Time management is broken. Here’s what we’re doing about it.

Time management is a pretty simple problem. People, generally, want help becoming more productive. It’s up there with “lose weight” and “spend more time with family” for generic, perennial goals.

In my life, there’s often a huge disconnect: I have a near-infinite list of things I’m expected to do, yet I often find myself sitting at my desk, with absolutely no clue what I ought to do next.

There are also thousands of solutions out there trying to connect “to do” with “done”. So why on earth would we throw our hat into such a crowded ring?

Although I’ve tilted at this windmill before, my friend Dave Brady and I felt like we had a new, unique philosophical take on this that might finally work for us, and perhaps for others.

What’s broken about time management

None of the solutions I’ve tried worked for me, and I’ve tried almost everything, from Franklin Covey to Getting Things Done. I’ve spent hundreds of dollars on apps, lists, and cool zipper binders for my “What matters most” planners. I set up a WebDAV server to sync my desktop OmniFocus with my iPhone version.

So what broke?

I skipped a day. Then a week. It was okay, since I had a pretty good handle on what  I was supposed to do, and tracking it all in a single place was just extra effort.

Then I came back to my management tool, and had to stare down a massive, irrelevant, stale backlog of tasks. I wound up marking tasks as complete that I just didn’t care about anymore. I started shifting priorities around to try to put everything in neat little boxes, but it didn’t work? Why? Because life is messy.

Then, I stopped knowing what to do next. And it doesn’t take me long to wear myself out on the panic that results from this kind of paralysis.

Enter Pomodoros.

Focus: It’s what the Pomodoro technique is known for (at least in circles that know it). In a nutshell, it’s a process by which you write down your day’s tasks on a piece of paper, estimate the number of 25-minute stretches of focused effort it will take to knock out each task, set a timer, and start doing these 25-minute stretches (called “pomodoros” or “poms”) with a 5-minute break in between.

This is, of course, very good for focus. Instead of looking for distraction-free writing or working environments, you sort of “distraction-proof” yourself. It operates on a principle that I hold close: that context is sacred, and no one should be allowed to break it (least of all yourself). I can shorten my personal leash and put Twitter on the bench for 25 minutes.

Interruptions from outside, too, tend to disappear after just a little bit of training. After just a few times hearing “I’m in the middle of a pomodoro, can I hit you back in 15 minutes?”, people get a sense of where boundaries are. This alone is worth the price of admission.

Pomodoro is very much a “live for today” technique. Much of what made Franklin Covey so popular, its focus on “big picture” items also sank it for me. With Pomodoro, I trust that I’m generally on the right course, and plan today’s tasks exclusively.

But for me, the Pomodoro technique solves a bigger problem. If I’m using Pomodoro, I have a pretty good idea of what to do next. Tasks that are too small to deserve a full pomodoro get swept up and done between poms, or they sort of fall by the wayside. As long as I made sure my tasks are truly valuable while planning them, I’m generally doing the right thing at a given time.

Anecdotally, I can vouch that this is a pretty good way to make sure that what you do during the day is an approximation of what you hoped to accomplish when you started.

Why ToDoGroove?

Very simply, Dave & I think that our vision for ToDoGroove is going to not just satisfy Pomodoro technique users hoping for a web-based solution, but introduce the principles and benefits of Pomodoro to a group of people who would never have tried it otherwise.

The philosophy and goals behind ToDoGroove can be summed up in 3 statements:

1. If you don’t know what to do next, your tools have failed you.

2. If you have to lie to your tools, they’ve failed you.

3. If you go home feeling like your day was stolen, your tools have failed you.

I’m not saying ToDoGroove accomplishes those perfectly yet (or even very well), but those are the clear pass/fail targets we’re aiming for.

Who’s it for?

A wood pulp enthusiast or moleskine-toting hipster can (and likely should) stick with the pen-and-paper flavor of the Pomodoro technique. On paper, you have the advantage of having to re-plan from scratch, every day, with no carryover of cruft.

But it’s easy to see where a digital version has advantages: possibilities suddenly open up for integration with other services, analytics, and automation (i.e. reminders).

Ultimately, I found several components in Pomodoro that worked, but pen-and-paper simply won’t cut it for me. That’s not where I live.

Our hope is that the people who have tried a lot of other stuff will find their home in Pomodoro like we have, and that ToDoGroove will be partially responsible for people feeling a sense of control over their day (and ultimately, their destiny).

A quick introduction

ToDoGroove works simply (thanks to some advice from a designer friend who freaked out at our overly-complicated mockups).

You log in, create tasks, tag them, and estimate effort. As you complete pomodoros on a task, you mark them off, and finally mark a task as complete.

How we use it now

The first thing I do in the morning, unless I’m being derelict, is to spend my first pomodoro planning the day’s poms.

I go through and mercilessly revise, delete, or archive prior tasks. I might dig through the archive to find tasks that might be worth reviving.

My tasks are tagged simply, with “work”, “home”, “todogroove”, etc. At work, I click the drop-down to jump into tasks tagged “work”.

Personally, I further drill down into Focus Mode to stay tied to the task I am working on at a given time, but Dave tends to get work done from his basic task list.

We use an external timer to track the 25-minute pom and the 5-minute break. I use a basic free one on the web, but you can get a really nice one for Mac for $5.

I find a lot of satisfaction in ticking a pom, and I typically force myself to take a break, check Twitter and email (briefly!), but try to clear my mind for the next pom.

My first day, I got 0 poms done. My second, I got 1. Third, I got 2. Then 4. Then 8. Now, I tend to get 6-10, depending on whether I have meetings to attend.

The Merlin Mann school of prioritization

You’ll notice a profound lack of “prioritization” in ToDoGroove. I subscribe to the Merlin Mann school, wherein there are two priorities: “I’m going to do it” or “it’s in the trash can”. I use the Archive as a trash can, and Delete as the incinerator. Planning one day of tasks at a time does a lot to keep me from obsessing over “priorities”.

That said, there may be need to order the tasks. Dave does this by prepending a number to his tasks. (So far, pretty much every feature we’ve built into ToDoGroove has been first hacked in and tested like this.)

So what’s next?

Seriously, a Pomodoro app without a timer? Dave thinks it’s a great idea, I don’t so much, though I do agree that timers are a commodity and shouldn’t be our main focus.

There are a lot of rough edges. A lot of the stuff we’re doing should be done via AJAX but isn’t yet, making our app feel a little janky and slow. There’s currently no way to reset your password or even view your archive.

We haven’t really kicked in analytics yet. Completed tasks hang around after they’re useful. Things like that.

We want to wipe the table of estimations every day, make tasks older than 3 days auto-archive, and make your first task every day auto-populate with “Plan today’s pomodoros”. But to feel comfortable doing that, I feel like you’ll need a place to configure settings or opt out of those.

Call for help

We can guess at this, but the reality is, we need your help. We’re creating the app we want, but we’d sure like to make sure it works for 80% of people. I’ve already gotten suggestions ranging from low-hanging fruit (recurring task lists) to some philosophically sticky wickets (using poms to let frustrated wives limit Minecraft time).

Really, the only way we’re going to make ToDoGroove capable of achieving its vision is to have you try it and to get your feedback. It’s very rough around the edges, but it is helping us wrest control of our lives back, so we are opening the door and letting people in, albeit slowly.

Please do hit us up if you want to join the beta. Offering more information about what you want to accomplish will help us pick people who are a good match for this stage of development.

Whether you try ToDoGroove or opt for the pen-and-paper approach, all we ask is to give it a week. You’ll know it’s working if the left side tingles if you start noticing more stuff gets done.

12 Killer Apps for iPad

I wasn’t going to write this post on my iPad. It felt like a bit of a cliché, you know? Plus, I thought it would be a bit like fighting with one hand tied behind my back. And it is, to some degree; I type about half as fast as I do on a laptop.

So why go through with it then? Because the iPad is so fun to use, I don’t feel like getting out my laptop.

I have my share of gripes and praises for the iPad, but it’s just 9.7 inches of blank screen without the apps to make it useful. And they do. In fact, “revolutionary” is not going too far.

So, with the aid of the iPad’s WordPress app, here are 12 apps I already can’t live without.

The first thing I want to say is that the iPad is an absolute joy to use. By that I mean that using the iPad elicits actual joy. Everyone was wondering what the killer app for the iPad would be. I think that the killer app might just be the experience of using an iPad, period. But to better answer the question, the answer is twofold:

– Everyone’s going to have their own version of the iPad’s killer app.
– You are going to find at least 10 killer apps within your first 48 hours

Here are 12 of mine.
I bought the iPad primarily as a reading device. It has already delivered on more than its promise. It’s not hard to imagine having an entire page of apps dedicated to the various types of reading I do. My favorites right now:

GoodReader ($1)
Without solid PDF support, I wouldn’t be able to read programming books on the iPad, and that would be a deal breaker (lame PDF support caused me to return both the Kindle and Sony Reader). Although the PDFs don’t render with lightning speed and the page turning mechanic is wonky (honestly, who turns pages from top to bottom?), this is an app that already shows maturity. I threw a 500MB PDF at it, and it cut through it with ease. GoodReader also has a raft of network-aware features, and although they’re a bit more geared toward power users, they handily circumvent Apple’s insane methods of getting files on and off the iPad.

iBooks (free)
iBooks is the app that always elicits the remark, “now they’re just showing off”. Graphical flourishes aside, it’s fast, beautiful, and fun to read books on. I had serious concerns about eyestrain, but those proved to be unfounded after fiddling with the brightness a bit. The included Winnie the Pooh book was a bit of unexpected genius; a sign of things to come as you dig deeper into the iPad experience.

Marvel Comics (free)
This is another app that really shows off what the iPad can do. I’m not a huge comic book fan, but they look so lovely on the iPad’s screen that I may pick one up from time to time.

Air Video ($3)
It’s an iPhone app, but while the team works on their iPad version, they deserve your 3 bucks. With a simple server app, you have access to all the media stored on your home computer anywhere, even over 3G. Media not encoded in iPad-compatible h.264? No sweat. It’ll convert on the fly while it streams your TV shows & movies, and even pixel-doubled, media looks fine.

Dear, departed Simplify Media ($N/A)
This one is a big WTF. Being able to access my music and photos remotely made this easily one of the most useful apps ever. Simplify not only streams your music from anywhere in the world to your iPad, it allows you to share your entire library with friends (and share theirs in turn). It’s the poster child for the idea that your media shouldn’t have to fill local storage to be accessible. But you can’t buy it, can’t download it, and even if you own it like I do, it will stop working in a couple of months. Rumors are swirling that these guys have been bought by Apple, and the mystery surrounding their disappearance is certainly consistent with past Apple acquisitions.

Sketchbook Pro ($8)
Smart controls and pro-caliber features make this the king of the sketch apps. Using it makes me wish I had more talent. I have seen it do amazing things in the hands of greater men than I.

SugarSync (free)
Apple has crippled this genius app. Access to all my documents, synced automatically from my desktop, anywhere… It’s a fantastic promise. On the iPhone, it doesn’t matter that the documents are read-only. But as soon as you need to edit a word document or save a PDF to GoodReader, you’re out of luck until you go through Apple’s convoluted manual sync process, or email it to yourself (and then it’s a crapshoot). Even with its limitations, SugarSync is a great app and helps point out the gaping hole in Apple’s cloud storage offering.

Instapaper (free)
There’s little to say about Instapaper other than that it’s nearly perfect. It’s a simple premise: save longer web articles for later reading. And what better place for all this to wind up than on your iPad? The “nearly” in “nearly perfect” is because Apple doesn’t allow in-app brightness control from third-party apps (though Kindle for iPad seems to have found a clever workaround).

Evernote (free)
Another simple-but-brilliant idea: all your notes, write once, sync everywhere. Clippings, links, anything you’d rather not forget goes into one safe place.

Games were the biggest surprise on the iPad. Aside from the week of my life I lost to fieldrunners, I’m not a big iPhone gamer. But with a larger screen, the games on iPad a compelling enough that I don’t foresee firing up my Xbox or Wii anytime soon.

Geometry Wars ($10)
This was the Xbox 360’s only memorable launch title, and it’s made quite a splash on the iPad. The dual-analog-stick-emulating controls are fantastic, though you need to place your thumbs well inside the bezel to get the best results. It’s quick to pick up, and I feel it pulling at me even now.

Top Gun ($5)
It’s dumb, retro fun. Tilt controls are a great way to experience this game that feels like a cross between Top Gun for NES and After Burner for arcade.

Touch Hockey ($3)
The iPad was made for moments like this. You pull out your tablet, set it on a table, and challenge a friend to a realistic, fast-paced round of air hockey. The highs and lows are just as visceral as the real thing, and it seems like a great way to strike up a conversation with a girl. Try doing that with your Kindle.

The iPad has tremendous potential for graphics capability, and I’m still holding out hope for a beautiful-looking, bumper-grinding arcade racer like Burnout (or an entry in the Burnout series).

Incidentally, the WordPress app for iPad (which I posted this from) is not yet a killer app; it’s a larger version of its iPhone cousin. Give us some HTML formatting help and better image handling, and we’ll talk.

I had to use one other app to make this post: Photogene ($4) to rotate and resize the photo I used in the post. Seems pretty cool, I look forward to using it more.

So there it is: for $30, a great way to start off your iPad experience. $40 if you include Pages, but I haven’t yet found occasion to use it.

I have a lot more to say about the iPad in general, but it can probably wait until I’m at a more comfortable keyboard.