What's worked for me:
0. General advice
- No negative self-talk!
Find more constructive ways to communicate your ideas _even to yourself_. "I wish I could communicate my ideas better" -> "Here's an idea I felt I did not communicate well, this time, in this context. Why do I feel this way? How could I have presented myself better? (Where can I gain competence?)"
- Write and rubber ducky!
Writing and rubber ducking are methods for practicing the linguistic aspects of communication. While verbalizing to the duck, play with the timbre, cadence, tone, etc., of your voice. Record yourself and listen to it. Have problems finding material to verbalize? Pick a poem. Memorize it. Recite it. This is, in my opinion, the calisthenics of social practice.
- The person with the most developed opinion of you- is you!
"He who despises himself will still respect his skills as a despiser." ~ Nietzsche, "Beyond Good And Evil" (paraphrased, can't be arsed to cite it just now)
The Spotlight Effect: https://en.wikipedia.org/wiki/Spotlight_effect
_You_ might notice every failure of your communique, but then again: you have an ideal for your communique. A goal, a reason, a vision of how it ought to manifest. To everyone else, however, it's an utterance like any other. The ultimate measure of your effectiveness isn't how closely you manifest your idea, but how much of an impact (and of what kind) it has on the audience.
=== 1. Practice, practice, practice. ===
It's a skill, like any other; and like any other, you succeed to the level and quality of your training. If you want to "get better at talking to people," then go talk to people; if you want to "get better at talking to people, in a book club, with a small number of friends" then do that!
How to do the first (i.e., practice speaking to people)? Communication is both observational and "applicative," in that you apply yourself in the actual doing. This suggests a good path in itself: practice your observations and also practice the doing.
How to observe strangers? (in a socially-conscious way?) The easiest way is to be conscientious of your interactions. I got started by making mental notes, pushing myself to take note of the most simple and basic details. "Oh, her nails are purple;" "It's midday and he's wearing shorts;" "He has a GameStop tag on his keyring." The simpler you can break down a situation, the more data you have for a fuller analysis.
Of course, simply having data does not an analysis make. Even with a habit of conscientiousness, I found myself struggling to derive actionable insights. Why? Likely because I was leaning too heavily on poor tools to make my analyses. This was during a phase in my life where I was very concerned with reducing as much as I could to logical and rational principles, including my interactions with others. "Assuming that people's statements reflect their internal state, that their internal state is logically consistent, and further assuming that some particular data X is included in their analysis, I can reasonably conclude that (by their statement) they must internally position themselves thusly with regards to X." This is a good general example of my internal dialogue during this period; it was helpful in some ways, fatal in many others. I now believe that there is no decision funnel you can induce, explicitly or otherwise, which makes this line of thinking safe.
I've since abandoned this project of rationalizing, because a key assumption I made was that every healthy, moral, person must have a logically consistent internal state. Indeed, I considered logical consistency to be a prerequisite for any kind of morality. I now believe this foolish; whereas I previously considered Man to be the rational animal, I'm now of the opinion that Man is much closer to the aesthetic animal.
This was a key insight for me. It has directly led to the most socially productive period of my life (which I'm thankfully still enjoying).
What does 'the aesthetic animal' entail? That people are, at base, motivated by their sensibilities. I take the most basic statement of logic to be equation: "this is that;" more specifically- "this is this." I believe the most basic statement of aesthetic is: "this pleases some sensibility I have."
People reveal their sensibilities- their aesthetic- with their genuine smiles, their sincere fashions, their honest jokes. Take note of these; my analytical habit these days is to capture as much of someone's aesthetic as I can. Again, it starts with conscious conscientiousness and observation.
=== 2. Perspective, perspective, perspective ===
You are distinct from every other person. I like to keep myself in perspective with counting the number of "distinction points" by which I differ from another. My love for the Beatles is one such point; that I know Sgt. Peppers' Lonely Hearts Club Band by heart, but none of their other albums, is another. That I program, when and how I started, what I'm doing now (with which languages)- all of these, too, and even the breakfast I had.
Don't try to store all this state at all times; just develop a habit and method of counting, and apply it where appropriate. Of course, the method, the habit, the application, understanding in which contexts it's appropriate: all of these are skills, too!
This is how I attempt to understand the differences between my perspective and others. From there, I spend a lot of my downtime acquiring alternate perspectives. I find Nietzsche ("Beyond Good And Evil") helpful to this end. (NOTE: I explicitly disavow and condemn Nietzsche's misogyny.) "Tuesdays With Morrie" is indispensable, in my opinion; specifically, Morrie's advice to embrace emotions. All of them.
Allow yourself to be embroiled in your feelings, until it finds its natural conclusion. Then practice conjuring your emotions, and be conscientious with your emotions. Observe their onsets and evolutions- _not_ to rationalize them, but to explore your own sensibilities and aesthetic.
Once you've made a habit of these observations and conjurations, seek out stimuli that alter your perspective, and then practice your perspective. Imagine how your relation to that stimuli might change if you were elsewise distinct. Conjure the emotions that you feel inherent to that you-but-else, and explore them as your own.
I treat it like a game; to these ends, the methods of acting are instructive.
This helps me explore a wider, but still woefully limited, aesthetic space. That, in turn, helps my conscientiousness of aesthetic (of both mine and others). Further, with my method of distinction, it gives me a much richer insight into how I perceive the aesthetics of others.
=== 3. Accept your mistakes, acknowledge your success ===
The possibility of failure is a precondition of any endeavor. Unfortunately, social failures can be particularly impactful to certain dispositions. Social failure can mean embarrassment, self-doubt, stigmatization, and (perhaps worst of all) emotional fallout in others.
An anecdote: I decided, for a period, to exercise my sense of humor. I visited a male cousin of mine, shortly after he had taken a new wife. His lot in life had been unhappy til then, filled with struggles and poverty. My visit was on the heels of his release from a half-year prison sentence. Imagine my happy surprise when I approached his address, to find a rather generous estate! Great land, a beautiful home, healthy children... I said to them- he and his wife- "What great success! But, I have to ask: who died and left you this land?"
She meekly replied, "My ex-husband."
It took me a while to feel comfortable making jokes. I was absolutely mortified for months thereafter. The mortification is appropriate! But it's not reasonable, nor healthy, to avoid an entire category of expression over a mistake- even such a horrid mistake as that. Perhaps _especially_ even for such a mistake. Accept it, take the L, and be more conservative in those expressions for a time thereafter: but don't define yourself by your missteps.
Likewise, acknowledge tho successes you have. Ultimately, only you can define what success looks like, and your successes must be operationalized to the context- but cherish these memories. Meditate upon them. Try to embrace the graces that led to it, on your end and the audiences'; yet, at the same time, refute the desire to embody these graces. Do not define yourself by your successes, either.
Ultimately: get out of your head and learn to love the strangeness of your fellow humans :) we are all a unique vintage, some more delicious than others (and a few that spoiled on the vine) yet all worthy of at least one honest snifter.
=== Recommended Materials ===
Nietzsche (specifically, "Beyond Good and Evil" [again, I categorically disavow his misogyny.]) "Tuesdays With Morrie," Mitch Albom
=== The Extremely Unorthodox ===
I recommend psychedelics.
Talk to your doctor, your therapist, your spiritual mentor, the neighbors' dog- whomever can help ease your mind. If you have any doubts, don't do it! And, of course, responsibly indulge where legal and when you are safe.
I also recommend "escorts," of any gender.
Not for the sex, but because escorts are by-and-large social professionals. Perhaps the _most_ social professional. They are experts of aesthetic, masters of perspective. Pay their fees, reassure them that they need not disrobe, and just go off. Ask all those little questions that you usually dare not vocalize. They've experienced stranger. It helps you exercise failure modes in a significantly safer space. "Adult entertainers" and bartenders are also choice for this.