How can one improve one's insight and judgment?

Listen and watch people mroe than you talk.

judgment is subjective and only practically objective in cases where facts govern opinion. You improve insight and judge rationally through being informed, observation, learning and a keen sense of collective analysis of a certain subject

Well-written fiction that depicts human emotions and interactions in an intelligent, insightful way contributes to a person’s understanding.

analysis

Well, the age-old saying is that “Good judgment comes from experience; experience comes from bad judgment.”

It’s cute, and there is an element of truth in it; it’s not entirely false.

But the best way that I have found to do it – the way that worked for me – was to argue (respectfully) with people I trusted. As a teenager I often argued (I do NOT mean “fought”) with my parents, and my father particularly. Don’t get me wrong; I always loved him, and I agreed with him more often than not, but I thought that I needed to test his hypotheses and judgments… by disagreeing with them, at least as far as taking opposite positions to his and arguing them as well as I could. I read a lot of “general thought”, history, economics, politics, you name it. And then I would sit down with him and argue about his closely held beliefs.

He understood – and supported – exactly what I was doing, so our arguments could last for days, weeks, even months sometimes, with timeouts (for me, usually) to acquire more ammunition, better thoughts and counters to (his, usually) ironclad arguments in favor of (more often than not his) positions. And we could always have these arguments with mutual love, respect and companionship. He never ridiculed my ideas, even when they were shot down around my ears in flames. In fact, as I think back on it, he never ridiculed ideas of mine that I now find ridiculous.

But I’ve had my own share of “experience” now, too, acquired in the way of that saying. Like I said, there is some validity to it.

As far as insight goes:
Always ask yourself who, what, where, when, and how, but mostly WHY???
Look for the reasons behind behaviors, especially those that don’t make sense on the surface. Most people behave for their own somewhat rational self interest. That may sound cynical but it explains a lot. I also look for hidden agendas.
Some insight is intuitive.

As far as judgement goes, much more difficult. Wisdom can be hard won. Trying to see things as they are, clear eyed, without prejudice is step one. Weighing and balancing sometimes disparate and conflicting info is important. I’m not sure if it can be taught. It’s a matter of practice. With practice and diligent information gathering and an innate sense of fairness, good judgement should, but does not always, result.

Throw yourself into as much experience as you can get. Always watch yourself. Try to understand your own motivations and other people’s motivations. Develop theories to explain human behavior and your own behavior and social movements. Study as much of every subject as you can. Constantly read. Always be curious.

You must also care. You must care about everyone and everything. Care about the universe as if it was yourself. In caring, you must look through everyone else’s eyes. You must be able to see things from everyone’s point of view and everything’s point of view if you hope to improve your insight and judgment.

I think caring is the most important thing. It isn’t about you any more. It’s about what’s best from all points of view. Or, if you want to do it from your point of view, acknowledge that and make it explicit to everyone.

Your job, in having good judgment, is to take the point of view that incorporates everyone and everyone’s interests. This must be done with love, or you can never get past yourself.

But to get there, you must live and you must have all kinds of experiences. In the process of living you will suffer. There will be pain, disappointment and heartbreak. You will run into brick walls (metaphorically) and be hurt badly. Don’t worry about making it happen. It will happen if you choose to live life fully, and to follow your bliss, as Joseph Campbell would put it.

Then you must be humble. This is probably hardest of all. For when you have good judgment, people will keep on complimenting you on it, and you must always resist feeling like it actually means anything. If you lose your humility, you will lose your insight.

Of course, this is what I believe, but it might be nonsense. I am probably deluded. But I try. And there is value in trying, even if you never meet the standard you set for yourself.

@wundayatta That is really well put! Amazing! you blow me away!

You ask how you can know your insight and judgement are improving. As for insight, I don’t know if you can count on a steady improvement. It takes a constant attention. There will be times that you feel you saw things clearly and were perceptive. There will be times when your attention flagged and you were way off the mark. When you are confirmed in your intuitive hunches, it will be exciting and gratifying. You’ll say to yourself “I called that one right!” When you’re wrong, it will be humbling. Such is life.

As for judgement…how will you know you’re improving you ask? It’s easier to see when you’re right when it is something connected to you personally.You’ll say to yourself, “Well, that worked out as I thought it would.” Sorry, not very specific I know. I’m running out of steam here!

Read as many different books from as many different people. Read all genres and discuss them with people. Analyze everything. Think of every situation from the point of view of others.