Todoist

For years and years, I managed all of my tasks, projects, goals and ideas using a handful of text files that I wrangled in the text editor BBEdit. It was nerdy and time-consuming, but also completely bespoke; the approach fit my workflow, and evolved over time as my working style did, too.

Along the way, I briefly tried out pretty much every task management software that existed. Some, like The Hit List or Omnifocus, I even stuck with for a couple of weeks. But, inevitably, I’d end up chafing under a program’s structure, or run into problems with its stability and data security, and return to my free-form text.

About six months ago, for reasons I can no longer recall, I decided to test out the online task management program Todoist. An extremely fast and fluid web app, it also boasted polished iPhone and iPad versions. So I dumped in my text files, and started using it. And then I kept using it. And using it. Two months in, I reverted to my text approach; after an hour, I started to feel that it was text, not Todoist, that fell short in comparison.

Six months later, I still use Todoist all day, ever day. If you haven’t tried it out, you should. (And sign up for the trial of the premium features; they make the app vastly more powerful, and are certainly worth the the $0.08 a day they cost if you decide to stick with it.)

Paradox

Recently, I stumbled across [Dance in a Year](http://danceinayear.com), an awesome single-page site from designer Karen Cheng. Atop the page, a video chronicles Karen’s dance skill progress over the course of a single year, from “embarrassing even alone in your room” to “ready to hit the club”.

Below the video, Karen shares her secret: practice every day, setting small goals along the way.

Or, in other words, the same advice that pretty much everyone ever gives on learning or doing anything at all.

Still, obvious isn’t the same as easy. Incremental progress is, by definition, slow. And daily hard work takes, well, daily hard work. So, instead, we Tweet and Facebook and Foursquare and Instagram our way through the day, chasing minor instant gratification, the sudden small changes that yield immediate inconsequential results.

And it seems we’re getting great at doing that! Problem is, it’s precisely the opposite of what it takes to actually be or do the things most of us really want out of life.

Backlog

And speaking of getting back on track:

In his excellent [*Do it Tomorrow*](http://amzn.com/0340909129), British time management guru Michael Forster observes that, on average, the number of incoming tasks, emails, whatever, that come into your life each day needs to line up with the number you can process, respond to, etc., over the course of that same average day. Otherwise, you end up progressively further and further behind with each day passing.

Once you’re behind, it’s increasingly tough to catch back up. It’s like bailing water out of a ship that’s already flooded. So Forster puts out an excellently elegant solution: declare a backlog, and move everything that’s come in prior to right this second to a separate list (or, for email, folder). Then focus, first, just on making sure you’re keeping up, day after day, with the new stuff as it comes in from here forward. After that, as time allows, then whittle away at the backlog.

Due to a slew of factors, which mostly boil down to me trying to juggle too much all at once, I realized earlier this week that I wasn’t even close to keeping up. My to-do list had hit 200 items – well beyond what I might hope to accomplish in a day, or even in a month. So, on Monday, I called shenanigans, and declared a backlog. I’m hitting new work as it comes in first, and slowly whittling away at those 200 items as the rest of my day allows.

If nothing else, it’s a good chance for me to watch carefully how much work comes in, and how much I can get back out, in a given day. If I can’t stay at inbox and task list zero, then I have to toss some commitments, or otherwise whittle away at the demands on my life.

Heart Felt

Perhaps due to my hacker roots, for more than a decade I’ve organized my life in a collection of text files. But when it comes to actually executing, I’ve discovered I’m far more productive working off a printed-out version of my Today.txt to-do list than I am with the same list on-screen.

For notes in meetings, too, I find paper and pen works better for me than an iPad or laptop. Much as for solo business strategy and planning sessions, where I tend to do my best work when I’m scrawling page after semi-legible page of ideas, mind-maps, outlines and diagrams. (Jess refers to this as my *Beautiful Mind* mode).

For years, I did my scribbling with blue Pilot G2 pens. Then about twelve months back, I switched abruptly to black Sharpie markers, usually writing on blank pieces of printer paper rather than yellow pad.

About three months ago, I ended up purchasing a variety pack of [Papermate Flair Felt-Tip Pens](http://www.amazon.com/Paper-Mate-Point-Guard-Assorted-8404452Pp/dp/B002R5AEIY/ref=sr_1_12?s=office-products&ie=UTF8&qid=1335062836&sr=1-12) to correct a document using the red pen. Though that pen was fine, and though the collection also included perfectly nice black and blue pens, I quickly found myself using only the green pen. I carried it in my pocket all day, using it at work, at home, to sign bills in restaurants.

A few times, I popped into Staples I happened to be passing by, hoping to find more green pens. But, in each case, the green was only available bundled in four-color packs. So, by now, a pile of unused black, blue and red Flairs sit unhappily in my desk, as I run through the ink in the couple of greens I own.

I don’t have a good explanation for why I like the green pen so much. It stands out? It’s easier on the eyes somehow than blue or back? It’s the color of money? It’s the logo color of Jess’ newly launched [Dobbin Clothing](http://www.dobbinclothing.com). (See what I did there, Jess?) But I do know that, soon, I need to start actually ordering these pens in twelve-packs online, because amassing unused other-colored felt-tips doesn’t seem like a particularly good long-term plan.

Kermit was right.

!Robots

Somewhere over the past couple of years, Gmail solved spam. I’m not sure when it happened, precisely, but by now spam in my inbox is so rare that it actually catches me off guard. How did that get through?

Still, about six months back, I realized that nearly half of my email was what’s sometimes called ‘bacn': those notices, newsletters, updates and alerts somewhere between spam and the ‘ham’ of real, human-sent emails. Shipping notices from Amazon, connection requests on LinkedIn, investor updates, retweets on Twitter, bills due to ConEd, Time Warner and AT&T, server status pings, all piling up at alarming speed. And though I wanted to at least glance at all those emails, few were crucial, few warranted immediate reading or response.

Still, because of their sheer volume, those bacn bits quickly gummed up the works, making it harder to spot and corral the messages that really did deserve quick attention.

So, using Gmail’s filter system, I fixed the problem:

I created a label called “!Robots” (with the ‘bang’ / exclamation point to alphabetize first).

Then, over the course of a month or so, as any email came in that wasn’t a personalized message from a real person, I’d click the little arrow at the top right of the message, choose “Filter messages like this”, then choose “Skip the Inbox” and “Apply the Label: !Robots”.

Voila.

Now, once every day or two, I head to the !Robots folder, and crank through the hundred or so messages that have inevitably accumulated. Most require nothing more than a quick glance. Others – say, an expiring domain – need a minute or two of action. Still, I can usually get through the folder in well under ten minutes.

And then, the rest of the time, when I check my email – whether in Gmail, in Sparrow, or on my iPhone – all I get is the good stuff. No weeding necessary.

Turns out, taking out the bacn has been as much of an improvement as taking out the spam.

5000, 4999, 4998, 4997…

I’ve been reading some kinesiology texts of late (yes, really), and stumbled across an interesting paper by Dr. Richard Schmidt [Motor Learning, 1988] about acquiring motor patterns through repetition.

Schmidt’s extensive research focused on the amount of practice necessary to learn a movement, to make it habit. A new pattern learned from scratch, he discovered, seemed to reliably take between 300 and 500 repetitions to become permanent. But new patterns learned to correct and replace an old, less efficient pattern instead consistently took between 3000 and 5000 repetitions – a literal order of magnitude difference.

I’ve thought about that recently as I’ve worked out, looking at the ways I move in basic exercises. But I’ve thought about it even more, looking at how I ‘move’ through the rest of my life.

Over the years of running companies, I’ve developed work habits, communications styles, and basic approaches to business. Most of those, on inspection, have served me very well. But a handful have not. And, indeed, I’ve increasingly noticed that I spend disproportionate amounts of time and energy undoing the problems cause by those handful of inefficient, bad patterns.

I’ve been focusing on correcting those patterns, replacing them with new, better, more efficient approaches. And, for the most part, I’ve been moving forward. But, of course, like with anything new, from time to time I misstep.

Before, I’d always believed the business self-help book saw that it takes 30 days to make a new behavior a habit. And, perhaps, in some cases, it does. But Schmidt’s research makes me think that time has nothing to do with it. Instead, it’s about volume of practice. And, in the case of re-learning something, it’s about a very, very large volume of practice.

Five thousand is an inordinate number of times to face a decision, and to make the right choice. In that context, those missteps seem inevitable. How can you do something new correctly five thousand times in a row?

And, just as important, in that context, it’s clearly only worth setting out for change when you’re ready to buckle down for a long-haul commitment, when you’re ready to start even knowing that you aren’t aren’t ‘done’, you aren’t finished thinking about your actions, until you’ve got things right again and again and again, three thousand to five thousand times.

Get to Work

“The advice I like to give young artists, or really anybody who’ll listen to me, is not to wait around for inspiration. Inspiration is for amateurs; the rest of us just show up and get to work. If you wait around for the clouds to part and a bolt of lightning to strike you in the brain, you are not going to make an awful lot of work. All the best ideas come out of the process; they come out of the work itself. Things occur to you. If you’re sitting around trying to dream up a great art idea, you can sit there a long time before anything happens. But if you just get to work, something will occur to you and something else will occur to you and somthing else that you reject will push you in another direction. Inspiration is absolutely unnecessary and somehow deceptive. You feel like you need this great idea before you can get down to work, and I find that’s almost never the case.”

– Chuck Close [Here, Via]

Freestyle Productivity

Recently, I stumbled back across a blog for students, called Study Hacks, that’s written by my friend Cal Newport. After getting sucked deep into the archives, I can definitively say it’s not only a great and well written site, but also one that’s genuinely and broadly useful for even those of us well out of college and into the ‘real world’. Go give it a read.

In particular, though, I’ve been thinking a lot about his Law of Action Planning: that no rigid rules or systems for figuring out “what to do when” can work effectively for more than a few weeks before becoming obsolete.

As Cal observes, (and as I have in the past) productivity largely boils down to two problems: capturing and organizing the stuff you have to do, than actually doing that stuff.

But, Cal goes on, while a simple system can solve that first ‘capture/organize’ problem for years and years with little change, it’s the second ‘do’ problem that constantly needs new solutions to keep up with the realities and demands of our lives.

Previously, I’d taken that as either a flaw inherent in a given system (like, say, David Allen’s Getting Things Done), or in myself. Now, I’m starting to see it’s perhaps just the way human brains are wired to work.

Admittedly, that doesn’t really change anything in terms of my actual productivity output. But it does, at very least, allow me to skip from one form of time management to another without all the mental angst. Don’t worry, I can tell myself; it’s a feature, not a bug.

Same Battle, New Tactics

There’s a great story about a guy who attends a Tony Robbins seminar, and complains to Robbins that, despite trying everything, he can’t lose weight.

“You’ve tried everything?” asks Robbins.

“Everything,” the guy replies.

“What were the last hundred things you tried?” asks Robbins.

“Well,” the guy admits, “I haven’t actually tried a hundred things.”

“Then what were the last twenty-five things you did?” asks Robbins.

“I haven’t tried twenty-five things, really, either,” the guy responds.

“So how many things have you actually tried?” asks Robbins.

“Well,” says the guy, sheepishly, “maybe five or six.”

Perhaps it’s an artifact of America’s Protestant work-ethic roots: when we fail, our first response is to try the same thing again, just harder, and with more resolve.

Problem is, that rarely works. If the strategy didn’t work the past five times, the sixth isn’t likely to work either, no matter how much energy, commitment, and enthusiasm you throw behind it.

Just observe the number of people making the same New Year’s resolutions year after year. If you’ve been vowing to lose weight each of the past five January’s, odds are good, by the next one you’ll still be a fat fuck.

As the old saying goes, if you always do what you always did, you always get what you always got. Or, in Einstein’s more eloquent words, “the thinking which created today’s problems is insufficient to solve them.”

So as you embark on this new year’s old resolutions, do some new thinking. Brainstorm about what you’re going to do differently, smarter. How you’re going to change your strategy. Because trying the same thing again – this time, with feeling! – just isn’t going to work at all.