The point of thinking well isn’t to think endlessly. It’s to prepare a fertile ground in which good things can be planted. But once planted, those crops must be tended – which requires a very different kind of mental discipline.

Thinking well is about finding concepts with value. Once you’ve found one, the goal shifts – you must now implement that concept. You must turn it into action in your life, or else the thinking part didn’t yield any benefit. You have to close the trap around it.

Converting concept into action can mean a lot of things, but if you aren’t taking some action then you’re just thinking for the sake of thinking. That isn’t the point. Building a better mousetrap has no point if it never catches mice.

The more complex your information ecosystem starts to become, the more you start to need a central place that all of that information leads to. But this can create some significant friction!

It’s an old trope; the physical “inbox” sitting on a desk with stratified layers of paper, towering enormously over the desk, with the bottom third dating back decades. It’s a cliche for a reason – when you bottleneck all of your information into a central place, it slows the flow of that information down.

A command center has to be more than just the information graveyard, a place where it goes to die. It has to be a processing center that, at minimum, acts on information at the same speed it receives it.

This alone takes time. If you’re collecting information from multiple spheres of your life, it’s not going to be an instantaneous process to move it where it needs to be in order to take appropriate action. There are plenty of ways to do this sort of thing and I won’t pretend my way is the best for everyone. But the most elemental mistake you can make is assuming that your system doesn’t need its own slot in your schedule for maintainence. It does.

I believe in experimental experiences. In other words, do things to try things! New things are good. At a certain point, you’re good at all the stuff you already do.

But because I like to think about my own experiences, I like to mull over how I know if I enjoyed something or not.

Good company makes things very enjoyable. But to that extent, if I’m with good company, am I biased towards the action itself? Let’s say I’d never ridden a roller coaster before. I decide to ride one with some of my dearest and most hilarious loved ones. We have a wonderful time. Later, it would be reasonable for me to ask if I actually enjoyed riding roller coasters!

The same is true in reverse, of course. I love camping, but if I had to go a whole weekend with someone I found really unbearable, that might sour the experience for me. And if it were the first time I went, I might judge camping a bit too harshly.

Good company is just one confounding factor – everything from my hydration level to how much sleep I’ve gotten recently can affect my perception of things.

Of course… if that’s true, is that bad? I mean, is the “problem” here that if I have good baseline physical and mental conditions and good company, I might “falsely” just enjoy everything I do, forever?

Maybe I’m onto something here.

Think about a topic you know a lot about. An area where you feel very confident in your expertise.

Think about why you feel that way. How do you know you’re an expert? Think about how many hours you’ve spent engrossed in the topic. How many books you’ve read, courses you’ve taken, hours of footage you’ve viewed, other experts you’ve conversed with, etc. Consider all the times you’ve had the opportunity to have your expertise tested and proved up to the challenge. Relive the lessons you’ve passed to others on that topic, and the number of times you’ve been asked directly to opine on it. In short, take a full and honest inventory of the proof of your knowledge.

Now, the next time you’re about to give an opinion on any other topic, ask yourself if you’ve committed the same level of investment into your expertise on this subject.

If the answer is no, replace your opinion with a question, and prepare your mind to hear the honest answer.

This advice, if followed, will make you a much better and happier person.

I sometimes see people blasting sales or marketing efforts with some variation of: “I would never buy this! What are these people thinking?”

My (internal) response: “What makes you think the goal is to get you to buy something?”

You aren’t the only person in the universe. If you see a marketing campaign that is completely uncompelling to you, remember that. My father was fond of pointing out that if people keep doing something, it’s probably working. If it isn’t working on you, then it might be an interesting exercise to try and imagine who it is working on.

There’s opportunity there.

My father would see an advertisement that didn’t appeal to him at all, and it would broaden his horizons. He’d say, “Wow, so there are people out there buying that stuff, huh? Could be money in that.” It didn’t matter that he didn’t see the lure himself. He knew a simple truth: If you spend $500 dollars on a billboard, it’s because you expect to make more than $500 dollars back in sales from it. And if you spend $500 dollars on a billboard a second time, then you did.

So the next time you see a billboard (or anything else) that seems so abjectly silly that you can’t imagine who would pay for such a thing, remember – the market of products, services, and ideas is great and wide, and you are but a tiny island. Get a ship.

Sometimes our lives just get a little hectic. Lots of chaotic things happen. They might not even be individually bad things (though even good things can be stressful), but they might be rapid, unconnected, demanding of attention, unpredictable, and uninvited.

You like ice cream cake, right? Someone just dropped one off for you at your office! But your office doesn’t have a freezer. What are you going to do with it? Hurry up, it’s melting! But you can’t figure it out now, because your boss just asked if you have fifteen minutes to talk about a promotion opportunity! But you can’t leave the cake in the break room, it’ll melt everywhere. But you can’t keep the boss waiting, you might miss the opportunity. And the person who works across the hall that you like seems to be flirting with you about the whole thing and this is the first time they’ve shown interest, but you can’t chat now, you’re dealing with an ice cream cake that’s melting…

You see? All individually good things can happen, but they can happen in chaotic ways. The above example was a little sitcom-y, sure, but the same thing can happen on a scale of weeks or even months. Things can just get a little out of control.

Of course, bad things can happen too. But that actually requires a different solution: bad things are problems to be solved. Good things aren’t; you want to keep the good things, you just want to tame the chaos.

How do you do it? How do you herd the chaotic flock?

First, put some umbrella concept over the whole thing. Unite them. They have to be a flock before you can herd them. An “umbrella concept” could be a mindset shift, like: “These aren’t individual things happening to me, this is all part of the ‘Story of the Craziest Year of My Life’ that I’ll tell at the New Year’s party this year.”

An umbrella concept can also be a project that you use as a catch-all. The ‘Story of the Craziest Year of My Life’ can be a mental model, but it can also be an actual book you start collecting notes for, a vlog series you record, etc. Then all of the chaotic pieces have a place. If you just dumped a bunch of cardboard scraps on my clean table, that might stress me out. But if it were a jigsaw puzzle, the same scenario would make me feel very serene and happy. It’s all about what those elements are making.

Once you have everything under an umbrella concept, you can start making decisions for the good of that concept, and for you as a whole. Instead of focusing on each individual piece and trying to make decisions about it in a vacuum (decisions that keep being interrupted by realizations that they’re conflicting with the best decisions about something else, etc.), you’re making big decisions about one big thing. That can cut down on the total number of decisions you have to make, which is often very helpful!

So if your life is feeling a little chaotic but it’s all or mostly good things, don’t fret. It’s not a storm that will destroy you. It’s a flock that you’ll gently herd home. You got this.

Whenever you have the opportunity to speak, the most valuable ten seconds you can possibly spend isn’t spent on collecting your own thoughts or deciding what phrasing you want to use. It’s the ten seconds spent taking a quick mental inventory of who can and will hear you.

You will save yourself enormous headache and heartache by knowing who’s listening when you speak (or who’s reading when you write). Sometimes you’ll realize the answer is “nobody,” and you’ll save yourself time. Other times you’ll note that there are far more people within literal or figurative earshot than just your narrow target. All of these things matter, and they matter far more than just what you were so keen to express.

Just as you should never fire a gun without knowing what’s downrange, you should never speak without getting an idea of who’s listening.

Innovation is good. If we didn’t invent new things, whether actual “things” or new ways to do things, we’d be in unlit caves dying as soon as we’re born. It’s easy to recognize that innovation is good, and innovation means carving out the new ways, and so it’s thusly easy to trick ourselves into thinking “new ways” are always good.

That’s a bad, bad trick. There’s a thing called “survivor bias,” which is where you judge whether it’s a good idea to do something based solely on the examples of the people who were successful in doing it. Every zebra on the other side of the river is fat and happy, so we should try to cross the river, too! That line of thinking ignores that four out of five zebras get eaten by crocodiles on the way over.

When you see a successful new thing, what you don’t see are the 999 other new things competing in that same space to be the best new thing in that category, all of which were enormous flaming disasters. The one left behind displaces the old, solidified way of thinking and turns out to be better, so we think “duh, of course, new is always better.”

Here’s the about that old way, though. The people who have been using that old way for a long time can usually tell you a lot about why a particular new way won’t work. But people ignore the old timers, thinking of them as relics of an antiquated way of thinking. Because those fools are stuck thinking that there’s one old way and one new way, and those are the competing methods.

But that one old way beat out 999 others to become the old wisdom. And your new way is just one of a thousand competing to do the same. The old timers, if you stopped to ask, can tell you where to put your bets.

What a scary, negative word – “ultimatum!”

I don’t mean it’s scary to hear one. For most people, it’s far scarier to give one. No one wants to be the big meanie that breaks the final relationship by giving an unreasonable ultimatum.

But look at that sneaky word – “unreasonable.”

It’s not unreasonable to explain your circumstances. If I say, “hey, I can’t make the meeting on Friday because my kid has surgery, so we either have to reschedule the meeting or I’ll have to sit out,” that’s not an ultimatum. That’s just me telling you what’s up. You can change the meeting or not.

Sometimes you have to bend around another person, and sometimes another person has to bend around you. That’s just life, not a series of ultimatums. So don’t be afraid to tell someone what’s what.