Since I went full-time freelance as a writer, designer, and consultant, a number of people have asked me how I manage my workload. It’s a fair question, since I juggle three consulting contracts and usually two to five projects at any one time. I thought I would write a few blog posts to detail my personal management process as it looks now. Maybe it will help other creative professionals as they get ready for the new year.
Yesterday I looked at how I use my board to track my task momentum. Today I’ll finish by talking about how I plan my tasks.
Jumping ahead a bit, I have a separate Trello board called “Backlog.” It’s much less structured than my Planning board, with vague columns for “Coming Soon,” “On The Horizon,” “Someday,” and “Blocked” (for long-term tasks that need something done before I can go ahead with them).
Whenever I get a new contract or a task that won’t be done this month, I make a simple card with the details and toss it on the Backlog — I don’t need to be thinking about what’s happening in March if I’m concentrating on January. But around the beginning of the month, I set aside an hour or two and pull tasks from the backlog for the month.
As I mentioned in my first post, I estimate 10 pomos of work a day. Each month, I count the days I expect to work (usually M-F, but skipping over conventions and other days I know I won’t be able to work) and multiply by 10 to get my pomo “budget” for the month — usually around 180-200 pomos. From there, I look at the tasks in front of me and start estimating.
Estimating tasks is 80% science, 20% art. Over the months I’ve gotten a good sense of how much I can write, edit, develop, and the like in a pomo, and I can use those metrics. I also track regular meetings with clients, and I can usually track how long those will last as well with pomos. Once in a while, though, I just have to guess. Some tasks I may not even have enough information to guess, which I mark with a “(?)” on my task.
Once I have a good idea of my estimates, I put the tasks in my “This Month” column of the main board. I whittle them down if they’re over my budget, or pull some more tasks from the backlog in if I’m under. From there, I break larger tasks down.
It’s possible to have a task like “(100) Book,” but it’s not very useful or flexible — I’ll be staring at that task for weeks in the “To Do” column. So I break large tasks into smaller tasks that I can more easily move around and see momentum on. Ideally I try to get tasks down to around to 10 pomos if I can (i.e., a one-day task), but no more than 30 (i.e., a three-day task). Sometimes these are natural breakdowns, like “Chapter 1,” “Chapter 2,” etc., or phase breakdowns like “Research,” “Writing,” “Revision.” Other times, though, I have to pick arbitrary milestones to give cut-offs, such as “every 5000 words” or even just “every 5 hours.”
Once those are all done, I usually give them a rough priority order in the “This Month” column, putting more urgent tasks at the top of the list. (I generally cycle meetings to the bottom, though — partly because those don’t move, so there’s no need to prioritize them, but partly because it’s a psychological need to remind myself that meetings are not really productivity).
I also have one tool outside of Trello I use: a small whiteboard in my office. There I project the next three months of work at a very high level — nothing more than the month’s pomo budget, titles of major projects, and a very rough pomo estimate. This is only so when a client asks me if I’m available, I can make a more informed decision on what my next three months look like.
And that’s it — my planning process as a freelancer. Feel free to use any of this in whatever way works best for you. It may seem like a lot of work, but once you get used to it, it makes planning very fast, and allows me to avoid the dreaded freelancer conundrum of taking on too much work or turning down work when I need it.
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