It's very hard for people to learn by interacting with other people directly. Two major reasons:

1. Interaction triggers people to behave and interpret socially. They put most of their effort into social hierarchy stuff instead of learning.
2. People are complex and flawed. It's a lot to deal with in addition to the subject itself (the subject is e.g. philosophy or physics concepts). People have to deal with miscommunication, scheduling, mutual benefit, different background knowledge, being able to think about other points of view, etc.

An impasse is a reason (from the speaker’s pov (point of view)) that the discussion isn’t working.

Impasses take logical priority over continuing the discussion. It doesn’t make sense to keep talking about the original topic when someone thinks that isn’t working.

An impasse chain is an impasse about a discussion of an impasse. The first impasse, about the original topic, is impasse 1. If discussion of impasse 1 reaches an impasse, that’s impasse 2. If discussion of impasse 2 reaches an impasse, that’s impasse 3. And so on.

A chain of impasses is different than multiple separate impasses. In a chain, each link is attached to the previous link. By contrast, multiple separate impasses would be if someone gives several reasons that the original discussion isn’t working. Each of those impasses is about the original discussion, rather than being linked to each other.

When there is a chain of impasses, the most recent (highest number) impasse takes priority over the previous impasses. Impasse 2 is a reason, from the speaker’s pov, that discussion of impasse 1 isn’t working. Responding about impasse 1 at that point doesn’t make sense from his pov. It comes off as trying to ignore him and his pov.

Sometimes people try to solve a problem without saying what they’re doing. Instead of discussing an impasse, they try to continue the prior discussion but make changes to fix the problem. But they don’t acknowledge the problem existed, say what they’re doing to fix it, ask if that is acceptable from the other person’s pov, etc. From the pov of the person who brought up the impasse, this looks like being ignored because the person doesn’t communicate about the impasse and tries to continue the original topic. The behavior looks very similar to a person who thinks the impasse is stupid and wants to ignore it for that reason. And usually when people try to silently solve the problem, they don’t actually know enough about it (since they asked no clarifying questions) in order to get it right on the first try (even if they weren’t confusing the other person by not explaining what they were doing, usually their first guess at a solution to the impasse won’t work).

This non-communicated-problem-solving-attempt problem is visible when people respond at the wrong level of discussion. Call the original topic level 0, the first impasse level 1, the second impasse level 2, the third impasse level 3, and so on. If level 3 has been reached and then someone responds to level 2, 1 or 0, then they’re not addressing the current impasse. They either are ignoring the problem or trying to solve it without explaining what they’re doing. Similarly, if the current level is 1, and someone responds at level 0, they’re making this error.

The above is already explained, in different words with more explanation, in my article Debates and Impasse Chains.

What constitutes "skipping steps" or "making assumptions" depends on context and perspective. We can't allocate conscious attention to all of reality – reality is too big, complex and varied.

To interact productively, people need some common ground – some shared knowledge and perspective – which specifies what sorts of assumptions are inappropriate to make. Shared culture is crucial for this.

Existing cultural defaults are adequate for working as a cashier. But our culture doesn't prepare people well for intellectual discussions. It's maybe pretty close to adequate for intellectual discussions, but some adjustments are needed.

As a starting point, for intellectual discussion, people should assume less than they normally do. Don't skip over some things you'd normally assume and then see which ones are or aren't an issue. But people are bad at assuming less, bad at judging which of their assumptions are riskier, and bad at updating their future behavior according to information gathered like this.

A good, generic strategy is to come up with some goals, then come up with some measurable criteria to judge success or failure for each goal. This helps you recognize problems, mistakes and inadequate plans (plans that somewhat work but not enough to reach the goal measurements).

Measurable criteria help with dishonesty and bias. Instead of moving the goalposts when you get there, or rationalizing how great you did, you clearly know in advance what the goal is (and write the goal and criteria down, often where other people can see it).

If your goal is "learn some stuff about physics" then it's hard to judge how well you're doing. It's pretty easy to fool yourself into thinking you succeeded when you didn't learn much. Or you could learn a fair amount but miss an opportunity to learn way more.

If you have measurable criteria, you can check whether you succeed at them. E.g.:

• spend 3 hours a week minimum on learning physics; miss zero weeks this year. (only solo learning counts for this time, not talking with people)
• post at least one physics question per week on stack exchange (at least 40 weeks this year).
• fully read the following physics books this year: X, Y, Z.
• do all practice problems in books X and W this year.
• at end of year, be able to get passing scores on the physics tests i found online (A, B and C).

This criteria aren't perfect. They don't measure everything I care about regarding my goal. I could succeed at these criteria and still have missed some opportunities.

But they have major advantages. They give me some clear guidelines. It'll be hard to lie to myself that I did one of these criteria when I didn't. They're easy to evaluate as either success or failure. Did I do it or not? I'm realistically going to be able to give a clear, correct answer, even if I'm pretty dumb and biased.

(What if I stop keeping track of time spent on physics, so I can't say if I succeeded? What if I don't keep track of what sections of what books I've read? You can take it as implied that that's a failure. Part of the goal is to keep track. Or you could write it into the goals that keeping track is a requirement.)

It's hard to measure everything we care about, and some goals are harder to make relevant measurements for than others. But measurements are useful and we can often get some benefit from them.

FYI you can find ideas similar to the above in various business management ideas. Regarding business management in general, I favor Theory of Constraints, from Eli Goldratt, who wrote a book actually titled The Goal.

"Get good at rational thinking" is a goal that's hard to measure progress, success or failure at.

With a business, you can measure stuff like sales, revenue, profit, widgets produced, number of widgets the factory throws out due to quality problems, number of late customer orders, price of raw materials required to build a widget, and much more. There are many things to attach numbers to. These measurements don't cover everything important but they help.

Websites can measure visitors per day, time on site, number of links clicked, number of visitors who return on a different day within 30 days, amount of people who sign up if shown marketing page A as opposed to signups for marketing page B, and much more. More intrusively and problematically, it's possible for software to e.g. monitor how much a user scrolls down on a web page and how long they spend with different parts of the page on screen.

But what do you measure when you're learning about rationality?

You can measure the time you spend on studying. You can measure words read and words written. You can measure whether you watched a list of videos and read a list of books. But those measurements don't tell you how well you understood the material. How effective was your learning? How much wiser and rational are you getting? It's hard to measure wisdom or rationality, or to measure anything very similar to them.

What's the solution? We must learn ways to think without measurement. We must get good at judging things in other ways besides measurement.

Measurement is useful and is something our culture is generally pretty good at. But it's certainly possible to think effectively in other ways. Measurement is resistant to bias, dishonesty and irrationality – it helps reduce those problems significantly – but it's not perfect at dealing with those problems and those problems can also be dealt with in other ways.

The main thing that's great about measurement is it's easy to be objective. It deals with facts that we can quantify with numbers. Often we have measuring tools to aid us, e.g. timers, rulers, microscopes, etc.

We measure some things without tools. If I'm loading boxes onto a truck, I can count them one by one as I load them, and I can write down the count at the end (or even update the written count after every box). We count this as a measurement. Similarly, "I read book X" is close enough to the concept of measurement, and easy enough to evaluate, that one can think of it as a measurement or as similar enough. (Note the issue isn't whether you understood the book or paid much attention or gave it much thought. What's easy to judge or measure is whether you went through it page by page and read what it said. There are borderline cases like how many pages can you skip before it doesn't count? But let's not worry about that now.)

Something that's easy to judge, and involves physical objects and facts, is identifying objects or their traits. Is that a cat, yes or no? I look at it and say yes. Is that an apple? I look at it and say no it's a strawberry. Is that object red? I look at it and say yes (I could also measure that using a digital camera, a computer, and some software – and actually we now have software that's pretty good at classifying pictures as various objects like cats or apples). Is it a type of "measurement" to say that object A in my room is a chair and object B is a chair? That's just terminology. It's not especially important what we call it. Regardless, that kind of thing can easily be judged and used in our goals. We're good at doing that without being biased. It's the kind of thing we find hard to get wrong or lie to ourselves about.

What are some things we can't "measure"? Judging whether an action is moral, pious, honest, wise or fair. Saying whether raspberries taste good to me. Judging how good my understanding of Socrates is. Deciding wether capitalism or socialism is better. Considering the best activities to start learning history with. These things require judgment and some involve things that some people consider a "matter of opinion", "subjective" or "arbitrary" (which they often say when they find it hard to be objective, rather than because they have arguments that objective judgment of the matter is impossible). These issues are getting away from facts like how long an object is, whether it's made of wood, what shape it is, how heavy it is, whether it's flat, etc. They're different and trickier.

Look for opportunities to use measurements to help your judgment. And also work on developing good judgment (about anything) and developing ways to prevent, detect and correct bias, dishonesty and irrationality.

How? Many ways. E.g. these articles could help:

• Lying
• Emotions
• Using Intellectual Processes to Combat Bias

Let's talk about a different way.

Assuming you're an adult, there are some things you're already good at judging. There are some areas where you're confident, competent, skilled, etc.

You can find more stuff which is similar or related and work on that. You can try to expand the good judgment you already have by applying it to more things.

Suppose you learn math to pass school tests. You might later find the math you already know is also useful for figuring out whether a system of pulleys will let you lift a large stone. And then later you you find the math you already know can help you analyze video game strategies, e.g. figuring out how much damage you can do in 60 seconds by casting different sequences of spells.

Skills often help with many things that weren't the original purpose you learned them for.

So you can take skills you already have and look for more stuff they can already help with. If the skill is related to judgment, and you find more ways to use it, then you're expanding the scope of what you can skillfully judge.

You can also expand on the skills as you apply them to more areas. E.g. you might find learning a few more mathematical techniques helps you with your pulleys or video games. Similarly, you could learn a few new things to help your judgment skills deal with new areas.