Ambition creates a natural alliance between young and old: Mentors want flattery; Protégés want to emulate

Ambition encourages friendships between the inexperienced and experienced, between old and young. All that success-seekers want to talk about is success, and those conversations transfer easily up and down. Those younger than them want to emulate them to get ahead. Those older want to be impressed. The status-seeker is thus likely to cultivate mentors and protégés rather than peers because neither party is close enough to each other to be threatened by them. Everybody at the same level would like to learn more about success, but to acknowledge the advice of peers is to risk getting tangled in insecurity. Thus the A-plus student is accused of being a brown-noser, and the precocious intern is labeled a climber.

The exception to this is the status-seeker who cultivates alliances to increase their power. But these are formal social connections, mediated by complicated postures and etiquette, and are not liable to become as genuine as the ones with asymmetrical power dynamics.

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A more powerful form of networking is just to find and make best friends like we used to on the playground

The image of networking is often that of collecting business cards, following up, having lunch meetings, going to parties and shaking hands, that sort of thing. But there is another kind of networking that may be more useful, not necessarily at making yourself super-connected, but for achieving the ultimate aims of networking, which are about creating unexpected opportunities. This alternative form of networking could be called the "best friend" method, where instead of collecting many leaves, you have one or a few best friends. When you visit a city where you supposedly have a lot of contacts, instead of "making the rounds," you continue and deepen your friendship with one signal friend there.

The introvert's experience with socializing could be called networking, even though it doesn't look like it. The continued deepening of interactions with a single friend can often lead to many more epiphany-like moments of collaboration that can fan out with the same exponential network effects than being a glad-handing politician.

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Empathy should precede all social interactions

People with poor social skills often forget they're talking to another person. Communicating is often a functional process. Here are some scenarios, with the function in italics:

"Oh man, I'm tired." "Why don't you sleep more?"

providing a solution

"I think we should go with plan B." "That's a stupid idea."

describing an observation

"I like this band." "They're okay."

correcting a misstatement

"I want to be a psychologist." "I hate psychologists."

mentioning personal opinion

This kind of communication is really unpleasant to be around. It's also not a great way to make friends. The trick to avoiding this pattern is to hold onto this principle: "Empathy should precede all social interaction." Before continuing with any social interaction, make sure to hold the other person's feelings in your heart.

By practicing empathy, you avoid simple functional responses. You start to move beyond simply responding to the content of someone's speech, and into responding to the person. This is similar to Martin Buber's I-Thou vs. I-It model of relationships. By doing this, you feel like you're speaking with the person and not at them.

Some techniques to practice empathy are to look at a person's tone, body language, and the flow of words, and to imagine what they're feeling. This is a better strategy than rehearsing your words in your head before saying them, which will make conversations flow unnaturally. And it's a better strategy than just having a general cautious social demeanor, which will just re-enforce social anxieties.

Once empathy is in check, the context of the conversation is set, and a new kind of conversation will naturally flow forward, one that will lead to self-confidence.

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Even though you never know what parties you aren't invited to, you might know subconsciously, which may partly explain social anxiety

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Friendships from middle school can resume at reunions because they were based on shared temperaments, not topics

Sometimes reconnecting with friends you had in middle school can have surprising results. Oftentimes there is an instant renewal of rapport, despite a gulf of a decade or more. During the gap period, both parties wandered off to forge their own paths, getting into different fields of interests. For example, one friend could be now into making movies, another into software development, and another could be living an ordinary corporate deskjob existence. And yet, when these friends re-connect, they might find it surprisingly easy to jump right into conversation or activities.

Some of the initial explanation for this could have to do low-level forces, such as adolescent imprinting, or simply nostalgia. However, oftentimes the renewed friends no longer resemble their childhood selves, or the shared memories are too far away to be remembered fondly.

Perhaps the real reason that friendships from middle school (between the ages of 11 and 14) can be easily renewed is that they were founded on temperament-matching, not interest-matching. Someone who speaks and moves fast is going to have friends who can keep up. Someone who seeks novelty is going to have comrades who like taking mechanical things apart, trying new video games, or exploring. Then, even after intervening gap years, during which concrete disciplines, interests, and hobbies manifest in each person, the friends still retain all of their childhood proclivities.

When the old friends reconnect, they might find it not only easy to resume their same conversational or interactive affinity, but also that there is now this massive interdisciplinary flow of information, since neither party is really acquainted with the other's current field of study or history.

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If you manipulate others, you manipulate yourself. After all, the person being manipulated spent no effort to change your behavior

Let's say you're in a domestic partnership, and you notice your partner is constantly leaving smelly clothes all over the place, despite you and them having discussions about this before. So you take a different tactic, and try soft manipulation, or "training," to make your partner behave differently. You stop your nagging, and instead you throw indifference at them. If they leave smelly things around, but then come around later to ask what's for dinner, you shrug or proceed to respond with a flat, hyphen-lip smile. Your actions may give your partner pause, who might then think, "Hmm, I wonder what's wrong," and maybe they respond by proactively cleaning up the house to cheer you up or get a reaction out of you.

This strategy is precisely what Amy Sutherland describes doing in What Shamu Taught Me About Life, Love, and Marriage. She drew from her background as an animal tamer to provide some lessons for relationship management. She learned that making a fuss when animals do something wrong encourages the negative behavior. So you turn it around, realize that the animal wants your attention, and withhold it until you get the desired behavior. She then applied this to her home and got her partner to pick up smelly socks.

Hearing this practice is naturally controversial. That's why Sutherland has to couch it in cute terminology from the animal kingdom. So what is exactly objectionable about it? Perhaps it's because the effort is self-defeating. By turning into a trainer who creatively figures out how to get what she wants from her partner using subtle techniques, in some ways, that means her partner trained her as well. By just "being himself," he got her to transform into a positive-reinforcing win-win communicator and is now rewarding the home with cleanliness.

Social manipulation is in many ways like a Chinese finger trap. The further you go down that road, the more it mires you in it. You can't deliberately bend others without in some ways bending yourself. It is perhaps why we often deride flatterers and social climbers as having no spine.

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Introversion has less to do with a disinterest in people, than it does with an interest in focus, something that groups lack

When socializing in groups, subjects randomly stream in and out, bringing in new perspectives and attitudes that lead the number of possible conversations to expand exponentially based on combinatorics. Turn-taking is tricky and determined on the insistence and volume of a dominating speaker. There is no steadiness or predictability as to where the conversation will go and who will speak.

When socializing one-on-one, the number of partners is fixed, and the topics change only gradually. Each partner takes turns leading the conversation, and the proportion that each partner spends speaking is relatively more equal than in a group. The difference between 2-person socializing and groups is much like the difference between sitting for an acoustic set at a coffee shop versus stadium rock.

Extroverts are hailed as charismatic leaders, whereas as introverts seem aloof or uninterested in others, and by extension, uninterested in the human race. But introverts love their friends just as dearly as extroverts. The perceived difference may just be a matter of temperament, not interest.

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Social skills lead to confidence which leads to extroversion which means that Jung's typologies aren't set in stone

In psychiatric literature, it is taboo to say social anxieties are related to social skills. Yet in folk therapy, i.e. by consulting your friends or reading controversial "underground" guides like The Game, if you explain that you have trouble talking with members of the opposite sex, your friends may suggest a makeover for you and that you take improv classes. It could be that more serious literature is designed to apply to as many people as possible, and a very specific recommendation like that is too unlikely to apply to you. (i.e. You may have already taken improv classes and may already dress well). Literature has to be context-free.

This notion of introversion vs. extroversion is one of those context-free memes that has become ingrained in people's consciousness. People say, "Oh, I'm an introvert" like it's a permanent part of their being. However, we don't have measurements about how flexible introvertedness is. Do people measure the same level of introvertedness one, two, or five years later?

In my personal experience, I noticed an uptick in my extroverted-ness that coincided with each uptick in social skills. When I read The Definitive Guide to Body Language. When I learned about empathetic listening. When I followed Fonzworth Bentley's principles of being a gentleman: "Style, Confidence, and Manners." After each seminar, I became more eager to socialize and make friends.

Now, it could be a confusion between causation and correlation. I may have been fundamentally eager to socialize, and therefore sought out self-help books to aid in that. On the other hand, then that means I wasn't an introvert to begin with, since my desires were so clear to me. So in a way, self-described introverts may cling to the label to resolve the tension between their desire to socialize more and the social anxieties that hold them back: "I don't know, I don't feel like going out, I guess I'm an introvert." In tandem, true introverts may use more blunt descriptions: "I have no interest in going out."

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There's a fine line between passive-aggressive feedback, and being vague enough to let the recipient save face

If you have to accuse or confront someone, one strategy is to couch your statements in such a way that it gives them a way out. In other words, it helps to be willfully vague when making an accusation.

As a programmer, there were so many times when I bumped up against someone else's code, and had to point out their mistakes. As a result, we used lots of indirect comments like, "What's happening with this error?" or "Should we tell quality assurance to double-check that?" These comments are, in some way, borderline passive-aggressive, and yet they're actually necessary to smooth out communication. At the very least, by giving the accused a way out, you're insuring yourself against possibly being wrong yourself, which if discovered, is almost a worse infraction.

Sometimes what you really want to accomplish is simply multi-faceted. On the one hand you want the other person to learn something, yet at the same time you don't want to flat out point out they did something wrong. For example, I asked a friend, who I wanted to accuse of saying negative things behind his friend's back, "You know, you were talking about our friend the other day. I was wondering if you could walk me through that. Because an uncharitable interpretation is that you were talking behind his back." He quickly back-pedaled, told me that him and our friend go way back, always with ups and downs, and that his criticism was more of a familial critique. That put me at ease, and yet I also feel I got through to him that he was kind of dragging his friend's name through the mud.

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While men and women are free to dress as they like, women have ten times more genres to choose from, including ones of their own personal invention

Men either have less freedom or more freedom when it comes to dress than women do. True, anybody can dress however they want, adorning themselves with all sorts of shapes and colors that fit their imagination, but to dress stylishly, one has to consider the existing, acceptable stylish genres for their gender.

For men in a cosmopolitan city, there are anywhere from 2-4 genres of attire that, when followed fully, lead to something that could be considered a stylish ensemble. For example, in Austin, TX, there are three genres to choose from. There is the hipster adorned with a willfully eclectic mix of styles, retro or ironic sunglasses, and unusual, but of-the-moment colors (at one point, it was purple, and recently it was maroon). There is the uniform that could be called "white liberal" from those who shop at Whole Foods, who like the hipness of hipsters, but don't like how loud they are, and at the moment, tend to wear shoes sold by Toms, the company that donates a pair of shoes for every one you buy. Thirdly, there is the stylish dress of the more traditionally employed, such as those working in finance, who tend to pick a blur of styles from the hipsters and white liberals, but from 5-10 years ago, while throwing in flairs of attitude and class, such as maintaining a popped collar, or still wearing Lacoste shirts.

If a man doesn't dress in a genre associated with his demographic, he can only create a facsimile of style. He can have matching colors, have forms that fit well, and pay for a coherent haircut, but if he doesn't fit within those above three genres, something will always seems off or incomplete about his ensemble.

Women also have genres to choose from. Two of the genres for men mentioned above also exist for women: the hipster and the white liberal. However, the number of genres for women are not on the order of 2-4, but on the order of 12-16. And since women spend more effort outdoing each other in fashion, appearing unique has larger currency for them. For a woman to appear stylish, she really has two options: to either choose from a pre-made genre for her demographic (whether it's a platinum-blonde inspired from The O.C. or a bangs-bedecked cutie-pie à la Zooey Deschanel), or she can create her own genre and ensemble, as long as it adheres to general principles of aesthetics.

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Women don't dress for men because to calculate how fashion choices affect reproductive chances would boggle the mind

When you ask women, "Why do you dress so well? Is it to impress guys?" they will most likely reply with a resounding, "No, I dress for myself." Technically this is true because when someone picks through their wardrobe, they are rarely visualizing some stranger of the opposite sex viewing them. Instead, they hold a mental image of themselves in the outfit and appraise their beauty in the same way that they would appraise a painting or a statue. So, in that sense, they are dressing for themselves. But dressing well garners more attention, raises social standing, and only "feels good" because it confers benefits in the form of increased likelihood of fortuitous connections.

But it's better that there's a disconnect between rhetoric and reality. Because to consider every encounter with a stranger as an opportunity to make a good impression so as to maximize one's social gain from that individual would boggle the mind. True, every connection you'll ever make starts with a stranger, but socializing is more of a numbers game. In the long-run, with enough iterations, dressing well will raise your social standing enough in some stranger's eye to start a conversation that could eventually lead to finding the love of your life. In other words, dressing well is an off-goal target. The real goal is to build good relationships, but instead, you focus on the side goal of sartorial excellence.

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Write eulogies for your loved ones, so that you may cherish them while they're alive

One big regret that people commonly express at funerals is that they didn't tell the deceased how much they really meant to them. To remedy this, what if we wrote a eulogy for each of our loved ones before they died, and then shared it with them?

There are some grim implications to this proposition, but they can be mitigated. Perhaps, after writing down a eulogy, you could distill the bullet points from it and ask yourself, "Does my loved one know that I think this highly of them?" For example, if you think your best friend is a really good listener, would they know that?

Then, instead of telling them outright, which could be awkward, you could drop hints every now and then or randomly mention the compliment in passing. People tend to cling onto such poignant lauds, even if uttered in a casual manner, and they have the possibility of changing the whole dynamic of your relationship.

Perhaps this should be the real "bucket list:" drop hints to everybody you know about the high esteem you really hold them in.