The Opposite of Loyalty is the Pick-Up Artist

The first rule of of negotiation that whoever cares less wins. Need proof? OK, Walk into a car dealership. Haggle. Say the price is too high. Then start to to walk off the lot. Watch them start to make concessions instantly. You might wind up with the deal of the century. They don’t want to lose you. Asking for a raise at your job? Be ready to go to a competitor if they don’t pay what you’re worth.

In short, the rule is to be non-commital in every situation, and to always have multiple options. It’s a maxim with broad applicability in many areas of business and in life. But like any good tool, it does more harm than good if you wield it wrong. As they say, when all you have is a hammer, everything looks like a nail.

Any good investor uses this principle all the time; it’s called diversification. Rather than just buy one stock or one property, you buy an assortment of investments with various levels of risk, because even though the market is uncertain, it’s much less likely for every one of them to turn own poorly than it is for just one to underperform. You protect yourself by relying on probability; some of your picks might be losers, but not all of them will be losers.

Apply it to your career. If you don’t get too hung up on one particular field or dream job or company, and instead guide yourself in the general direction of the things that excite you, you’re less likely to be devastated when something goes wrong, when you don’t get that promotion, or whatever. You will be able to take your skills to the firm down the street and try again, maybe in a slightly different way that benefits from your prior experience.

Silicon Valley startup types love to talk about “pivoting.” This buzzword is just a fancy way of saying that they are adaptable. And adaptability comes from having multiple options. It means that your startup might discover that the people who you thought were your customers aren’t your real customers, and oh hey, there’s this market over here that you totally overlooked. So you shift your business to address their needs. The moral is that you can’t get too hung up on the original idea.

At it’s core, this is about realism. It’s about being impersonal and realizing that the world behaves how the world behaves, not how you want it to. So if a situation sucks or isn’t working, you have to be ready to walk away and try something else.

Nassim Nicholas Taleb calls this the approach of the “rational flâneur”, a concept that he elevates it to a life philosophy. The flâneur is someone who does not have a fixed path. So unlike a tourist with an itinerary, the flâneur makes a decision at every step to revise his schedule based on new information. He plans, but he is not beholden to a plan. He keep the good and ditches the bad, because it’s a big wide world and there’s no use getting bogged down in any one part of it.

But as powerful as this approach is, you run into trouble if you apply it to broadly. Take pick-up community for example, the self-proclaimed “pick up artists (PUAs)” that were both inspired by and documented in Neil Strauss’s modern classic “The Game.” Here is a group that applies the flaneur approch to dating. On the whole, it works extremely well— it’s an approach implicit in the old adage “there are plenty of fish in the sea.” The premise is that men on the prowl never commit to a single female (the dreaded psychological hang-up called “one-itis”), and so if they are rejected, they are stregically and emotionally free to pursue others with equal zeal.

This is the way of the flaneur— keeping everthing at arm’s length lest one become too commited to a particular outcome. It’s indistinguishable from what might commonly be called “opportunism” or “being a dick.”

In his book, Strauss openly admits that despite the success he had with women by following the pick-up methodology, he felt something was missing. He realized that his relationships lacked depth. Essentially, he reached the limits of flaneur-style living, and realized that although it may be a sound economic principle, it’s just not wise to apply the same logic to personal relationships.

In fact Taleb cautions us against the same thing. In Antifragile, he writes: “The opposite of opportunism in human relations is loyal, a noble sentiment— but one that needs to be invested in the right places, that is, in human relations and moral commitments.”

I fear that too many men of my generation to not see this distinction. Too many of us aspire to be pick-up artists or men’s rights activists. There are too many men who do not realize that there is wide gulf between being picky with a job or making smart investments and choosing your life partner. It’s OK to console yourself after a breakup by realizing that there that there are plenty of fish in the sea. But it’s another thing entirely to accept it so fully that you are unable to express loyalty and commitment to another human being because you are deliberately being noncommital.

Commitment to a particular objective is dangerous, unless that objective is a human being. Then everything changes. I always try to remind myself: In negotiation, whoever cares less wins. In love and in friendship, it’s exactly the opposite.