There’s an old adage: “shirtsleeves to shirtsleeves in three generations.” The idea behind the adage is that an industrious person works hard to build wealth in order to leave it to their children. Their children grew up around hard work and saw the benefits so they’re responsible with the money they’ve inherited, but they don’t have to work nearly as hard themselves. As a result, their children grow up wealthy but don’t learn commensurate responsibility; they squander their money and are poor again.

It’s not always true, of course. But it’s true often enough to have created the adage. Leaving things better for your kids (and even if you don’t have them yourself, leaving the world better for all the kids) is humanity’s most noble pursuit. I think most of the most salient problems on Earth are generation-length problems, and we could solve them in a generation if we accepted that. But people are often selfish, and so they want to choose “solutions” that are anything but, sold by snake-oil salesmen who promise that you can have everything better today if you just sign here.

But you should not only be shepherding resources towards your children, you should also be teaching them to be shepherds. I would never hand over the car keys to my child without first making sure that child was a responsible driver. But I will work hard to make sure my children have cars, because early access to reliable transportation opens up many opportunities for them.

Give resources. Teach their use. Teach the teaching of their use. And share the values and vision of a better world. Lay yourself on that altar if you get the opportunity. You will not live forever anyway, but any sacrifice you can make for your kin will echo for eternity.

The first time you accomplish something amazing, it feels amazing. The second time, even if you complete the exact same amazing accomplishment, it feels… okay?

It doesn’t matter how objectively incredible the actual accomplishment is. Because there is no objective measure of “amazing.” Picking up your foot and putting it back down in front of you without falling on your face is a pretty simple task that you do thousands of times a day without even thinking about it, but the very first time you did it the people who love you went absolutely bananas.

Accomplishing anything new pretty much serves two purposes. One is “proof of concept.” You climb Mount Everest to prove that you can. The other purpose is to start a habit. You take your first step because you want to take millions more.

So when you take your second step, and the cheering seems to drop off, even in yourself – do not despair. If the accomplishment is no longer shocking, then that means you’re doing exactly what you want to do. What once was incredible is now routine, because you’re incorporating the incredible into your everyday. That’s the way to an amazing life.

The world is full of middlemen.

In a very oversimplified view of the world, for every product or service there exists the person who provides it and the person who consumes it. And then there are a bunch of people in the middle, sometimes.

Wildly reductive, but true enough in many cases. I don’t buy my eggs (most of the time) directly from a farmer. I buy them from a grocery store – so the grocery store is a “middleman.”

While not always the case, often the term “middleman” is used in a pejorative way; whether it’s commercials for companies who “cut out the middleman, and pass the savings on to YOU” or folks who simply curse their existence and blame them for every inconvenience. And the fact is, many middlemen are parasitic rent-seekers. But others are so incredibly helpful that you’d be crazy to “cut them out!”

Take the grocery store example. What a glorious middleman! Imagine going to the store and picking up twenty items. Relatively simple errand. Now imagine that instead, you had to go to the factory or farm where each of those twenty items was produced in order to buy it. Ugh!

The good kind of middleman collects, organizes, and bundles for you. They reduce the space in the middle! They aren’t adding one step to a process; they’re removing 19.

So what’s the bad kind?

Picture ticket scalpers. Here’s a concert venue with five thousand tickets to sell for an upcoming show. They can sell to you directly, and in fact, would like to do so. But before they get the chance, an unscrupulous person buys all five thousand tickets the second they go on sale. Then they turn around and re-sell them at a much higher price than the one originally set by the venue.

This is the bad kind of middleman – someone who creates more middle solely for the purpose of extracting some value for themselves. They aren’t providing any actual benefit to either side (unlike grocery stores, which provide tremendous benefit to both the consumers of the products and their producers). They’re just parasites.

Grocery stores and ticket scalpers are obvious. They’re easy to spot for what they are. Not so with all middlemen. Especially as you get deeper and deeper into niche industries, there can be some weird examples of different steps in the long process between original producer and end consumer. It won’t always be so obvious which ones are adding value and which ones aren’t, because they’ll almost all have a story for why they’re the former and not the latter.

So here’s a quick mental check: say “if this person didn’t exist, would it be easier to get what I want or harder?” Follow this question for grocery stores (way harder) or ticket scalpers (way easier – mostly; there’s a case to be made that some level of scalping just helps shift goods from time-preference to money-preference but that’s a different subject altogether). Now you can run that basic check on any proposed service someone tries to sell you. Usually you’ll be happy you did.

See, I helped you get closer to your end goal – and I didn’t even charge you. Praise the middle!

Messages should be ways to communicate about things, ways to encourage actions. When the message itself becomes the product, run.

If someone sells painted rocks for a living and does well, then that person is unlikely to stop painting rocks and selling them. Likewise, if someone’s message has become elevated to the point where they make a decent living off of simply transmitting that message, then they’re unlikely to stop. That means you can safely ignore them, forever. And you should, even if you agree with the message.

Why? Because it won’t change, won’t produce new information, won’t adjust to reality. Here’s a hypothetical: let’s say some public figure is strongly anti-cigarette. Strongly! So strongly that it’s their whole public brand – they’re publicly well-known as the “anti-smoking guy” and they post on social media all the time about it. He leads an anti-smoking foundation and he’s always protesting tobacco companies. He does lecture series on the dangers of smoking in high schools across the country, etc.

I don’t have a particular problem with this guy’s message. I think smoking is bad, generally! But I would absolutely ignore this guy because not only don’t I need to listen to him to gather information, but there’s a very strong chance he’ll lie to me.

If some famous celebrity were to die, and in their apartment the police found drugs, alcohol, and cigarettes – what do you think Anti-Smoking Guy would tweet about? You could probably guess, and you’d be right. Anti-Smoking Guy would tweet about the dangers of smoking – and even if a later autopsy revealed a drug overdose or alcohol poisoning to be the cause of death, Anti-Smoking Guy would tweet about how cigarettes led to those things, were a “gateway habit,” or whatever. You could predict that, and you would be right, and that tweet wouldn’t contain any new information that would be helpful to you, so you can safely unfollow.

And you should, because that’s just the most benign version. The more malign version is this: imagine that some new research emerges that says that smoking cigarettes, if combined with the right daily vitamin regimen, not only has no adverse health effects but tremendous health benefits? What if it added 20 points to your IQ and thirty years to your lifespan? What if it cured other diseases? What if it turns out that with the right additive, cigarettes became one of the greatest boons to mankind in history?

Do you think Anti-Smoking Guy would care? Do you think he’d pack his things and go home?

Of course not. Once your message is your living, you’re chained to it. So in the best-case scenario, cigarettes are poison, you already know they’re poison, and Anti-Smoking Guy just exaggerates (note, that doesn’t mean that Anti-Smoking Guy isn’t possibly doing some good by spreading the message itself to people who might not have heard it yet, just that you don’t need to listen to it). In the worst-case scenario, Anti-Smoking Guy actually impedes progress.

Heck, Anti-Smoking Guy doesn’t even want cigarettes to go away. Then he’d be out of a job. His personal best-case scenario is that cigarettes stay around forever so he can just keep on advocating against them… and maintain his grift.

Because it is a grift. Even if the message is true and good, most of the messengers are grifters. There’s a difference between someone who actually works to increase public health, regardless of what form that takes, and Anti-Smoking Guy. ASG just wants to get paid to yell; he doesn’t want to make anything, doesn’t want to produce alternatives, doesn’t even want to pursue a goal like “public health.” He just picked a thing that a lot of people don’t like and publicly disliked it with enough passion and charisma that its other detractors started paying him – paying him in attention, in clicks and likes, in lecture fees, in notoriety, in book sales.

But you know what? Pro-Smoking Guy gets the same deal. So the fervor of the message alone isn’t enough to prove truth. You have to find that out on your own – and the grifters are the first people you should ignore in your search for truth.

I grew up in a pretty small town with a very tiny school. The upshot is that my grade had about 12 kids in it (including me) in any given year. They were fine, as kids go. But we didn’t have a ton of shared interests and so I wasn’t much more than casual friends with any of them.

In the summer between 6th and 7th grade, I met someone who would become one of my closest friends to this day. He was a year older than me (going into 8th grade), but we had a ton of shared interests and met as a result of them. We became hangout-every-single-day friends quickly.

The next year, he graduated up into high school while I still had a year to go. We still hung out every day (we lived only a few blocks from each other) but we also saw lots of new people. So when I joined him in high school a year later, he introduced me to a cadre of new people. Some of them were older than him – he’d met this person in math class, who had a brother two years older who was cool, and that brother’s friends became our friends, and one of them had a sister one year older, so we were friends with her, so her friends became our friends. One of them had a younger sister who was close in age to my younger sister, so they melded in. My cousins were between those ages so we absorbed them. The web grew and grew, and to think that it would have been even possible, let alone good to only hang out with people the exact same age as me plus or minus six months would be ludicrous.

Over the course of the time between that 7th-grade year and my first year as a parent, my friend group has ranged easily 15 years in either direction of my own age. My sister is eight years younger than I am, but our closeness, in turn, drew our respective friend groups together, and since both of ours had decent age ranges by themselves the total group’s range was very wide indeed. At my family’s annual 4th of July party (the party of the year by all standards), it wasn’t uncommon for the 40 or more “kids” to be as young as 5 or as old as their late 20s.

This was a group dynamic, of course. The range is more understandable when it’s fifteen people getting together than if it’s three, but it wasn’t unheard of for two or three people hanging out to have ten years between the youngest and oldest.

And all of this was very, very good. Older kids with good hearts are the kind of loyal guardian parents can’t ever really be and dream of having for their offspring. Younger kids with good intentions help older kids step into maturity and responsibility – and often keep them honest and humble. When people say “it takes a village,” that doesn’t just mean that it takes a village of adults to supervise the kids. It means that those kids are good for each other.

Let me say that again: kids are good for each other. It’s good to put the kids together that like each other and let them run around town, finding adventures and yes, even getting into a little trouble. They will protect each other. They’ll protect each other from the very things you’re most afraid of when you think about your precious little darling hanging out with “the older kids,” as if anyone older than your own kid was automatically a wicked influence. The first time I experimented with alcohol (and yes, shocker, your kid will probably do that), I had an army of older kids telling me how to take care of myself, not drink too much, not get “wasted,” and so on. I had an older kid smack a cigarette out of my hand – and I’ve smacked a few out of the hands of younger kids. I’ve had younger friends who tried drugs call me to come get them, knowing they couldn’t call their own parents, and so were able to be transported somewhere safe rather than stay where they might not have been.

And those are the extreme things! In between those big dramatic moments were a thousand tiny ones, helping each other and learning together and growing together. Becoming better adults for our society we made. Adapting to different interests, learning social cues and graces, building up each others’ confidence.

Now we have our own kids, and they play together – regardless of age. I have more of a link to them than my parents had to me, but I never use it. And I don’t warn my kids about some silly, imagined dangers of “older kids.” I encourage them to make friends wherever they find them, and most of the social lessons I give them are about how they can become better “older friends” to those they meet.

There is evil and wickedness in the world. Some of it will target kids, and some of it will even reside within them. That is a very poor reason to try to hide your kids from the world. Evil and wickedness are a very, very, very tiny percentage of the world. The only chance it has to grow is if all the good in the world hides from it. But if you flood the world with good, there’s nowhere left for evil to be. Train your children to be shepherds and send them out into the flock. They will be neither the oldest nor the youngest, ever. Sleep well at night, knowing that.

The most productive days create the most productive moods, and vice versa.

Though they’re uncommon, I do occasionally have “lazy days” where I accomplish very little. Truthfully 100% of these days are “hang out with the kids all day” days, so I certainly don’t think they’re wasted (in fact, I think they’re vital and wonderful), but I certainly wouldn’t call them “productive.”

That tends to make them infertile soil for growing ambition. Late spring days with no agenda with my children are just about paradise, and the thing about paradise is that it’s the end goal. It’s the Last Thing, not an input to something else. Sure, time marches ever onward and these children I’m raising will one day navigate complex lives with impacts all their own – perhaps even on their own children. And so even on these days I must attend to fatherly duties and make sure I’m raising heroes. But the very time itself, the natural way we interact, already gently propels us towards that end. By and large, what I get to do on these days is enjoy them.

It means my writing on these days tends to be less “advice” and more “reflection,” because without crashing into challenges and obstacles, I learn very little that’s useful in avoiding them. That’s okay, though – the world is not short on obstacles, and I need not wish more into existence. They’ll come.

But not today. Today, my life is not interesting. But it’s vital and wonderful, and I am thankful.

The way time interacts with money has always been a point of fascination for me. While I’ve often thought about how to go about buying time with money, recently I’ve been thinking a lot more about buying money with time – and without it.

Time is an input into all productive processes that eventually will be exchanged for money. It might be an initial investment or it might be a unit cost, and your final pricing philosophy should be different depending on which.

If you sell something that requires your time as a unit cost, you should charge more. For instance, if you are a plumber, you’re not charging enough. Virtually everyone who sells their time directly would do better if they doubled their prices. When you have a business, there’s always the inclination to lower your prices because of a universal fear of “losing business.” But here’s the thing: if you’re not losing any business, then almost by definition you’re not charging enough. You should lose business.

Why? Let’s say you charge $20/hour as a freelancer doing whatever it is you do, and at that price your calendar is full – you work 50 hours a week consistently. Cool, you make a thousand bucks a week. Now let’s say you raise your prices to $25/hour and as a result, you lose 20% of your business. Those canceling clients scare you, but… you still make a thousand bucks a week. And you work ten fewer hours. So now you can either just enjoy making the same money in less time, or you can spend the extra ten hours hustling for new clients and make even more money.

(And hey, don’t forget – with every passing month you’re getting more experienced and better at what you do, so those prices should be going up anyway.)

If you double your prices and lose half your business as a result… good! Time is your ultimate bottleneck, not “number of clients.” There will always be a range of available customers at a variety of price ranges, but time is a unit cost for you, then there are only so many you can ever serve. Your goal shouldn’t be to maximize the number of clients, it should be to maximize the total value of your book of business, and that means moving up the hierarchy.

Now, if time isn’t a unit cost for you, you should lower your prices!

The easiest example: if you write a book, then you should probably lower the cost of digital copies. Time was an initial investment, but there’s no per-unit cost in time to sell additional e-reader copies. Your goal is to get the book read, and beyond a certain minimum threshold, everything is profit. So you want to get more copies out there. If lowering the price of your book from $10 to $8 doubles the number of units sold, that’s an incredible move. (Of course, if lowering the book from $10 to $8 doesn’t change the number sold, then don’t – but the point is that there’s a “sweet spot” and it’s probably lower than your initial assessment.)

There are, of course, a bajillion considerations when it comes to determining the final price of any product or service. I don’t mean to reduce all of that here to one simple decision. But I do think this guiding philosophy would help most people evaluate all those other factors more effectively, especially the early entrepreneurs and small business owners out there. If you sell your time, charge more. If you don’t, charge less. Start there, and go make more money!

You can use time to plan a day or a week. Maybe you can use time to plan a month, but probably not. You definitely can’t use time to plan a year – or your whole life.

Too many things change, there are too many variables. You can pretty confidently plan out a schedule for tomorrow, but you can’t schedule out the next five years of your life. “Five-Year Plans” are a joke. The problem is that people do them anyway, and then they don’t survive contact with the enemy, and people fall back on nothing at all.

Here’s your tip: stop planning using time. Start planning using conditions.

Don’t say, “I’ll stay in this job for three years, then I’ll transition to this other role where I’ll spend 4 years gaining XYZ skills, and then…” because it just won’t happen.

Instead, say, “I’ll stay in this role until I’ve met A, B, and C criteria. Once those are satisfied, however long that takes, I’ll move into a different role based on the next thing I want to accomplish. Then I’ll stay there until I find this specific kind of opportunity,” etc.

Conditions. Timelines may change, but that’s okay. If you know what you want you can be moving towards it – faster or slower. Think of it like this: if someone tells you which series of busses to take but never actually tells you where you’re going, what do you do if you miss a bus? You have no idea how to adapt. But if you know your destination, it’s easy to say “my first step is to get to downtown Main Street, and once I’m there I take whichever the next bus is that’s headed east.”

“If, then” is greater than “when.”

You: “I think we should swim across the ocean.”

Me: “What?”

You: “Yeah, there’s lots of great stuff over there. We should swim over and get it.”

Me: “Um, I don’t think–“

You: “Do you not want the stuff?”

Me: “The stuff would be great, sure. It’s just–“

You: “I think you don’t want the stuff. Or maybe you just don’t want ME to have the stuff. Is that it? You don’t want me to be happy?”

Me: “What? Of course I want you to be happy. I just don’t think you attempting to swim across the ocean is the way to make that happen.”

You: “So you admit that you don’t want me to swim across the ocean.”

Me: “I didn’t say I don’t want it. I don’t think it will happen.”

You: “So you don’t support it.”

Me: “I think you’re being deliberately obtuse. Something being impossible is different from me not wanting it. I would love gold to spontaneously appear in my house, but that doesn’t mean I expect it.”

You: “Then why not voice your support for it, at least? It might not happen, but you send the right message.”

Me: “Well for one, I don’t necessarily think that loudly wishing for gold to appear in my house ‘sends the right message,’ whatever that means. But in your case, there are more than just empty platitudes at stake. You can’t swim across the ocean, and if you try, you’ll probably drown. I don’t want you to drown, and that’s a pretty big unintended consequence of ‘sending the right message,’ don’t you think?”