There are two main methods to organizing your daily tasks. First, you can have a todo list. Second, you can block out time for all the tasks you must do in a calendar.

A checklist is sufficient if your list of tasks is:

  1. Small. Only three or four ‘need to do’ items that are easy to understand. Tasks like ‘roast the coffee’ work fine in todo lists. It takes ten minutes, and I can do it anytime before the day ends. A list of fourteen items will feel like climbing a mountain.
  2. Simple. Tasks with a lot of emotional baggage don’t work well with todo lists. If your list includes items like ‘resolve that lingering issue with my boss,’ you’ll probably avoid it all day and decide tomorrow will be better. It won’t be.
  3. Known. All the tasks need to be things you know exactly how to do. Tasks like ‘determine strategy for blah blah’ don’t work well here. Open-ended brainstorming or big projects without clear endings make for imposing items on a checklist. They are the items you’ll want to do last and conveniently run out of time for.

Once in a while, the work day will conform to these requirements, and a simple todo list is enough organization to get through it all. Since no clock times are assigned to anything, there is room for reshuffling the order or adding a few new tasks as the day progresses.

Blocking time on the calendar becomes necessary when the three requirements above no longer apply.

Assigning time requires more mental energy and makes improvising throughout the day more difficult. The higher overhead is well worth it when working on long-term projects or anything complex. However, in the weekend chores example, planning to roast the coffee at exactly 10:15 a.m. and feeling behind because you don’t do it exactly at that time is overkill.

To put together a calendar-based daily plan:

  1. List all your tasks for the day.
  2. Look at the calendar and make sure all your appointments are up to date.
  3. Review the open slots in the calendar and assign your todo list tasks to them.

This system can handle larger and more complex tasks. If you’re writing a large program, blocking an hour to make progress may be enough. Open-ended tasks can be organized around how much time to spend rather than specific outcomes.

Sounds great in theory, but using the calendar is prone to failure and frustration. Here’s what to avoid:

  1. Assuming things will go to plan. Be willing to change the plan when things happen. A boss will throw something unexpected at you. Roll with it. At least you had a plan in the first place. If you’re lucky, you can keep your plan and throw the new task into a later calendar block.
  2. Being overly optimistic about how long things take. Double your initial time estimates. Seriously. A daily plan with some slack to fill in is good. Finishing things ahead of schedule feels good. The odds are that this will be much closer to reality than the initial estimates.
  3. Optimizing for maximum tasks. It seems like having a daily plan is a great method for increasing the number of things you can get done. Resist the urge. A couple of packed days in a row, and you’ll be ready to throw out your calendar. Don’t add more just because you can.

If the day ends with a sense of “I got all the necessary stuff done, made some incremental progress on important things, and wasn’t overwhelmed,” consider it a win. A planning system that accomplishes that is working.