Juggling jobs: How do you handle project management and balance?

A moving GIF showing a basic 3 ball-cascade juggling pattern: good for juggling explanation. (Photo credit: Wikipedia)

We’ve talked before about how you manage your To Do List but now I want to know your favorite strategies or apps for project management. I recently signed up for the free Trello which is a simple way of managing multiple To Do lists but it’s not really what I’m after so I want to know what you use.

I’m trying to figure out a good way to track a couple of different elements of my business. At the most basic, I’ve got:

Things that directly lead to money (ie listing things for sale, readying an ebook for sale)
Things that indirectly lead to money (such as blogging, website maintenance, etc)
Things that may never lead to money (working on a novel, experimenting with a new play, etc)

Obviously, I want to make sure the majority of how I spent my time and resources is on #1 but #2 is still a necessity to keep things running and, for my own general happiness, I want to continue to find time for #3. I want to be able to track my progress on a wide variety of projects in these three categories but, and here’s the kicker that I can’t seem to find an app to help me with, I want to make sure I’m giving each project category a proportional amount of time. Say 40% on #1, 30% each on #2 and #3 just to pull some numbers out of the air.

So a variety of projects in three basic categories and I want to make sure I’m giving each the amount of attention they need/warrant. And the system has to be easy so that I can just pick it up quickly in the few spare seconds here and there that are really all I have to work. Ideally, it would somehow track automatically without my having to do anything.

See, my biggest flaw has always been that I tend to just work on whatever I’m pointed at when I sit down to work. Say I notice something wrong with my website. It’s a 5 minute fix and then I should move on to the next thing but then I’m in Website Fixing Mode and I use up my entire work window doing web stuff, most of which could really have waited because this thing over here was really the higher priority to do that day. What I really need is a system where I can specify that, say, no more than 5% of my day should be spent on web stuff that turns red or otherwise gives me a warning when I go over that so I know to work on something else.

I also like a system that rewards you for meeting goals, even if that reward is just a box that turns green instead of red. I have a system of my own that I’ve devised that I use for writing that does this very thing (turns red or green depending on whether I’m caught up) but I just can’t figure out a way to adapt it to work. I find it weirdly satisfying to hit daily/weekly/monthly goals but I can’t figure out a way to do that without inputting everything I do into a spreadsheet and I do NOT have time for that extra work. I tried RescueTime* for a while (which automatically tracks everything you do on your computer and gives you reports) and, while a very useful program, it’s got a couple of big disadvantages that limited its usefulness for me.

*=I’ll do a full review of RescueTime sometime in the future if people are interested.

I tried just going as low tech as possible and just designated days (say, Monday, Wednesday and Friday are all category #1 things while I work on #2 things on Tuesday, #3 on Thursday) but the fundamental flaw with this, at least in my situation, is that there’s no guarantee I’ll get any time to work on a given day at all and if the little one doesn’t nap two Tuesdays in a row, category 2 suffers. I suspect the solution is to just train myself to only work on any one thing for a few minutes and then move onto the next with a rock solid plan always in front of me showing what’s the highest priority but that’s easier said than done.

Anyway, these are just some of the problems I run into when it comes to balancing multiple projects and I’m sure you have all of these and more. What’s your system for keeping all your different balls in the air? How do you manage hobbies and real work and make sure you’re making time for each? Is there an app or other service that you’d recommend?