The art of the to-do list

A step-by-step walkthrough of Hamm's system for managing all of the tasks of a person who manages a fairly complicated schedule.

Yesterday, I answered a question in the Reader Mailbag describing how I manage several to-do lists at once. By the end of the day, I had received several follow-up questions by email asking all kinds of questions about how I manage tasks and my workflow, so I thought I would explain my entire system for getting all of my personal and professional tasks in order and completed in the appropriate time.

This is a step-by-step walkthrough of my system for managing all of the tasks of a person who manages a fairly complicated freelancing career, an involved parent of three young children, a good husband, an active presence in the community, a homeowner, and a few other personal projects in the spare time that remains. 

Things To Do Today: My Daily To-Do List
One of the last things I do each day is to prepare a to-do list for the following day.

For my own purposes, I use TOPS form 2170 for my to-do list. It essentially gives you space to list twelve items with some detail, along with a spot to check them off as you finish. I’ve found that twelve is just about the perfect number for an upper limit on a daily to-do list.

Of course, an ordinary piece of paper will work just fine for this. I would simply suggest that you not make the list any longer than twelve, and that should only occur if the items are a mix of professional and personal tasks.If you make the list too long, there is a strong tendency to simply not do some of the items on the list, and that creates a terrible habit. You’re much better off completing your list each day and then seeking out other less important things to do on your own.

Earlier in the day, I will sometimes start tomorrow’s to-do list and sometimes even the to-do list of the day after that. However, if there’s anything going on beyond that, I save it for other tools.

Things To Deal With: My Inbox
In a given day, lots of things come in that need to be dealt with. Emails. Physical mail. Notes in a child’s backpack. Notes from phone calls. The list goes on and on.

About three times a day, I stop and process everything that’s accumulated. I go through emails, mark the ones that actually need some more attention, and delete the rest. Every physical item – notes, physical mail, and so on – is kept in the metal inbox on my desk, so I dig through that and do the same, keeping the important items and tossing the rest in the trash.

After that, I go through each item that has to actually be dealt with. If it takes more than a minute to deal with and it’s not mind-blowingly urgent, then I usually add it either to today’s to-do list near the bottom if there’s room, or I stick it on tomorrow’s to-do list. If it needs to be filed, I file it.

A side note about filing: if there’s one weak spot in my system, it’s this. I’m not particularly good at keeping up with filing. In fact, my filing cabinet has a “catch-all” drawer where I put things that should someday be filed and organized, but actually doing that is a pretty low priority for me.

Plans for the Future
So, what about all the tasks that aren’t really appropriate for today? What about the lower-urgency tasks? What about the big ongoing projects? How do I handle all of these things?

I use an online list manager for all of these things.

My preferred list manager is Remember the Milk, which I’ve used for many years. I’ve experimented with other systems, but I’ve never found one that just hits home quite like Remember the Milk.

Within Remember the Milk, I keep a big pile of to-do lists. I’ll talk about each one in order.

Tasks is my big list. Whenever I have a task that I need to do that’s not incredibly urgent, not part of a bigger ongoing project, and doesn’t have a specific due date assigned to it, I stick it on my “Tasks” list. Here, you’ll find things like minor home repairs, people I need to write a thoughtful letter to, things I need to research a little and think about, small errands I need to run, and so on.

Dated Tasks is another big list. It’s similar to Tasks, but it’s filled with things that have specific due dates. I keep this list ordered by the due date.

Someday is a list filled with things that are very low priority. It’s just a place to collect all the things that I might want to do someday. Usually, these things are pretty big and nebulous – they would be large projects unto themselves. Whenever I feel like my plate is relatively empty (it does happen!), I go through this list and pick out an item or two to start tackling.

Projects is another major list. It simply lists all of the ongoing projects I have going on in my life. This is more of a reference thing than anything else, though it feels really good to mark something off of here. My novel is an item on this list, as is The Simple Dollar. I have several other ongoing personal and professional projects listed here as well.

Each project has its own to-do list. This is a checklist of steps that I’ll need to take to finish the project. Usually, the next few steps are pretty specific and the later steps become larger and more nebulous. From time to time, I’ll break down an upcoming nebulous bit into more specific steps just to keep things flowing.

So, each day, when I’m making my daily to-do list on a piece of paper, I start with the Dated Tasks and copy over anything that’s due the next day. I then move to the regular tasks and copy down an item or two from there. I then look at each project. I take the very next action needed on each of those projects and add it to my daily to-do list that’s sitting on the table in front of me.

That to-do list ends up telling me exactly what I need to do each day. It moves me forward on a few projects and takes care of the important things of the day.

On top of that, I have four lists that I keep around to simply help me think about my life: Areas of Focus, Goals, Vision, and Purpose/Principles. Each one of these lists has between seven to ten items on it that outline the future direction of my life.

Areas of Focus are the things that I view as important in my life right now and over the next year or two. For example, one area of focus right now is helping my oldest child master reading to the point of being an independent reader of youth fiction and nonfiction books. Another one is figuring out the direction of writing on The Simple Dollar once the “365″ series is finished. These are big things on my mind that usually stretch over the next year or so. Often, these areas of focus help me pick out and define new projects when I complete old ones.

Goals are things I want to achieve in the next five years. Quite often, I’ve talked about how I like to paint a detailed picture of my life in five years. What will it look like? This list is made up of specific things that I would like to see in my life after five years. For example, one goal is to cultivate my children into avid readers and independent and self-directed learners. Often, these goals help me to figure out areas of focus as I outgrow old ones and seek new ones.

Vision is essentially where I want my life to go over the next ten to fifteen years. It’s really a stretch to call these things goals because so much can change between now and then. Instead, these tend to be things that I know I want in a general sense from my future. Here, I have items that broadly describe some of the things I want for my children over the rest of their childhood and far-reaching career and personal goals. One of my visions is for my children to see and understand the world as a broad and diverse and varied place, and also for them to have self-reliance. Again, these visions often help inform my goals.

Finally, Purpose and Principles basically describes what I want on my tombstone at the end of my life. What things do I want people to say about me at my funeral? Was I kind? Was I giving? Was I truly a good parent and a good spouse? Did I help people with my writings or how I spent my time? I hope the answers to all of these questions is yes, and I keep this list as a reminder of those principles. These inform my life all through the other lists I keep.

Once every two weeks or so, I spend some time really reflecting on all of the lists. I’ll spend part of an afternoon going through lists, asking myself if this is what I truly want to be doing, and evaluting whether or not I’m fulfilling the things I want out of life. It really helps me find motivation to take all of the little steps when I see, step by step, how they all tie to the big things I want in my life.

Bringing It All Together
So, when I’m sitting at my desk, what do I do? On a given day, I usually follow my to-do list pretty carefully. If I have an idea, I jot it down on a piece of scratch paper and toss it in my inbox. I process that inbox regularly and put the things in there where they need to be.

Those little steps are each connected to a somewhat bigger thing I have in mind – a project, let’s say. Each piece is connected to something bigger in some direct fashion until everything connects back to the big purposes I have for my life.

Doing this, for me, keeps everything organized quite well and helps me feel deep motivation for even the smallest tasks.