How To Cross Every Item Off Your To-Do List In One Night

For the entire year that I have lived in this suite, a cardboard-velvet box piled over with envelopes and mail sat on the floor between my filing cabinet and my entertainment unit. Today it is gone because yesterday I took twenty minutes to file it all.

It feels very different in here now. Cleaner karma. Better Feng Shui. It almost feels like I removed something from my head.

That box was, ostensibly, an active part of my “workflow system.” Any file that ended up out of its home was to be dropped in there, the whole lot to be re-filed at the end of every day.

All of the other components of my system have been in a similar state of stasis for a similarly long time. It was months ago that my master to-do list grew so stagnant and irrelevant that I stopped even looking at it, which reveals an interesting fact about our to-do items: they often don’t really need to be done at all.

There are items on it that have been “urgent” for months. I have certainly experienced inconveniences and lost opportunities because of my ridiculous level of procrastination, but clearly none of the eighty forgotten items on my list were life or death, or I’d be dead. Life has been generally pleasant.

So the bulk of my supposed must-do items (and probably yours too) were completely optional, benign opportunities to get ahead, rather than the creeping imperatives they seemed to be.

Still, their undoneness imposes a persistent mental burden, on the clarity of your mind and your self-esteem. Unmet commitments represent personal shortcomings.

I am a career procrastinator. So are many of you, I gather. None of the articles I’ve written has inspired more heartfelt “Oh my god that’s me!” responses than one I wrote about procrastination. In the article I argued that procrastination is not laziness, but a symptom of certain kinds of private fear.

Fear is much less a part of my day-to-day consciousness now than it was when I wrote that. I feel like I’m game to take on my concerns as they emerge in life, including the fuzzier, scarier projects that made my to-do items into more of a permanent collection than a rolling list.

The two approaches

Everyone experiences a steady stream of to-do items in their lives. People generally subscribe to one of two philosophies in dealing with them: acting on them arbitrarily as they become salient, or by using a system to organize them. In other words, they either keep their list of concerns in their head or they put them on paper.

Some people manage to live relaxed, productive lives allowing their workload to float freely in their minds. They do what needs doing whenever it feels like it needs doing.

For the rest of us, this feels too crazy. It’s hard to walk around with the persistent feeling that you’re not doing something that needs doing. When there are eighty things that feel like they need doing, it’s hard to regard them as a finite list of concerns that can each be dealt with. So naturally, we want to write them down, and see that there are only thirty-seven concerns right now, and you can do one or two or ten today. A list alone constitutes a workflow system.

A system only works when it feels like everything is accounted for somewhere outside your head. Even if your system is a cubicle wall plastered with yellow post-its, if you have faith that it’s all there, and nothing is floating unarticulated in your head that may fall through the cracks, then you can work through them and feel in control.

Most people find that a simple list isn’t detailed enough. It doesn’t articulate priorities, it makes it look like everything is on today’s plate. A lot of people have tiers of lists. A list of phone calls to make. A list of purchases to make. A list of things to do before you die.

Probably the most popular comprehensive workflow system is David Allan’s Getting Things Done. I have long fantasized about mastering the GTD system and the “mind like water” state that is supposed to arise once you’ve properly implemented it. This achievement even had a place on my own bucket list for a while.

The general idea is that you catch all incoming requests on your time in a series of inboxes: mail goes into an in-tray on your desk, email goes into its own inbox, notes when you’re out and about go into your smartphone. Any event that causes a feeling of “I should do something about that” — an order from your boss, an unsettling knock in your car’s engine, or a recurring dream about getting your prostate checked — is written down and sent to its appropriate inbox.

Every few days, you go through these inboxes and decide what you’re going to do about them. There are four options: do something about it right now, decide you’re going to do it later, delegate it to someone else, or decide not to bother doing anything at all.

If you can capture on paper anything that tugs on your conscience, and get it to its appropriate inbox, then you can know that no concern will escape your decisionmaking process. Properly implemented, the GTD system creates a workflow that lets you relax in the moment, knowing that every single concern will end up in front of you at your desk when you are alert and prepared to make a decision on it.

Your habits ensure it all gets into the funnel at some stage. The system hinges on eradicating escapees. If you have a concerning thought and you don’t write it down, some part of you will know that there is a free-floating problem out there that you haven’t addressed, and which could blow up at any time. Your personal world feels dangerous again, out of your sphere of control, and stress returns.

Weekly, you review the whole machine for leaks.

Presumably, once the crucial routines are established, you reach a point of balance, where sharpened habits process the inflow of emerging commitments into completed goals and realized dreams.

I envy people who make this complex system work. When those of us who are attempting to work a system begin to lose control of that system, we end up inadvertently using the other approach — trying to keep all our commitments organized in our heads.

Procrastinators and other people without a track-record of steady productivity will have trouble with GTD, for a particular reason: the system is unsympathetic to your emotional state. If you have any problems with procrastination or motivation, the system will fall apart quickly for you. Slag off one weekly review or let your inbox pile up for a whole week even once, then resuming the system becomes daunting enough that you wait to do them until you have a clear three-hour stretch, and very quickly your workflow system is back to a react-as-it-comes basis.

It’s still totally worth learning GTD, if only so you can use it as a basis for your own system, one that is not so inflexible and doesn’t require so many simultaneous habit changes.

I’m taking a much simpler approach now. Keep all the same inboxes, go through them once a week and put them on a big, single-category list. No more subcategories and priority rankings to get lost in. Look at the list every evening and decide what to do the next day. If I need time-specific reminders I’ll set them up in Google Calendar on my phone. A cabinet for files. A regular day weekly to get up to date.

The problem is that I’ve got a six-month backlog to work through before I can bring this leaner system to bear on today’s concerns as they arise in real time. It’s something like starting your first job, in retail, on Black Friday, when the closer last night forgot to do everything.

How to deal with a stagnant backlog of work in a single evening

In finance, when you need a clean slate, you take the drastic action of bankruptcy. I recently learned of the concept of task bankruptcy. Given that you’ve already delayed a ridiculously long time on an ridiculous number of tasks, you just decide you aren’t going to ever do those things, and you start a list again from zero.

As with financial bankruptcy, there are commitments on your list you won’t be able to reasonably discharge. But these are uncommon. Identify them and decide where to go from here with them.

Everything else is gone. If learning to knit or selling all those boxes of CDs on ebay or assembling the family tree really were important, they will recapture your conscience at some point later in life. For now — and maybe forever — they are no longer important. No need to remember what was once there, what you used to feel compelled to (eventually) do.

You let it all drop, and start from where you are. Those emails will simply go unreturned, those short stories will be allowed to die unfinished, and the world will go on.

After declaring task bankruptcy, I went through all my old “debts” with a sense of detachment and freedom and found that most of them didn’t seem important any more. But until I ceremoniously terminated them, each one had a little hook in my conscience.

Some of them still made sense to do. So I put them consciously, voluntarily on my new list, but only once I had truly cleaned my docket, and only if I felt a fresh commitment to doing them. If it was just lingering guilt, I let them die.

It may not even occur to a lot of people that almost all longstanding to-do items can be abandoned without your becoming a disgraced deadbeat. Dumping them will probably put you immediately into a better position to complete the important things. There will be some repercussions from letting certain tasks die, but they’re probably minor compared to the cost of continuing to bleed.

Streamline the system and declare task bankruptcy. GTD is a robust system that’s designed to catch absolutely everything, and it may be just too much personal bureaucracy for a lot of people. If you’ve been struggling with it, try Leo Babauta’s Zen to Done — a minimalist rebuttal to GTD and its complexity.

If you’ve got an unmanageable backlog, you’re paying all kinds of interest until you’re solvent again. Might as well swallow your pride and begin the rest of your life now.