Disclaimer The opinions expressed herein are my own personal opinions and do not represent my employer's view in any way.
In today's world of missed deadlines, project cost overruns, missed new year's resolutions, pounds of fat not coming off and so on, it sometimes seems like the most truly awe inspiring a human being can experience or witness is someone actually meeting a goal or deadline.
I'm sure that's a rather unrealistically negative viewpoint, but that's how I feel sometimes. I know I take on too much or set my schedules or deadlines too aggressive and so I suffer the consequences of missing it, and then in my mind its a failure, even if I did my best and actually was very heroic in my efforts to achieve what I was striving for. When the finish line is way out of reach, its disheartening to know you can't reach it. Conversely, if you set it too low, its actually better because you're more motivated since the end is in sight, you're much more likely to hit the goal and then you get that mental high of achieving the goal you set out for.
Anywho, that is what I'm focusing on more, lately. My organizational system, using GTD is working well. I just need to apply another spoonful of reality when setting schedules. I tried this out recently when I fleshed out my 5 year plan. We've all had that question in an interview: "Where do you see yourself in 5 years?".
Well I sat down and tried to answer that. I busted out a trusty Google spreadsheet, making a row for each goal. A goal can be specific "Conquer Canada" or vague "get more better in shape". Vague is fine here because we'll flesh out the milestones in a sec. I then made columns for every month from 1-6, then every year from 1-5. In each cell I set a specific goal for the 5 year mark, then filled out every cell before it starting at 1 month. I went over them again and again until it looked like I had a REASONABLE set of milestone stepping stones to reach the lofty 5 year milestone. Then I took the 1 month goals and either made them projects on my GTD projects list or put them straight on my Remember The Milk to do list. I don't know about everyone else, but I feel like I have to constantly be improving myself, even if its just a little bit. So every day I wake up, I've bettered myself from the day before. Its like level grinding in real life, which was actually one of my favorite parts of Diablo 2. (Sidenote: I can't wait for Diablo3 and Starcraft2! I think I may take a week of vacation time just to play them right release)