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.