Break down tasks into manageable chunks.

Many organizational systems advise separating large projects into parts, making each part of the project a separate to-do list task. This makes it less daunting to approach a big project, and easier to see progress while working on one. It can also help avoid scope creep. I totally do this with big projects, for instance when I have massive amounts of grading - I'll write "mark 10 papers!" on my to-do list three times (instead of writing "mark 30 papers!" once, or even writing just "mark papers!" a few times). That way I can budget three smaller and easier units of time, and each time there is an exact goal to meet.

I have realized recently, however, that I work better when I subdivide even small tasks. My employer offers a Flex Spending program for medical costs. I would like to enroll in this program. It will save me money. However, the deadline for enrollment is fast approaching and I have not yet completed the task. I had "enroll flex spending!" on my to-do list every work day for weeks, and I just never got around to it.

I realized that perhaps that task - probably about an hour's worth of work overall - was still too big for me to fit into my already-full office hours in a single day. Plus, I do not enjoy dealing with forms, so I had a built-in affinity for pushing the task off day after day. So, to combat this tendency, I broke it into component parts even though it is not a large project. I assigned each part to one day. Here are the new to-do list items I created:

• Read emails about flex spending; plan tasks. (Done!) 
• Call flex spending company; confirm reimbursement eligibility for specific costs. (Done!)
• Download, print, fill out flex spending enrollment forms. (Next!) 
• Submit flex spending forms. (And then it will be over.) 

Each of these tasks is discrete enough and small enough that it won't be a burden to fit into my workday, and while the project is spread out over more time, it will be completed by the deadline, and won't keep getting moved to the next day over and over again.

Several weeks ago when I was discussing my two-column to-do list with a Very Organized Friend, she asked if I rewrote items on my list. I was doing that with "apply flex spending!" It had become something to move from one day's list to another, rather than something to do. When that happens, it's time to divide the task.