It's really essential that one have (1) down (to be self-constituted) down in order for (3) not to lead to a circle of confusion. If I feel very assured in my own relationship with the universe, that doesn't depend on how anybody else sees me, and my security does not depend on others being happy with me. And when I don't need to make anybody happy, connection and compassion arise naturally from a place of curiosity--there are feelings of abundance and security underlying it rather than confusion or anxiety.

That sounds simple but the self-constitution part takes years of serious searching and work; some things (good therapists, good meditation teachers, good books, consistent practice, etc.) help the journey along, but there is no quick route.

Any particular books you recommend? people keep mentioning _how to win friends and influence people_ and I am not sure if it's just mindless productivity gurus hype

Right now I'm reading As It Is by Tulku Urgyen Rinpoche (if you don't have previous experience with Buddhism I'd recommend starting with something broader like Zen Mind Beginner's Mind, and find yourself a Buddhist meditation group!), and Self-Therapy by Jay Earley. Something else very much written for an intellectually-oriented audience but that gives inklings of a ladder into non-intellectual being, is Unwinding Anxiety by Judson A. Brewer. I liked it at the time, though I found I needed more help practicing the things that that book suggests, which led me deeper into Buddhism and eventually towards Dzogchen.

I wouldn't recommend How to Win Friends and Influence People, it is all about fine-tuning behavior to make a better impression on people, and that doesn't sound like the heart of the issue you described. The heart of that issue _could_ be that one clings to mind-concepts rather than trusting the whole being and feeling a connection with the universe. If so, one must slowly learn to trust the felt experience of life, to know that gut feelings and open-heartedness are just as important as thoughts (moreso in many respects), to trust that one can relax one's whole being and be carried by an infinite love within. It is a gradual progression.

As a lifelong obsequious people pleaser, I have realized that I make it about me by trying to figure out what people want from me, or I'm focused on how I can look better in their eyes. Instead, truly trying to understand how someone is feeling and reflecting that to them has been so much more gratifying for me (and hopefully for my friends and family.)

+1. I say this jokingly, but in a sense being a people-pleaser vs being empathetic is a “skill issue.”

Being focused on how people might think of you is shallow and tastes like narcissism. Even if in your own mind you are “thinking about others” too much you are really only thinking about yourself through their eyes.

Being present in the moment with someone and their feelings involves getting out of your own narrative.

This section was the hardest for me to understand. I personally don't like the idea of building a mental theory of mind and then evaluating your responses based on how you think someone might react. I prefer to be authentic in my action even when I know it is going to be ill received or not be in my advantage. I do what I do for a reason and I have to trust my internal compass. If after all that my actions are taken the wrong way then I accept that. Self reflection to keep myself in check, most of the time i stand by what I said. You cant live life without being mean, rude, offensive sometimes thats what the situation calls for.

But maybe im an asshole, I genuinely have no idea.