This post was largely inspired by the On taking advice and learning from people we admire and This productivity advice won’t help you but you should read it anyway.
A tweet summarizing a post from TJCX that I like a lot, which is related to your section on “When simple advice does work”:
This is why it’s useful e.g. to reread Scott Adams periodically – to keep the obvious stuff top of mind.
Edit: also cf
When giving advice to friends:
~10% of the time the “advice” is just reaffirming a good decision the other party completely planned and has yet to execute
~10% of the time the “advice” is obvious “why do you whack yourself in the head with a hammer every morning, stop doing that” kind of advice
~80% is stuff I’m totally unsure of that is much more about building my relationship with that friend (and I make sure they know this so they don’t take it)
Also, I have rarely received worse advice than that received from my best friends, which was always designed to strengthen our friendship rather than achieve any good for me. I do not regret following most, if any, of this advice. I cherish these memories.
The only advice I have heard worse than that advice was from people who prided themselves on giving advice. I regret following most, if not all, of this advice.