Luke_Grecki comments on Discuss: Meta-Thinking Skills - Less Wrong
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One way I've done this is via the meta-level skill of recognizing a familiar pattern in the structure of my thoughts about a problem. This familiar pattern can be addressed with my existing meta-skills (which is one reason I remember it), and so I just apply them. This is what I think Eliezer means by "routine meta-thinking".
It's harder to identify when one should engage in original meta-level thinking. If you try to use the outside view, and recognize thinking patterns that can be treated on the meta-level, you most likely end up doing what I described above. If you can recognize a thinking pattern it means you've seen it (at least) a few times before, and probably know how to deal with it.
One could also approach this decision using a coarser outside view. You could ask yourself:
An simple heuristic to use is to go meta periodically, with longer periods between higher meta-level thinking modes.
In this comment nickerst mentions using this heuristic in structured planning: