Regarding Project Management

The Hunt for Progress on Many Simultaneous Projects

Recorded on July 13th, 2016

One thing that continually bugs me is that I don’t have a way to plan, achieve, and track daily progress on multiple projects. This is a problem whether I’m at work or at home. You’d think that Trello, Google Spreadsheets, Todoist or TaskPaper could solve this, but all of these systems are only as good as the person using them (me, unfortunately).

My mental model is like this: The end of a project is like the destination of a road trip. Let’s say we need to drive from Richmond, Virginia to San Francisco, California. Our trip starts tomorrow, and for whatever reason we have six full days to get there. We could fairly easily plan out how many miles we’d need to cover each day, how many hotels to stay at, etc. One trip (or a project) like that is pretty easy. You check in with yourself at multiple times along the way, and you can self-correct if you’re falling behind.

But what if you have five simultaneous trips (projects) going on, you’re not quite sure how many miles are necessary for each trip because there are no maps for that territory, and you don’t have good milestones planned out along the way? (Ignore the fact that this analogy breaks down because one person can’t physically be on multiple road trips at the same time.) If you’re like me, you abandon planning, figure out 100 miles at a time, and drive 1000 miles on Trip X in one day. Then you switch gears the next day because you realize Trip Y has been ignored, and pour in 1200 miles to that trip to make up for lost time, thereby ignoring the rest of the ongoing trips. You have no overall picture of how each day should be going.

Or, you do plan, you have a really good picture of what needs to happen each day, you do great for Day 1, and then on Day 2 your car breaks down and you don’t have the sense to renegotiate the outcomes, even though you realize there’s no way all these trips are going to reach their destination on time.

I have no answers here. Only weak analogies and a vague sense that I’m sticking my head in the sand, hoping for the best.