We love lists. It's a way for us to keep score, but also to keep track. There are wish lists, bucket lists, check lists, and of course, to-do lists. These last lists can give us anxiety, if we let them. They can be a repository of everything we have on our mind, if we let them. But these to-do lists should not ever be used in their raw form as a working document.
The obvious reality is that not all items on your list are created equal. Dropping something off at the dry cleaners or making a doctor's appointment are both errands, but they shouldn't really be on the "same" list as "plan family vacation" or "have conversation with daughter about dating." All of these are things that need to be done, but if they all simply live on a to-do list, not only will that list be very long (and hence disheartening), but from a getting things done perspective, it will be useless.
The phrase "measure twice, cut once" was a reminder to carpenters that once a cut was made, errors would be costly. Better to double check that measurement than risk imprecision. So to with to-do lists: divide twice, accomplish once.
The first division can be quite simply "now" vs "later." Something that should be done "now" must be done in the next week. Something "later" would simply be anything that doesn't have to be done in the next seven days. This instantly takes the massive to-do list you may have compiled and makes it intelligible in terms of what is urgent and what can wait.
The second division concerns what you need to get done on any given day. You make a list for the next day the night before, with three divisions, depending on how long your estimate of the task is. For example, you can use 5 minutes, 15 minutes, 1 hour+. Five minute tasks can be things like making a medical appointment, paying a bill, or starting a load of laundry. Fifteen minute tasks might include sending an email of one or two paragraphs, booking a flight or hotel room that you have already researched, or reading an important article you had bookmarked. One hour plus tasks can include creating work flow for a project, travel planning for a family vacation, or a reply to a letter from a friend. By creating time estimates, you've further parsed the tasks, but you've also given yourself a range of what is possible. If you know, for example, that you only have four working hours the following day (perhaps you have some personal appointments and responsibilities already) then you know that you cannot schedule six 1 hour+ items. You'll already be over.
If the number and times assigned to the tasks exceed what you have available, you're setting yourself up to fail. If you give yourself a bit of slack, you allow for challenges and difficulties throughout the day. And you're always welcome to go back to the "now" vs "later" list if you have accomplished everything you've assigned for the day AND have decided to
As with all areas of productivity, you will have good days and bad days, not because the system or technique is flawed, but because we as humans are. We may overestimate the amount of time it takes to do one task and underestimate the time it takes to do another. We may be overly ambitious with our list and max out the time we have available to work and load ourselves up with tasks. As we said in a previous article, peak, high performance productivity is never about getting a lot of things done, but rather getting a relative few things done well.
Your giant to-do list will now be revised weekly and will serve as a touchstone for your daily priorities. No longer will you be subject to a vague worry that you aren't getting to all you need to accomplish, as you'll be working through the list each day, and each week you can eliminate what has been accomplished and move some of the "later" tasks that merit it into the "now" side. Productivity isn't always easy, but it doesn't need to be hard, either.