I don’t have a suggestion as to how you can get the behavior that you’re looking for, nor do I have a work-around to get something similar.
Instead, I’d like to suggest that OF is designed so that you can get your work done without you having to explicitly order your list.
Omnifocus was not really designed to be a to-do list program, it was designed as a program to help people organize their projects and tasks using the GTD methodology. An important aspect of GTD is “focus”, hence the name itself of the program: Omnifocus. The idea behind GTD in a teeny-tiny nutshell is to organize your material so that any point in time you have a clear overview of what needs to be and can be done right here and right now.
Over the years I have also learned how extremely important it is to cut down on my currently active projects. If I have more on my plate than I can realistically handle, I get frustrated and demotivated because the list of tasks is so long. If there are too many things staring me in the face yelling, “Do me!”, I just feel stressed. If I start out with fewer active projects, once I take care of a few projects I can always add more.
So let’s say I’ve trimmed my focus of active things down to where I have a list of 20 actions that I want to do. — That’s actually a very large number and I hope that I have less than that!
The next thing is to decide what I want to do right now. If I’m lucky, my contexts can help me divvy these 20 things into smaller groups that might give me a better idea where I want to start. — Contexts are really an important tool I learned from the GTD book!
The next step is to select, say, three tasks that I want to do right now. When I see the complete selection in front of me, it shouldn’t be too hard to decide on the spur of the moment what are the most important things to start with. I select these three tasks, hit Shift-CMD-F to focus in on them and I’m left with a super short list. It’s so short that I don’t need to rearrange it because a quick glance at the list is enough to tell me what the next thing is I should do.
I take care of those three things, concentrate on them, complete them or get them to a point where I see, “OK, now I need to move on to something different”. Unfocus the list, take another look at the longer list, redecide what’s most important to be done next, and refocus.
Once things are no longer in focus, I can ignore them while I work, knowing that they’re still there when I need them, and I can trust myself to pick the next few tasks when the time comes.
Another thing I do for urgent things that I really need or want to be sure to do first is set their starting date to today. These tasks show up in my tickler window, reminding me how important they are so I don’t lose track of them.
So that’s the way I work without having to keep a list of things in the order of when I want/need to do them. If I did have a list like that, my guess is that I would wind up reorganizing the list in the course of the day anyway when it turns out that the order I started out with doesn’t work because of the real-life world. With the approach I use, I get the same effect when I refocus.
I can think of two scenarios in which the strategy I describe won’t work:
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If you print the list out on paper and just work from the printout. You can’t refocus on paper. The way I work, I always have OF open and available to look at when I need it.
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If you use the iPhone or iPad version of OF. I don’t believe you can focus using the iOS versions of the software.