After many conversations with people both inside and outside the office, I thought it might be useful for me to describe exactly how I approach my work and why the traditional 9-to-5 day hasn't cut it for me for almost a decade.

From a high level, how well I'm doing with my work is not a function of how many hours I've put into a given week, but rather the state of one artifact: my to-do list. I've used Remember the Milk for over seven years to keep track of what I'm responsible for and how I'm doing meeting my obligations.

I settled on Remember the Milk after abandoning the Omni Group's OmniFocus when I needed a to-do list that was accessible in as many places and on as many devices as possible (more on this below). Prior to using a dedicated to-do list system, my task management consisted of a haphazard combination of e-mails and using whatever list functionality was available in my local calendaring app. This original combination of e-mail+calendar system originated in college and lasted through one stint working for "The Man" into my first year of graduate school.

The transition from e-mail+calendar to a dedicated to-do list was driven by an unfortunate incident of me losing track of what I needed to do in graduate school and vowing to never again drop the ball in such an egregious manner. The fumbled task consisted of a collection of things I needed to do to host a visiting speaker, including arranging meetings with local faculty, sending out travel plans and itineraries, and a couple of other tasks that I had to rush to recall and complete the week before he was set to visit our Media, Technology, and Society program. My organization was a mess and the chewing-out I received was well deserved.

After that incident, I read David Allen's "Getting Things Done" and was successful implementing his entire system for several months before abandoning some of the less-useful aspects and keeping the valuable ones. The most valuable thing for me to come out of Allen's GTD methodology was the idea of "ubiquitous capture". The fundamental concept behind this idea is that when you think of something you need to do, you record/capture it immediately in a persistent form (like an item in a to-do list) and you no longer worry about "remembering to remember it". During graduate school, I was still using an early generation iPhone, so I adopted OmniFocus for both the Mac desktop and iPhone as my capture technology and this technique is been at the core of how I get things done ever since.

When I started dabbling in Android, I switched from OmniFocus to Remember the Milk (RTM) mainly because I could access RTM from their native Android and iOS apps, as well as their web site from a desktop. I've been with the service ever since and it's a $25 yearly fee that I gleefully pay.

At its core, RTM is a very simple service. It consists of an Inbox list and you are free to create other manual lists as well as smart lists that are saved queries. You can tag tasks, assign them geographic locations, set up reminders, and more. Despite all this richness, I've settled on a very simple pattern that I've found works well for me.

First of all, I don't worry about breaking my task list into sublists or spend too much time organizing the tasks. So, I primarily park things in the Inbox and use the due date feature and priority to keep things organized. In reality this manifests itself as me setting any items that I could be working on now (or feel like should already be done) as due today (or earlier) with an orange-red priority of 1. Items that are more things to think about than calls to action don't get a due date, but may get a priority of 1. Ideas that still need fleshing out (without any urgency) get added to the list without any due dates or priorities. These sink to the bottom of the list and may get promoted to actual task status if I feel like I have time and mental energy to address them.

I have two numbers that I look at for keeping score of how I'm doing. The most important number is the number of items overdue. This represents the count of things that I would like to have already finished and the main items I'll tackle during the day. The second score is the number of tasks completed. This is the total number of items I've marked completed since I started using the app and the rate at which it rises serves as a rough estimate of my task velocity. I keep track of particular milestones (completion count is a multiple of 500 or 1000) and this helps me estimate how quickly I'm getting through my tasks.

Remember the Milk Screenshot

My current scores are 77 overdue, 6385 completed. The 77 overdue items is much higher than my historical preference of an overdue count between 15 and 30. I'm in the end phases of a project and most of those 77 items represent small things that need to be done (fix a particular bug, make a phone call) instead of larger items that will eventually be broken into smaller tasks (write an app that does X). The overall count of 6385 lets me know that I've completed 385 tasks since November 12. This is a faster pace than I'm historically used to and reflects the war of attrition I'm current waging in my working life. My current task completion rate is roughly double what I'm used to in less busy times. I don't intend to maintain this pace, but I need to get through the current slog before I can reach a more desired "chill" state.

While the overdue and completed counts have internal meaning for me, I'm extremely hesitant to use them to make any more generalized representations about my productivity or agenda to outside parties (the paragraph above being an obvious exception). The main reason for this is that not all tasks are the same size and extrapolating a time estimate or other effort figure for pending items based on past items is pretty suspect. One task may represent many other tasks (e.g. "IC: Random recommender w/ Conductor integration", while another task may be a simple action that can be completed in less than a minute (e.g. "PT: Take Vitamins"). Completing one task may spawn others, such as a software refactor that may identify new issues to address after the refactor itself is complete.

To an outside observer, I'm sure that this instantiation of the things that I have to do is somewhat baroque, undocumented, and poorly-organized (especially given all the tools available: sublists, priorities, locations, tags, and so on). However, it is the way it is because it's not designed to be a shining example of project management, it's designed to enable effective ubiquitous capture (record the task when you think of it - don't wait.) This effectively means that I try to keep the amount of ceremony down to a minimum and not spend a lot of time worrying about organizing where each task fits. This allows me to easily record what needs to get done in just about any environment. For example, I just remembered that I need to take down Christmas decorations. To record this task, I open RTM on either my mobile device or desktop and type:

Take down Christmas decorations !1 today

"Take down Christmas decorations" is the task. "!1" is RTM shorthand for assigning it the highest priority. "today" tells RTM to set the due date to today. That's typically all that is required to get the item into my agenda. If I need to add some other organizational information, I've adopted a convention where I'll attach a prefix to the task. For example:

IC: List Intellicare apps on CBITs Tech Facebook page !1 today

The "IC:" prefix is a note to myself that this is an Intellicare task. If I'm looking for things that need to be done with Intellicare, I can quickly scan the list for items with that prefix.

Once I go through the actions above, the tasks are in my list, sufficiently organized, and have incremented the overdue counter that I have an ongoing compulsion to decrement down to zero.

Questions others have asked about this approach or questions I've asked myself about this way of getting things done:

Q: How does this approach work with vacation and/or time-off?

A: My approach basically doesn't accommodate time-off or vacation all that well. Basically, vacation days are days where I don't look at the list nearly as often or focus my energy towards knocking off items that are not work related like things around the house or projects of my own. ("Laundry" is often a popular item.)

Q: How do you delegate using this approach?

A: My RTM list is intended for one user – myself. If there's an item on the list that I want to delegate, one of two things happens. If I can trust that the person I'm delegating the item to will be able to take it over without any further intervention on my part, I mark the task done. If the task is something I'll have to review or otherwise be engaged with, I'll change the task's description and set the due date to a time in the future when I should expect to received the results and review them.

Q: What about work/life separation?

I don't find a lot of use trying to compartmentalize my "job" and the rest of my life. Some people I know keep separate personal and work lists and only engage with each "on" or "off" the clock. Personally, I like to spread my misery around (I'm joking) and don't really worry about the borders between "work" and "home". If I have an opportunity to knock off a "work" item at home the evening before, I'll do that because it will make my next day at work a bit better.

To be a bit clearer, rather than try to match "work tasks" to "work time" and "other tasks" to "other time", I try to take care of the most challenging tasks I have in the queue based upon my personal context and mental energy at that moment. For example, when I was with my wife at the hospital and she was lightly napping, I took that opportunity to update the icons in the Intellicare suite from to previous Holo style to new icons in the new Material Design style. It was fairly tedious work (especially when managing the various display densities – 4 copies per icon), but something that I could do without a lot of thought while sitting in the chair. I knocked it out then rather than spend a couple of hours at work wasting a higher-capacity mental state during the regular workday.

Q: Would a more structured methodology like Scrum or tools like Pivotal Tracker provide some structure that would make your life easier?

A: We use Pivotal Tracker in the office for general project management and I've been a bit of a curmudgeon in adopting it wholesale. While I think it's a decent (not great) tool for communicating with clients, I haven't adopted it as my go-to task management system primarily because its lack of ubiquitous capture. There are no acceptable mobile clients and the desktop experience erects a lot more "ceremony" around logging an item than I find useful:

Is this task a bug, feature, chore or something else?

If this is a feature, on a scale of 0-4, what is the effort required?

Who is assigned this issue?

And so on.

Given that my bread and butter are mobile apps, I spend a lot of time during my commutes poking apps and logging issues in RTM. There's simply no analogue in the Pivotal Tracker world. Incidentally, the amount of similar complexity was one of the reasons I was happy to originally leave OmniFocus in 2009 for RTM. I think Pivotal Tracker is a useful tool for coordinating teams, but more as a report for what's been done or on the overall agenda, instead of being an actual tool to ingest the items to be done and serve as an ongoing tool to help get work done.

Q: Why are fifteen to thirty "overdue" items a sweet spot?

A: I find it useful to always have something in the queue because if I were ever able to get to the point where I had an empty list, I'd find myself prone to bikeshedding small things instead of looking for and achieving larger goals. I also don't really believe in the mythical 0-item to-do list. That either means that I'm not being sought after to do something (my services are not in demand) or I lack the vision to take something of my own and make it better. Neither are appealing situations.

Currently, my fifteen most "overdue" items in my list consist of

  • 3 updates to my Shion home automation software

  • 3 improvements to Fresh Comics

  • 3 improvements to the Pnakotic Atlas

  • 2 new Purple Robot features

  • 2 favors for friends

  • 1 household improvement

  • 1 belated blog post (not this one)

All of these are items - some captured as early as 3 years ago - are worthwhile things to do, but my priorities haven't been aligned in such a way to do them. As I keep knocking out higher-priority items, these will rise and eventually be completed.

The upper bound of my comfort level – thirty items – is a figure I've arrived out experientially. Once my to-do list exceeds that level, I've traditionally needed to buckle down and get to work so that things don't overwhelm me. It's a signal that I need to begin limiting what obligations I'm willing to take on until that number is approaching the low twenties.

My current overdue count of 77 is a clear signal that I'm unable to take on any new projects or obligations at this point. I'm optimistic that I can clear it – I've already completed 5x that number of tasks since the middle of November – I just need to work to limit the number of new items that get added.

Q: Why not just give your best effort from 9am to 5pm and take some satisfaction in that?

A: I think my inability to do this stems from a couple of things:

First of all, I'm fortunate in that I have the kinds of projects that keep me thinking about them throughout the day. If I get an idea to improve one of my apps out in the field, I'd rather get started with that improvement while the energy and enthusiasm is fresh instead of postponing it until the next morning.

Secondly, I don't believe that my job is "trading hours of effort for a paycheck", rather it's "trading results for a paycheck". I don't want my career to grow based upon a resume that's largely trading on time spent at one place or another with some callout to skills. I want trade on a resume that highlights specific results achieved instead. This is one reason that I think software developers would be smart to pitch portfolios of results instead of lists of skills when looking for new opportunities.

Another major thing that I think imprinted on me was my father's whiteboard growing up. Next to his desk, he had a whiteboard listing the windmills and other wells that needed service. At the end of the day, how well things went were not really a function of hours spent or distance travelled – it was whether he knocked off a bunch of small jobs or completed a large job that was on the board. My RTM list is just an updated iteration of that basic tool.

Q: When do you expect to be back in the "comfort zone"? You're almost fifty tasks away from your sweet spot.

A: I'm in the process of putting together my plan for 2015 where I can devote some time to projects I've been neglecting. I've set aside January as my mop-up month and hope to begin on February 1 improving Fresh Comics, The Pnakotic Atlas, Shion, as well as working on my temporarily neglected novel.


In the end, I'm not advocating that anyone else adopt this method. It's worked well for me, but it's also been crafted to take advantage of my own personal values and peculiarities. This is not an approach I adopted overnight – it's the outcome of many years of trial and error. It works well for me and is a core part of my working persona. I'm still learning how to interface it with other systems (like Pivotal Tracker) and still working out ways to keep using my individual approach while improving its ability to support delegation. Like everything else I do, it's a work in progress, and if you're interested in monitoring my progress, check out the To-Do List bar in my Goal Tracker section on the front page. Hopefully if you're reading this in January 2015, it's shrinking down to the sweet spot. If you're reading this after that, hopefully you see it hovering in that 15-30 task comfort zone.

Image courtesy Wikimedia Commons: Encana's Bow skyscraper construction progress in May of '09

comments powered by Disqus