Schematic and Circuit Design
I got into circuit design with a the help of a friend. He would show me his home made boards and I would go to him with questions as I made mine. I guess this is the order you will need to go in to get comfortable with circuits.
1. Learn the schematic symbols - Radio Shack has a decent book called "Electronic Formulas, Symbols and Circuits" it is a beginners guide to learning the symbols and seeing many common circuits. It is a way to learn through example. Radio Shack # 62-5031
2. Now that you can read schematics it is time to start drawing them. There are really two pieces of software that the DIY world uses for schematic capture. Make some schematics with one of these programs.
A) gschem - www.geda.seul.org/download.html - This is great software if you come from a background of using only open source code and are really a UNIX person at heart. If this is not the case move onto the next option.
B) eagle - www.cadsoftusa.com/ - Eagle is sort of shareware. You pay for the software once your circuit boards are larger than 4" in any direction. It is very popular in the Make world.
3. Schematics can be exported into PCB (Printed Circuit Board) layout programs like PCB for gschem and eagle has its own built in board layout. The idea being once you have laid out the logical connections and parts in the schematic side you then need to place each component.
That is all you need to work on for becoming comfortable with making circuits. It will be frustrating to use the software at first just because there is so much to get used to, but if you spent some time looking at lots of schematics in the Radio Shack book it will make things go smoother.
The next step after learning how to design and layout circuits is to have your circuit boards printed. I use barebonespcb to print my boards. They are in your area (Colorado) and don't charge much if you are doing runs of 10.
Finally you need to get into programming microcontrollers to start having a lot of fun. That is another hurdle, but if you have some experience programming software it will greatly reduce the learning curve.
Let me know how this goes for you and feel free to ask questions. This is sort of like how to become a electrical engineer over spring break.