Maybe this is related: A crucial step in the workflow of Getting Things Done is to clarify the task. Many of the tasks you mention are not clearly specified. I suppose morphing them into questions means that the task becomes to first clarify the task.
Each brick = one uncertainty
TL;DR
Maybe instead of writing task lists, reframe macro objectives in terms of nested questions until you reach 'root' testable experiments.
Putting this into practice
I built a tool for myself, ‘Thought-Tree’ here, to try and systematise what I wrote in this post. Maybe it works out for you as well?
Essays I am Thinking About, and that Inspired this Post
Related essays by me
What I am planning to read
Setting 'questions' instead of goals?
I want to contribute to the world in the best way I can.
I really think that this is super hard. And in general, I think phrases like 'I want to do X' or 'I want to be Y' actually might be pretty ineffective ways of phrasing targets because it doesn't give you any hints on how to do it. My evidence for 'not knowing how to reach really ambitious targets' is a weak reductio ad absurdum one - implicitly, if I knew how to do it, I probably would've already got there (or busy working away at what needs to be done, and not writing an essay on what I don't know on Casual Physics Enjoyer ;)).
But since I am writing this, I (and maybe you) are not in that position, which implies that there's stuff that we don't know. And in my case of 'contributing to the world in the best way I can), there is a shit ton of stuff I don't know about
I don't know how to measure positive contribution, in the sense that I don't know how I would set up reasonable feedback loops which would signal somehow that I am actually doing a good job, kind of like the OODA framework in Ben Kuhn, Impact, agency, and taste.
Maybe this is why to-do lists for big actions have pretty ineffective for me
The more I think about it, the more I realise this is why task lists and goal setting have primarily been useless exercises for me, and why I never have been able to stick to any structured task plan phrased in terms of 'do X'. It's because most of the time, if you're trying to do anything new, then by definition you don't know how to do it. This seems to be because novelty seems to be a big part of building new stuff that is important. Paul Graham, What to Do Casual Physics Enjoyer, On Good Writing
So prematurely setting a 'goal' like 'contribute to the world positively' isn't a very helpful exercise. I've tried adding more 'detail' to goals, in an effort to make them clearer and try to make it more well defined, but I tend to run into the same problem - I just don't know enough stuff to accomplish them.
This can feel overwhelming and pushes me to give up - so I wanted to try and find a better way to make 'planning' more useful to me. (Check out some more planning and prioritisation thoughts from Ben Kuhn, Impact, agency, and taste). I've also tried doing it the other way and go into just random 'do mode', but that doesn't feel right either.
But then I thought - even though we don't know how to do things, we DO know what we don't know, and that, for me, gives me a better place to start than just 'do X'. And so, recently for a given 'macro statement' like 'contribute to the world positively', I've been trying to write down 'questions / uncertainties' instead of goals instead.
Here are some of my macro statements rephrased as questions.
And then for each question / uncertainty, I nest more questions until I can find an 'experiment' to test what the answer to that question is. It works doubly well if that question has a fairly binary answer, and usually that is a sign that the nesting can stop and I can try to come up with a list of experiments. The 'answer' is then a probability that the statement is a 'yes'.
I found this approach lends itself reasonably well to time boxing, where you can just set a time limit for one of your questions, or parent questions once you get a better idea of what's involved.
An example of my current tree
Here is an example of the tree that I'm currently working on. I haven't put all the stuff here for brevity but I plan to have a website that has my tree, and hopefully helps other people make trees.
And then after that, actually try and do the things in the allotted time.
Again, this is something I've only recently been doing for maybe half a year, but I've been trying to better stick to task lists for since I was in primary school. So it's probably time for a new approach!
Positive side effects
One possible criticism of this approach is that it could be seen as 'procrastination' towards 'actually doing things'. This is similar to the trope of 'analysis paralysis', where over analysing might bias one towards this action. But I argue that doing this correctly is 'just doing things'!
Because
On the first point: I think this approach also has some positive side effects, in that, if you have those questions, other people likely have those problems as well. And so exposing the experiments online on a blog or publication is a free 'DO' action. I also think, if the question is somewhat meaningful at all, then resolving it is a creative process in itself. And I think doing things that are biased towards creation feels good.
Am I just lazy?
I have asked myself this question many times. Am I just finding ways to cope / rationalise a way to avoid 'schlep'? Schlep being the necessary boring, hard work to actually do things? Well, here is my TREE that helps me answer that question
I think so
Time boxing detail
Super rough notes On Designing Experiments