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 through it over the course of an afternoon, spending however much time on each prompt feels appropriate (this’ll depend on how recently you’ve done a “big picture step-back-and-look-with-fresh-eyes” type exercise).

(Reminder: If you’re interested in the full version of the corresponding workshop, please fill out this interest form)

Part 1. Breadth First

1. If you were doing something radically different than what you’re currently doing, what would it be?

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

(Examples of different strategic frames: “Reduce x-risk”, “maximize chance of a glorious future”, “find things that feel wholesome and do those”, “follow your heart”, “gain useful information as fast as you can”, “fuck around and see if good stuff happens”)

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.

4. What are you afraid might turn out to be the right thing to do?

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?

6. What are some important problems that it seems nobody has the ball on?

7. How could you be gaining information way faster than you currently are?

8. Can you make your feedback loop faster, or less noisy, or have richer data?

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

10. What plans would you be most motivated to do?

11. What plans would be most fun?

12. What plans would donors or customers pay me for?

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

Recursively asking “Why is That Impossible?”

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?

B. What makes them so hard?

C. Are the things that make them hard also impossible to deal with?

(try asking this question about each subsequent answer a few times until you hit something that feels merely “very hard,” instead of impossible, and then think about whether you could make a plan to deal with it)

More on Impossibility

What are things you don’t have any traction on, either because they are confusing or because they feel awful/scary/sad/too-big-a-sacrifice?

You don’t have to delve into this right now, but flag it as something you might want to get help later taking a look at from someone you trust, to help you explore “how could we strategize to make this less costly/scary/confusing/sad”?

What are things you have trouble looking at, because if you looked at them, you’d have to do something about it and that would be horrible?

What if you could look at it without doing something about it? (Again, don’t need to delve into now, but think about how you might pursue it later)

Part II: Actually make 2+ plans at 3 strategic levels

i. What high level strategies seem at least interesting to consider?

i.e. things you might orient your plans around for months or years.

ii. What plans seem interesting to consider?

i.e. things you might orient your day-to-day actions around for weeks or months. Pick at least one of the high-level-strategies and brainstorm/braindump your possible alternate plans for it. If it seems alive, maybe try brainstorming some alternate plans for a second high-level-strategy.

iii. What tactical next-actions might make sense, for your favorite, and second-favorite plans?

You may not work with these today, but they can help make plans feel more real/concrete.

Uncertainty Reduction, and/or
“How would you know if you’re wrong?”

For all likely plans:
What are you uncertain about?

What cheap experiments would reduce your uncertainty?

Can you pose clear, concrete questions that will prompt your intuition to tell you “oh yeah, that’s not actually gonna work” or “I basically do expect this to work.”

See: Fluent, Cruxy Predictions

For the most likely plans:
What are the earliest signs you might see, that you’ree subtly on the wrong track?

What are some tiny confusions in your heart, or clues in the world that you might miss, if you aren’t paying attention?

For plans you don’t currently expect to do:
What are the earliest bits of evidence you might find that should make you reevaluate, and consider if actually, you should shift to that one?