[Jables]

First of all, thank you all again so much for the input. I know a lot of this is learning what works for you but I find that I work much better when I'm able to bounce ideas off people and get input along the way. This is all very helpful.

Originally Posted by DrJJWMac

Why the urgency? My process of discovering how
to use OmniFocus in the best way possible for me took a few months to settle. Many excellent (longer term) plans are destroyed in the pursuit of perfection (in the immediate time frame).JJW

That's good to know. I guess my initial concern was just waiting around too long to start taking action. It seemed better to sort of jump into it and figure it out as I go along.

Originally Posted by DrJJWMac

My first thoughts are ... Are you depending too much on projects to define your areas of focus? What would happen if you set up your areas of focus absent any considerations about the projects you have? IOW, what would happen if you first defined fully the areas of your life that provide you with fulfillment (and what that means in each case), and then defined in each area the projects that are necessary to achieve that fulfillment in that area only.JJW

That's a really profound and interesting question that I hadn't really thought too much about. Up until this point, I've just had a lot of "things" that I wanted to get done, for one reason or another. I want to learn Guitar because, well...I want to learn guitar. I want to improve my skills at Lightroom because I like taking pictures with my DSLR and want to take better pictures. I want to learn C# because I think it will help me in my career. When I started out setting up Omnifocus I basically was able to break up my life into three major categories that consume my time, Home (stuff I do around the house or projects involving my wife and kids), Work (anything relating to the things I need to get done at my job) and Personal Time (all of the stuff that interests me or that I want to do with my free time including hobbies, things I'd like to improve on or things I'd like to get better at). Maybe this is the wrong approach. I've seen some Project setups based around the "20,000 Ft" concept of GTD but on paper these just seemed a little odd to me for defining projects from that point. I find it a little odd to think of things in terms of "fulfillment" since there are some responsibilities that I have which frankly don't necessarily give me much fulfillment (other than actually completing them) but still need to be done, Finances, Travel Plans, some Work related tasks, etc.

Originally Posted by DrJJWMac

Are you mixing up the sense of Goals and Projects? To me, a Goal is the driving force behind setting up Projects. I put my "goals" as general statements in a Someday "project" (example: Someday: Action Statement -> learn to play the classical guitar for personal enjoyment). When I review, I can decide whether to establish a project that will help me meet that goal.JJW

Again, this sort of ties into the above but maybe this is my problem. This is the setup I've gone with thus far.

Home (Upkeep, Vehicles, Home Misc, Home Ideas)
Work (Projects, One Pagers, Work Misc, Work Ideas)
Finances (Budget, Bills, Retirement, Insurance, Taxes, Future Purchases, Finance Misc, Finance Ideas)
Travel (Travel Misc, Travel Ideas)
Relationships (Wife, Kids, Family, Friends, Pets, Professional)
Personal (Health, Photography, Brewing, Cooking, Reading, Fitness, Gaming, Game Dev, Creative Writing, Guitar, Productivity, Education)

Originally Posted by Lizard

Actually, I meant literal calendar events, in the Calendar app (or on a paper calendar if you prefer), not OmniFocus actions at all. Most GTD advice advocates not jumbling your actions and scheduled events all together in one list.

If you create events in the Calendar app, you can then opt to show them directly in the Forecast view in OmniFocus for iPhone or iPad.

Hmm, I hadn't thought of that. I know that they suggested using a calendar to give you a hard landscape of the things that needed to be done for that day so I assumed it made sense to put in things like Workout Class schedules and Appointments (doctors, dentists, etc). Perhaps this isn't the way to go.

Originally Posted by whpalmer4

Right, so this is like an appointment — you've decided that Thursday morning you will hit the gym on the way to work. Because that's an action that needs to be performed at a certain time, rather than at any time, or by a specific time, it should move out of your GTD system and onto your calendar. OF/GTD will help you decide what to do with the time that isn't spoken for in advance on your calendar.

This does make a lot more sense and probably is a lot less of a hassle than "completing" a bunch of obvious tasks that I know I'm going to do anyways while dodging any guilt that might come up if I have to miss a class for some reason...