[This one’s for the 43Folders-ites and GTD dorks; apologies if readers less obsessed with life-hacking find it far too anal retentive to sustain their interest.]

Though I’ve been GTD’ing for about three years, I’ve recently stumbled across two things that have done wonders for inching me towards a watery mind and away from my naturally procrastinatory ways. Thought I’d toss them up, in the off chance that others might find them useful.

The first is the power of the checklist. Though David Allen mentions checklists throughout GTD, I and (from the implementations I’ve seen) most others seem to give them short shrift.

In my myriad approaches to wrangling GTD details, I’ve always had particular trouble with recurring tasks. I play the trumpet on the side, for example, and try to put the horn on my chops for at least a half hour of daily practice. When I was using to-do managers with recurring task capabilities, I was able to set recurrence daily, and check off trumpet each day. But, using VoodooPad as I do now, I didn’t have a good approach.

So, I initially set up a daily checklist as a way of managing the larger recurring tasks in my life, things like trumpet practice, blogging, or hitting the gym, which I wanted to do each day, and which didn’t lead from one action to the next, but required the same action again and again. Each morning, I’d paste my daily checklist across to my Next Actions list, and then get to work.

As I started doing that, however, I realized there were any number of other things I did (or, at least, should) daily. Things like taking a vitamin. Obviously, popping a vitamin is a ridiculously minor task, and well under the two minute time cutoff, so I’d initially left it off my task list. But, as it was something I wanted to do daily, I’d been unwittingly carrying around the obligation mentally. Further, there were a number of similarly small action obligations inherent in my approach to GTD itself: emptying my in basket each morning, checking the prior night’s voicemails, or copying the hard landscape of my day across from iCal.

Very quickly, my checklist began to expand, from major recurring daily to-do’s, to the very small ones. And the cognitive energy freed up by getting all of those out of my mental RAM was on par with the initial surge that hooked me when I first implemented GTD. Eventually, I added in weekly (including an action-by-action break-down of the weekly review), monthly and yearly checklists, all of which have been slowly populating with the small, inane tasks that otherwise didn’t seem to fit well into the GTD framework. My brain feels vastly emptier (in a good way!) as a result.

In the process, I also discovered a second, equally powerful, use of checklists: scheduling procrastinatory tasks. One huge time suck for me, for example, is Bloglines. I’d load the site throughout the day, derailing my attempts at staying on task. So, on a lark, I added surfing Bloglines to my daily checklist. Each day, I was giving myself not just the permission, but the obligation, to pull up the site, and read through everything that popped in.

The amazing thing was, the rest of the time, Bloglines didn’t hold nearly the draw it previously did. Knowing that I’d get to check it at least once a day, the constant impulse to make sure I hadn’t missed anything abated.

I added scheduled requirements of other procrastinatory ploys to my checklist, and found the same thing. In retrospect, that makes a lot of sense. I tend to procrastinate not by doing things that are bad, things that I shouldn’t be doing at all, but by doing things that are less good, that I shouldn’t be doing preferentially to my more important tasks.

Still, as those procrastination escapes were things I really did want to do, I was carrying around the mental obligation to them as heavily as I’d been carrying around any other unrecorded project or next-action. No wonder the urge to do them had been popping into my brain at the least opportune moment!

So, fellow GTD acolytes, I’d urge you to give the same hack a try: put together a checklist of the things you want to do each day, each week, month or year. Put really small, stupid things on the lists, every single one you can think of, to free up mental RAM. Then add in a regular obligation to do the things that make you waste time. Do them regularly, do them like you mean them, and discover you’re unbothered by them until you’re required to do them again.

Go to it.

Recently, I’ve been finding that I’m actually far more productive on weekends than I am during the work week. In a quasi-observance of Shabbat, I take Saturday off from doing any Cyan or Long Tail work, instead banging out all the other details of my life; then, Sunday, I start cranking through the upcoming week’s works tasks. Holed up inside for those two days, I inevitably get more done than in the next five combined.

Though I don’t know why, exactly, that’s the case, I’ve started to take advantage of it as much as possible: clearing out my weekends of brunches and dinners and even Saturday evening parties in favor of long, uninterrupted stretches where I can crank through my backlog of tasks. Which, I suppose, I’d feel worse about, were I not making up for that lost social time (by which I mean, binge drinking) through the rest of the week.

On occasion, I’ll refer to myself as an underachiever.

Which, inevitably, draws a round of guffaws. But, honestly, I am.

Not, perhaps, against some external standard, against some outside set of average expectations. But, certainly, against my own expectations, against my sense of what I could be getting done if I didn’t piss away huge percentages of each of my days.

Over the past few years, I’ve pulled together a collection of anal-retentive organization systems and pro-productivity mind hacks to fight that. But my gains have been, to be honest, incremental at best.

Very recently, however, I’ve come to realize that a focus on building the right tools means little until I’m ready to wield them. Sure, those elaborate systems can help me work far more effectively, but only if I can actually force myself to sit down and get to work in the first place.

So, as of today, I’m officially launching a war on procrastination. (Or maybe as of tomorrow. [Hah! I kid. Just a bit of procrastination humor there.]) For the next few weeks, at least, I’ll be keeping a minute-by-minute time journal of my work day, tracking my ‘billable hours’, even if I’m just billing those hours to myself. If, indeed, awareness is the first step in the process of change, then perhaps by becoming fully aware of how I actually spend and waste time, by regularly rubbing my own nose in the stupid shit I manage to convince myself to do instead of productive work, I can actually set myself on the path to getting things done.

Wish me luck.

In the past few years, I’ve become increasingly enamored with the voluntary simplicity movement, which builds on the idea that paring away from our lives – be it reducing possessions or reducing commitments – lets us more fully enjoy those that are left.

In some ways, this flies against my genetic code. My parents are such pack-rats that they converted their two-car garage into storage space, then overflowed into a rented storage facility as well. (My father often jokes that, if he and my mother were suddenly plowed down in traffic, my brother and I would need to take the next year off from work just to sift through the piles they’ve accumulated.)

But, contrary to upbringing as it may be, I’ve slowly developed the habit of ruthless de-stuff-ing. A few times a year, I try to view everything I own with a dispassionate eye. A pair of jeans I haven’t worn for over a year? To Goodwill they go. A book on my shelf I realize I’m increasingly unlikely to re-read? Trotted down to the local library’s donation bin.

Still, in moving into my new apartment last month, a process that involved carefully looking at literally everything I own as I boxed and unboxed it, I started to appreciate that the things I own are more than just things; they’re behaviors waiting to happen.

Psychologists call this ‘affordance’: what an object suggests for us to do with it. A well designed door, for example, lets us know to pull rather than push it even before we read the ‘pull’ sign. As I unpacked item after boxed item, I started to realize that nearly all of them, by conscious design or otherwise, seemed to afford a specific set of behaviors. And while I’d previously accumulated and sloughed off ‘stuff’ with an eye mainly towards frequency of use, more recently, I’ve started to look at things in terms of type of use. If, at least to some degree, my behaviors are shaped by what my surroundings ‘afford’, can I change my behavior just by changing my surroundings?

In other words, does the right tool not just help get the job done, but spur on the job itself? I’ve found it certainly does, as in the case of the garbage can under my desk: for the past few years, I’ve had a small one that looked great, but filled up remarkably quickly. And, as it began to overflow, I found myself subtly slowing down my discarding of unneeded work papers. Inane as it may sound, I found that switching to a much larger desk garbage helped me suddenly clear off my often overflowing desk. The problem hadn’t been that I didn’t want to trash papers, but that my little garbage can didn’t ‘want’ me to throw any more away.

Or consider the Look skillet my father (a fellow kitchen gadgeteer) recently sent me as a gift. While I had long meant to integrate scrambled eggs into my breakfast rotation (great, paleo-friendly source of protein that they are), I had somehow never stuck with the idea. The Look, however, with its flawless non-stick coating and slow, even cooking, just begs to be scrambled upon whenever I see it. I’ve taken to leaving it out on the stove, and suddenly scrambled eggs are a regular morning choice.

Thinking about affordance in cooking tools reminds me that this incredibly basic advice – how you behave is based, to some degree, on what you do or don’t have around – is something I’ve long pointed out in the world of nutrition. My first tip for friends looking to eat more healthfully? Go through your cabinets and throw away all the junk. Don’t buy any more. You’ll naturally end up eating better when you only indulge those cravings that can motivate you to put your pants back on to head to the supermarket.

The new thought, for me, was how broadly this principle applies to everything else. In nearly every facet of my life, given a behavior I want to encourage, or a bad habit I want to break, perhaps by very carefully acquiring or discarding the right tools, the relevant ‘stuff’, I can give myself a boost well past will-power alone.

And, increasingly, I’m starting to think it works. Last week, I was having trouble falling asleep with the stress and excitement of starting Long Tail. Each time I found myself staring at the ceiling, I’d pick up some bedtime reading, and end up keeping myself up even later. Despite self-chastising, I didn’t cut it out until I reasoned through affordance to a simple yet powerful solution: I took the bulb out of my bedside lamp.

When I was in elementary school, my mother referred to me as the ‘absent minded professor’. I lost jackets and umbrellas, couldn’t keep track of school projects, and was generally an organizational mess.

Over time, I built up elaborate systems and anal retentive habits to counter my natural state. And, in the last few years, with the help of Getting Things Done and an endless array of trivial hacks, I’ve gotten to the point where I finally have a good sense, at any given moment, of exactly what I should be doing.

Unfortunately, at any given moment, I’m usually doing something else entirely. Even with a list of next actions in front of me, I have an awfully hard time sitting down and forcing myself to work my way through that list.

In part, I blame my job, which is enormously amorphous. There’s very little in the way of procrastination that I can’t somehow rationalize away as at least vaguely productive. Reading an old Malcolm Gladwell article on marketing khakis? Why, a deeper understanding of buyers’ psychology certainly will come in handy selling Cyan and Long Tail’s films!

In other words, the problem isn’t that the procrastination expeditions I talk myself into are necessarily bad; it’s simply that they’re less good than what I should be doing instead. Still, knowing that, rationally, doesn’t seem to help. For me, at least, ‘integrity in the moment of choice’ is tough stuff.

For the past year or so, I’ve tried to push my way through with logic and brute force:

“Listen,” the smarter part of my brain says. “You’d be much better off if you put down that article and went back to drafting the script option term sheet.”

“Absolutely,” the less smart part agrees. “As soon as I finish this khakis article, I’ll get right on it.”

Very recently, however, I’ve discovered a way that I can trick myself into listening to the smarter part: I schedule, on the half hour, tiny little increments of work, then let myself go back to ‘productively’ goofing off as soon as I’ve done each little increment, at least until the next half hour mark chimes.

Let’s say, as I did earlier today, that I have thirty theaters I need to call to check their base screen rental rates. I’ll sit down and break the list into chunks of three or four theaters, and list them out over the afternoon. These four at 1:00, these three at 1:30, etc. I’ve found it works the best to set the first chunk about ten, fifteen minutes in the future.

So, 1:00 rolls around, I bang out the first four, and then get back to whatever I’ve stupidly escaped into doing, like rearranging a shelf of DVDs. Ding! 1:30. I make the three calls, then do another one or two to lighten the encroaching 2:00 load. Ding! Back to calling, so I crank through the remainder of the 2:00 list, then, with momentum building, hit the lists for 2:30, 3:00 and 3:30.

My brain spent, I go back to DVD re-arranging, until the 2:30 ding, when I get back to calling, and decide to just make the last eight or nine calls to be done with it. And now, thrilled to have finished the calling I’d been avoiding all weekend, I crank out a few pressing emails for good measure, and build effortlessly from there.

Holy reclaimed afternoon, Batman! Somehow I’ve gone from a day where my brain seemed permanently out to lunch to one where I’m startlingly productive.

The secret, for me, seems to be the safety of the worst case scenario: even if I’m not picked up by the surge of forward motion, I know I’ll at least manage to slog through each of the small, on-the-half-hour actions. Which, for whatever reason, seems to take off enough of the pressure to perform that, about 95% percent of the time, I do get picked up by the productivity surge, pushing towards the best case scenario instead.

For the first time, I seem to have discovered my subconscious resistance to getting started: the inherent internal commitment to keep going past that first step. Take away that commitment, and the getting started seems far less terrifying. After which, apparently, the keeping going sort of takes care of itself.

Like most internet users, I get spam. Unlike most, I get ridiculous, overwhelming amounts of it: on average days, upwards of a thousand pieces. Consider it an occupational hazard. To find the screenwriters, directors, actors, producers and slew of other collaborators on which Cyan’s (and now Long Tail’s) projects depend, I need my email address flung far and wide through the cybersphere. But, in that flinging, it inevitably ends up on junk mail lists everywhere.

For the past year or so, I’ve been getting around the problem using KnowSpam.net, a server-side challenge-response system. Which basically means that, every time someone sent me an email, if I hadn’t previously received an email from them, KnowSpam would ask them to demonstrate they were human by answering a question on their website. And, on the plus side, it worked exceedingly well in cutting my spam down to zero. On the minus, it also started to increasingly piss off the humans whose humanity was being verified.

So, yesterday evening, I downloaded SpamSieve, a Bayesian filter for the Mac. Bayesian filters (near and dear to my heart from the neuroscience and computer science days back at Yale) essentially figure out the fuzzy overall similarity between two things – in this case, the similarity between an incoming piece of email, and the entire body of previously received email already sorted into spam and ham. Bayesian filtering, in theory, works remarkably well. But, like communism, it rarely seems to pan out quite as nicely in practice.

Which is why I was more than pleasantly surprised by SpamSieve; I was joyously shocked. After training the filters on a stack of old emails, it caught all but one of the 313 pieces of spam I received since midnight. Now, perversely, I’m taking pleasure not in the real email I receive, but in the flow of penis enlargement ads and mortgage refinancing offers, as they pile up, message by unmissed message, in my junk folder.

Finding happiness in watching good technology at work. Further proof that, hide out in the world of film as I may, I’m still pretty much 100% dork.

As the history of great men is littered with inveterate nappers – Albert Einstein, Napoleon Bonaparte, Thomas Edison, Winston Churchill – it pains me to admit that I nap rather poorly. It isn’t that I can’t fall asleep in the middle of the day, but rather that I can’t wake back up.

Of course, at some point, I do awake; but, invariably, it’s feeling far more tired than when I dozed off. My rare naps, then, are usually driven by extreme situations – after a particularly long night on the town, or following a work-driven all-nighter. Then, groggy and cotton-mouthed as a half-hour stretch of zzz’s may leave me, I’m at least no worse off than I would otherwise have been.

There is, however, one other sort of nap I do take more regularly, albeit unintentionally: it is the post-workout pass-out. On occasion, while hitting the gym, I manage to push myself well past my rational limits. Returning home, I lie down for a minute while untying my sneakers, then open my eyes to discover an hour and a half has suddenly disappeared. This happened to me yesterday, and, as my eyes opened, I felt a bit like a computer must (if, indeed, computers feel) upon crashing and rebooting. Unlike my other naps – ones where I put myself to bed and eventually wake myself back up – these post-workout pass-outs catch me suddenly, then dump me back into the world, essentially the same, though with the exercise-induced cobwebs cleaned from my body and brain.

And it is through those gym-driven nods that I can, at least to some degree, understand and envy the great nappers. Surely, I would more than make up for twenty minutes lost to sleep if I emerged from each at a fresh mid-day beginning. Which leads some horrible part of my subconscious to secretly wish for a late onset of narcolepsy. If it is the sudden start – that capture by sleep, thoroughly unawares – that differentiates my gym-driven napping from my other less successful attempts, then perhaps as a narcoleptic, I might be able to nap like a pro.

Sure, unexpected fits of sleep might complicate driving, or lead to some awkward dating moments. But nobody said that achieving greatness would come easy. It clearly takes hard work. Apparently the sort of hard work you can sleep through.

During my month in Israel, I had the odd impression that someone had hit the pause button in my life. Aside from the documentary, nothing else seemed to exist; everything appeared frozen, in stand-still. Yet, not surprisingly, during that month the parts of my life were still rolling ahead, piling up in surprisingly exciting ways. I came back to a flurry of breakfasts, lunches, coffees, dinners and drinks, to a calendar filled past breaking with friends and family, colleagues and competitors. I’m booked near solid for weeks to come, and with each passing day, I’m rediscovering how much I like the people I haven’t seen for far too long, shocking myself with the ready-to-move-ahead-at-the-push-of-a-button potential stored up in the various business projects I’ve kept brewing in my head.

When it rains, it pours. And, during the slower patches of my life, I constantly wonder what I can do to speed it all back up, to get the drizzle started. Apparently, all I have to do is simply fall off the face of the earth for a while. Because, now, the first showers have started, the rainclouds keep rolling in, and I’m ready to get drenched.

I receive a fairly insane number of emails a day, and have always been rather slow in responding to them. I’ve recently started getting much better, however, and wanted to quickly share what works for me in case it helps anyone else.

1. Get a good spam filter. I use Knowspam.net – as I check email on both my computer and phone, I wanted something server-side. It’s a challenge/response system, so literally no spam gets through. I loaded up my address book when I joined, and it scans my outgoing mail for new addresses, so only people who have never emailed me before and have never received an email from me are hit with an authentication request, and then only the first time. Having something automatically separate the wheat from the chaff makes wading through all the email I receive merely extremely tough, rather absolutely impossible.

2. Read the emails you receive. If any require less than two sentences of response, or absolutely require immediate attention, reply as soon as you read them. Doing so guarantees you respond to the time-sensitive messages in a timely manner, and it keeps easy ones from piling up.

3. Make a ‘reply’ folder, and move everything else there. Your inbox then stays clean, making it easy to triage incoming mail.

4. When you have some free time, pull up the reply folder and start working through the messages one by one, bottom up. That is, open the oldest email, and reply to it before going on to the next. This keeps you from saving the hard-to-write ones, saving them even longer, and then realizing you’ve gone weeks or months without replying to them.

5. If you find the reply box is getting particularly full, and you have a laptop, I find it helps immensely to get out of the office (or home workspace) and head to a coffee shop or restaurant instead, as it reduces all the possible procrastination-friendly distractions to a bare minimum. Plop down somewhere, and do nothing but chip away at the reply folder.

6. Another quick time saver: don’t save old emails in specific folders or categorize them or whatever else. Just delete everything, but set Outlook (or whichever program you’re using) to archive rather than delete the mail in your ‘deleted items’ folder, and set the archive date out eight or twelve months. This way, you can sort by sender and quickly find specific exchanges by skimming the list of emails from that sender; or, if you can’t remember who sent it, you can always search for the content the email contained. Either way, it’s likely faster than devising and sticking to an elaborate system of folder categorization.

Between these six things, I’m starting to feel like I’m no longer drowning in emails – now I’m only, say, neck deep. Still, that’s a big improvement. Try it out, and see if it works for you.