During my metastrategy workshop, Day Two was focused on taking a step back and asking "okay, wait, what am I actually doing and why?". Choosing what area to focus, and what your mid-level strategy is for achieving it, determine at least as much (and I think often much more) of the value you create, than how well you operationally succeed.

If you're going to pivot to a plan that's 10x better than your current plan, it'll probably be because you considered a much wider swath of possible-plan-space.

This post is the series of prompts that I gave people to work through, to help them take a step back and revisit their big picture thinking with fresh eyes.

I recommend:

Skimming each question once, to get a rough sense of which ones feel most juicy to you.
Copying this into a google doc, or your preferred writing setup.
Working [...]

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Outline:

(01:07) Part 1. Breadth First

(01:12) 1. If you were doing something radically different than what you’re currently doing, what would it be?

(01:19) 2. If you were to look at the world through a radically different strategic frame, what would it be? (Try brainstorming 5-10)

(01:44) 3. Pick a frame from the previous exercise that feels appealing, but different from what you normally do. Generate some ideas for plans based around it.

(01:55) 4. What are you afraid might turn out to be the right thing to do?

(02:01) 5. What are the most important problems in the world that you’re (deliberately) not currently working on? Why aren’t you working on them? What would be your cruxes for shifting to work on them?

(02:15) 6. What are some important problems that it seems nobody has the ball on?

(02:21) 7. How could you be gaining information way faster than you currently are?

(02:28) 8. Can you make your feedback loop faster, or less noisy, or have richer data?

(02:35) 9. What are some people you respect who might suggest something different if you talked to them? What would they say?

(02:44) 10. What plans would you be most motivated to do?

(02:50) 11. What plans would be most fun?

(03:00) 13. What are some other prompts I should have asked, but didn’t? Try making some up and answering them

(03:09) Recursively asking “Why is That Impossible?”

(03:14) A. What are some important things in the world that feel so impossible to deal with, you haven’t even bothered making plans about them?

(03:23) B. What makes them so hard?

(03:27) C. Are the things that make them hard also impossible to deal with?

(03:44) Part II: Actually make 2+ plans at 3 strategic levels

(03:51) i. What high level strategies seem at least interesting to consider?

(04:01) ii. What plans seem interesting to consider?

(04:23) iii. What tactical next-actions might make sense, for your favorite, and second-favorite plans?

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First published:
April 13th, 2024

Source:
https://www.lesswrong.com/posts/KLsKaywDDLRSLgdFC/prompts-for-big-picture-planning

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Narrated by TYPE III AUDIO.

“Prompts for Big-Picture Planning” by Raemon

LessWrong (30+ Karma)

“Prompts for Big-Picture Planning” by Raemon