The Friendship Challenge

The Limits of Friendship” is primarily about the Dunbar number, and the article’s attendant Hacker News discussion evolved or devolved toward discussing friendship more generally (“Reading the comments, I’d say many members of HN should probably invest more time fostering friendships”). Both remind me of discussions with friends, about the nature of friendship, and how most people seem ill-prepared for social life after school.

In American and perhaps Western society as a whole like-minded people at similar life stages continuously mix together from age five up to at least age 18 and often well into the 20s through school. Then people often stop routinely mixing with new people, different people find themselves in different stages of life, and the friend machine often stops.* Yet it doesn’t have to, but making friends and meeting people becomes a skill more than a side effect of being.

A friend observed that I have a “gift” for talking to strangers, which would probably be a funny observation to my family or people who knew me in high school. Still I thought the comment was awesome because I’m quite the opposite: when I was a teenager I was pathologically shy for a lot of my life, and it’s taken a lot of effort to cultivate the ability to be social with strangers. I wrote to the friend that casually and regularly making friends is a learned behavior for me.

I used to never do it (flirting with women was also a learned behavior, as extensively and embarrassingly discussed here). Now that I do, however, I’ve noticed that people think I’m automatically good at it. A lot of things people now identify as characteristic Jake behaviors are really, really learned. I think that the temptation to see them as innate is attractive because it excuses us from doing the work necessary to cultivate and practice them.

I don’t want to be one of those people who hit 30 and are like, “Gee, I don’t have any friends anymore…” Part of the challenge comes from friendships being defined by time-of-life. Single people want to party and mingle with other single people. Couples (often) with couples, since single people can be threatening to relationship stability. Parents of young children rarely hit the bars at 10:00 p.m. on Thursday night.

Generalizations are obviously not universally applicable to all people all the time, but they exist for a reason. People with kids identify with other people with kids and so on. Parents talk about babysitting and their children’s shitting habits (I seriously hope to never do that). Your best friend at 20 might have nothing in common by 30 depending on when / where / how you evolve.

I see more and more lonely people who are like “Why am I lonely?!?” Let me be harsh for a moment and say they’re like fat people who are like, “Why am I fat?” and “I want to lose weight.” Some people have medical or medication issues, but for most the answers are straightforward: “Stop eating cookies and drinking soda and do some pushups and ride your bike instead of driving your car.” The response is usually, “I don’t have time blah blah blah.” Problems have solutions and there are many ways to falsely divide people into two groups, and one of those ways is between people who do the shit necessary to be effective and the ones who don’t.

Everything I have learned I feel like I have learned the hard way, through enormous amounts of error. That’s one reason I’m not too pissed about being told I’m a novice lifter at the gym. Chances are the trainer is right and I need to practice. Practice is everything. I suck at everything until I try, really hard and really repeatedly, to get better at it.

Friendship also isn’t quantifiable, which probably dissuades some high achievers who want everything measured in grades, dollars, or some other metric (that Facebook can be measured in this way may be one problem with it). There are still guides to becoming better at people. For example, How to Win Friends and Influence People is surprisingly good. I heard about it through reputation and assumed it would be stupid. I was wrong. Read it, annotate it, read it again in three months. There is a reason it has endured for (literally) generations—I think it first came out in the 1920s or 1930s—and that’s because its advice is timeless.

How to Be Polite” has one or two paragraphs that are brilliant (it also has some other paragraphs):

Here’s a polite person’s trick, one that has never failed me. I will share it with you because I like and respect you, and it is clear to me that you’ll know how to apply it wisely: When you are at a party and are thrust into conversation with someone, see how long you can hold off before talking about what they do for a living. And when that painful lull arrives, be the master of it. I have come to revel in that agonizing first pause, because I know that I can push a conversation through. Just ask the other person what they do, and right after they tell you, say: “Wow. That sounds hard.”

Because nearly everyone in the world believes their job to be difficult. I once went to a party and met a very beautiful woman whose job was to help celebrities wear Harry Winston jewelry. I could tell that she was disappointed to be introduced to this rumpled giant in an off-brand shirt, but when I told her that her job sounded difficult to me she brightened and spoke for 30 straight minutes about sapphires and Jessica Simpson. She kept touching me as she talked. I forgave her for that. I didn’t reveal a single detail about myself, including my name. Eventually someone pulled me back into the party. The celebrity jewelry coordinator smiled and grabbed my hand and said, “I like you!” She seemed so relieved to have unburdened herself. I counted it as a great accomplishment. Maybe a hundred times since I’ve said, “wow, that sounds hard” to a stranger, always to great effect. I stay home with my kids and have no life left to me, so take this party trick, my gift to you.

The resources are there. The challenge is implementation. Let me repeat myself: Making and keeping friends is a learned skill, which many of us never learn and some of us learn much later than we should.


* (Adolescence is hard because it scrambles all the rules and principles learn about friendship from approximately toddlerhood to say age 12. Tom Perrotta’s Election has a great line in which a character observes that sex habitually turns friends into strangers and strangers into friends. Francine Prose’s young adult novel Touch hits similar themes. It may be that many people are unhappy that we never really return to those pre-puberty rules and roles because our desires and incentives change, and we have powerful evolutionarily shaped drives to do certain things and behave in certain ways.)

The appeal of “pickup” or “game” or “The Redpill” is a failure of education and socialization

Since posting “The inequality that matters II: Why does dating in Seattle get left out?” and “Men are where women were 30 years ago?” I’ve gotten into a couple discussions about why Neil Strauss’s The Game is popular and why adjacent subjects like “pickup” and the “Redpill” have become more popular too. One friend wrote, “It’s so tedious to see how resentful men get—a subject much in the news lately because of the Santa Barbara shooting…”

That’s somewhat true, but underlying, longer-term trends are still worth examining. The world is more complex than it used to be in many respects, and that includes sex and dating. Until relatively recently—probably the late 60s / early 70s—it was common for most guys to marry a local girl, maybe straight out of high school, and marry a girl whose parents the guy probably knows and her parents probably know the guy’s. Parents, families, and religious authorities probably had a strong effect on what their children did, and a lot of men and women married as virgins. The dating script was relatively easy to follow and relatively many people paired early. In the 60s an explosion of divorces began, and that complicated matters in ways that are still being sorting out.

Today there are more hookups for a longer period of time and fewer universal scripts that everyone follows, or is supposed to be following. Instead, one sees a proliferation of possibilities, from the adventurous player—which is not solely a male role—to early marriage (though those early marriages tend to end in divorce).

Dating “inequality” has probably increased, since the top guys are certainly having a lot more sex than the median or bottom guys. To some extent high-status guys have always had more sex, but now “top” could mean dozens of partners at a relatively early age, and the numerical top is more readily available to guys who want it. In the old regime it was probably possible for almost everyone to find a significant other of some sort (and I think families had more sway and say). Now that may be harder, especially for guys towards the bottom who don’t want to realize that if they’re towards the bottom the women they’re likely to attract are likely to be around the same place. We don’t all get a Hollywood ending, and Hollywood itself is unrealistic.

Guys who notice that movies, TV shows, and some books portray an unlikely or unrealistic set of dating and marriage patterns should start to wonder what the “real thing” looks like. The Game isn’t bad, though it is dated, and I expect Tucker Max and Geoffrey Miller’s book Mate to be popular for reasons similar to the ones that made The Game popular.

I’ve also noticed an elegiac sense that a weirdly large number of the “pickup artists” or “Red Pill” (sometimes it’s used as two words, sometimes as one) or “manosphere” guys have about the past, and how back then it was relatively easy to find, date, and marry a woman. Much of this is probably mythological, and I don’t think most of them would be happy marrying at 20 or 24 and having two or three kids by 28 or 29.

Like all generalizations, the stereotype above are riddled with holes and exceptions—see further the oeuvre of John Updike—but I’m examining broad trends rather than specific details. Today almost no one gets married straight out of high school. Routine moves from city to city are normal, and each move often rips someone from the social networks that provide romantic connections. Families play a smaller and smaller role. Twenty-somethings, and especially women, don’t listen to their parents’s romantic advice.

If you don’t have the infrastructure of school, how do you meet lots of new people? Jobs are one possibility but looking for romantic prospects at work has obvious pitfalls. Online dating is another, but people who can’t effectively date offline often aren’t any better on—and are often worse.

Technology matters too. Technologies take a long time—decades, at least—to really reach fruition and for their ripples to be felt throughout societies and cultures. Virtually all big ideas start small.* That’s an important lesson from Where Good Ideas Come From, The Great Stagnation, The Enlightened Economy, and similar books about technological, economic, and social history.

A suite of interrelated technologies around birth control (like hormonal birth control itself, better forms of it, and easy condom distribution and acquisition) are still playing out. Same with antibiotics and vaccines against STIs. VOX offers one way to think about this in “From shame to game in one hundred years: An economic model of the rise in premarital sex and its de-stigmatisation.” It begins:

The last one hundred years have witnessed a revolution in sexual behaviour. In 1900, only 6% of US women would have engaged in premarital sex by the age of 19, compared to 75% today . . . Public acceptance of premarital sex has reacted with a lag.

Culture is still catching up. Pickup, game, and the Redpill, regardless of what you personally think of them, are part of the the cultural catchup. They’re responses from guys frustrated by the way their own efforts fail while some of their peers’s efforts succeed. A lot of women appear less interested in an okay guy with an okay job and an okay but not that exciting or fun life, relative to guys with a different set of qualities. Men invest in what they think women want and women invest in what they think men want, and relative wants have changed over time.

Almost every guy sees or knows at least one guy and often a couple who do spectacularly well with women. Guys who are frustrated or who can’t achieve the romantic life they want start to ask, “What are the successful guys doing that I’m not?” Pickup or game or the Redpill are different strains of systematic answers. All three may have things wrong with them, but all three are better than nothing. Saying “Women are mysterious” or “No one knows what women want” is bullshit, and guys only have to look around to notice it.

Pickup artists and those who read them are responding to a cultural milieu in which most guys get terrible socialization regarding dating and women. Pickup artists are stepping into that gap. They’re trying to answer questions in a concrete way, which most people, including their detractors, aren’t. In a review of Clarisse Thorn’s Confessions of a Pickup Artist Chaser I wrote:

feminism does very little to describe, let alone evaluate, how micro, day-to-day interactions are structured. Pickup artists, or whatever one may want to call guys who are consciously building their skills at going out and getting women, are describing the specific comments, conversations, styles, and venues women respond to. The pickup artists are saying, “This is how you approach a woman in a bar, this is how you strike up a conversation at the grocery store, and so forth.” In other words, they’re looking at how people actually go about the business of getting laid. Their work is often very detailed, and the overall thrust is toward the effectiveness of getting laid rather than how male-female interactions work in theory. Feminism, in Thorn’s view, appears to be silent, or mostly silent, on the day-to-day interactions.

Who else is doing that? Almost no one. As with virtually any other topic, one can muddle along through trial and error (and mostly error) or one can try to systematically learn about it and apply that learning to the problem domain, along with the learning others have done.

To be sure, the worst of the group if just trying to sell shit, and sell as much of it as possible to fools. The best of the group is saying things that almost no one else is saying. They also say it’s hard. Look at “Krauser:”

The PUA cartel saw you coming and will sell you magic pills and 3 Secrets To Make Her Wet as long as your credit card is below it’s limit. If you’re looking to score something for nothing, you’ll end up with nothing. Daygame is hard. Very very hard.

He calls out the “hack mentality” in the same post. Caricature is easy, but the guys who are really paying attention aren’t easily caricatured.

As noted above, Max, Miller, and Nils Parker are writing Mate: The Young Man’s Guide To Sex And Dating, which is, among other things, a description of modern dating and a description of why so many guys do it so badly for so long. Confusion reigns, and the book promises to be the sort of fun-but-comprehensive read that can be given to unhappy, puzzled guys who understand something is wrong but don’t know how to fix it.

One strategy in response to new social circumstances is to figure out what you should do to be reasonably successful and what you can do to make yourself more appealing. This is not a male-only question: virtually every issue of Cosmo is about how to attract men, retain men, and deal with female friends and rivals. Another is to blame women, or withdraw from dating, or kill innocents because of your own frustration.

If you think half the population isn’t into you, the problem is with you, not the population. There’s an important similarity to business here: If you start a business and no one wants to buy your products or services, you can blame the market or you can realize that you’re not doing what people want.

It’s easier to blame women than it is to make real changes, and there is a tendency among some of the self-proclaimed “Redpill”-types to do that. Paul Graham says the real secret to making wealth is to “Make something people want.” In dating the real “secret” (which isn’t a secret) is to be a person people like. How to do that can be a whole book’s worth of material.

Blame is easy and improvement is hard. Short guys do have it harder than tall guys—but so what? Go ask a fat girl, or a flat-chested one, how much fun dating is for her, compared to her slenderer or better-endowed competitors. Honesty in those conversations is probably rare, but it is out there: usually in late-night conversations after a couple drinks.

I don’t hate “pickup artists” as a group, though I dislike the term and wish there was something better. Many of the critics are accurate. But so what? criticizing without recognizing the impetus for the development in the first place is attacking the plant while ignoring the roots. This post, like so many of the posts I write, is looking at or attempting to look at the root.

Feminism didn’t come from nowhere. Neither has pickup.


* Which is not to say that all small ideas will automatically become big. Most don’t. But ideas, technologies, practices, and cultures spread much more slowly than is sometimes assumed, especially among the rah-rah tech press.

Most volunteering is a waste of time for anyone except the volunteer

Volunteering is primarily driven by the need of the volunteer to feel good about themselves, not to do the most good; the way to really do the most good is to know how to do something valuable, like make a computer do what a person wants, or building things. Not that many people can or choose to learn how to do something really valuable, but many people can rehab trails or serve meals to the homeless.

Nonprofit and public agencies know this and many don’t really want volunteers, though they also can’t really turn volunteers away for PR reasons.* Nonprofit and public agencies want cash, which is fungible and can then be spent hiring professionals who don’t consume a lot of time and energy. Programmers know that the smallest number of programmers possible should work on a given project, because each additional programmer increases the communication overhead of the project. Sufficiently large projects often collapse because programmers cannot communicate effectively and ensure their code works coherently together. Volunteers face a similar problem, albeit to a lesser extent.

Low-wage labor is also widely available. Someone with a skill that can be sold for a couple hundred dollars an hour is better off doing that, and then donating their wages to hire at least ten people for ten dollars an hour. That’s much more useful to society as a whole. We’re in the habit of automatically admiring volunteers and volunteerism, to the extent that claiming volunteer hours has become yet another way of gaming college admissions through dubious altruism.

The primary way to usefully volunteer is to have a specialized skill that can be effectively deployed by the organization, but that rarely seems to happen. If the organization really needs a given skill, it tends to pay for it, because it needs that skill delivered reliably and, often, to precise specifications.

Mastering a complex skill, however, is a labor-intensive process; it’s famously been said to take ten years. Maybe one can master a skill in less time, but certainly it takes thousands of hours of dedicated practice. No one can wake up and decide to write a (good) novel or (good) operating system or whatever. One can go off and seal envelopes or make cold calls or serve meals for a couple hours.

One sees this at work in the misguided efforts to send expensive American teenagers to developing countries to build houses. Developing countries by and large do not have a shortage of effective construction workers (the U.S. imports plenty of Mexican construction workers)—they have a shortage of money. The thousands of dollars it takes to feed, secure, and transport American teenagers or twenty-somethings would be much more effectively spent on local labor and materials. But the purpose of volunteer trips is of course not about building houses but about making the volunteers feel good and useful.

Still, if the choice is between volunteering or watching T.V., volunteering is probably a “better” thing, but if the choice is between volunteering and mastering a unique skill, master that skill (and perhaps teach it to others). Be an example to others by becoming an expert, instead of by sacrificing time that should be optimally spent doing something useful for a large number of people.


* I’m a grant writing consultant. Many nonprofit and public agencies will admit in private that they don’t want volunteers. I suspect all or nearly all professions generate uncommon or counter-intuitive knowledge. The Internet is pretty good at letting people discuss that knowledge in a pseudonymous environment.

If someone is angry you may be doing something right: Alain de Botton edition

Early negative reviews of his work [How Proust Can Change Your Life], by Proust professors and philosophy dons, devastated him, admitted de Botton. “It was very surprising and upsetting. Then my wife, who is very wise, said to me, ‘It’s obvious, this is a fight.’ This is a turf war, and the battle is about what culture should mean to us.”*

If you’re a) doing significant work and b) making people angry, then you may c) be doing something right. I think the first component is particularly important because it’s easy to needlessly or cruelly piss people off—through rude remarks or punching someone, for example. We’re taught that making other people angry is a bad thing and in most contexts it probably is, but in some it isn’t and may actually be a sign of importance.

Anger is a powerful response and a common one to someone who feels threatened: suggest to a public school teacher that teachers shouldn’t be granted de facto lifetime employment after three years, or that teachers’ unions are serious impediments to education, and you’re not likely to get a reasoned discussion about policy. You’re likely to be treated as someone who violates taboo. To most of us discussions about education policy are benign, but to teachers they’re often sacred (the “benign-violation theory” of humor is similar, as discussed in The Humor Code).

I’ve gotten weirdly vituperative responses from English professors about this blog. Usually those responses are couched in language about being unprofessional or low quality or a waste of time that could be better spent advancing my career. In that worldview, having anyone read your work doesn’t matter. At first I took those responses at face value, but now I’m not so sure: they might have been unhappy that I think most English journals bogus and, worse, treat them as such. It’s dangerous to have people work outside the system they’re highly invested in. If you don’t have the apparatus of peer review and journals and so forth, what separates paid professors from blogger rabble? Some answers to that question may be terrifying.

Philosophers probably guard their jewel basket carefully because there is nothing inside.

To return to de Botton, I also think he calibrates his work towards accessibility. It is easy for a normal person to understand what he says and to judge its truth value. Many philosophers seem to take pride in doing the opposite. In addition, de Botton reaches for a relatively low-knowledge audience; I found his book about architecture charming, for example, but How to Think More About Sex was inane, mostly because of it lacked any familiarity with evolutionary biology. Over the last couple decades, that’s been where the action is. Writing about sex without reading evolutionary biology is pointless, and I know enough to know that. Alternately, even compelling writers produce some bad books, and this could be de Botton’s off book.


* From “The empire of Alain de Botton.”

How I learned about assertiveness and reality from being a consultant

Like many people with such businesses, some friends with a design consulting business say they’re getting jerked around by potential clients, they’re worried about offending potential clients, and most importantly they’re discovering that the lessons they’ve taken from school and every day life are wrong or at least not optimal. So I described my own experiences as a consultant and how that taught me about reality and money.

A lot of people—including me—are told from an early age to be polite, take turns, be considerate of other people’s feelings, etc. This is good advice in many but not all circumstances. In the business / consultant worlds it often leads other people to take advantage of you. Consultants need one very important skill: they need to figure out who is going to give them money and who isn’t, and they need to do so relatively quickly. Clients will often press to get as much free stuff—often in the form of time and opinions—as they can. They lose nothing by dallying and often gain stuff. Consultants need to learn the killer instinct necessary to know when to stop and say “send me a contract and check or don’t call me until you want to.”

(c) Victor WeFoto.com

(c) Victor WeFoto.com

“Talk is cheap” is a cliché for a reason: it doesn’t mean anything. Any talk that’s not a billable hour should be leading, rapidly, to a billable hour. At some point—a point sooner than most novices realize—it’s time to pay or go away. Money talks (and it isn’t cheap): I’ve been on numerous calls about “collaborations” and what not, when the real thing happens is through subcontracts. Show me the money, or it doesn’t exist.

Someone who wants to hire you knows relatively quickly whether they want to hire you. Anything other than “yes” means “no.” “Maybe” means no. That’s a hard thing for many of us to accept. My parents founded Seliger + Associates 20 years ago and they certainly had to learn such lessons the hard way; a lot of potential clients will dangle work that never arrives and waste a lot of valuable time and energy in the process. That means consultants have to get to “no.”

Getting to “no” is actually quite useful and a big improvement over a nebulous maybe.

Drawing a clear line can actually turn some “maybes” in “yeses.” Clients will respect you more if you eventually stop negotiating or talking unless they pay up. Because of the issues described in the paragraphs above, anyone experienced learns when to stop talking and say “money or nothing.” That means continuing to flirt without cash in hand is also a signal of being inexperienced. The line between being brusque and being direct is thin but when it doubt err on the side of directness rather than meekness.

Directness can actually be a kind of politeness. “Professional courtesy” has an adjective before “courtesy” because it’s different from regular courtesy; professional courtesy is there to indicate that there is a different way of being courteous than the conventional way, and one aspect of professional courtesy is there to avoid time wasting people.

That being said, it can be worth exploring new ventures even when those new ventures aren’t immediately remunerative. But money and contracts separate exploration from reality.

These lessons aren’t only applicable to consultant. They apply to almost any form of business and for that matter in dating: if she says “I like you but not in that way,” she means no. I think men tend to learn this faster then women do.

(c) looking4poetry

(c) looking4poetry

My friends are women, and from what I’ve observed guys in their teens have to learn to approach women and risk rejection if they’re going to get anywhere, and a lot of women wait for guys to approach them. Consequently guys who want to get anywhere have to get used to rejection in a way a lot of women don’t, and that socialization is probably part of the reason why women like Sheryl Sandberg write books like Lean In. Men figure out relatively early that they have to lean in—or suffer. Like a lot of guys I spent time suffering. I also learned, however, that with women too anything other than “yes” means “no” and that I should move on quickly. Sticking around to beg and plead only worsens the situation.

Disengagement is underrated. In many endeavors one important ingredient in success is fire and motion.

Your hours

Raymond Chen has a hilarious and quietly insightful post in “I wrote FAT on an airplane, for heaven’s sake,” which ends this way:

During the development of Windows 3.0, it was customary to have regular meetings with Bill Gates to brief him on the status of the project. At one of the reviews, the topic was performance, and Bill complained, “You guys are spending all this time with your segment tuning tinkering. I could teach a twelve-year-old to segment-tune. I want to see some real optimization, not this segment tuning nonsense. I wrote FAT on an airplane, for heaven’s sake.”

(I can’t believe I had to write this: This is a dramatization, not a courtroom transcript.)

This “I wrote FAT on an airplane” line was apparently one Bill used when he wanted to complain that what other people was doing wasn’t Real Programming. But this time, the development manager decided she’d had enough.

“Fine, Bill. We’ll set you up with a machine fully enlisted in the Windows source code, and you can help us out with some of your programming magic, why don’t you.”

One deeper point: Bill “wrote” FAT on an airplane, but in a sense he’d been learning how to write it for a decade or decades. Any complex thing anyone does is built on a wide, deep, specialized foundation. Writing works that way too—I may “write” a given post or essay or proposal in a few hours or days, but in a sense I’ve been learning how to write for at least a decade. Maybe longer. When a post is executed cleanly and well, it’s not because I have some magical ability. It’s because any time spent at the keyboard is the tip of a spear that extends back through thousands of books and hours spent practicing things I’ve done wrong or seen other people do wrong.

Everyone has or should have a skill like that, or should be developing one. What’s yours?

(Chen wrote a similar follow-up post.)

How not to choose a college: Frank Bruni ignores the really important stuff

Frank Bruni wrote an essay called “How to Choose a College” without mentioning the most important fact about college for the life outcomes of many students: debt. That’s liking writing about the Titanic and ignoring the whole iceberg thing.

In How to Win at the Sport of Business, Mark Cuban writes, “financial debt is the ultimate dream killer. Your first house, car, whatever you might want to buy, is going to be the primary reason you stop looking for what makes you the happiest.” He’s right about debt often being “the ultimate dream killer,” but he should add student loans to his roster of “whatever you might want to buy,” especially because student loans are effectively impossible to discharge through bankruptcy. I don’t think most 18 year olds really understand what tens or hundreds of thousands of dollars of debt will really mean to them five years, ten years, twenty years after they graduate.

To me, the most interesting metric a university could offer these days is the mean, median, and mode debt of students upon graduation.

Money shouldn’t be the only factor in choosing a college, but it should be a major one, unless one has uncommonly wealthy parents.

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