Holy smokes, you guys are really awesome! Thank you so much for the quick and in depth responses! Very helpful stuff.

@vbampton - Looking at things from a series of "hats" is a refreshing viewpoint but still somewhat difficult to wrap my head around. In my first attempt at organizing my folders, I looked at things from an "area of focus" perspective. At a high level, I see my life broken up into three separate areas; Home - Personal area of my life dealing with my responsibilities as a husband, father, homeowner, etc, Work - The part of my life dealing with things regarding work and myself as an employee, Personal - all of MY stuff, hobbies wishes, dreams etc. However, when I started to think about this stuff in terms of High Level Folders, I started to feel like it wasn't granular enough...and I went a little overboard. I ended up creating 6 Top Level Folders (Home, Work, Finances, Travel, Relationships, and Personal) that have a vast number of subfolders. All said and done...I have about 50+ Folders and Subfolders...not even joking. I'm not entirely sure why but I felt compelled to eliminate any overlaps and try to get down to the most granular level. This made sense when I started to look at all my projects from the Folder Hierarchy structure, however now I just feel like things are OVER organized and it's too difficult to find anything.

I'm having a really hard time finding some middle ground here but finding it really difficult to do so. I have a hard time processing the folders when there's so much potential overlap. Perhaps this is something I need to just "get over" but it's tough for me to do so. If I managed to break things down into just Home and Work, I'd be highly compelled to add a thousand subfolders.

You definitely have a point about the projects though, and this is a point that vicve and Gardener also touched on as well...as much as I'd like to think I could move all those projects forward at once I certainly don't believe it was something that was ACTUALLY going to get done and probably ended up being more of a "setting myself up for failure" situation than it should have been. I think the key moving forward is definitely going to involve picking a project or two and putting them on the front burners while the others are put in the back Someday/Maybe/On Hold until I want to do something about them. There are still a few concerns regarding unexpected actions however. For example, Becoming a Better Brewer and Becoming a Better Photographer are two high level goals/projects. Brewing and photography are two activities that I partake in somewhat randomly from time to time. Figuring a way to balance this somewhat randomness with the system is another thing I feel needs some clarity.

I've done a fairly good job with adding things to my inbox as it comes to mind, though there's still a part of me that gets a bit of anxiety when it comes to processing these. I can only hope this has to do with the poor "foundation" I've setup for myself regarding Projects and Contexts.

I've signed up for GTD Connect and look forward to checking it out a bit more, though part of me hopes to avoid over researching some of this stuff and spending all my time doing that instead of putting my foot down and moving forward with implementing a solid system.

@vicve

Your New Years Resolution example is spot in. In fact, that's exactly why I picked up GTD and OmniFocus at the beginning of the year, I set a goal to try and make myself more productive this year! Trying to work that brain muscle instead of my flabby arms...for now.

I first ended up buying OmniFocus because while I liked the core concepts of the GTD system, some of the implementations described in the book (filing cabinets, paper trays, folders, etc) seemed a bit out of date for myself. I was really looking for a solid digital system I could track so I went with OmniFocus.

I really appreciate you bringing up the whole "being OK with NOT doing something" aspect of GTD. I think it's easy to forget and to be honest it IS something I let slide. That's something I certainly have to work on. As someone who constantly procrastinates and has always put off trying to complete my goals, putting things "On Hold" sort of feels like a defeat, that I'm just going to let them sit there and stew without ever actually doing anything about them. I think I need to find a way to be OK with things being On Hold and really trusting the system, because trying to do everything at once is really just overwhelming me and getting me nowhere.

As someone with so many ambitions I'd be intrigued to see how you went about setting up your high level priorities for your System.

@Gardener

Perspectives are amazing and they make tons of sense. However, I've not really gotten around to using them or setting them up just yet because I'm not 100% confident in the Project Hierarchy Foundation. I can totally see their use and it's like a light at the end of the tunnel, but my brain is consumed by the "half-@$$ed" attempt I've currently got for my Projects and Contexts that it seems wrong to try implementing Perspectives at this point.

As I mentioned above, my Folder Hierarchy is currently...well...ridiculous. I'd love to work it toward being more shallow but my brain seems to fight me every step of the way when overlaps occur thinking, "Well...that could actually be broken down a little further because it's REALLY thing a and thing b..." It's maddening.

I do greatly appreciate the list of examples you provided though. They're helpful for thinking about things in terms of a Next Action and your critique of C# being too big of a goal is absolutely correct. I really should focus on breaking this down into actionable tasks. At that point though, I wonder if it even makes sense to have "Learn C#" as a viewable Project anywhere or if I should just have a folder relating to C#. The over-organized side of my brain wants to have a Main Project called Learn C# with nested/grouped tasks for each of the actual steps I'd like to partake in toward the end goal of learning C#.

Reading is a whole other bag of frustration for me when it comes to organizing projects, as I have both "entertainment/pleasure" reading as well as "research/enrichment" reading that need to be done. That even begins to shine a bit of a spotlight on something some of my high level goals. Be a better Designer is a goal I have that relates to Work, but really has to do with Enrichement and Career development regardless of Work and is something I Want to do because Game Design is important to me as as a hobby. So where the heck does it go?!

I'm going to take a stab at trying to make my project hierarchy a bit simpler as a first step but again, it's a bit difficult to wrap my head around. If anyone else has examples for defining Areas of Focus that worked for them, I'd love to see/hear.