The Art of Spending Money: Simple Choices for a Richer Life

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Highlights & Notes

Money is less about numbers and more about stories—stories we tell ourselves about what matters, what makes us happy, and how we measure success.

It’s astounding to witness someone gain what they thought they always wanted only to realize that happiness is more complicated than they first assumed. And, my gosh, that is so true with money. There’s an old saying that nothing’s worse than getting what you want but not what you need.

Winston Churchill famously said that he got more out of alcohol than alcohol got out of him.

Many people have figured out how to use money as a tool to provide things that actually make them happier in life. But the rich chair guy had it right: What society tells us we’re supposed to do with money is not always what we should be doing to get the most out of it.

Carl Jung, one of the most influential psychologists to ever live, was once asked, “What do you consider to be more or less basic factors making for happiness in the human mind?” Jung listed them off: Good physical and mental health. Good personal and intimate relationships, such as those of marriage, the family, and friendships. The faculty for perceiving beauty in art and nature. Reasonable standards of living and satisfactory work. A philosophic or religious point of view capable of coping successfully with the vicissitudes of life.

There are two ways to use money. One is as a tool to live a better life. The other is as a yardstick of status to measure yourself against others. Many people aspire for the former but spend their life chasing the latter.

Enduring happiness is found in contentment, so those happiest with money tend to be those who have found a way to stop thinking about it. You can value it, appreciate it, even marvel at it. But if money never leaves your mind, it’s likely you’ve found yourself with an obsession, where it controls you. The best use of money is as a tool to leverage who you are, but never to define who you are.

Money is so tangible that it’s an easy goal to strive for, and pursuing it can become the path of least resistance for those who haven’t discovered what truly feeds their soul.

“After meeting our basic needs as creatures, we enter into the human universe of desire. And knowing what to want is much harder than knowing what to need.”

Benjamin Franklin put this so well when he wrote: “Many a man thinks he is buying pleasure, when he is really selling himself a slave to it.”

The quest of your own simple life—however you choose to live it—starts with a deep understanding and examination of yourself.

Most debates about what’s worth spending money on are actually just people with different life experiences talking over each other.

What have you experienced that I haven’t that makes you believe what you do? And would I believe the same if I experienced what you have? It applies to so many things in life. Including money.

Never make fun of someone for mispronouncing a word, because it means they learned it from reading. As a corollary: Never make fun of how someone spends their money, because they learned it from living.

All behavior makes sense with enough information.

she suffers from “post-traumatic broke syndrome.” It’s made it hard for her to spend her newfound wealth. “I was broke for so long, and it was so hard, that I’m afraid of going back there,” she says.

I have noticed that those most capable of delayed gratification are often those who enjoy their work. The pay might be good, but the urge to compensate for your hard work with heavy spending isn’t there.

“People are not rational. They are rationalizing. Once you understand this simple fact, all the oddest human behavior will suddenly make way more sense.”

The important thing is that emotions are learned. They are a product of the culture and environment we are raised in.

Behavior that embarrasses you might make me proud. What I fear might be a thrill to you. Your goals might be my nightmares.

“consensus realities are mostly the result of geography.”

  1. Don’t let anyone tell you what you should or shouldn’t spend money on. There is no “right” way. You have to figure out what makes you happy and fulfilled (more on that later).

A lot of money problems come from people spending or saving money in a way they think they’re supposed to but that doesn’t match their personality. They look for a one-size-fits-all answer to a problem that’s deeply personal. It’s like going through life forcing yourself to be someone you’re not.

  1. Be careful judging how other people spend their money.

A healthy financial philosophy is having respect for others’ experiences, an appreciation of your own, and an understanding that all behavior makes sense with enough information.

May I Have Your Attention Please You think you want nice stuff, but what you really want is respect, admiration, and attention.

But the desire for more money and the things it can buy often obscures what you actually want: respect and admiration from other people.

Write down what you want your obituary to say, then figure out how to live up to it. It’s the cleanest, simplest way to plot out what you want in life and what truly matters.

We value the attention money brings us more than we value the comfort and convenience of stuff that money can buy.

If you gain your respect and admiration for who you are rather than what you own, your desire to spend more money on flashy things plunges.

“The appetite for applause counts amongst the lowest of human character traits.”

Resume virtues are things like salary, job title, net worth, and how fancy your possessions are. Eulogy virtues can be boiled down to how much people actually respect and admire you.

“When you get to my age, you’ll really measure your success in life by how many of the people you want to have love you actually do love you.”

Maybe You Already Have Enough One of the most powerful money tales is the parable of the Mexican fisherman. An American businessman visits Mexico and meets a local fisherman. The American is shocked to learn the fisherman only works a few hours a day. “What do you do with the rest of your time?” the American asks. “I sleep late, hang out with my family, read, take naps, and play guitar with my friends,” the fisherman says. “You’re doing this all wrong. I have an idea,” says the American. “You should work all day. Borrow money and buy another boat. Hire more fishermen to work for you. You could make so much money you’ll be retired in ten years.” “What would I do in retirement?” the fisherman asks. “You could sleep late, hang out with your family, read, take naps, and play guitar with your friends,” says the American.

The Happiest People I Know If your expectations grow faster than your income, you will never be happy with your money.

True happiness is when you stop asking what else you need to be happy. When you think of it like that, you become eager to spend less time asking what’s missing and more time enjoying what you already have—regardless of how much or how little that might be. You realize that the key to happiness is being content with what you have, and its antidote is focusing on what you don’t.

Appreciating what’s in front of you rather than dwelling on what you don’t have. What a wonderful analogy for money too.

Psychological wealth is such an important concept, and with money it comes from proper expectations. Happiness is contentment. Contentment is what you have relative to what you want. Everyone’s life follows that formula, in one direction or another. All happiness in life is just the gap between expectations and circumstances.

The key is realizing that happiness is the state when nothing is missing, regardless of the lifestyle you’re living. The more you say to yourself, “I would be happier if I had this new car,” the more you’re just focusing on the fact that you’re not happy right now. Desire is a hidden form of debt that must be repaid before you get to feel any happiness.

When you don’t appreciate what you already have and only focus on what’s missing, nothing ever feels good enough. Happiness remains elusive. There’s a Stoic saying: “Not needing wealth is more valuable than wealth itself.”

Nothing is as desired as much as the thing you want but can’t have. In fact, for most people there’s a hierarchy of spending that goes something like this: If you don’t want something and don’t have it, you don’t think about it. If you want something and have it, you might feel OK. If you want something and don’t have it, you might feel motivated. If you want something and can’t have it, you drive yourself absolutely mad.

I’ll leave it to the excellent book The Molecule of More to describe the process: Dopamine is the chemical of desire that always asks for more—more stuff, more stimulation, and more surprises. In pursuit of these things, it is undeterred by emotion, fear, or morality. From dopamine’s point of view, it’s not the having that matters; it’s getting something—anything—that’s new. Your brain doesn’t want stuff. It doesn’t even want new stuff. It wants to engage in the process and anticipation of getting new stuff.

If you don’t have those things, then they can mean a great deal to you. When you do have them, they mean nothing to you.

People often chase the wrong emotion. They go for a buzz of happiness, which is fun but fleeting. It’s better to go for contentment, which feels even better and is much more durable.

“Happiness is that feeling you get right before you need more happiness.”

Once you view contentment as the ultimate psychological mountaintop, your goals change. You recognize that the dopamine game can never be won—there’s always a next level you’re striving for—and so the only way to win is to stop playing. To be content. And let me tell you: There are few greater monetary joys than realizing that you have everything you need, right now, to be as satisfied—even as happy—as you can be. The best measure of wealth is what you have minus what you want.

The most powerful definition of wealth is not what you have. What actually matters is the gap between what you have and what you want.

Everything You Don’t See Happiness depends on so much more than income. There are thirteen divorces among the ten richest men in the world.

Music executive Rick Rubin once echoed something similar: It’s hard to get really depressed until your dreams come true. Once your dreams come true and you realize you feel the same way you did before, then you get a feeling of hopelessness.

I think we mistakenly think that some kind of outward success is going to change something in us. And it does not. It may make life more comfortable. But it doesn’t change who we are. And any hole in ourselves that we’re hoping to fill does not get filled. And let’s say you spend 20 years of your life working towards something that’s going to solve everything, and then you finally achieve what you’ve been trying to do for 20 years, toiling away…and nothing changes. That’s when you get hopeless.

The late psychologist Daniel Kahneman once said, “Nothing in life is as important as you think it is when you are thinking about it.” He pointed out that “paraplegics are often unhappy, but they are not unhappy all the time, because they spend most of the time experiencing and thinking about things other than their disability.”

On average, individuals with high incomes are in a better mood than people with lower income, but the difference is about a third as large as most people expect. When you think of rich and poor people, your thoughts are inevitably focused on circumstances in which income is important. But happiness depends on other factors more than it depends on income.

If you’re already an unhappy person, it’s unlikely that more money will ever fix your problems.

A related point is that the core ingredients that truly make people happy—friends, family, health, meaning, a clear mind—cannot be purchased, only earned. When spending more money does make you happier, it’s usually for indirect reasons.

Never focus on what money can do for you without a clear understanding of the cost of acquiring more of it.

“Everyone is jealous of what you’ve got, no one is jealous of how you got it.”

Looking back, whether you lived a good life will likely have little to do with how much money you made or spent.

The Most Valuable Financial Asset Is Not Needing to Impress Anyone The ability to not need to prove yourself to strangers is priceless.

There are always two benchmarks to measure yourself against to determine how well you’re doing in life: internal and external. The first is how happy you are with yourself, the other is what other people think of you.

Warren Buffett once said: “The big question about how people behave is whether they’ve got an Inner Scorecard or an Outer Scorecard. It helps if you can be satisfied with an Inner Scorecard.”

Every decision we make when spending money falls into one of two buckets: Are you spending money on something because it makes people think differently of you—like you more, be more impressed with you, maybe even jealous of you—or because it actually feeds your soul and makes you happy?

What Makes You Happy A good life is everything you need and some of what you want. If you have everything you want, you appreciate none of what you have.

A weird thing is that everyone strives for a good life because they think it will make them happy. But what actually brings happiness is the contrast between what you have now and whatever you were just experiencing.

There is no such thing as an objectively good experience—every amount of “good” is just the gap between expectations and reality. It’s the distance between what you have now and what you either had or expected before. The contrast, not the amount, is what makes you happy. Few things are as important to keep in mind while spending money. A good life is everything you need and some of what you want. If you have everything you want, you appreciate none of what you have.

The thing that is least perceived about wealth is that all pleasure in money ends at the point where economy becomes unnecessary. The man who can buy anything he covets, without any consultation with his banker, values nothing that he buys.

Going from nothing to something can be so much more powerful than going from a lot to even more. Contrast, contrast, contrast. Once you see how powerful it is, you appreciate how important it is.

So much of being happy with your money is battling the hedonic treadmill—the ability to become accustomed to something you once considered a luxury. One way to fight back is respecting the idea that occasional treats can generate more joy than perpetual luxury.

When you expect nothing, everything is a surprise. When everything is a surprise, you walk around like Michael May, ecstatic over the littlest things you’d otherwise take for granted.

When you live a simple and modest life, your occasional experience with nice things can generate more joy than if you had those things all the time.

Christmas morning, the Fourth of July, birthdays, and the last day of school feel great because they happen just once a year. The same joy can be had when the luxury items in your life become occasional treats rather than constant needs.

A simple life can be the most potent way to enjoy luxury items.

When you are content with a simple life, the occasional treat truly feels like magic. The power of contrast can make ordinary things feel incredible and extraordinary things feel bland.

When you have no contrast against current experiences, amazing things can feel completely ordinary. When you realize how powerful expectations are, you put as much effort into keeping them low as you do into improving your circumstances. Happiness, contentment, joy…all of those things come from experiencing a gap between expectations and reality.

“In this lonely world of ice and emptiness, they had achieved at least a limited kind of contentment. They had been tested and found not wanting.” That’s about as good as it gets. The Rich and the Wealthy Being controlled by money is a hidden form of debt. And like all debt, it will eventually be repaid plus interest.

If you are rich, you have money in the bank that allows you to buy the stuff you want. If you are wealthy, you have a level of control over what that money does to your personality, your freedom, your desires, ambitions, morals, friendships, and mental health.

(Back to the tool: If someone asked why you’re using a screwdriver, you would not say, “Because I can.” You would say, “Because it helps me hang pictures on the wall and put furniture together.” The master-versus-tool framework is so powerful once you look for it.)

To be happy, you have to be yourself. If you blindly accept money’s ability to persuade your personality and dictate how you spend your day, it will quickly take control.

you can’t be happy with a partner if you can’t be happy without them. It’s the same for spending money.

If you’re already satisfied with who you are, you naturally view money as a tool to be used to make things even better. That’s when you become wealthy.

Separate what you like from what you want. They can be very different things. Many people like cigarettes because they feel good, but few actually want them. I like aimlessly scrolling through social media, but I don’t necessarily want to do it—these things are just addictive, and they control the person rather than becoming tools to help to enhance the person’s life.

There’s a Stoic saying—“You are unlikely to have a good and meaningful life unless you can overcome your insatiability”—that fits well here.

Don’t be proud of your consumption. Be proud of what you’ve built.

Utility vs. Status The value of anything is its ability to help you live the life you want. Nothing more. I once heard someone say that a high-end Toyota is a nicer car than an entry-level BMW, because the Toyota is filled with things that make driving more pleasant—plush seats, a great sound system, a moonroof—while the low-end BMW is mostly just bragging rights. I love that framing.

You’d want a high-end Toyota, not an entry-level BMW. You’d want utility over status.

Buying things for their utility gives you the ability to express your own identity, while chasing status often makes you conform to others’ identity.

Utility, by contrast, is deeply selfish in a beautiful way. Your top goal becomes bettering your own life and those you care about, the opinions and attention of others be damned.

The pleasure you get from utility can be more durable than pleasure gained from status.

know that when I’m ninety years old I will value a home with a nice view and memories with my kids—so I can invest in the utility those things provide.

Risk and Regret Good advice is never as simple as saying “Live for today” or “Save for the future.” The only good advice is “Minimize future regret.”

When dealing with money, risk isn’t how much you might lose. It’s not even necessarily how you’ll feel when you lose it—over time, a lot of painful experiences turn into cherished lessons. Real risk is the regret (or lack thereof) that might come years or decades later.

One of the biggest conflicts when managing money is finding the delicate balance between the two most powerful forces in the world: Compound interest, which turns patience today into fortunes tomorrow. The fact that you are one day closer to death than you were yesterday, so make the most of your short time here and enjoy every day you’re lucky enough to be alive. There is a Scottish proverb: “Be happy while you are living, for you are a long time dead.” The struggle is knowing how much you should invest for the future versus spend today.

I met someone a few years ago. When we parted ways he said, “Life is long. I hope we stay in touch.” Life is long. No one says that. They always say, “Life is short.” But obviously it could be either. We have no idea.

Good advice is never as simple as saying “Live for today” or “Save for the future.” The only good advice is “Minimize future regret.”

Amazon founder Jeff Bezos once described his decision to start an online bookstore in the 1990s: The framework I found which made the decision incredibly easy was what I called the regret minimization framework. I wanted to project myself forward to age 80 and look back on my life and I want to have minimized the number of regrets I have. And I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the internet that I thought was going to be a really big deal. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me every day. So when I thought about it that way it was an incredibly easy decision.

Good memories are the closest thing to living for today while compounding for tomorrow.

“The purpose of life is to experience things for which you will later experience nostalgia.”

I once heard an elderly woman say that the benefit to growing old was the ability to time travel in your head—to

Children are rich in health but poor in life memories; as you age, that flips.

I try to keep in mind that the things I am most likely to regret in the future will be the time I didn’t spend with my kids, the relationships with friends I didn’t put enough effort into, and certain things I’m stressed and anxious about today that I’ll eventually realize deserved more self-forgiveness.

People love to gawk at the power of compounding when investing their money. It’s much harder to think about the value of compounding memories you get by trading money for time, but the results can be just as incredible.

Saving for the future creates independence today.

Once you view savings as providing the benefit of independence, you stop viewing saving for tomorrow as sacrificing today.

A parable: A teacher stands before her class and says, “Here’s a math problem. There are ten sheep on a farm. One sheep runs away. How many sheep are left?” A student raises his hand and says, “Zero. There are no sheep left.” “It appears you don’t understand math,” the teacher says. “No, it appears you don’t understand sheep,” replies the boy. The urge to watch other people and copy what they’re doing without asking questions is so powerful, so pervasive, and explains so much of modern life.

Look at Them Jealousy, envy, and the priceless art of not caring what others think.

There’s a fine line between being motivated by what others have and you don’t (potentially good) and being envious of what they have and you want (always dangerous). Being motivated by what others have can be fun—their success is like an effective form of advertising for things you didn’t know existed. But being envious of others is mental torture, like a contract you’ve made with yourself to be miserable.

It’s nearly impossible to “win” the status game. What’s unique and enviable in one period becomes common and bland in the next.

Being jealous of what others have and assuming your life would be better if you were like them is misleading because you are not getting a full picture of their lives.

Being jealous of what others have is outsourcing your critical thinking to strangers.

Envy is inversely correlated with self-examination. The less you know yourself, the more you look to others to get an idea of your worth. But the more you delve into who you are, the less you seek from others, and the dissolution of envy begins.

The more you know yourself and become closer to what you want, the less you envy others even when they have what you don’t.

FOMO—the fear of missing out—is one of the most dangerous financial reactions that exists.

Dwight Eisenhower used to quote Napoleon, who said a military genius is “the man who can do the average thing when everyone else around him is losing his mind.” It’s the same with money.

Remove FOMO from the equation and what’s left? You only care about your own financial goals. You only care about the opinions of those you care about. You think long term and avoid getting sucked into fads and bubbles. And you don’t need much else to do well over time. Your propensity to be jealous of what others have can increase as you become wealthier.

When you have everything you need, you immediately shift to focusing on everything you might want, which is a never-ending list.

Everything worthwhile in life is just the gap between expectations and reality, and when your frame of reference is rich people trying to impress each other, that gap can close quickly.

The simplest formula for a pretty nice life is independence plus purpose. Independence plus purpose. Independence plus purpose. Independence plus purpose. The independence to do what you want, and the wisdom to want to do meaningful things. It’s not everything, but, boy, does it move the needle.

Spending on independence can be the most wonderful thing money can buy. And it’s more in your control than you might think.

Wealth Without Independence Is a Unique Form of Poverty Money you haven’t spent buys something intangible but valuable: freedom, independence, and being able to spend time in your own way.

Money you haven’t spent buys something intangible but valuable: freedom, independence, and being able to spend time in your own way. Every dollar of savings buys a claim check on the future. (And every dollar of debt you hold is a piece of your future that someone else controls.)

I view every cent of savings as a ticket toward a greater degree of financial independence, which is my true goal.

That whole idea—trading money for time, rather than trading it for stuff, because having more time is going to provide greater joy in your life—is probably the most overlooked aspect of spending money, because to most people the extra time and mental clarity you get from independence and savings doesn’t feel like “spent” money.

Nassim Taleb says, “What matters isn’t what a person has or doesn’t have; it is what he or she is afraid of losing. The more you have to lose, the more fragile you are.”

Wealth without independence is a unique form of poverty.

The trick is viewing every bit of savings as having actively purchased something, even if it doesn’t come with a receipt: You have purchased the ability to do what you want, when you want, with whom you want, for as long as you want. And it is priceless. Hush Money I think bragging is the inverse of how satisfied you are with life. It’s one of the most reliable psychological formulas around. In the movie Broadcast News, Tom Grunick asks, “What do you do when your real life exceeds your dreams?” Aaron Altman replies: “Keep it to yourself.” The more you want people’s attention, and the more you try to focus that attention on how smart, rich, and successful you are, the higher the odds that you’re trying to fill some sort of emotional hole. When I see people clearly bragging about how much money they make or spend, I try not to judge. I’d rather ask: Who are you trying to impress, what do they actually think of your boasts, and is your bragging unintentionally doing more harm than good? Social Debt When how you spend your money influences what people think of you in unwanted ways.

“It’s very expensive to be rich,” which is as true as it is absurd. The expense comes when people desperately try to keep up with spiraling social debt that’s attached to living a rich lifestyle.

The point is not to say you should avoid nice cars and nice homes—I like both. It’s a realization that once money goes from being a tool you can use to make yourself happy to a symbol of what other people measure you by, you’ve lost the game.

I want you to know that possessions are chameleons that change from fantasies into responsibilities once you hold them in your hands and that they take your eye from the heavens and rivet it squarely on the earth.

Naval Ravikant once said: The best position to be in is rich and anonymous.

Quiet Compounding The fastest way to get rich is to go slow.

“Nature is not in a hurry, yet everything is accomplished,” said Chinese philosopher Lao Tzu.

Let me reiterate the two ways to use money: One is as a tool to live a better life. The other is as a yardstick of success to measure yourself against other people. The first is quiet and personal, the second is loud and performative. It’s so obvious which leads to a happier life.

I’ve found it helpful to always ask, “Would I be happy with this result if no one other than me and my family could see it, and I didn’t compare the result to the appearance of other people’s success?”

Christopher Morley said, “There is only one success—to be able to spend your life in your own way.”

I’d rather wake up and be able to do anything I want, with whom I want, for as long as I want, than try to impress you with nice stuff.

Blitz-scaling? Blitz-failing.

That’s why old money wants a tax shelter and new money wants a Lambo.

A great irony in finance is that the fastest way to get rich is often to go slow. You’re never in a rush, never impatient, rarely worried or influenced by others doing things differently. You know that longevity and the ability to keep something going for the longest period of time is the true magic of finance. Like so many things in life, speed gets all the attention but slow has all the power.

You’re not in a hurry, yet everything is accomplished.

Identity When money controls who you are.

I paid twenty-five dollars a month for a little house—our grocery bill hardly averaged five dollars a week. Sometimes it seems that it might be better to go back to those simpler days, that one might get more out of a less complex life…. But it cannot be done…. One changes with prosperity. We all think we should like to lead the simple life, and then we find that we have picked up a thousand little habits which we are quite unconscious of because they are a part of our very being. There is no going back—except as a broken man.

I call it frugality inertia. It’s what happens when a lifetime of good saving habits can’t be transitioned to a reasonable spending phase.

If you develop an early system of saving and living well below your means—congratulations, that’s great. But if you can never break away from that system, and insist on a heavy saving regimen well into your retirement years…what is that? Is it still winning? Those whose ultimate goal is to stop thinking about money are stuck. Refusing to recognize that you’ve met your goal can be as bad as never meeting the goal to begin with.

  • Importante

Nature is very good at promoting one behavior even if it comes with some harm down the road.

And then you have to ask: Is the money serving you, or are you serving it? Is it your tool, or your master? Does it serve you, or do you serve it?

Value the ability to change your mind, change your lifestyle, alter your spending, and try something new.

The surest sign that something has become a dangerous part of your identity, and controls you rather than the other way around, is the inability to change your mind when you or the facts change.

“A belief is not dangerous until it turns absolute.”

“We are built with an almost infinite capacity to believe things because the beliefs are advantageous for us to hold, rather than because they are even remotely related to the truth.”

The strategy of having strong beliefs, weakly held, is often helpful.

Money should always be a tool to leverage who you are, not a goal in itself.

Try Something New I can’t recommend this enough: Within the confines of your budget, experiment with as many types of spending as you can, cutting quickly and without mercy the things that aren’t working for you.

Find what works and just do that. Ignore the rest.

When finding a new book to read, my strategy is to have a wide funnel and a strong filter. I want to start reading as many books as possible, but finish few of them.

“The man who doesn’t read good books has no advantage over the man who can’t read them,” said Mark Twain. Every smart person I know is a voracious reader who also says, “Every smart person I know is a voracious reader.” There are so few exceptions to this rule.

It’s impossible to know what you’re going to like until you try it, so you have to try everything. But the only way to try a million new things is to have a strong filter that immediately rejects what isn’t for you.

You should spend extravagantly on the things you love as long as you mercilessly cut the things you don’t.

If you can’t find your “thing,” there is a good chance that money has entrapped you, controlling your personality, and you are either addicted to saving money or ignorant of its potential, becoming unable to use it as a tool to provide joy in your life.

It’s common for people to default to whatever society tells them they should like.

Premium prices are often found on branded products, and the purpose of a brand is not to signal quality. It’s to signal consistency.

Learning what to quickly say no to can be more important than what to buy.

Monotony makes time speed up, variety makes it slow.

Anthony De Mello, always wise, says, “If you learn to enjoy the scent of a thousand flowers you will not cling to one or suffer when you cannot get it.”

Your Money and Your Kids Values, hard work, support, and the opposite of spoiled.

One nuance here is that it’s dangerous for you, as a parent, to live one lifestyle while you demand your kids live a different, more modest one.

Lead by example, not by humiliation.

“The parent-child bond is the most important relationship for a child’s mental health. When a child cannot meet a parent’s high expectations, that bond becomes jeopardized.” Find your own way—I don’t judge—but consider these points and pick your lifestyle carefully.

So much of success in life is learning how to fail without failing so hard you can’t recover. I want to prevent collapse. But I never want to use money as a crutch for my kids to avoid learning—on their own—the values of hard work, dignity, and managing failure.

noble goal as a parent should not be to raise successful children—success should be an offshoot of raising children who feel confident enough to find success on their own.

No amount of money can compensate for a lack of character, honesty, and genuine empathy toward others.

Warren Buffett says it’s good to have people in your life who you don’t want to disappoint.

I want to show my kids how you can use money as a tool to live a better life. I do not want to burden—or even poison—them with displays of insecurity and greed.

Kids may want your money, but what they’ll come to value—and remember you by—are the deeper values that money can’t buy. Spreadsheets Don’t Care About Your Feelings When emotions are more insightful than numbers.

Spreadsheets don’t care about your feelings. But sometimes those feelings are the most important part of a big financial decision.

I actually think managing money becomes easier when you come to terms with how emotional it can be. Instead of a math problem to solve, you view it as an emotional problem to fulfill, within the confines of some budgetary boundaries.

The Finer Things The wisdom, and futility, of obsessing over small purchases. Author Rory Sutherland writes, “The opposite of a good idea can also be a good idea.”

Author Kevin Kelly writes, “Tend to the small things. More people are defeated by blisters than mountains.”

The point is that small changes at scale yield massive impact.

The small, easy-to-ignore expenses add up to be so profound over time that they overwhelm the large, obvious costs you pay the most attention to. Price is easy to calculate. It’s just whatever you paid initially and sold for eventually. Cost is harder to figure out, because it tends to be a slow drip over time, which is easy to ignore but adds up quickly. Same for cars, boats, and hobbies. You can even say the cost of smoking cigarettes is the price of a pack plus the long-term cost of medical care associated with the habit. One is easy to calculate, the other is very difficult.

There’s a saying I love: Save a little bit of money each month, and at the end of the year you’ll be surprised at how little you still have.

Parkinson’s Law of Triviality. It states: “The amount of attention a problem gets is the inverse of its importance.”

Author Ramit Sethi says too many people ask 30,000 questions (what college should I go to?).

The amount of attention a problem gets is the inverse of its importance.

For the vast majority of people, a handful of budget items make up the vast majority of expenses: College Home Car Health insurance Childcare

Tending to small expenses can compound into a fortune. They can also suck your attention away from much larger problems. I don’t think these two points contradict each other. Remember, the opposite of a good idea can also be a good idea. They are equally important.

Save like a pessimist and invest like an optimist. Expect the worst, hope for the best. Live for today, prepare for tomorrow. Let me offer another: It’s almost impossible to build wealth without controlling your biggest expenses. And it’s very difficult to grow wealth without caring about smaller expenses.

The Life Cycle of Greed and Fear It begins innocent, turns crazy, and ends up right where you began.

Some she at once crushes beneath her cruel feet; others she condemns to a fate like that of galley slaves; a few she favors and fondles, riding them high on the bubbles of fortune; then with a sudden breath she blows the bubbles out and laughs mockingly as she watches them fall. —James Weldon Johnson on New York City

Greed and fear control so much in life. I think of it like this: There is no amount of success that can’t be destroyed by the temptation to grab too much of it. And there is no opportunity so appealing that it will catch the eye of someone who refuses to look.

Spending money often requires optimism; saving often requires pessimism.

So much of success in life is finding the delicate balance of when optimism turns into greed and pessimism turns into fear.

All greed begins with the most innocent idea: that you deserve to be right.

It’s hard to make it through the day admitting you don’t know how the world works. So almost no one does it. We tell ourselves that our beliefs are correct, and correct views will be rewarded. The conviction that whatever you believe is right, and you deserve to be right because you’ve put in so much effort to form those beliefs, and correct beliefs will be rewarded by the world, is such a common and innocent idea. And it’s where things start to get messy.

When you are rewarded for being right, a door opens inside your head that invites delusion to step inside.

way. This is an important part of greed: People justify their actions, even when in hindsight those actions were clearly excessive or crazy.

The common form of innocent greed is extrapolating with enthusiasm what worked in the past.

Greed happens when you double down on actions that at one time worked but aren’t sustainable, or that cause you to overestimate how influential your actions were on outcomes.

Peak greed is expecting to get back more than you deserve given what you put in. Which is exactly what happens when you overestimate your ability to do things that will directly lead to rewards.

Being locked into a single view is fatal in an economy where reversion to the mean and competition constantly dismantle old strategies.

After multiple failures, you begin to view yourself as a victim.

Admitting you were wrong is painful.

When you were greedy you believed that 100 percent of what you did influenced the gains you received. Now you think there’s nothing you can do that’s in your control that will deliver upside.

Fear does the most damage when your biggest fear is wondering what else you should be fearful about.

How to Be Miserable Spending Your Money A brief guide to bad decisions.

An important fact of life is that it’s often difficult to know what will make you happy, but quite easy to identify what will make you miserable.

Succeed by first knowing what to avoid.

Direct your gaze at the socioeconomic group just above you, assuming that within it you will find a level of durable happiness.

Have such a fierce saving ideology that you’re never able to treat yourself to a good life you can afford. Act like money’s only purpose is to accumulate in your bank account, where instead of a tool to live a better life you’ve essentially formed an accounting hobby.

The Luckier You Are, the Nicer You Should Be My simple path to a good financial life.

My only financial goal is to go to bed every night with a sense of calm, knowing my family is OK and that I can spend the next day doing what I want, when I want, with whom I want, for as long as I want.

Independence offers the highest ROI that money can buy, and I don’t think it’s even close.

Spend less than you make. Quietly compound. Money serves you, not the other way around. No one is thinking about you as much as you are. Independence is wealth. Health is wealth. Aim to be a good ancestor. Love your family.

So let me propose one last thought about money: The luckier you are, the nicer you should be. Having money can accentuate who you are, but it can also blind you to who others are.