I have learned— if you must give advice to others, it's useful to think of Kahneman's remembering vs. experiencing self: Don't give advice from your remembering self. In hindsight your simplified lessons feel certain; to those experiencing the immediate, they feel irrelevant
In chronological order
Do give advice that serves as *tools* for the experiencing self. The experiencing self is fraught with continuous ambiguity; it's hard to see patterns while in the thick of it. This stage needs concrete tools to deal with the volatile froth and eery ephemeral still
My favorite example of an experiencing self tool: In evaluating a new relationship-- go on a trip to an equally new destination early on, to test how both sides deal with the wonder and unexpected challenges of travel (read: new situations)
Even my use of Twitter is as an experiencing self tool. I sense intuitively that certain ideas are related and might have greater meaning once interlaced with others, but I'm not entirely sure how. Linking ideas as a start hopefully helps paint a clearer, grander picture.
Another experiencing self tool-- saying yes to more situations that are on the *edge* of discomfort. It's like doing Turkish Getups w/ a kettlebell that's on the edge of too heavy. It grabs your focus, and with each discrete posture you quickly learn what your imbalances are.