If you really want to get to know someone, you have to do something with them that forces them to rely on who they really are. Build something frustrating together, or compete with one another. Playing poker against someone is a better exercise for getting to know them than a thousand hours of them telling you what they want you to know.

One person can care for one tree. One person can care for a hundred trees. But one hundred people can’t care for a hundred trees.

It’s just not in our nature to be emotionally invested properly in things that we can’t conceptualize as “ours.” That doesn’t have to be in a selfish, greedy ownership way. It can be in terms of responsibility.

When someone is given a partial stake in a large domain, they tend to want to carve out subdomains for themselves. If you tell a hundred people to collectively care for a hundred trees, the natural and immediate response is for them to start picking individual trees to care for. Expecting them to each care 1% for each tree is absurd. It’s not how people act.

Remember that when faced with large collectives. If you meet a company leader who expects every employee to care equally about all aspects of the company, that’s a foolish leader. People need to have domains, or they’ll make them themselves. And if they do, it will often be at the larger collective’s expense.

If you tell all one hundred people that they each need to care for one tree, and give them access to the resources to do so and organize them, you’ll have a bunch of healthy trees. If you just tell all hundred people to care for all hundred trees, they’ll still split them up, but now they’ll become competitive and zero-sum.

Design the domains and you’ll achieve the goal.

People hoard information for too long. They want a big dramatic curtain flourish and thunderous applause, but that’s not what they get. They get confusion and fear.

Do you want the meeting to run well? Then tell people what it’s about a week in advance. When you ambush them they can’t be prepared and their attention and responses are scattered. You don’t need to outflank people. They aren’t your battlefield opponents.

This is a reminder mostly to myself.

If you get one question about something you’ve explained, it’s for clarification or context. If you get two or more, you’ve explained it badly.

Not always true, of course – but true often enough to be a helpful reminder. When someone asks a question, it’s for a reason. (And never forget one of the primary rules of teaching: for each person who asks a question, ten more had the question but didn’t ask it out loud.)

When someone asks a clarifying question, that’s your cue to pivot into examples and practice. Make sure everyone actually gets it. Don’t just answer the question and move on.

A question is a gift and an olive branch. Don’t ignore it.

There’s this pithy quote from Carl Sagan: “If you wish to make an apple pie from scratch, you must first invent the universe.” I like that quote. It’s a good reminder that nothing is really “square one.” Everything builds on something else, is made from something else, was learned somewhere else. All starting points are more or less arbitrary.

Because of that, people sometimes pick bad ones.

Here’s a rule: if you’re doing something to learn, start as small as you can. If you’re doing something to get it done, start big.

If you want to learn woodworking, start with just a knife and a small stick and carve it up a little. Get a feel for how wood moves. Small, small.

If you want to have a house, start with understanding how a house fits in your life and consider location, style, scope. Big, big.

In other words, go from the inside out if you want to learn in an open-ended way so you can build on your skills and never box yourself in. Start with the outside in if you want to accomplish a specific goal so you can understand the proper context and then zero in without scope creep.

Pick the right starting point. And enjoy your pie.

Sometimes we don’t realize how bad something is until we experience a much better version. “Good” and “Bad” are relative terms, right? We look back on the way people did certain things a hundred years ago and we laugh at how horrible it was to, for example, take a long journey on a steamship or get Polio or whatever. But certain things are normalized for their context; intellectually you may be aware that travel and medicine will certainly improve over the next hundred years too, but you don’t really feel it.

In fact, the only way you think of something as good or bad is if it’s better or worse than the norms you’ve already experienced. You don’t think of air travel as inherently good or bad, it just is. But if you take an especially bumpy or late flight or have a very good hospital experience you’re aware of it – and you become aware of the standard you’re measuring that experience against, all of a sudden. A great doctor’s visit makes you say “Why can’t they all be like this?” A crappy flight makes you say “Most flights are enjoyable, why did this one fall short?”

But if you never take that horrible flight or get that great doctor’s attention, you may never know. A hundred times a day you probably experience something that could be much better or worse and you have no idea.

An upshot of this: often whatever you deliver could be much better, and you have no idea.

I mean, let’s say you make sandwiches in a cafeteria. Maybe they’re fine. They could be way better though – but you have no idea unless someone else comes in and, with the exact same ingredients, puts together a way better gourmet meal. And it’s very easy to accidentally engineer our lives so that never happens.

In many ways, I think it would be great if more people had to be like barbers. A barber can’t cut their own hair, so they have to pretty regularly interact with someone else who does what they do professionally. That’s not a bad thing, and most of us don’t do it. Most of us deliver something professionally for years or even decades without necessarily experiencing someone else delivering the same thing, but much better.

It’s worth looking out for. The bubble can be an average-making machine, and how would you know better unless you saw it?

When someone “gets lucky,” we often forget that there’s skill even in that. If you’ve ever heard the phrase, “He wouldn’t know what to do with good luck if he got it,” just remember that we have that phrase for a reason. Just because someone throws something at you doesn’t mean you can catch it.

When you’re down on your luck, it can be hard to remember. But it’s crucial – you can never stop being ready to catch a lucky break when it’s thrown to you. Opportunities ebb and flow, but when you’re in a slump it’s easy to stop looking for them. And then you miss them even when they practically drop into your lap.

You are much less complex than you think you are. Everything else is much more.

We view things we don’t know about as monoliths, simple entities with simple rules. The reality couldn’t be further from the truth. At the same time, we think of ourselves as these deep beings with rich tapestries of motivations, but we’re mostly just status-seeking machines who eat sometimes.

Anyway, it’s a good thing to keep in mind. Don’t make too many assumptions about the world until you go and look, and remember to be a bit more humble about yourself.

There is an art to speaking as one person, but listening as another. It’s hard to do; not everyone gets it. But it’s the true secret to effective communication and engaging your audience. Whether it’s a one-on-one conversation, a sales pitch, or a keynote address, it’s an opportunity.

First, let’s assume for a moment that you realize that every time you speak, it should be with purpose. (And I’m using “speak” as shorthand for all communication, not just verbal speech.) If you’re just doing it to hear yourself talk, well… mission accomplished, I suppose. Plenty of people want to just be visible. They speak for their own status. This isn’t advice for that. If that’s your goal, I’m probably not much help.

Often, people don’t explicitly begin communicating with the singular goal of hearing their own echo, but they sure act like it. They start with the question, “What do I want to talk about,” and go from there. Once they’ve picked a topic, it’s on to, “What do I have to say about this topic,” and now you’re giving a great speech or writing an amazing newsletter for an audience of exactly yourself.

Understand these truths:

1. No one else necessarily cares about what you care about.
2. No one else has the same background or foundational knowledge as you.
3. No one else “lives in your context;” the information they get affects them differently than it affects you.
4. No one else shares your assumptions about language, style, or the value of your time spent speaking versus their time spent listening.
5. All of these things are your responsibility if you want to communicate.

The first question you need to ask is: “What do I want to happen as a result of this communication?”

If you’re a professor, for example, you should have several goals when you communicate. You have a goal of students absorbing information in a useful and applicable way. You have a goal of those students being able to communicate that information back in the form of whatever assignments and tests will certify that knowledge. And you want them to engage with an active learning process that advances the field as a whole over time.

Those are reasonable goals, so now we have to run those goals through the “Truths” from above. If my goal is for students to learn about economics in a way that enables them to retain knowledge, pass tests, and ultimately do economic work, I need to first understand that they don’t automatically care about that. Even if they’ve signed up for my class, that doesn’t guarantee it! That just means they needed the credits from Econ 101, or it was the only class available, or they mistakenly thought it would be easy, or a hundred other potential reasons. Their starting motivation is probably closer to “I just need to get through this class with at least a C so I can move on.”

And here’s the first major fail point for most communicators: they dismiss that whole point. They scoff and say something like “Well if they’re not showing up eager to learn in the first place, then why should I bother?” Look, no one’s telling you that you have to take responsibility for communicating well. But if you don’t, you own the results. Sometimes those results won’t matter to you directly – maybe this professor has tenure and they truly don’t care if people learn or not. But again, if you don’t care about communicating better, I’m not helping you. If you do, keep reading.

So you have a goal, and your audience’s initial motivation doesn’t align with that goal. You want the students to truly learn, retain, and practice. They want to get through to the other side of the class with a passing grade. If you want those two goals to align, it is on you to align them.

Speak to their goal. Start with an understanding of the realities, and communicate your understanding of them without being condescending or dismissive. “Welcome everyone to Econ 101. I know many of you are already trying to figure out if it’s not too late to switch classes, and a few of you are excited about the world of economics. No matter your level of excitement when you came in, I’m going to let you know that the same standards apply to everyone. If you want the surest way to leave this class with a passing grade and no more grey hairs than when you came in, I’m going to speak to that today. One thing I will promise you: I will not give lectures that you can largely snooze through, and then selectively draw nuggets from to pass multiple-choice tests. If you want to pass, you will do real work in this room, and the quality of that work will determine your success.”

There. You’ve started to align the goals. You’ve taken their incentive and attached it firmly to the thing you want to happen. You’ve spoken to their motivations, not yours. You didn’t assume they wanted to hear (and could retain!) all your advanced knowledge of economics starting from day one.

It’s the same all over. A CEO and ground-level employees don’t care about the same things, don’t have the same background context, don’t value their time the same way. No matter the context, the rule is simple: If you want people to listen, you have to speak for them, not to them.

I think it’s easy to use “At least I tried” as an excuse to not really attempt to succeed. It seems counterintuitive, but sometimes people aren’t afraid of effort, but they’re afraid of sacrifice. So they do the former without the latter, enabling a sort of social validation of their inevitable – and predictable – failure.

If you’re going to try, make sure it’s because you really do want to succeed. If the cost is too high, that’s fine – not all juice is worth the squeeze. But then walk away.