I'm a firm kanban person, and I think it might help you. I happen to use the tool KanbanFlow for this. [1] But I also have done it with index cards on a wall [2], and Trello's ok, too.
Boiling it down, Kanban approaches require you to 1) break big things down into small deliverables, 2) describe your workflow in columns, placing the units of work in the correct columns, and 3) setting strong work-in-process limits on the columns.
For example, my main board has these columns and WIP limits: backlog (∞), soon (12), today (5), pending (3), in progress (3), and done (∞). Work normally flows from left to right, with the exception of the pending column, which is used when something in progress gets stuck because I'm waiting on some external event.
If I've finished working on something, I try to look first in the in progress column, so that I can finish off something on going. Next, I'll check the pending column, to see if I can unstick anything. Only if those two are solid will I look at the today column. Last thing at night or first thing in the morning, I'll look everything, load up the today column, and make sure it reflects my current priorities.
I should note that the WIP limits are integral to this. There are two basic ways you can run a workflow. One is a pull system, where running out of things to do means I pull something forward. I'm mentally standing at the "done" end of the board and pulling things through one at a time. This is very different than a push system, where I mentally stand at the backlog end and stuff things in, hoping useful work gets squeeze out the other end. WIP limits help keep me honest, in that the board is not about what I want to accomplish; it's what I am accomplishing.
I think the Kanban approach will be helpful to you in two ways. One, because it's a pull system, the amount of time one spends reorganizing is limited. At worse, I reorganize every time I finish something. But hopefully, because I already have small numbers of top priorities in the today and soon columns, it'll be easy for me to pull without working about everything I have to do.
Two, it sounds like you're trying to do more than you can. Executive you has made a grand annual plan, but worker you is struggling to juggle priorities and allocate time. This is not just stressful; as you say, it's inefficient. Optimize for worker you, because that's where things actually happen.
In addition to the Kanban board, I also use Evernote to keep a "projects" notebook. It's one page per project idea, and for active projects that page turns into a journal. I'll often describe future plans there, which I will mine for to-do entries as I pull things in. But those future visions aren't consistent or complete; they're just top-of-head notions. That much more efficient than trying to express my ever-changing vision in work-management tools.
Boiling it down, Kanban approaches require you to 1) break big things down into small deliverables, 2) describe your workflow in columns, placing the units of work in the correct columns, and 3) setting strong work-in-process limits on the columns.
For example, my main board has these columns and WIP limits: backlog (∞), soon (12), today (5), pending (3), in progress (3), and done (∞). Work normally flows from left to right, with the exception of the pending column, which is used when something in progress gets stuck because I'm waiting on some external event.
If I've finished working on something, I try to look first in the in progress column, so that I can finish off something on going. Next, I'll check the pending column, to see if I can unstick anything. Only if those two are solid will I look at the today column. Last thing at night or first thing in the morning, I'll look everything, load up the today column, and make sure it reflects my current priorities.
I should note that the WIP limits are integral to this. There are two basic ways you can run a workflow. One is a pull system, where running out of things to do means I pull something forward. I'm mentally standing at the "done" end of the board and pulling things through one at a time. This is very different than a push system, where I mentally stand at the backlog end and stuff things in, hoping useful work gets squeeze out the other end. WIP limits help keep me honest, in that the board is not about what I want to accomplish; it's what I am accomplishing.
I think the Kanban approach will be helpful to you in two ways. One, because it's a pull system, the amount of time one spends reorganizing is limited. At worse, I reorganize every time I finish something. But hopefully, because I already have small numbers of top priorities in the today and soon columns, it'll be easy for me to pull without working about everything I have to do.
Two, it sounds like you're trying to do more than you can. Executive you has made a grand annual plan, but worker you is struggling to juggle priorities and allocate time. This is not just stressful; as you say, it's inefficient. Optimize for worker you, because that's where things actually happen.
In addition to the Kanban board, I also use Evernote to keep a "projects" notebook. It's one page per project idea, and for active projects that page turns into a journal. I'll often describe future plans there, which I will mine for to-do entries as I pull things in. But those future visions aren't consistent or complete; they're just top-of-head notions. That much more efficient than trying to express my ever-changing vision in work-management tools.
I hope that helps!
[1] https://kanbanflow.com/
[2] http://williampietri.com/writing/2015/the-big-board/