In software development, this is known as being "Agile." Originally, software was designed mostly in head-land (a "Big Design Up Front"), but gradually a different process was pushed wherein a smaller, prototype design would first be constructed, then evaluated for its effects in real-land, and then improved upon, repeatedly. I find it interesting that unlike in the world of sports, where "one step at a time" can be almost universally agreed upon, software development is rife with controversy over whether "Agile software development methods" have any real advantages.

IAWYC and your examples reflect my own experience.

But unless there's some difference between the amount of planning, thinking, and daydreaming necessary for our ancestral environment and the amount of those things necessary now, evolutionary psychology at least provides some weak evidence that humans on average plan, think, and daydream about the right amount. That suggests that maybe the costs to asking people on dates and getting stuff done is balanced by benefits elsewhere.

I upvoted this partly because it was really well written and I would love to see more articles of this caliber.

As for the topic... I guess I don't disagree on any particular point and I think the insights are good to note. Personally I seemed to head in the opposite direction when faced with this problem:

One might grant that while responding that running models in head-land is nevertheless the best predictor of real-land events that any individual has. And that's true, but it doesn't change our apparent tendency to place far more trust in our head-land models than their dismal accuracy could ever warrant.

Instead of throwing out the head-land models and simulations as not helpful I look for ways to make the head-land models more accurate. The success of specific head-land models is more or less easy to measure: Did the predictions occur? The solution is two-pronged: look for better accuracy and ditch the apparently accuracy-bias.

The danger of head-land catastrophes that poison real-land endeavors looms over every step of the path. The possibility of being metaphorically laughed out of the classroom, though probably only illusory to begin with, never quite leaves one's mind.

Agreed; a major obstacle to measuring the success of head-land predictors comes when the predictions themselves affect the outcome of real-land. Namely, both fear of failures imagined and the relaxing opium of daydreams.

In my experience, it is possible to shoo the metaphorical laughter away. Furthermore, it is possible to let the head-land simulations run and remain emotionally abstracted from the results. Instead of responding to imagined failure with real-land fear, forge onward with the intent of measuring the success of your head-land.

Fearing head-land failures to the degree of not acting in the real-world truly is poison. But shutting off our best predictor because it may predict inaccurate failure seems to be letting a valuable tool fall away. It is better to not emulate than to not act but is it not possible to increase our accuracy?

I suppose my point can be boiled into this: My head-land has been known to guess correctly. Are these successes a false pattern? Are they evidence of a talent that can be honed into something useful to my real-land self? My head-land is telling me the latter.

Could I get step by step instructions on how to more active in real-land instead of head-land?

I finally created an account just so I could 'up-vote' this post, which I enjoyed. I think it shows a depth of thought and introspection that is very helpful. Perhaps this post could be the start of a series?

I thought that was on purpose.

Minor typo : it seems there's a missing word in this sentence:

Head-land is the world in which I constructing an image of what this sentence will look like when complete

I really enjoyed reading this.

First off, welcome to Less Wrong! Check out the welcome thread if you haven't already.

You have a good writing style, but I hope you'll pardon me if I make a few suggestions based on the usual audience for Less Wrong posts:

Typically, a post of this length should be broken up into a sequence; you run the risk of "too long; didn't read" reactions after 1000 words, let alone 3000, and the conversation in the comments is usually sharper if the post has a single narrow focus. Usually, the analysis of a situation and the recommendations become separate posts if both are substantial.

Secondly, with the notable exception (sometimes) of P.J. Eby, we're often mistrustful of theories borne of introspection and anecdotes, and especially of recommendations based on such theories. There's therefore a norm of looking for and linking to experimental confirmation where it exists, and being doubly cautious if it doesn't. In this case, for instance, you could find some experimental evidence on choking that supports your thesis. This also forces you to think carefully about what sort of things your model predicts and doesn't predict, since at first glance it seems vague to the point of danger. The more specific you can get about these phenomena, the more useful your post will be.

Excellent. This is precisely why I'm always ranting here about actually trying things, and deferring True Theory until you've first had Useful Practice. Otherwise, it's all too likely your models are bullshit based on previously-learned bullshit and entirely unrelated to what would actually happen if you Just Did It Already.

One quibble:

The classic example would be approaching the girl one likes in middle school

I suspect that this might've been better phrased as "The classic example of a guy approaching the girl he likes in middle school", as the way it's phrased now implies the reader is a heterosexual male, and is less inclusive than it'd otherwise be. (It also could've been phrased as "The classic example of me approaching the girl I liked in middle school".)

I think the rest of your statements about that scenario didn't imply the reader was the one doing it, but I'm not 100% positive of that.