I loved this blog post, and I started to respond on Twitter but it rapidly became a blog-length thought, so here we are.

People hate simple rules and meritocracy for a lot of reasons. Some thoughts:

• By definition, the majority of people will be outworked and outperformed by a small minority. The majority don’t like the constant arms race of hard work; they’d rather use their mass influence to cap the benefits of it. That’s why 40-hour work weeks exist. Because if you can get ahead of me by working 50 hours, then I’ll have to work 50 hours to keep up, and I don’t want to. I’d rather force you to only work 40.
• Clear rules eliminate excuses, and people cling to their excuses like a security blanket. If the rules are murky and I don’t get what I want, I can cry “Injustice!” or “Bias!” and sometimes it will even work – and if it doesn’t, I can count on a lot of sympathy. Or at least I can be righteously indignant. But if the rules were simple and fair from the start, I have no excuse when I break them or fail. I think this is the biggest contributing factor.
• People think they’re more deserving than others, and also that they have good reasons for doing bad things that others do for bad reasons. Example: “I smoke marijuana because I have chronic back pain and it helps me be a more productive worker, but they smoke marijuana because they’re worthless pot heads.” People want the ability to enforce laws on others but skate themselves because they legitimately believe that’s just.
• Many rules can’t be objective. Especially in things like college admissions or tenure considerations, it’s often a matter of relative ranking rather than objective standard, which makes fair rules nearly impossible. The real standard is “better than X% of your peers,” which means it’s malleable.
• My (totally anecdotal) observation: The people who most want clear rules are the people that would excel in a meritocracy. They want clear rules because they don’t expect to need special consideration, and don’t want special consideration for someone else getting in the way of their earned success.
• Conversely to the last point, some people want clear rules so they know the bare minimum they need to do.

The ultimate example of the downside of unclear rules:

I care about being right.

I care about the truthfulness of my statements, for many reasons. I want to know that people that may take my advice find that advice genuinely helpful to them. I care about my professional reputation, and don’t want it sullied if I’m wrong too often. I care about knowledge, and the don’t like the idea of walking around with a bunch of incorrect information taking up limited space in my brain.

But there’s so much to know! So much to potentially be wrong about. How do you make sure you’re right?

There’s no certain way to always be right, but there’s definitely a method that helps improve your record: make sure you suffer a cost if you’re wrong.

Or to put it another way: get some skin in the game!

Let’s say you’re a sports fan. You’d like to make predictions about sports, and you’d like those predictions to be right. If that’s the case, you should bet. Bet money, and bet a decent amount. If you consistently put money on your own decisions, you’ll work a lot harder to be right than if you were just making predictions with no cost attached to them. For instance, if you’re an Eagles fan, you might be tempted to say “The Birds are going all the way this year! I’m 100% sure of it!” But you’re really just signaling loyalty to your team; the decision comes from hope and love, not from actual information – even if in the heat of the moment you truly believe what you say. Now if someone responded to that statement with “If you’re 100% sure, how about putting your money where your mouth is? Want to bet?” Suddenly you’re no longer 100% sure, and before you put real money on it, you might take some time to do a little real research.

We’re flawed beings. We’re not computers, and we’re subject to all sorts of biases. Those biases are usually the reasons we’re wrong about stuff. So the way to be right more often is to give our brains a reason to put those biases aside. Put simply, we’re biased because being biased is often either free or has costs we don’t see and thus don’t respond to. If we put the cost front and center, suddenly we’ll be less biased.

There are many, many ways to bet, to get skin in the game. The traditional “bet” is only one of them. If you find yourself saying, “that company is going to crash and burn, mark my words,” then there’s a way to make money from that! Get that ball rolling and suddenly you have a much higher incentive to be guided by actual information instead of hunches. There are companies that will allow you to bet on yourself losing weight – you give them money and a weight loss goal. If you succeed you get extra money back, but if you fail you lose your stake.

This extends to the political realm, too. Politics is mostly about people with no skin in the game and no incentive to be right trying to impose rules and regulations on people that do. Industry regulations always crack me up, being written by people who have never even used the product or service in question (let alone provided it) trying to tell an entire market what’s best for them.

One of the reasons I talk confidently about things like career coaching is that I have skin in the game. That’s my profession, and if I’m wrong about it I lose income and career potential. I have an incentive to be right, and that motivates me to constantly learn, improve, and be careful with my advice. It might not make you right about everything, but people with skin in the game are right more often than people without.

If you don’t believe me – want to bet?

Companies love a yes man.

I don’t mean a spineless sycophant, though of course some organizations and their leaders like those, too. I just mean that in general, optimism tends to be rewarded. And with good reason! Optimists are the risk-takers, the innovators, the ones that make the world move.

But there’s absolutely a role for informed pessimism in some cases. Sometimes ideas are just bad. The closer you are to something, the harder it can be to see the bad ideas. Unfortunately, that can sometimes mean that the leader of a project or even head of a company can be the person most blind to the realities of a particular project.

Good leaders try to avoid this problem by actively encouraging their teams to give honest feedback, and not to just tell the leader what they want to hear. But even good leaders that do this run into a problem: even if they want honest feedback, people can be afraid to give it for a variety of reasons.

First, no one wants to be unpopular. If everyone is excited about a new initiative, being the one voice saying “I think our budget projections are way too conservative and this is going to cost us 3x as much as we think, thus rending the project a huge loss instead of a modest win” isn’t winning any popularity contests. If the project moves forward anyway and the pessimist was right, he’ll win no extra friends saying “I told you so,” and people might even blame the pessimist, accusing him of anything from not being invested enough to outright sabotage. If the project goes forward anyway and the pessimist was wrong, he’ll lose credibility and social capital. If the project doesn’t move forward due to his opinion, people will never be sure if the project might not have succeeded, and many will think he crushed a good idea. In short, there’s no hero’s path for the pessimist, even if he’s totally correct.

Smart people know that, and often keep their mouths shut even when the leader is insistent that they want honest feedback. If you’re a leader, you don’t want your smart people keeping their mouths shut! So how do you make it safe for them to give you their specialized knowledge without it possibly hurting the social capital they’ve built in their team?

A research psychologist named Gary Klein invented a spectacular technique for overcoming this problem, and if you’re a team, project, or company leader this is something you should definitely have in your toolbox. It’s called the “Pre-Mortem.”

A “post-mortem” is an examination of a dead body to determine the cause of death, and from that the Pre-mortem gets its name; it’s an examination to determine how a project is going to die. It works like this: When a major decision hasn’t yet been made but is near to the deadline for an answer, you get the team together – everyone who has or might have valuable input. You say, “Okay everyone. We’re nearing the time where we have to make a firm call on going ahead with Project X. Let’s assume we say yes, and now it’s one year from today. I want everyone to start with the assumption that Project X was an unmitigated disaster. Went down in flames. In front of you is a piece of paper – write down the history of that disaster. Explain how it all went wrong.”

This solves all of the problems detailed above. First, it makes everyone the voice of opposition instead of a lone pessimist or small group, so no one loses social capital for stating their opinion. Second, because it was specifically requested, the dissent can’t be seen as any level of disloyalty. It gets your smart people talking instead of keeping quiet, and best of all it puts them all in a room together to brainstorm ideas.

The end result: if there are any problems with the upcoming project that anyone can see, you’ll know about them! It doesn’t even have to spell doom for the project; in many cases, catching and talking about these problems early is exactly the thing that saves the project, because they can be corrected for before they’re an issue. And it builds great trust with your team – it’s one thing to say you want honest feedback, but too many people have had leaders that said that with one side of their mouth, and then scolded an employee for disloyalty with the other side.

It’s good to be an optimist. But when it comes time for really big decisions, take a little time to listen to the pessimists, and let them stress-test your ideas. If you surround yourself with smart people but don’t create an environment where they can disagree with you, you’re wasting them.

I was once advising a small-business client on her pricing models. She had purchased the business from someone else, and wanted to revisit prices that hadn’t been touched in some time.

As part of the adjustment, she wanted to eliminate a product line entirely. It was already a product they didn’t make in-house, but rather farmed out and resold when ordered. She didn’t think it was worth the hassle.

“At that price,” I said.

She asked what I meant. “You don’t think it’s worth the hassle at that price. So raise the price; don’t eliminate the product. If you eliminate the product you never make money from that customer demo. If you just raise the price to a level where you’d be happy to do it, you might make something.”

She said at the price point she’d be happy with, no one would buy. But so what? No one will buy if you don’t offer it at all either, and since you farm this product out it doesn’t cost you anything to offer it; there’s no stock or overhead. Plus just offering it can have some fringe benefits like showing up in Google searches for that item, etc.

The lesson is: it’s better to set a price than to say no. Prices say you’re open for business, and that’s ultimately the message businesses want to send.

If you’re not familiar with it, Social Desirability Bias is the tendency for people to slightly exaggerate or outright lie in the direction of socially-acceptable answers. For instance, if you talk to your mother once a month, and someone asks how often you call your mom, you might fudge a little and say “every week” or “a few times a month.” You’re very unlikely to lie in the other direction – you’re not likely to lie and say “only twice a year,” because why would you?

Social Desirability Bias explains a LOT of stuff, by the way. It’s definitely one of those things where once you learn about it, you see it everywhere. One version of it that almost everyone is aware of is the “follow the money” thought process, where we sort of inherently distrust people that stand to make money if we believe them. Think of TV salesmen on infomercials. We take what they say with a grain of salt, because there’s an obvious incentive for them to lie in a particular direction.

The reverse of that, of course, is that you can be much more certain that someone is telling the truth if they’re saying something you don’t want to hear, or that damages their reputation in some way. If I tell you that the product I’m selling is bad for you and you shouldn’t buy it, you have an easier time trusting that because I have no obvious incentive to lie about that.

I think about SDB a lot. As someone who communicates for a living, who is sort of geeky about politics, and who reads lots of economics and social science books for fun, I end up thinking about it almost daily.

There’s a big negative side effect to that. I’m overly critical of the things I say, no matter how sincere.

For instance, a very true fact about myself (almost core to my personality) is that I get enormous pleasure out of watching other people succeed. Other people’s thrill at their accomplishments is really contagious to me, and it improves by a factor of ten when I was involved. Seeing someone I coached accomplish the thing I was coaching them on might be my favorite thing in the world.

But if that wasn’t true, it would still be socially desirable for me to say it. If I said “I hate other people’s success, and I want everyone else to fail,” few people would think I was lying. They would think I was a jerk, but an honest jerk.

But when I say “I love other people’s success,” it sounds hollow to me. No matter how true I know it is, I know that talk is cheap. You shouldn’t just believe me because I say it.

But here’s the positive: That gives me a huge bias for action. How do you counter someone else’s Social Desirability Bias? You follow their actions, not their words. Someone who talks a lot about the plight of the homeless but never donates a dollar isn’t being sincere. But if they donate a huge chunk of their income to causes they believe will help, then you can be more sure they mean what they say.

So I don’t just say I love other people’s success. I help them accomplish it. I am terrified of becoming a hypocrite, and that motivates me to make sure my deeds match my words. I am certain I will fall short at times, but it won’t ever be for lack of sincerity in my attempt.

Do you want more money?

Let’s assume you said “yes,” because most people would. You might be that one Buddhist monk who lives on a mountaintop and doesn’t, but then how are you reading this blog?

If I gave you a bunch of money, what would you do with it? Would you put it in stacks on your table and stare at it lovingly? Would you roll around in it? Would you eat it? Probably not, I’m guessing. I’m guessing you’d spend it. (Or you’d save or invest it, but for this thought experiment that can count as “spending,” in that you’d do something with it other than enjoying the actual physical bank notes.)

Okay, so you didn’t really want money. You wanted stuff – a new car, a different outfit, a fancy toy or a night out or a vacation or whatever. Even if you save/invest it, you don’t want a savings or investment account for their own sake; you have them because you want a new car, different outfit, vacation or whatever, but you want more of them later as opposed to fewer of them now.

So that’s “one why deeper.” You say you want money. I ask why. You say “because I want a new car.”

But we can go another why deeper. “Why do you want a new car?”

Maybe as we go deeper and deeper, you discover that you want a new car because your older brother loved cars, and he was your hero growing up, and he passed away a few years ago and getting a fast car lets you remember him and know he’d be proud of you for all you accomplished. (And if you go even deeper, you’ll realize that your brother would be proud of you no matter what, so do what makes you happy, not what he would have liked.)

Maybe as you go deeper and deeper, you discover that you want a new car because the kind of potential mates you find attractive are the kind that like fast, fancy muscle cars, and you want to use it as an ice-breaker to meet those potential mates. (And if you go even deeper, maybe you realize that what you really want is just a mate that thinks you’re cool and builds up your self-esteem, and there are lots of ways to pursue that goal.)

Maybe as you go deeper and deeper, you realize that you’re perfectly happy with your 2008 Toyota Corolla but you’ve been caught up in the constant race of keeping up with the Joneses for so long that you’ve started to judge yourself based on how others perceive you, and what you’d really rather do with that money is visit your mom in Jacksonville. (And if you go even deeper, maybe you realize there are a lot of things you spend money on that you’d rather abandon in favor of more family time.)

All dollars are not the same. Things and experiences make us happy and give our lives fulfillment, and to earn them we do things that are valuable to others. I make your life better, and in exchange I get the means to make my own life better. That’s the core concept of all of society. No matter how we organize the point system and exchange rates, ultimately society is built on this concept – give a little, get a little.

But if you give to the world, and then when it’s your turn to get something you pick things that don’t actually make you happy… what are you doing?

It’s worth going “one why deeper” until you get to the bottom, because that’s where you see who you really are. Most of us don’t. All of us should.

Momentum is very powerful. Building up steam.

Have you ever had to push something very heavy, maybe a piece of furniture or something, and you had that moment where you had to “just get it started?” That initial first push to get it moving that took a lot of effort, but then it seemed easier to keep going?

Guess what? It WAS easier! One of my favorite “learning memories” was when I learned about Static Friction versus Kinetic Friction. If you don’t know, here’s the quick-and-dirty: Static Friction is the force that acts against a stationary object, making it hard to move. Kinetic Friction is the force that against against a moving object, making it hard to move. But Kinetic Friction is weaker than Static Friction! So it’s not just in your head – it actually does require more force to start pushing that couch than it does to keep it in motion once you’ve got it started.

There’s a huge life lesson in there. It can be hard to start stuff, but it’s easier to continue stuff. The problem most people face is that they make it really difficult for themselves to start stuff.

Last year I lost 40 pounds. I’ve kept it off, too, and I’m pretty proud of myself. But I’d been trying for a long time and failing. What did I change? I stopped trying to lose 40 pounds. Instead, I decided to lose 1 pound, in one week.

One pound is SO EASY to lose. Skip one dessert and take the stairs instead of the elevator for a week and you’ll lose a pound. Drink water. But once you lose that pound, you’re so happy! And you’re also saying, “wow, that was super easy. I can do that again.” So I lost another pound. I never, ever let myself think about the total weight I wanted to lose. I just said, “one pound, each week.” And I plateaued after around 40 pounds of loss, and I feel great.

When you build up these great big barriers for yourself, you increase your Static Friction. It’s hard to lose 40 pounds, but it’s easy to lose 1. And once you lose one, now you don’t have to “start” losing weight any more. You just keep losing weight, which is way easier. Try running. Put on your sneakers and say, “I’m going to run to the end of my driveway.” That’s a super short goal, it’s not daunting at all. But here’s what will happen: You’ll run to the end of your driveway, and you won’t want to stop. You’ll keep going until you want to stop, and that will be fine, because you already demolished your goal.

Are you feeling overwhelmed by a huge to-do list? Take just one item on it, and say “I’m just going to do this one thing today. That’s it, just the one.” Then you’ll do it, feel great about yourself, and you’ll just say “Weeeeellll, okay I can do one more.” And then before you know it the whole list will be gone. Instead of climbing out of a hole just to get to ground level, you’ll be triumphantly scaling a mountain to see to the beautiful horizon.

Get that momentum going!

I just had a wonderful conversation with someone who I used to career coach. She’s learning about podcasting, and her reasons are spectacular. She’s crushing it at her job, but she’s an ambitious person, hungry for new skills beyond the ones she’s practicing there. She wants to find more ways to be valuable every day, so she’s hitting that goal in two ways – first, by learning about podcasting to begin with, and second with the subject of that podcast. Her idea is to interview someone successful every day, and ask them how they become more valuable every day.

Anyone with half of her ambition and drive will do very well in this world. That’s why I was so thrilled to talk to her. She’s part of The River.

What is The River? Imagine a drop of water hitting you. Does it do much to change your momentum, to move you in any particular direction? Despite the fact that in a very technical sense it does a little, you’d never notice it. Its impact would be negligible. No matter what direction that drop came from, your path wouldn’t change a bit.

But step into the river rapids, and the story is quite different. Whichever direction that river is going, you’re going that way too. Maybe you can fight the current, but it will always be pushing you with tremendous force. Maybe the current will be so strong you can’t resist it at all.

So you should only step in rivers that are pushing in the direction you want to go!

Individual people you interact with are like those drops of water. By themselves, none of them move you much. But all of the people you interact with together – that’s The River. If you surround yourself with people going in a negative direction, making bad or irresponsible choices, then that’s where your River will push you. You can fight it, but even if your own personal goals lay in a positive direction, you’re swimming upstream. But if you surround yourself with people going the way you want to go, if you surround yourself with ambitious, positive and curious people, then your River can push you to wondrous places.

Just as even a single drop of water raises the sea, each person contributes to the flow of The River. Make sure you’re choosing people that push the flow in the direction you want.

This is one of the most brilliant pieces of comedy I’ve ever seen. (NSFW: Language)