Reader Jeff asks:

I keep trying and failing to use something for task management… I keep trying OmniFocus (and other task management apps) but the problem is I enter things, I watch screencasts, I get everything setup nice - and then I never see that window again…

What is it that makes you look at OmniFocus? I’m sure it is second nature to you by now, but how did you come to use it and rely on it in the first place? Was it something you had to adapt to or did it just fall into your life like a perfect Tetris piece?

I’m tired of not getting anything done - or at least I say I’m tired of it. Then I watch a screencast, put a bunch of things into OmniFocus, and then don’t look at them ever again for the umpteenth time. Maybe I just don’t actually want to do anything. I hope not, though.

I loved this question. For one thing, it’s just so beautifully honest. It’s superficially simple, yet it slices through the evangelistic aura that enshrines any popular productivity system.

I especially liked it because it made me think.

What is it that makes you look at OmniFocus? After all, what good is any system if you don’t want to look at it? What makes it enjoyable?

What follows is my answer. Maybe it's yours, too. Maybe it's not.

Defining OmniFocus

Forget about GTD canon. Forget the apps. Forget sync, AppleScript plugins, and themes. Let’s call it what it is.

OmniFocus is a brainless messenger. It’s a channel through which my planning self directs my doing self. When I’m creating projects and actions, I’m a manager. When I’m checking off actions, I’m a worker.

OmniFocus is not a manager. It doesn’t ship with a ball-busting boss that can threaten to make my life worse if I don’t do things.[1] And so using OmniFocus for self-management requires a lot of self-discipline.

I believe good self-discipline falls naturally out of self-trust: knowing that I’m doing the right thing, right now. Worker-me trusts manager-me. I’ll come back to this in a second. (Trust me.)

Good cop >> OmniFocus << bad cop

In a very idealistic sense, I think all tasks in OmniFocus should fit into one of two categories: 1) things I enjoy doing right now or 2) things that will lead to later rewards (or avoid negative outcomes).

I would probably look at OmniFocus a lot less if I only put the un-fun there. So I don’t make it the bad cop:

Mylife of1 pe

Instead, I tell OmniFocus to tell me good news, too:

Mylife of2 pe

For me, OmniFocus doesn’t just include reminders to pay bills or make unpleasant phone calls. I put reminders to Huffduff podcasts, try interesting apps, and to watch videos. You know, fun things that I want to do—not now, but later.

Syncing it all, starting with me

If my life had an extremely narrow focus, I’m not sure I would need a system like OmniFocus.

But I don’t have a one-dimensional life. I have a family. I have a full-time corporate job as an actuary. I work on the side. I volunteer. And I have an irrepressible urge to write stuff.

I do all of these things because I’m fulfilled by all of them in their own special way. My life challenges me to constantly to rebalance my attention, to sharpen my focus on the now—whatever that now happens to be any moment of the day.

OmniFocus continues to be a daily presence in my life not because it’s a very well-made product, not because it’s used by people I respect, and not because I think I should use it. The honest, if unintuitive truth is that OmniFocus works for me because I’ve made a choice to pursue things I care about.

OmniFocus can’t make me love what I do each day of my life. And OmniFocus can’t make me look at OmniFocus. OmniFocus can only tell me what I’ve told it to tell me. I just have to look and listen.

And I look because I trust myself.

  1. Maybe someone can write a plugin.  ↩