Preparation not only has diminishing marginal returns, it has – for most people – negative returns after a certain point.

If you’re going to give a speech on Friday, you should practice. You should practice until it sounds natural and you can deliver it while paying more attention to your audience than to yourself or your words. And then you should stop.

If you practice it four thousand more times beyond that point, you’re going to make yourself worse. You’re going to get in your own head, words are going to start sounding weird, you’ll get distracted by minute changes at the actual event, etc. Someone will cough and you’ll lose your whole rhythm because it didn’t happen exactly as you rehearsed – rehearsed so many times it wore ruts in your brain.

Some things, most things, only have so much of a range of possible results anyway. If you’re giving a toast at a buddy’s retirement party, there’s no way to do that so well that they build a statue of you or so poorly that your buddy has to go back to work for five more years. I’m not saying it doesn’t matter, I’m just saying that you can reach the maximum level of “good” it can be pretty quickly.

That’s a valuable lesson in itself. Figure out the maximum positive result that’s realistic, practice until you’re good enough to hit that result, and then… go do something else. The minutes of your life are finite!

Context matters. Whether it’s linguistically, culturally, or anything else – when and where and how you say something matters. It’s the carrier for the vitamins, the vessel for the astronauts. You can’t deliver what you want without it.

And it doesn’t always translate. When I meet someone who grew up where I grew up, is around my age, and roughly my socio-economic class, I can talk to them in a weird patois of Simpsons references and 1337-speak and they’ll understand it perfectly. In a different country, to a different age group, etc.? Definitely not. And we’re not even discussing language yet.

It’s not just about adjusting the context, either. I can’t say a great idea is a “home run” to your average German and have it mean anything, but I also can’t just change that phrase to “goal” just because the German likes soccer. A goal and a home run are different, and they mean different things as an analogy. In other words, some contexts can’t carry certain information at all.

Communication is hard. But it’s even harder if you assume it’s universal. Respect the limits, and ask about context more than you assume it.

There is a very basic rule of the universe that most people seem to forget. If you remember it, your life will be much better – largely because you’ll avoid wasting a lot of effort. Here’s the rule: The easier something is, the more people will do it.

Why is that rule important? Because people often lament that something is too hard, onerous, or bothersome – and then also complain that too many people are doing it. But one of those things is balanced against the other!

The example that shows up for me most frequently is career-related: people want job applications to be easier. And sure, some of the requirements these days are ridiculous. People don’t want to fill out eight forms, record five videos, design an app, interview sixteen times, and take a blood test just to try to get a job. They want to push one button called “Apply” and be done with it!

But if you pay attention, you discover that the other side of the problem is that ten thousand people apply to every job in the first five minutes that it’s posted. And look, I know you don’t want to hear this, but… you cannot solve both of those problems at once.

Anything that makes it easier to apply to jobs will increase the number of people who do so. And the only way to decrease that number is to make the application process more involved. Those are two sides of one scale.

This has nothing to do with whether the process is even good. Forget about whether whatever hoops companies are creating actually find good candidates or filter out bad ones. We aren’t even at that problem yet. We’re just talking about the math. And the math at this stage is – unfortunately – simple.

The economics language around this is “there are no twenty-dollar bills on the sidewalk.” Think like this: if a twenty-dollar bill was on top of Mount Everest, it would stay there for a long time, because very few people could get it and it wouldn’t be worth it for anyone to try. On the other side of the spectrum, a twenty-dollar bill just laying on the sidewalk would be picked up instantly – by someone else. The easier the bill is to reach, the more people are reaching for it.

If you want getting the bill to be easy, someone else got it. If you want no one else to be competing with you for the bill, then it has to be so hard to get that it’s not worth it – even for you.

Now, I’m not a doom-and-gloom guy. I offer solutions and opportunities.

The world is complex, and in that complexity there are opportunities for improvements – maybe not to an entire system, but definitely to your own life. Don’t lament that the mountain is too hard to climb or the sidewalk is too crowded – find a third way. There may be two ten-dollar bills just down the street, you just have to play a different game.

In practical terms, remember: There is almost always someone on the other side of the problem. To go back to the job example, this is also a problem for companies. It’s a different problem, but it’s a problem. Believe it or not, companies aren’t making this hard as a punishment for you specifically. When they make their application processes difficult and weird, they’re doing it because they’re trying (and I grant you, often trying very ham-fistedly) to reduce the number of candidates to a manageable level while still retaining the best ones. Most of them fail miserably (that’s a whole other post on why), but they’re definitely looking for solutions. That’s your angle.

Don’t play rigged games. If a process is crazy difficult and five hundred people are still engaging in it, then that means the process simply can’t sustain the weight of the math. So skip the process. Email the CEO directly. Do something weird and a little difficult, but that you want to do. Cut the line, in other words. It might not work! But the main process definitely won’t.

But understand this problem when you see it. This math dilemma is a brick wall, but it’s not universal. Go around it whenever you can.

People can deploy falsehoods so easily that they have no choice but to fall back on emotional tactics if challenged. If someone says something in support of their overall position, but you think that thing is untrue, you need to be prepared sometimes to be attacked.

This is true even if you agree with the position! I agree, for instance, that we jail non-violent offenders too readily. But if someone says “Police in this country jail non-violent offenders over a million times per week for an average of fifteen years,” I would point out that this probably isn’t true. I would challenge it, ask for sources, etc. And the speaker might say something like, “What are you, in favor of the police state?! Why are you making such a big deal about this?!”

That’s an old trick. My desire to be accurate and know the truth isn’t the same as support for one position or another. How can I even know what positions to take if I don’t know the truth? That has to be upstream.

If you’re getting upset because someone wants more information, then that’s a sign that you need to reevaluate. And if someone gets mad at you for wanting it, then that’s a sign that they’re not a source of truth.

“I love talking to you. It’s like watching a TED talk.” – my daughter, age 12.

I can’t remember a better compliment from a more important source. Some days you just feel like you’re doing it right.

Happy New Month!

My goal this month is to build new independencies in my children. Their own walking patterns to school, library cards, new bikes, anything that gives them more keys to the world. It’s a great month for it. And they’re great kids.

May you be independent too!

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.