty screens. The back end guy is the one doing the algorithms, database work, etc. You can outsource everything, though the results are usually not even on the same league as the worst results you can get from a good team that clicks working together. You can always have a contractor come in and work with you or your team if needed, and that can sometimes be a better compromise than outsourcing per se. D)I started as a programmer at an early age, but I was also an artist. What put me on that path is that I wanted to know how to do everything. From Photoshop to Rails to C to server security and deployment. I started learning by doing. Don't look for guidance man, just work on a project and when you need something you're not comfortable doing, freaking do it anyways. Need to do graphics, test layouts, a/b testing? Read on it and start doing it asap. At some point you'll become decent at it, and then one day you're actually good at doing it too! Obstacles? There are no obstacles, only challenges. Challenge yourself and you'll come out a winner.