Quote Originally Posted by Oogiem View Post
I also use omnifocus and I have a fairly flat system of folders. So what f something can fit in several place, instead I just put it where I am most likely to look for it first and go with it.

You will have to adapt GTD to you so create a project to Tweak and adapt GTD to my working style or something that will be a place to put all the new skills you are learning as you do this.
Thank you very much for the additional input. I think these were two of the most important takeaways for myself.

So I've actually been re-organizing things here and there over the past few days and I'm starting to feel a bit better about the organization. For starters, I've gone from about 50+ folders/subfolders down to only twenty or so. I also realized that I had created a lot of single action projects "just in case" that actually never got populated after my mind dump. This seemed a bit odd, as if I was creating additional work for myself before I even had something tangible to populate it with.

As it stands here are my High Level Folders...
  • Family - Anything relating to my wife, kids, parents, siblings, etc. previously this was a folder called "relationships" but I decided to break it out temporarily into Family and Friends.
  • Home - Tasks relating to my home itself. Chores, Maintenance, Landscaping, things that need to be done with the house itself. I've also lumped tasks relating to my vehicles here as well. I've seen some people label this folder "Owner" which makes a little sense but feels like it could potentially get a little muddy. I own several things, what does and does not make that list?
  • Finances - Pretty straight-forward, anything regarding money. Retirement accounts, bills, insurance, taxes are all under here.
  • Work - This one is a little tricky but for now I keep it strictly to tasks that revolve around things that need to get done at work.
  • Hobbies - My "fun stuff" including Brewing, Photography, Gaming and Reading. Things that I do for entertainment.
  • Career - This sort of ties into "Work" in terms of trickiness. I've separated these out for now because I sort of see them separately. Work are things that I have to do as a designer, but my career relates to things that I want to do on my own as a designer. This relates to things like Networking and Personal development to some degree (Learning C#, Unity, improving Math skills). However It's still a little fuzzy how these things should be setup.
  • Health & Fitness - Anything relating to physical activities I take part in, Jiu-Jitsu, CrossFit, Hiking, Running, etc.
  • Travel - This one is a little weird as well for the moment. I had initially thought of putting it under Home or something like that, but my wife and I are transplants from the midwest living in Colorado so we travel pretty regularly to visit our families.
  • Friends - Again, previously this was under a Relationships folder that I had but I decided to break the Family and Friends out into separate folders of focus. I guess we'll see how it plays out.

That's where I'm sitting right now. The inspiration for this new setup came much from the advice posted here and another link that a fellow GTD/OmniFocus user had shared with me... http://andrewminer.tumblr.com/omnifocus

However there is still some work to do/questions to answer regarding a few of my projects and organization.
  1. It's obvious I need to utilize some sort of Someday/Maybe list for certain projects. However, I'm curious if I should just create an entirely separate folder for all the goals/projects I hope to tackle someday, or if I should have something for those within each of the high level folders themselves (Someday/Maybe for Home, Finanaces, Hobbies, Career, etc.)
  2. Work, Career and Personal Development sort of seem to blend together. I work as a designer and I have tasks that need to be accomplished there, however I have career aspirations and side projects that exist outside of my everyday 9-5 work schedule. I have things I'd like to accomplish in hopes of being a better designer. These are things that I need to learn though, so they could potentially be labeled under a Personal Development folder but again, they're more focused on my career/role/"hat" as a designer.
  3. There still seem to be a few holes in my structure when thinking about certain projects though. Learn Guitar, for example is one that I have a difficult time placing in this hierarchy. I don't really consider it "Personal Development" because it's not something really needed or necessary in my life, it's more of a "hey that would be cool!" thing. Also, I'm hesitant to label it a hobby because it's something I don't yet know and I'm not even entirely sure it will become a hobby. Maybe I don't enjoy it. Maybe I don't have time for it. Maybe I can't afford the lessons. It feels like I'm missing some sort of High Level folder to classify projects like this under. Another example might be a project to learn Japanese. Something I've always wanted to do, but not entirely necessary.
  4. Then there are several 1-off sort of tasks that don't really seem to fit into any particular area. Again these are things that don't really NEED to be done but that I'd like to do eventually or would be nice to do. One example is organizing the NAS I have at home. It's not really something that has to be done, but I feel the need to organize all the files and data there for clarity's sake. Other tasks would be things like research building a new PC for myself, organize my bookmarks on my various PCs, checking in on things that I've lent out to friends. These just feel very nebulous in terms of categorization and I'm not sure where I should stick them.

I can't thank you all enough again for all the help you've provided thus far. I'm sure I'll continue to have questions and I'll continue to post them here, if for nothing else than the fact that it sort of forces me to think in detail about what my problems are so I might better understand how I can fix them on my own. As always, thoughts, feedback and critiques are always appreciated.