Assured Misery

Collaborative Blog


People tend to know what makes them angry with more certainty than what might make them happy. Happiness is complicated because you keep moving the goalposts. Misery is more durable.

So you can move the needle a lot by focusing on what not to do in life.

A few little things to avoid:

1. The inability to deal with petty criticisms.

Alexander Hamilton was one of the most talented Americans to ever live. But he had a flaw: Born into nothing without a prominent family name to leverage, he was hypersensitive to anyone criticizing his reputation.

The first time this backfired was when a judge named Aedanus Burke called Hamilton a liar. Hamilton challenged the judge to a duel. Burke quickly apologized, but congressmen were stunned at Hamilton’s willingness to die over a petty exchange.

A decade later Hamilton’s 20-year-old son, Philip, heard a speech where a lawyer claimed the Hamiltons might try to overthrow the presidency. Philip was so shaken that he continued the family tradition, challenging the lawyer, George Eacker, to a duel. Alexander wasn’t just aware of the duel; he counseled his son on how to do it properly. But these things are 50-50: Philip died.

Three years later Hamilton claimed Aaron Burr had no principles and would do anything for power. Burr asked for an apology, which Hamilton seemed to interpret as an insult to his dignity. He called for a duel, which took place at the same spot Philip was shot. An hour later the same surgeon who tried to save Philip was operating on a wounded Alexander, with the same outcome. The most talented American would not live to see his 50th birthday.

The inability to deal with criticism, even when it’s unwarranted, is a sure path to misery.

The line between “protecting your honor” and “dangerously thin skin” is pale.

Warren Buffett says the definition of success is when the people you want to love you do love you. A corollary is not to sweat it when people you don’t care about don’t love you.

2. Envy of others’ success without having a full picture of their lives.

Most things you envy look better from the outside, because everyone crafts a selected image of what they’re doing and they are. A lot of time you’re envious of someone specifically because that person has done a good job crafting the image of their life. But since they’re crafting the image, it’s not a complete view. There’s a filter. Skills are advertised, flaws are hidden.

Instagram is full of beach vacation photos, not flight delay photos. Resumes highlight career wins but are silent on doubt and worry. Investing gurus are easy to elevate to mythical status because you don’t know them well enough to witness times when their decision-making process was ordinary, if not awful.

The problem is that when you are keenly aware of your own struggles but blind to others’, it’s easy to assume you’re missing some skill or secret that others have. It’s a sure path to feeling inadequate.

Everyone’s dealing with problems they don’t advertise, at least until you get to know them well. Keep that in mind and you become less envious and more forgiving – to yourself and others.

3. The inability to deal with hassle, delay, setback, and nonsense, caused by a desire to squeeze maximum efficiency out of everything we do.

Just-in-time manufacturing – where companies don’t stock the parts they need to build products, relying instead on last-minute shipments of components – was the epitome of efficient operations over the last 20 years. Then Covid hit, and virtually every manufacturer found itself dreadfully short of what it needs.

A sneaky kind of assured misery is when you have no room for error in your life, which feels like maximizing efficiency but actually just means you’re guaranteeing disappointment when the world inevitably wobbles.

There’s always an optimal amount of hassle in life – a rate of imperfection you should embrace. This is partly because it’s realistic; people you work with have bad days and difficult personalities, which have to be dealt with if you want to get anything done. And it’s partly protective: Once you accept a certain level of baloney, you stop denying its existence and have a clearer view of how the world works.

4. Being persuaded by the advice of those who need or want something you don’t.

No one criticizes marathon runners for training and eating, differently from powerlifters, despite both being athletes. ESPN covers sports, yet no anchor pretends golf and mixed martial arts are remotely similar. People playing different games want different things and play by different rules.

But that logic breaks down when we talk about things like investing and careers.

What you want might not be what I want.

What’s fun to you might be miserable to me.

Your family’s different from mine. Your job’s different from mine. You have different life experiences than I do, different role models, different risk tolerances and goals and social ambitions, work-life balance targets, career incentives, on and on.

If you view investing as a single game, then you think every deviation from that game’s rules, strategies, or skills is wrong. But most of the time you’re just a marathon runner yelling at a powerlifter. So much of what we consider investing debates and disagreements are actually just people playing different games unintentionally talking over each other.

Two things come from this.

One is that if you accept that people play different games, you become less cynical and upset that people manage their lives differently from your own.

The second is more important.

If you don’t realize that people play different games you might be persuaded by advice and tactics of people who want or need something you don’t.

It can be a miserable path, because you might be getting advice from good, honest, well-meaning people, and the advice they give can be excellent for them and others playing their game. So it checks all the boxes. But it can still be disastrous to you.

Define what game you’re playing and play it (and only it).

5. Expectations rise equal or faster than results, leading to constant disappointment no matter how much you’ve accomplished.

All wealth, all success, all accomplishment, is a two-part equation: A result relative to expectations. What you have and what you expected to have.

When you realize that each part is equally important, you realize that the overwhelming attention we pay to getting more and the negligible attention we put on managing expectations makes little sense, especially because the expectations side is more in your control.

Warren Buffett once told a group of college students that they all lived better than John D. Rockefeller:


I mean you’re warm in winter and cool in summer and can watch the World Series on TV. You can do anything in the world. You literally live better than Rockefeller. His unparalleled fortune couldn’t buy what we now take for granted, whether the field is—to name just a few—transportation, entertainment, communication or medical services. Rockefeller certainly had power and fame; he could not, however, live as well as my neighbors now do.

This is one of those technically-right-but- contextually wrong problems. Rockefeller never had Advil or sunscreen or penicillin. But nobody today wakes up feeling richer than Rockefeller because everyone judges how well they’re doing relative to those around them. And since somebody is always getting richer than you, faster than you, with what appears like less effort than you’ve put in, and what looks like more enjoyment than you’re getting, it’s so easy for the goalpost to move even if you’re technically doing well in life.

Managing expectations and getting the goalpost to stop moving is one of the hardest tricks in life. But it’s so essential. A big part of it is realizing that managing expectations doesn’t have to mean being conservative or unambitious. It’s just realizing that an insatiable appetite for more will always push you to the point of disappointment and regret – always, every single time. So having some ability to deny an extra dollar of work, or a potential opportunity, a bigger house or a nicer car, is essential if you want to use money to make a better life.