It’s either been a slow week for Pittsburgh Startups and Social Media or I’ve been too busy to track it, hard to tell from where I’m sitting.  So instead of either of those, I’m going to give you some friendly advice and solicit your feedback on it.  The topic, how to manage a post-modern, project-based life.  I’m imagining that at least a few of the people who read this blog, like me, tend to be running with 6-12 projects at a time (for me there’s 3 projects around my day job, this blog, running a marathon and a few others I prefer not to comment on just yet).  Of these projects, you might be in a holding pattern on three of them, be the bottleneck on three of them, and just plodding along on the rest.

I WANT to live the ADD lifestyle described above, and I recommend it if you’re considering it.  I love my work (well, most of it) and consequently I’m willing to put in the kind of time that it takes to deal with that many projects.  I began the project-based way of thinking about life when I started my MBA in January 2009 and the first few months were AWFUL.  I almost quit the MBA and I seriously considered getting out of the high-paced world of startups altogether.  I had three primary problems.  First, I didn’t prioritize well, I would finish the least important task exceptionally well and never get to the most important task.  Second, I fell victim to “out of sight, out of mind”, I would draft something a week before it was due and send it off for review only to remember the day after it was due that I never heard back about it and never turned it in.  Third, I never started new projects, when you’re busy with a bunch of projects its easy to miss opportunities when they come around.

I dedicated one of my whiteboards to solving these issues, and over the next two years I evolved to the system pictured above (click the pic for a larger version).  Here’s a brief description of each of the sections:

• Each project has its own column.  In that column I list the two or three things that I can do right now to help that project.  From a granularity perspective, I try to keep these at things that I can accomplish in a half-day or less.  These “Immediate Actions” are all candidates to be accomplished today.  Each project also has, in red, one or more significant dates.  These dates are typically things I’m waiting on (e.g. “12/5 Should hear back about my Application”).  Under those red dates are the actions I’ll have to perform once that date has passed.  Writing things down like that is important for two reasons.  First, for budgeting time in the few days around that significant date.  Second, for remembering that the date is supposed to happen and, if it doesn’t, remembering to remind whomever it was who was supposed to review your application.  Some projects are so contingent on those upcoming dates that they can’t be worked on presently.  Those have a red dot above them (projects with immediate actions have a green dot).  I do this because I ABSOLUTELY HATE RED DOT PROJECTS, and having the red dot glare at me all day reminds me to keep agitating whoever I am dependent on; it’s my project after all and I don’t want it to lose steam.  This system seems to resolve my second problem (“out of sight, out of mind”) by reminding me when I’m going to have to resume a project that has faded to the background.
• The section for today’s to do list is where prioritization occurs.  I wipe this clean every morning and start from scratch.  I look through the “immediate actions” in each project and select the first most important one and put it first, second one and put it second, third…  I have way to much ADD to actually attack the tasks in that order during the day, but at least I have taken the time to prioritize and I know what NEEDS to be done today and what I’d LIKE to get done today.  This addresses my first problem, prioritization.
• The last section, “Potential Project Ideas” is something I only started using about a year ago, but it has been invaluable.  To give credit where it’s due, I was inspired by this Chris Dixon post.  Essentially, I want to know the 5 or 10 projects that I can’t work on now, but I would be doing if I had the time.  For example, right now I have blowing out this scorecard in to a Wiki that can keep track of all of the resources in the Pittsburgh Startup Community.  I don’t have time to do it or any of the projects on my list right now, but simply thinking about what I would do if I had time encourages me to make sure the projects that I am working on are worth my time.  Too often you complete a project only to learn that you should have abandoned it halfway for a better opportunity.  This addresses my third problem, working so hard that you miss opportunities.

Each morning I update every column and then build my to do list and I try to carefully consider my “Potential Project Ideas” at least once a week.

Anyone have a way for me to improve?  Have your own way?  (I’d even encourage a guest post if someone has a good thought on how they deal with the same problem)