Task Management Systems


One thing I’ve learned from 20+ years of using different task management approaches is to keep expectations in check. It is unlikely that any system or software is going to bring meaningful change to core problems of disorganization, lack of motivation, or just plain laziness. But that shouldn’t discourage one from trying different tools as part of the quest to get organized, get more done, or just get some peace of mind. Something is probably better than nothing.

Reviews of individual tools–and I’ve used plenty–are boring and have a short shelf life because these things change, die, and are supplanted regularly. Let’s instead look at some broad categories.

Paper

Every so often paper comes around presenting itself as an option. Who can resist the appeal of Moleskines and nice pens, not to mention ditching electronica for a little bit? This infatuation is short-lived. Soon after adoption the impracticality of paper is remembered, we realize that computers are useful for stuff like this, and the remaining 98% of the notebook will be left empty. I will allow that something like a Post-It for the tasks at hand right now can be pretty effective. But I have little interest in notebooks systems or planners.

Documents

Using a single text file, Word/Google Doc, or personal wiki, is not a bad approach at all. There is low barrier to use, they’re searchable, and they tend to keep recent information in one place (top or bottom), which is a useful trait. The main disadvantage is that it is difficult to resist using free form docs for random snippets, thoughts, reference information and the like. This dilutes their use as a task management system.

A subcategory of documents is outlines. This is the structure that I always want to love but never actually do. Rarely does my task list benefit from hierachy, and trying to force it into this form usually just adds work and consternation about the right way to do it.

Simple and complicated lists

The mass of “todo” apps fall into this category, and there are surely thousands of options. I consider simple lists to be those that just capture individual items, maybe with multiple lists to provide a little organization. More complicated options start bringing is tags, GTD stuff like projects, contexts, “areas”, date management (due, threshold), etc.

These tools are fine and usually helpful. Not fine is switching between them too much. Usually there are few differences except for cosmetics and gimmicks. Churn within this space wastes time.

Databases

The “big” apps like Things, Omnifocus, 2Do are sophisticated databases that offer a task management interface. Sometimes it’s very prescriptive, others are more roll-your-own. They often have polished, cross-platform apps and can be an enticing “fix your task management problems once and for all” option, for a comparatively hefty price (always justified by the amount of time you’ll save…).

I’ve gotten into these systems and they’re certainly powerful if they align with how you tend to work. The ubiquity that some offer (desktop/mobile/web) is undeniably useful. But there are some things to watch out for:

  • Beware of big learning curves, and of fiddling with the tool forever in search for the perfect setup. They give you more than enough opportunity to waste time.

  • Don’t sign up for a data entry job. I call these tools databases because most have a huge number of fields you can chose to fill out. Adding a ton of metadata will probably not pay off. And if you feel bad because the tool is encouraging this, find something else.

  • Beware of lock-in. Your tool becomes abandonware, or you switch to some unsupported platform. What now? Even export options may leave you with a not-terribly-useful CSV or XML file. That said, live for today. Migrating data sucks but is hopefully not that common (provided you’re not hopping around voluntarily). I would pick the superior tool even if the export path is weak.

Other considerations

Don’t overweight portability

Once phones became smart, the base expectation was that everything should be available everywhere. While I generally accept this, it became too strict a filter: any tool that didn’t have a world class mobile app was disqualified. This could be the right choice for a lot of people, but be mindful of what portability you really need. It’s impressive to have all task-related information at hand and beautifully presented, but it not necessary for me. What is necessary is to capture data, and to a lesser degree, being able to check things off.

Let go of the all-in-one dream

It is tempting to try to shoehorn as much as possible into the one tool to rule them all. This is often suboptimal. Some purpose-built tools are really good, such as OurGroceries for a shared groceries list. Jamming those thing into my task management system would miss out on all of the family shopping optimized goodness. And on the flip side, some very broad utility tools don’t make good task managers. I’ve found the little checklists in Evernote and Onenote—both very good tools in general—to be nearly useless for task management.

Recommendations

Give apps a decent try, with enough time to see how well they fit into your workflow. I’m always amused at the tech bloggers who write reviews after a couple days of use. These are the same people often guilty of churning through gobs of apps, singing all their praises along the way. Of course you should reject obviously bad apps right away, but in most cases I need to really use a tool for at least a month to get past initial impressions and infatuation to really judge it.