Let’s say you’re a rational, intelligent human being – so naturally, you like the middle parts of the brownies. They’re superior, and preferring them reflects upon you as a person of culture. Now imagine you’re looking for a romantic partner. Surely you also want someone cultured and intelligent, so you should seek out someone else who also prefers the middle parts of the brownies, right?

No! Despite the fact that liking the edge pieces is indicative of an unhinged personality, that’s probably who would make the best partner for you (at least, in this one area). If you both like the middle parts, then you’ll fight over them and the edge pieces will go uneaten.

The point is that the right person to complement you is not necessarily the person most similar to you. If you want to start a bakery to make your own brownies all the time, you don’t necessarily want business partners who also have a deep love of baking. You want business partners who have a deep love of operational organization, or finance, or workforce management, or any of the other things that are required to run a successful small business. If you all love baking but hate doing the books then the business is doomed.

To put it another way: when two jigsaw puzzle pieces are the same shape, they don’t fit together.

This is yet another reason to diversify your life. Get out of your echo chamber. Sure, it might be intellectually satisfying to hear other people agree with you about which parts of the brownies are the best. But when the hands start reaching for the pan, that intellectual satisfaction dries up real quick. Just like the dry, disgusting edges of the brownies.

Free Your Work

In your life, you will do work for free. This is amazing.

When you work for free, you free your work. You work without permission, you work without constraint. At least, if you do it early.

Here’s the life cycle: in order for someone to want to exchange with you, they have to have some confidence that they’ll get what they want. In order for that to happen, you need to have some evidence to present. This is the classic paradox: “I can’t get a job without experience, and I can’t get experience without a job.”

Of course, that paradox is easily solved, but it’s the opposite of what most people making that statement want. Most people lamenting the existence of that paradox are wishing that someone would just give them the job without the experience, but that’s not the false part. The false part is thinking that you can’t get experience without a job.

Of course you can! In fact, you can get much more. You can do whatever you want if no one is paying you; it’s up to you to realize how beneficial that is.

You don’t need an audience to speak. You speak, and then an audience will come. We live in a glorious golden age of social proof – it’s so easy to do things in a way that others can witness. You can write, or speak, or build, or create, or anything. Others can witness in the present or (more likely) the future. You don’t trade your labor for money; you trade control of your labor for money. You can always labor, you can always think, you can always do. How wonderful it is to be free!

And the more you take advantage of that now, the more control you will retain when it comes time to trade. If you wait until someone pays you before you do anything, you yield not only control over your work, but over the development of the identity of your work. If someone pays you to paint houses, now you’re a painter – whether you wanted to be or not. That will start to stick to you, start to carve you. But if you do what you want when you can, then that will be what people generally pay you to do later.

This isn’t just advice for young people, by the way. You died yesterday, every single one of you, and you die every day. Every new day you are born again, ready to choose the expression of this new life, this new freedom.

The world conspires to rob you of your freedom at every turn. Nature makes you hungry and lashes your labor to the pursuit of food, shelter, security. Do not squander what freedom you retain! Do not yearn for more chains, simply because they may give more slack to those you started with. Do what you love and let the world follow. But no matter what, do – before anyone asks.

Rational Risk

Something like 80% of small businesses fail in the first year. Those aren’t good odds. So why do people start small businesses?

Let’s assume for a moment that it’s not total ignorance of the statistic. Some of it might be, of course, but even for people who know that 80% fail, some try anyway. To begin with, the 80% distribution of failures isn’t random. There aren’t 100 equally-viable businesses, of which 80 crumble through no fault of their own. Sure, the slings and arrows of outrageous fortune play some part in any business’s success or failure, but they’re not as big of a factor as all of the controllables are.

No, what makes people start businesses isn’t ignorance of the statistic, it’s the awareness of the fact that it isn’t random combined with the general faith that they, personally, are in the 20% of viable businesses. Of course, 100% of people can’t be right about being in the 20% minority, but that doesn’t shake people.

And it shouldn’t! It’s good that people take these risks – if no one took the risk, we’d have zero new businesses. The process of sorting through them is what advances us.

Humans are bad at risk assessment, as a general rule. We don’t have intuitive calculating machines in our brains, we’re not great at “gut-level statistics,” we don’t evaluate probability well. Often I lament this and work hard to try to train myself to do it better. But to some extent, I think a lot of our species-level survival has depended on the very fact that we’re bad at knowing when not to jump.

We very often think there’s more risk than there is, and we frequently think there’s less. If you’re going to have to make one of those errors, make the second one. The worst that can happen if you jump when you shouldn’t is that you die. That’s not nearly as bad as what will happen if you don’t jump when you should, which is that you never live.

Desperate Measures

In physics, there’s a concept called the “observer effect,” which basically means that to accurately measure something you very often change it a little through the actions of your measurement. We can’t really be “passive observers” most of the time; in order to study something, we have to interact with it at least a little. Think of checking tire pressure – the very act of attaching the pressure gauge to the valve lets out just a smidge of air. So by measuring the air pressure you also changed it, if only a bit.

This isn’t just a physics thing. If you study animals in their natural habitat, you have to disrupt that habitat, if only in a minor way. You have to sneak in a camera or something, and get your smell on things and scare away a bird that might have been the next meal of the tiger you’re trying to study, etc.

And it’s not just a hard science thing, either. In fact, the problem is much, much worse in the realm of human interaction. Because in addition to everything else, humans can usually observe that they’re being measured – especially if you tell them!

Let’s talk about resumes for a moment. Most people that use resumes have the core idea of them completely wrong. Most people think that a resume is an impartial record of their professional life. They think of a resume almost as if it was created by an outside observer who’s been watching their career. If that was actually how resumes got made, that would be fine – but it isn’t. Because if that were how resumes were made (by impartial, outside observers) then employers could use them as a measure of a candidate’s ability and experience.

But that’s not what they are at all. They’re self-created marketing documents, and that changes things a lot. You see, what employers generally want to see on resumes is generally pretty known (or at least discoverable). Their standards of measure are public information, for the most part. And that means, for the most part, that they’re bad standards of measure.

Let me go deeper into this tangent for a moment. Let’s say an eccentric billionaire walks into a sleepy town one day (without announcing anything about his wealth), and asks around until he finds the person who has worked hardest to become a painter. Discovering an artist toiling away on brilliance in poverty-level conditions, the billionaire bequeaths a million dollars on this person in a public display of support, speaking about how much the billionaire values the artistic pursuits and why they’re so important. The billionaire then says that he’ll return to the town next year.

What would you expect that town to look like, a year hence? The place would probably be overrun with artists! But here’s the problem – that very first artist was pursuing art out of a genuine love of it. You could be sure of this because the artist had no expectation of a sudden windfall. Meanwhile, every other artist in the city now has their motives sullied by the fact that they know that there’s a major reward lurking if they paint hard enough. Incentives change behavior. The people of the city know that the measure of “best artist” would be rewarded, and so they changed their behaviors appropriately in response to the measure. That means that the measure is no longer the measure the billionaire wants it to be – it’s no longer a measure of “who loves art the most,” but rather “who wants a million dollars the most.” Since those two measures will reflect different people, the point is lost.

So, back up to resumes. If a measurement becomes a target you can adjust to, it stops being a good measure. That is extra true when it comes to measurements that are very easy to change and very hard to quantify in the first place, which is like 99% of what shows up on resumes.

I can read a resume, but what I’m reading is a piece of paper written entirely by a person who wants a specific thing that I have to offer, and who knew in advance exactly what I wanted to see. I’m not saying that all people who turn in resumes are shameless liars or anything (though certainly a few are, and their resumes will look the same as those of the people who aren’t), but I’m saying that even if the resume is 100% truthful and accurate, even doing the actual stuff you’ve written about was informed by the fact that someone else would want to read it, not because you wanted to do it or it had value.

For example, I’ve talked to a number of people who worked at Facebook, and I heard this story many times: it was a good idea to work at Facebook for two years, even though Facebook was a terrible employer and everyone hated working there, because it looked so good on your resume. Many of these people did nothing of value while they were there. They “phoned it in” and did just enough to not get fired for two years (or close enough to round up) and then bounced, knowing that future employers would look at their resume and go “Ooooh, Facebook! How impressive!” No lying involved – the resume was accurate – but the actions of the person in question were deadweight loss to everyone involved.

See, that’s the other problem with targeting a measure – in most cases, you have to do wasteful things in order to do it. In the example of the town full of artists, a LOT of time is being wasted. I don’t think “art” is a waste or anything. But I think that garbage art that you don’t even want to make and no one else wants to see that you’re creating in a frenzy just because one of you out of hundreds will get a million dollars for doing so is just about the definition of wasteful. All of those people, absent the million-dollar prize, would have been doing significantly more valuable things with their year. In fact, if you added up the value of all the things those people could have built or accomplished in that year, the total would certainly be more than a million dollars.

Of course, in some cases point of measuring things in an observable way is to encourage changes in behavior. Measuring grades in school is meant not only to be an observation of ability but also an encouragement to improve ability. And of course… it doesn’t work. For exactly all the reasons I’ve stated. What grades measure is precise. “How well you’re learning” or “how smart you are” are very imprecise things that only very loosely correlate to your grades in school, but they do make sure that children spend all of their time and energy not actually learning, but trying to get good grades. Actual knowledge retention of the things children are graded on is abysmal (remember that show “Are You Smarter Than a Fifth Grader?”), because grades don’t measure how well you retain stuff, just how well you pass tests.

So here’s the upshot of all this rambling: as soon as the subject of your measurement knows that they’re being measured (assuming that some reward is also tied to the measurement), they will bend towards appeasing the yardstick. If you aren’t fully aware of that when you try to measure, you’re wasting your time – and probably everyone else’s, too. In a real way, you’re inflicting harm. Of course, our understanding and operation in the world requires that we have data and that requires measurement. At some point, you simply have to. But you have to know that this effect exists. You have to know that you cannot be an impartial observer – your observation will change the outcomes. The easier it is to bend to the yardstick, the more of exactly that you will get.


Sherlock Holmes said: “When you have eliminated all which is impossible, then whatever remains, however improbable, must be the truth.”

Here’s a version of that to apply to your life: “When you have eliminated all which will not happen, then whatever remains, no matter how you feel about it, are the possibilities for the future.”

Want to make yourself really miserable all the time? Then expect things that won’t ever happen, and get mad when they don’t. Note that the question of whether something is likely to happen is totally separate from the question of whether it should happen (or whether or not you want it to). Don’t confuse them.

Your high school bully should call you, out of the blue, twenty years after graduation to apologize for the way they treated you and offer to make amends. But if you sit around mad that they aren’t, it’s because you were foolish enough to somehow confuse the question of whether or not they should with whether or not they will.

This is the source of, I’d say, maybe 90% of people’s unhappiness? If not more! Expecting something to happen just because it should happen. If you want contentment, learn to not expect things that aren’t going to happen. “Should” is a stupid question when you apply it to other people – if you decide that you should do something, you have the power to make it so. But the question of whether anyone else “should” do anything is purely academic and theoretical. Eliminate such thoughts, for they consume your time as well as your contentment.

Lots of things just happen, and lots of other things just don’t. You can’t control the storm that happens, but you can control how you stand against it.

Plato’s Thanksgiving

As I reflect on the nature of gratitude today, I’m reminded of the views on the topic expressed by one of the founders of Western philosophy, Plato. Plato should be unfamiliar to no one, even if you don’t know the full breadth and depth of his work. He lived for eight decades, spending the lion’s share of that time in philosophical pursuits. His work spanned the nature of love, thought, mathematics, and a wide variety of other topics. Yet in all that time, he never once wrote or – as far as any records indicate – even spoke the words “thank you.”

Do you know why?

He didn’t speak English.

The Sweet Spot

My middle kid is 4. She is a constant, never-ending stream of absolute side-splitting hilarity. That’s not just me saying “my kid is special,” in the standard parent-bragging way. In fact, as far as I can tell, my kid is very much not special in this regard.

Right around this age, give or take a few months, kids seem to be absolutely hilarious (my oldest kid certainly was at this age, and I expect my youngest will be as well). A few moments of reflection and it’s easy to see why: much earlier than this, and they can’t really talk at all. Much later than this, and their language ability develops to the point where they speak “normally” and don’t say the funny not-quite-right charmers that are such a hallmark of this particular development stage. This is the sweet spot.

I think this principle is easy to see when you’re looking at the hysterical half-nonsense spewed by a four-year-old, but it’s present everywhere. Between “not knowing anything” and the point where your knowledge levels out and joins the “general consensus” is a sweet spot where the most creative things can happen. You know enough to be dangerous, but you don’t know so much that you’ve started following familiar pathways all the time just because they’re familiar.

Capitalize on that. Lots of people get frustrated in exactly this stage because it feels like you’ve emerged from the stuff that’s easy to learn and you’re on the precipice where expertise feels elusive, like there’s so much more to absorb that you don’t have yet. In your race to avoid that discomfort you grab anything that looks like expertise, but what looks like expertise is often just the standard model of whatever it is you’re doing. In order to avoid looking or feeling foolish, you surrender your freedom to do really creative things in the nonsense-space.

Part of why kids are hilarious at that age is because they don’t know what things, exactly, they’re wrong about – and they don’t care. They’re trying to get their point across, express themselves, and use language to manipulate their conditions. They’re not yet focused on status or whether there’s a “right” way to do things that might be separate from the “effective” way. Be like them. Don’t rush out of the sweet spot. Stay there and play for as long as you can.

Thoughts & Feelings

Are our thoughts primary to our feelings, or do our feelings inform our thoughts?

There’s definitely truth to the idea that we are riders on elephants – i.e. we are constantly trying to retroactively justify our gut reactions with intellectual reasoning and then claiming that the reasoning was primary (like a person helplessly riding around on an elephant but trying to claim that they wanted to go that way the whole time). At the same time, sometimes I definitely have thoughts that clearly cause an emotional reaction where no particularly strong emotion existed before.

Or have I? Maybe that’s part of me justifying my elephant.

It’s an important question, especially as it relates to controlling our own motivations. I’m a realist in the sense that I know many of my actions are going to be heavily influenced by unseen biases, heuristics, and other factors besides my conscious and rational decision-making. That, in and of itself, is inevitable – but the more I learn about it the more I can at least predict it. Since I want my actions to mostly follow the motivations that I dictate in my most clear-headed moments rather than at my most emotional.

At least, that’s how I feel.


I frequently do things that I consider good, but would be very very bad if everyone did them. That’s not a reason for me not to – in fact, it’s part of the reason I do.

There’s always someone saying “What if EVERYONE acted like you?” Well, then I wouldn’t act like me. Part of the calculation of how I believe I should act is what everyone else is doing.

Consider a stadium full of people watching a game. If one person stands up, they see better. If everyone stands up, then no one sees any better. So if I stand up, it might sort of make sense for someone to say “what if EVERYONE stood up, huh??” But if everyone stood up, I wouldn’t – I’d probably just leave. Part of what I do, every day, is respond to the movement of my society.

Sometimes a lot of people doing something is a reason for me to do it, or at least try it. Very often it’s a reason for me to run the other way.

Society thrives on diversity, specialization, and individuality. If I do things that other people aren’t doing, there’s a good chance I’m adding value somewhere. The guy that cleans septic tanks for a living adds a LOT of value, but if everyone did it, he’d probably do something else.

This argument works the other way, too. Sometimes people complain that things would be amazing if just “everyone would…” Well, the answer to that is the same.

“Everyone” will never do anything. People will never unify. You can’t expect it, and you shouldn’t fear it. Both the admonition of “what if EVERYONE acted like you?!” and the lament of “if only EVERYONE acted like me” are foolish. People are different, and you can feel free to choose your path without worrying or hoping that it will become a universal standard.

Heart of Hearts

Thoughts can lead to feelings or they can lead to actions. Sometimes both and sometimes neither, but those are their influence on the world – on your world.

A thought itself can harm no one. Your most evil thought cannot murder, and your most righteous thought cannot heal. You curate your thoughts to the extent that you want to feel and act certain ways because you know that those thoughts lead to those feelings and actions.

Outside of you, the rest of the world cannot experience your thoughts directly. It can only experience your actions. Good and evil that you do must naturally happen in the rest of the world, so it is your actions that determine this.

A person might think “the only thing in the world that matters to me is that other people look at and admire me; I crave their attention and adoration because it makes me feel better than them.” We wouldn’t view that as a “good” thought, but if that thought motivates the person to save a bunch of lives as a surgeon or to donate a ton of money to Malaria research, then hooray! I will admire that person and consider their life well-lived.

That same thought could lead someone to be a brutal tyrant, of course. In fact, in the grand scheme of things, thoughts like that might be more likely to lead someone down the road to villainy than heroics. But that’s the only reason we, as outsiders, should care – and if the person has already “beaten the odds” and done heroic things then we should applaud them. We shouldn’t retroactively decry their accomplishments because they thought bad thoughts.

If a person has nothing but love and care in their heart but never acts – then they aren’t “good” to the world. My genuinely altruistic desire to help others, uncoupled from appropriate action, does not outweigh someone’s very selfishly-motivated construction of a homeless shelter that makes a real impact on peoples’ lives.

In other words, the whole “good things for bad reasons” concept is bunk. There are no bad reasons to do good things, unless we’re talking about some sort of trap – i.e. if someone built a homeless shelter so that they could lure people in and then blow it up, yeah, that’s a bad reason. But in the way most people talk about it, pssshh. “Oh, he only wanted to build a homeless shelter so he could name it after himself.” That’s fine! Pride, status, tax breaks – these things don’t matter to the people who get a roof and a warm bed tonight, that otherwise would not have.

I think that when most people decry others for doing “good things for bad reasons” like that, it’s usually because they didn’t do anything at all. They don’t like comparing themselves unfavorably to someone they want to dislike, so they reflexively make up a reason why that person who actually improved the world isn’t better than me after all. “Sure, they built a homeless shelter while I sat on the couch and ate Cheetos, but my heart was in the right place and there’s wasn’t.”

Hogwash, of course. You should absolutely care about your own thoughts. You should cultivate ones that inspire you to good deeds and that don’t darken your own soul. Even if you don’t act on them, you should keep evil thoughts from polluting your heart to the best of your ability. But thoughts must be grappled with, they must be engaged. You cannot run from your own mind, and you must by nature struggle with your own chaos. But don’t confuse your own battle with demons for something you have any ability or right to judge in others. That battle is yours, and yours alone – and so it goes for every soul. For everyone but yourself, judge the wake of their actions and the wake of their actions alone, for that is what touches the world. And remember always that you must be judged thereby: what you carry to the grave in your heart of hearts is for no one else to ever know.