This idea reminds me very much of Oblique Strategies. I guess the idea of that set of cards is to help with creative work—you draw a card when you’re feeling stuck or uninspired, and the cards say something oblique like “not building a wall, making a brick”, allowing you to give your thoughts a big shove in a pretty arbitrary direction in thought-space, which can push you out of a local optimum and get things moving again.
Inspired by this, I’ve thought about trying to do exactly what you’re doing, and I can share the list I wrote down (with no claims whatsoever about their quality or suitability):
Compare the outside and inside views
Has this problem been solved before?
Is this the right problem to solve?
Have you tried the obvious things?
Ask someone else for obvious things to try
Your future self visits to tell you your plan failed. What went wrong?
Who would be better at this than you? Pick a specific person. What would they do?
Stop and make a list or two
Consider the opportunity costs
What are you avoiding thinking about?
Be more specific
Name three examples
Come up with a concrete example
Why are you drawing a card? Ask yourself “why?” to the response, 4 more times.
What would convince you that you are wrong?
What assumptions are you relying on?
What other problem is this most similar to?
Do a Fermi calculation
Go meta
Separate the parts of you that disagree, and let them have a conversation
This idea reminds me very much of Oblique Strategies. I guess the idea of that set of cards is to help with creative work—you draw a card when you’re feeling stuck or uninspired, and the cards say something oblique like “not building a wall, making a brick”, allowing you to give your thoughts a big shove in a pretty arbitrary direction in thought-space, which can push you out of a local optimum and get things moving again.
Inspired by this, I’ve thought about trying to do exactly what you’re doing, and I can share the list I wrote down (with no claims whatsoever about their quality or suitability):
Compare the outside and inside views
Has this problem been solved before?
Is this the right problem to solve?
Have you tried the obvious things?
Ask someone else for obvious things to try
Your future self visits to tell you your plan failed. What went wrong?
Who would be better at this than you? Pick a specific person. What would they do?
Stop and make a list or two
Consider the opportunity costs
What are you avoiding thinking about?
Be more specific
Name three examples
Come up with a concrete example
Why are you drawing a card? Ask yourself “why?” to the response, 4 more times.
What would convince you that you are wrong?
What assumptions are you relying on?
What other problem is this most similar to?
Do a Fermi calculation
Go meta
Separate the parts of you that disagree, and let them have a conversation
Break the problem into smaller sub-problems
Take the contrapositive