In my downtime while travelling, I read about two years worth of Less Wrong, a rationalist community blog that Kat Walsh introduced me to. It’s a great read, especially for people who fall into what Less Wrong co-founder Eliezer Yudkowsky hilariously and aptly labels “the atheist/libertarian/technophile/sf-fan/Silicon-Valley/programmer/early-adopter crowd” – and there are a couple of posts I think are particularly worth calling to the attention of experienced, committed Wikimedia community members.
Here are four posts I think every Wikimedian should read.
1. How to Save the World lays out a rationalist approach to making the world a better place. My favourite –and the most applicable to us– “identify a cause with lots of leverage.” In the words of the author:
It’s noble to try and save the world, but it’s ineffective and unrealistic to try and do it all on your own. So let’s start out by joining forces with an established organization who’s already working on what you care about. Seriously, unless you’re already ridiculously rich + brilliant or ludicrously influential, going solo or further fragmenting the philanthropic world by creating US-Charity#1,238,202 is almost certainly a mistake. Now that we’re all working together here, let’s keep in mind that only a few charitable organizations are truly great investments — and the vast majority just aren’t. So maximize your leverage by investing your time and money into supporting the best non-profits with the largest expected pay-offs.
2. Defecting By Accident: A Flaw Common to Analytical People lays out the author’s view that highly analytical people tend to frequently “defect by accident” – basically, they hurt their ability to advance their own agenda by alienating others with unnecessary pedantry, sarcasm, and disagreeableness. The author offers eight tips for behavioural changes to make accidental defectors more effective, and recommends three books to increase influence persuasive ability — including Robert Cialdini’s excellent Influence: The Psychology of Persuasion .
3. Why Our Kind Can’t Cooperate. A post that argues that yes, a group which can’t tolerate disagreement isn’t rational. But also that a group that tolerates only disagreement is equally irrational.
Our culture puts all the emphasis on heroic disagreement and heroic defiance, and none on heroic agreement or heroic group consensus. We signal our superior intelligence and our membership in the nonconformist community by inventing clever objections to others’ arguments. Perhaps that is why the atheist/libertarian/technophile/sf-fan/Silicon-Valley/programmer/early-adopter crowd stays marginalized, losing battles with less nonconformist factions in larger society. No, we’re not losing because we’re so superior, we’re losing because our exclusively individualist traditions sabotage our ability to cooperate.
4. Your Price For Joining. This picks up where Poul-Henning Kamp’s Why Should I Care What Color the Bikeshed Is? leaves off, arguing that “people in the atheist/libertarian/technophile/sf-fan/etcetera cluster often set their joining prices way way way too high.” In the words of the author:
I observe that people underestimate the costs of what they ask for, or perhaps just act on instinct, and set their prices way way way too high. If the nonconformist crowd ever wants to get anything done together, we need to move in the direction of joining groups and staying there at least a little more easily. Even in the face of annoyances and imperfections! Even in the face of unresponsiveness to our own better ideas!
These are themes I think about / write about, a lot: collaboration, dissent, how groups can work together productively. I worry sometimes that Wikimedians think I’m hyper-critical and don’t see the strengths of our (argumentative, lively, sometimes ungenerous) culture. So to be super-clear: no! I very much value our culture, scrappiness and all. That doesn’t mean I don’t see its limitations though, and I do think we should always be aiming to improve and make ourselves more effective. That’s what these essays are about, and that’s why I’m recommending them.
 I e-mailed Robert Cialdini once looking for advice about a particular problem I was having working well with some Wikimedia community members. Surprisingly to me, he called me within just a few minutes, and we talked for more than an hour while I walked through an airport. I wouldn’t say he was able to fully solve my problem, but it was a helpful conversation and I was amazed by his generosity.