Sometimes you tell someone something not to inform or convince them, but rather to demonstrate how they can inform or convince someone else.

A wonderful mentor I had back in my sales days explained it like this: sometimes you’re selling something to someone who really, really wants it – imagine selling a sports car to a guy who is very much in favor of getting one. Selling to him is easy – but his wife, who is not with him, is very much opposed to him buying a sports car. You can sell to him all you want, but he’s not going to make the final decision without talking to her. So the real sale is going to be made that night, in that couple’s living room, and you won’t be there.

So you spend the next 15 minutes talking to the guy anyway, going through all the great features of the car – and if you’re smart, you tell him about all the great features that his wife might like. You’re doing this not because he needs to be closed, but to give him the tools to convince his wife when he gets home.

Like any attempt at convincing or transferring information, this doesn’t always work, of course. But it will never work if you’re not aware that’s what you’re doing. Explaining to someone how to work a machine they’re unfamiliar with is a very different task than explaining to someone how to explain to someone how to work said machine. You need to anticipate a different set of difficulties and prepare for different mistakes. You need to do more than deliver your message; you need to grant that message to the other person in a way that will transfer.

A lot of what people think of you won’t just be based on the information they get, but on how they get that information.

If you’ve ever been advised to “get ahead of it,” you know what I mean. Sometimes something bad happens, and sometimes it’s your fault. It happens; we’re not perfect. When the error is yours, it’s always better to get ahead of it. Someone always finds out, and the best way for them to find out is from you.

If they find out from you, then you not only get to control the narrative itself, making sure that no one is misstating the events or that the rumor mill isn’t grinding you to dust, but you also get to show people that you own it. Transparency matters in people’s reactions.

It’s a rough band-aid to rip off, but you just have to. The longer it takes, the worse it gets. Get ahead of it.

How much you strive to impress someone should be directly proportional to how much you admire them and their importance in your life. Your close friends, your family, your valued mentors – you absolutely should try to impress them! That’s part of their role in your life. If they’re noble people, then they’ll be impressed by nobility, and that will cause you to strive for good qualities and noble deeds.

That means don’t waste time trying to impress people you don’t admire, even if it feels like in the short term you’ll get something. The cost will be high as you pursue foul works to impress foul people. And certainly don’t waste time trying to impress people who can’t even observe you – don’t think “oh, my favorite celebrity would love this!” They won’t.

Want a good compass for life? Do good deeds, and watch who becomes impressed. Grow closer with them. And then impress them more. The virtuous cycle will carry you far.

I never worry about people not taking my advice. I worry about it when they do.

People ignoring you is the default state. Eight billion people spend their whole lives not listening to me, and only a handful of people might. But to those handful, I owe a great debt of responsibility. On the off chance that someone might take my advice, I do my best to give it carefully and thoughtfully.

There are certain phrases and conversations that have stuck with me across decades. I don’t think their speakers necessarily intended that when they spoke those words to me, but here they are. You never know which moment will have just the right shape and just the right trajectory to stick in someone’s mind forever.

Speak less, speak more carefully. Think more, and think more carefully, too. You never know who depends on it.

The sense of being confused is the sense of not knowing what the rules are to the game you’re playing. We trust that sense too much. Just because you don’t know the rules doesn’t mean there are rules to know!

You might be confused because you expect rules when there aren’t any. You might just be in a very fluid situation or have a very nebulous goal.

So lean into it! When you’re confused, that might mean that there are many ways to solve your problem. If you’ve given an honest effort to learn the rules and you can’t seem to figure them out, entertain the notion that there simply aren’t any. And if there are no rules, you can’t break them – so get the job done your way and gather information after.

Be careful not to accidentally back yourself into “hard mode” too often. It’s good to challenge yourself, and it’s good to try to overcome your flaws. But it’s also fine to acknowledge that certain paths through life are just harder than you need to deal with and don’t lead anywhere better.

Every once in a while, it’s good to take the “road less taken” just to prove to yourself that you can when you need to. But I promise you, there’s no merit badge for taking that harder path every single time if it’s just making you miserable. You’re allowed to stroll on easy mode when the cheerier path takes you to the same clearing.

Every experience in your past colors how you perceive similar scenarios in the future. This is pretty hard-wired into our instincts by evolution, and it generally served a good purpose in that context. If you narrowly escaped being eaten by a bear once, then anything that sounds like a bear in the future should frighten you.

Of course, that same evolutionary wiring leads us to all sorts of unpleasant biases and prejudices in the modern world, which is one of the reasons we have to be aware of our own wiring – because it isn’t always helpful. Sometimes, in fact, it’s downright detrimental. In our ancient past, if someone from a neighboring tribe attacked you or stole from you, the safest route was to never trust anyone from that tribe again, because the risk of being “got” was so high and tribes were much more mono-cultural. Now, one person wronging you doesn’t affect the odds of a similar-looking person doing the same at all, but the evolutionary wiring is still there – and that’s one of the reasons people with lower self-awareness become tricked into prejudice by their own brains.

You are susceptible to this. And so are other people.

It’s important to be self-aware as a way of rising above our own baser natures. Our instincts tell us to do a lot of things that we absolutely should not do – morally or practically. We need to build habits and structures for ourselves to keep us away from those instincts that we’ve deemed counter-productive to a healthy and moral way of life.

Consider: our instincts tell us to claim resources that are within our reach. Look at any young child – they’ll grab any food they can get their hands on, plus any object they want. It’s in our nature, but “ownership” and “permission” are concepts we have to develop and learn. As an adult, if you see someone’s unattended, delicious-looking sandwich, you still have the instinct to grab it and eat it. You just don’t (hopefully), because you’ve learned and/or developed a moral framework that supersedes the instinct.

Now think about this: we don’t just have existing instincts to contend with. We also have our natural inclination to take every past experience and make it a general fact about the world. And this will hurt you in two ways.

First, this will just make you wrong about stuff. Mostly about people. You’ll attribute aspects to people you’ve never met based on people you have met. The people you’ve met in the past and the people you’re interacting with now don’t even have to have anything in common except the nature of their interaction with your life! Want an example? Imagine a cashier at a local fast food place was rude to you. The next time you go into a different location of that same chain, some part of you will assume the cashier there is going to be rude. You’ll brace for it, you might even treat them poorly to begin with in your interaction (and oh, that’s even worse – because then it might become a self-fulfilling prophecy and you’ll be even more certain that you’ve figured out some general case about the world). But the first cashier had nothing to do with the second!

People don’t even generalize in the same way. Some people encounter one rude cashier and think “all cashiers are rude.” Others think “all people of that age category are rude.” And so on. None of them are right. But it’s so, so easy to fall into that trap. Once you declare a general case in your mind, confirmation bias takes over and you’ll never run out of reinforcing data points if you want to find them. If a BMW cuts you off and you decide “BMW drivers are all jerks,” then you’ll never run out of occasions in the future where a BMW does something else you don’t like – and you’ll never notice all the BMWs that drive perfectly well.

So letting the experience from any one person spill over into your expectations about encounters with other people will almost always result in you harming yourself. The harm, of course, is in lost opportunities. This sort of bias is almost always negative (consider that a pleasant cashier has probably never made you think ‘all cashiers are pleasant;’ positive traits tend to be attributed to the individual unless they’re already part of a confirmation bias pattern you’ve established prior), so it almost always results in you creating diminished interpersonal interactions before they’ve had the chance to take their own shape.

In our modern lives, the gains from positive interpersonal relationships far outweigh the negative risks from bad ones. You are much safer in your modern life than our ancient ancestors. They may have had little to gain from making a friend from another tribe, and an incredible amount to lose in the zero-sum, resource-poor environment in which they lived while developing these instincts. You, on the other hand, have relatively little to fear from a cashier at a local store, and potentially a lot of upside from making that friend.

Okay, so that’s the first way this hurts you. Here’s the second: sometimes you are the person someone else is unfairly biased about. And this is the situation where you can have the most impact if you know what you’re dealing with.

• “My girlfriend is constantly nagging me to know exactly where I am at all times, to give her my phone every time I see her, and to send me pictures of myself whenever I’m out without her. I hate being treated like a criminal; we’ve barely been dating a few months and I’ve done absolutely nothing to deserve this treatment.“
• “I’ve only just been promoted to manager of this team, but they already seem to hate me. They’re constantly going over my head to confirm my instructions with my boss, they don’t offer any input even when I ask their opinions, and they won’t do anything without me expressly giving them permission. What have I done to make them not trust me already?“
• “I took over the Johnson account, and the client treats me like I’m an idiot. He emails me, then texts me to make sure I got the email, and then wants to call me to discuss the contents of the email. And that’s for every little change! He won’t just give me the full scope and let me work. We’ve only been working together a few days, why does he already think I’m stupid?“

Do any of these sound familiar? Have you encountered situations like one or more of these in your own life? They’re frustrating. You feel like the other person has formed this very unfair, quick opinion of you – and you can’t figure out why. Many people do what these quotes indicate: they blame themselves and try to figure out what they’ve done wrong to offend the other person.

The answer, quite often, is nothing. Talk to anyone who’s ever rescued a foster dog: sometimes that dog is terrified. You can be the sweetest, kindest pet owner in the world, but the last owner wasn’t. The last owner might have done some pretty terrible things – that’s why the dog is being fostered in the first place. It’s not that the dog has a reason to be afraid of you, specifically. It’s that the dog is instinctually terrified of entities that are similar – or even in a similar position – to the last entity that hurt it.

Your girlfriend might not be mistrustful of you, but maybe she was cheated on by her last partner and hasn’t yet separated that baggage from the general category of “boyfriends.” Maybe the last manager of your new team was a micro-manager and manipulator and your team has developed habits to protect them from that behavior. Maybe the last account manager for the Johnson client was an idiot who needed things explained several times and the client started doing things that way to ensure results.

In most scenarios, you aren’t the first “whatever you are” to the other person. You won’t always be someone else’s first significant other, first manager, first account rep, first customer, or first fan. Whatever you are to them, they’ve probably had at least one other – and you’re inheriting the baggage from that relationship.

As soon as you acknowledge that, it breaks an enormous barrier. If you treat the other person’s behavior as if they were basing it on your behavior, you’re going to spiral into a very negative pattern. For example: You think your girlfriend is reacting to something you’ve done, but since you haven’t done anything to deserve this reaction, you naturally assume she’s overreacting or being unreasonable. This leads you to invalidate or diminish her feelings as you dismiss the concerns leading to her behavior. And now, of course, she has even more reason to react the way she does and even more validation that her general opinion of “men” or “boyfriends” as a category is justified.

If instead, you acknowledge that from her perspective she has what seems like a perfectly reasonable mental framework for interacting with the category of “boyfriends,” then you can interact with that framework in a respectful way. You can accept that she’s carrying baggage from real past harm, and you can assure her that you won’t harm her in that way without invalidating her past experiences. You can separate yourself from her experience, in other words, without invalidating it. You can ask her to share about what hurt her, and agree that it was bad and her pain was real. You can avoid blaming her for “putting that on you,” and instead give her the space to not.

Is this fair? Should you have to carry the responsibility of doing this? Who cares? Trying to constantly seek fairness will make you deeply unhappy, and instead of worrying about who’s to blame and therefore who’s responsibility it should be, you should just take the fastest, most magnanimous route to happiness. (Note from Johnny: Huh, it turns out I write about that particular theme a lot.)

If you want other people to not take their own negative baggage and foist it upon their relationship with you, you have to acknowledge that baggage exists. You can’t act like you’re the first person they’ve ever met and expect that they’re going to base all their interactions with you solely on a calm, calculated evaluation of your behavior and your behavior alone. You don’t even do that with others, even when you’re aware of it and you try, because you’re a human and humans are imperfect machines. So have some grace about others who probably haven’t even read this insightful blog post and thus don’t know what you know (but go ahead and share it with them if it will help you create some shared language to help you talk about the topic).

If you’re at the beginning of a new interpersonal relationship with an individual or group that is likely to last into the foreseeable future, it is incredibly good practice to get this out in the open right away. Share with each other your experiences, positive and negative, with past people in similar roles in your life. Talk about the way they might color your perceptions of each other, and acknowledge both that those experiences were valid and that bringing that baggage forward instinctively is understandable. That’s the most direct way to overcome those instincts and to leave the baggage in the past where it belongs.

Imagine gathering together one hundred people who all wanted to build a bridge across a canyon. They’ve never met before, and the only thing they know about one another is that they share this goal. You drop them off at the edge of the canyon and leave, leaving behind no instructions or directions, but plenty of tools and resources.

What do you think will happen?

I’ll tell you what won’t happen – they won’t flawlessly and immediately get to work. This isn’t a hive of bees or a colony of ants with a prior, established social order. These are one hundred humans, and before one hundred humans can work together on anything, someone will have to establish order.

And with one hundred humans, that’s no small feat.

Even if you imagine that the desire to build the bridge is so strong in every individual that they’re willing to stick it out, it still might take weeks before the group has organized into anything cohesive enough to begin. Who’s in charge? Who will do what? Who will decide those things? How can they change? How will the rewards be split?

If you repeated this experiment one hundred times, with one hundred different groups, the final quality of each bridge would be far, far more dependent on how each group handled this initial organization than it would be on, for example, the actual engineering abilities of the individuals in the group.

That skill – the ability to organize people – is incredibly rare. And most people don’t even understand it, let alone have it. People use the phrase “herding cats,” but that always makes me laugh. Herding cats is way easier. Most cats share the same motivations, for one. And for two, most cats are smaller than you, and can’t object to being tricked or forced. If I want a hundred cats to go into a barn, I could manage that far easier than I could manage to get a hundred humans to build that barn.

This is one of those things that most people simply can’t believe is that difficult until they’ve tried it and failed miserably. It’s one of those tasks that looks so much easier on paper, because on paper all the different people are profiles and you’re just trying to solve an organizational puzzle. That’s tricky enough, but it’s solvable. But then once you start to put your fancy little org chart into practice and people just… don’t do it, then you realize all the different layers of communication, buy-in, negotiation, motivation, conflict resolution, and rapport you need to manage to be even mildly successful.

People are so harsh on “bosses” – managers are seen as this parasite class of people that contribute nothing but steal credit and value. And look, sure, some are really bad. Some are a hindrance and are doing more harm than good. But that’s just further demonstration of how hard it is to be good at this.

The next time you see something impressive get done by any group of people larger than about five, just take a moment and remember how incredibly impressive it is that anyone managed to organize that effort. Maybe one person out of a hundred is good at it – if that.

If you’ve been going back to the same well for a long time, it can be a bit of a shock when it goes dry. But no well lasts forever; things change.

It’s natural in life that the shape of the world sometimes shifts in a way that isn’t convenient for you. Sometimes you have to dig a new well. But that will be a joyous day – the new water is always sweeter than the last dregs you drank when you were fighting off the idea that you had to change.

Here is a good habit: When you are in someone else’s home, do more than just obey their rules. Observe their customs.

Participate in their way of life. Follow them without picking everything apart; just soak it in, especially if it’s your first visit. And “home” here can mean a lot more than just someone’s house. It can be any rabbit hole into which you’ve followed them – if they are more native to the space than you, then let yourself be led.

We carve such deep grooves and ruts into our own lives that very few things can shake us out of them. One little trick is to just step over into someone else’s groove. Something that is common for another can be wondrous for you.