How I Plan
This is something I’ve started doing to help me work on careerish stuff. I’ve been doing it for a couple of months now, and it works pretty well, as proven by the existence of this blog among other things.

The first column lists things I want to accomplish by the end of the current month. (I rewrite the chart every month.)
The second column lists things I want to accomplish by the end of the current year.
The third column lists things I want to accomplish by Dec. 31, 2012 (roughly three years from now).
The rows going across are money, talk, code, and learning.
Money is mainly my plan for how much I need to save each month to get to a place where I can support myself for a year without working. (I may not actually not-work for a year, but I’d like to have the option to just go travel around the world if I choose to.) There’s also a secondary goal there around getting a new car, which I need to do this year.
Talk is everything I try to do to “make a name for myself” – blogging, writing articles, and eventually conference speaking. One of these items is always a specific goal for how many blog posts I want to make that month. I’ve been at 6; this month I went down to 4 because I’m feeling unwordly. This is how I make myself blog.
Code is obvious, it’s about things that I want to make and do. Longer-term, it’s about building up both my portfolio and my freelance network.
Learning tends to be shorter-term, and usually includes things that I want to read or watch that aren’t just “for me”. Mostly this is technical stuff, although this month I have a work-related book up there as well.
I picked these four categories because they seem like the main areas that I need to work on in order to advance my career.
The hardest part was getting that 3-year column down. This past fall I went away for a long weekend and hiked part of the Appalachian Trail (for real, not Mark Sanford-style) and did a lot of thinking and writing, and that’s when I came up with a better idea of where I wanted to be in three years. Once I knew that, figuring out what I needed to do to get there was relatively easy.