I got this question from TJudge:

It seems like you’re always involved in a ton of projects at once.  I can barely remember to tie my shoes in the morning.  Do you use some kind of program to keep track of all the stuff you do?

The answer to that question is, of course, constantly evolving, as anybody in a creative field I’m sure can tell you.  I think the biggest challenge when managing multiple tasks is in finding a way to keep track of those tasks without getting overwhelmed.  There are a lot of philosophies on this subject, but the increasingly dominant one comes from a book called Getting Things Done by David Allen.  The common term for this, in true internet abbreviation style, is “GTD.”

The GTD philosophy is complex, but it essentially boils down to keeping close track of what actions you need to take, when you need to take them, and what dependencies exist for these tasks.  It’s about structuring your time to maximize your resources and focus on the tasks at hand.

For this purpose, I recommend one of three bits of software (all for Mac, sorry) - OmniFocus, The Hit List, and Things.

I’m not going to fully review them all here, because there are plenty of posts on the internet doing exactly that.  Instead, I’ll give you what I consider to be the main points of each:

  1. OmniFocus - This is the most managed of the three GTD programs, and the one that adheres most closely to the original Getting Things Done book.  I used it for a while, but in the end it was too managed for me - I found I spent too much time trying to structure my tasks, and not enough time actually doing them.  It’s great if you’re a hardcore GTD freak, or if you have one of those scattered brains that absolutely requires that level of structure to keep yourself organized.  It has a ton of features that the others don’t, including inter-task dependencies (sub-tasks that need to be accomplished in a certain order) which is great if you don’t want to look at tasks you can’t accomplish yet because other tasks have not been completed.  I can see how others would enjoy this, but I needed a more flexible solution that didn’t require so much effort to reorder when things went sideways, as they often do with projects like the ones I have on my plate.
  2. The Hit List - This is the least managed, and the most freeform, of the three GTD programs.  The Hit List focuses primarily on getting the UI out of your way so you can work, and is probably the most flexible.  It has a strong “desk” metaphor to the UI, with interfaces that look like lined paper and notecards.  I like The Hit List a lot, but I found I wanted a little more structure to both the UI and the tasks than it provided.  My mind is reasonably ordered by nature, but I still want a program that’s capable of showing me just what I need to be doing at the moment - it’s too easy for me to start “chasing rabbits,” as one of my old professors used to say.  Also, the lack of a companion iPhone app (which the other two have, and which The Hit List is apparently working on) was a bit frustrating.
  3. Things - This one falls smack in the middle of the other two.  Its UI is less managed than OmniFocus, but not as freeform as The Hit List, and I found a Goldilocks sort of fit to this program.  I sometimes miss the task dependencies of OmniFocus, as well as the uncluttered UI of The Hit List, but overall, I like the strong focus on “what do I have to do today?” On the whole, it requires less maintenance than OmniFocus and allows for more focused use than The Hit List.

When I was selecting an alternative to OmniFocus, I came across this question a lot on the interwebz: “Yeah, but which is the best?” And the truth is, there isn’t one.  You really can’t say that one is better than the other across the board, because organization is such a subjective field.  I have lots of colleagues who love OmniFocus - it’s certainly the most feature-rich of the applications, capable of serving just about any specific need you have and able to force even the most disorganized minds into GTD submission.  And The Hit List is great for folks who crave a more freeform approach and prefer hotkey combinations to dedicated UI buttons.

The best bit of advice I can give is to try each fully.  Each, as far as I know, has a trial (I got The Hit List with MacHeist, so I don’t know the terms of the trial).  Here are two tips in that regard:

  1. When trying them out, commit to them. There’s a strong tendency with trial software to download it, poke at it for an hour, and decide based on first impressions, and this really doesn’t work with GTD software.  You need to use it fully for a while to get a full sense of the software’s philosophy.  Within an hour of using OmniFocus, I remember hating it.  Three days later, I was in love with it.  A week after that, and I was irritated by its interface but able to leverage it competently.  A few months after that, I felt I needed to reassess.  You’ve typically got two weeks to decide on the trial; use those to really commit to the software, and decide when the trial is up whether or not it worked for your needs.
  2. Don’t download all three at once. If you do that, your trials will all run out at the same time, and you won’t have had a chance to commit to any of them for a sufficient amount of time.  Instead, you’ll be going back and forth between the three of them, directly comparing features without fully experiencing any of them.  See tip #1.
  3. Don’t give up on a missing feature.  If there’s a missing feature in the software you’re currently using, do a bit of Googling before giving up.  GTD freaks love to talk about their workflows (take the length of this post as evidence), and many have come up with really interesting workarounds for lacking features that they’re happy to share.  For instance, OmniFocus doesn’t have a tagging system (the way the other two do), but one user pointed out that it has full-text search so it’s possible to use hash tagging (”#mytag”) in the Notes field and search by “tag.”  Things doesn’t have multi-computer syncing, but I got the idea from a forum to use Dropbox to sync the database between my desktop and laptop.
  4. Don’t give too much credence to reviews. Remember that GTD is extremely subjective, and what frustrates one user may really please another.  I’ve seen a lot of reviewers rant about quirks in the Things UI that I actually find quite helpful.  I’ve also seen reviewers rave about features in OmniFocus that seemed to just get in my way.

If you have thoughts on your favorite GTD workflow (or suggestions for Windows users), please sound off in the comments; I’d love to hear them.