Published on November 4, 2025 10:15 PM GMT

Or: “Who, what, when, where?” -> “Why?”

In “What’s hard about this? What can I do about that?”, I talk about how, when you’re facing a difficult situation, it’s often useful to list exactly what’s difficult about it. And then, systematically brainstorm ideas for dealing with those difficult things.

Then, the problem becomes easy.

But, there is a secret subskill necessary for this to work. The first few people I pitched “What’s hard about this and what can I do about that?” to happened to already have the subskill, so I didn’t notice for awhile.

The subskill is “being a useful kind of ‘concrete.’”

Often, people who are ostensibly problem-solving, will say things that are either vague, or concrete but in a way that doesn’t help. (This doesn’t just apply to “why is this hard?”, it’s more general).

Here’s some examples of vague things:

• “I need to eat better.”
• “I’m stuck on this math problem.”
• “I’m not someone who really has ideas.”
• “This task fell through the cracks.”

Here are some examples of somewhat-concrete-but-not-that-helpful things you might say, about each of those, if you were trying to ask “what’s hard about that?”

• “I love sugar too much.”
• “I’m just so confused. I have no traction.”
• “I only get ideas when I talk to other people and they basically give me the ideas.”
• “No one was paying attention to this task.”

Here are some more helpfully concrete things:

• “I get sugar cravings in the afternoon.”
• “When I try to look at the math problem, my eyes glaze over, and then I’m just suddenly over on facebook.”
• “Alice mentioned ‘oh, someone should do Task X’, and then we went to talk about other things, and then neither Alice nor Bob nor Charlie remembered to do Task X later.”

(I’m going to come back to “I only get ideas when I talk to other people and they basically give me the ideas”, because the problem there is a bit differently shaped)

Usefully concrete things typically have at least a “who”, a “what [happened]” and a “when and/or where”. When you have those things, it’s a lot easier to notice which followup questions are useful. Such as:

• “Why do I get sugar cravings in the afternoon, specifically?”
• “Why do my eyes glaze over when I look at the math problem?”
• “Why didn’t Alice, Bob or Charlie remember to do Task X?”

The Who/What/Where gives you enough concrete detail to start forming a model of:

• “Who, specifically, had the opportunity to do something different here?”.
• “What, specifically, where they doing, when they had that opportunity?”.
• “When/Where” tells us what sort of situation it took place in.

This puts you in a much better position to start investigating and gathering followup data. You know who was involved, you know what situation they were in, that’s specific enough to pay more attention the next time you end up in that situation.

By contrast, if I ask “why do you love sugar so much?” (as opposed to “why do you get sugar cravings in the afternoon?”), the answer-space is wider and less obviously useful. “Because… my mom fed me too much sugar and I got used to it?”. “Because it tastes good?”. It suggests some kind of essentialist answer instead of a mechanistic answer.

“Why do I get sugar cravings in the afternoon?” suggests that either something specifically interesting is happening in the afternoon, or, maybe it’s happening a few hours earlier every day. Or, something about my biochemistry is just real “afternoon-sugar-craving” shaped, but at least that can prompt some followup questions about why is my biochemistry like that.

Noticing the empty space

What’s wrong with “I only get ideas when I talk to other people and they basically give me the ideas?”. It’s located where the problem isn’t. You talk to people, you either come up with or get new ideas. Great.

I was recently talking to someone who said the “only get ideas around others” sentence. I asked “what happens when you try to have ideas?” and at first they sort of shrugged and moved on without answering the question, and eventually I pinned them down and they said “I… guess I don’t try to have ideas?”

And then I asked “what do you expect would happen, if you tried?”

And they said “I dunno, I wouldn’t have any. It wouldn’t work”

And I asked “Can you be more specific about that? What wouldn’t work?”. They didn’t quite know how to answer the question, I tried to explain something like “what cognitive motions do you think you’d do, if you were trying to have ideas? What questions would you ask yourself? What places would you look?”

Eventually they said “okay, I guess yeah upon reflection I basically just haven’t tried even at all and when I try even at all, things come up like ‘I’d look for books or papers to read that might have interesting concepts I could build on’ or ’I’d ask why I don’t understand something that feels confusing.”

In this case it was hard to get started down the journey, because there was no specific time that they might have gone and tried to generate novel ideas. 

Noticing a vacuum is harder than noticing when something goes wrong. But, when you’re going to try and articulate your problem, you can notice if you have failed to state a situation where the problem is occurring, and widen your search space.

(There’s a similar-but-less-extreme version with Alice, Bob and Charlie. Where first, there was an opportunity to, say, decide who was doing Task X, or write it down to remember later, or something, and they just didn’t notice that as an inflection point at all)

Problem solutions also need a Who/What/Where/When, and maybe also “How?”

Dumb/vague solutions: 

• “I’ll eat less sugar.”
• “I’ll focus harder on the math problems next time.”
• “Okay, we’ll remember to do Task X next time.”

There’s no way that’ll actually work reliably. A somewhat better set:

• “When I notice a sugar craving, I’ll eat some other food I like instead.”
• “When I notice my eyes glazing over a math problem, I’ll look more carefully at it.”
• “When we mention a task, we’ll write it down.”

The reason problem solutions should be concrete is partly so it’s easier to form a plan to actually do them. i.e. who is actually doing what? When is it time to do that?

But, another reason to do it is that, if something is sufficiently concrete, your brain can actually simulate it, and then you get to leverage your fast intuitions may immediately get a sense of whether it’ll work. For example, when I look at the above statements, I immediately imagine:

• No, they won’t eat some other food instead, because that requires willpower, and there will be days they don’t have enough willpower and then the habit will break, if it doesn’t immediately.
• No, they won’t successfully focus on the math problem, because they didn’t actually solve the problem of “something is causing their eyes to glaze over in the first place” and they don’t have a plan other than powering through.
• They probably won’t remember the task just because they wrote it down, unless they have a system for bumping written-down-things into their mind at the moment they are actually needed.

To deal with each of those, I’d ask “Okay, what’s hard about this situation, and what can we do about it?”. But, it’s much easier to ask that question when you can clearly visualize the situation, and your imagined interventions on it.