Hacks are hard because shortcuts rarely exist. Prizes take time and effort.

The personal finance industry – filled with advice that sounds and feels good without moving the needle – needs to recognize this.

These aren’t fun hacks, but no one said this was easy.

Luck plays such a big role in the world. But few people want to talk about it. If I say you got lucky, I look jealous. If I tell myself that I got lucky, I feel diminished.

Maybe a better way to frame luck is by asking: what isn’t repeatable?

And maybe better yet: The way to get luckier is to find what’s repeatable.

The fun part of behavioral finance is learning about how flawed other people can be. The hard part is trying to figure out how flawed you are, and what stories make sense to you but would seem crazy to others.

A few of the best and most insightful things I've read lately. 

Woodrow Wilson was the only president with a Ph.D. in political science.

He came to office having thought more about how a government functions than most before him or since.

One of his complaints was that too many people in government held the belief that it was a Big Machine: that once you set up a series of rules you could take your hands off the wheel and let the government run on its own forever. They viewed government like physics, with a set of customs and laws that required no updating or second-guessing because they were believed to be precise and perfect as they were.

Wilson thought that was wrong. He viewed government as being a living thing that adapted and evolved. 

I really don't care about politics. But he had a theory that I think is so important, and so applicable, to us ordinary people managing our money. 

Mae West said, “Too much of a good thing can be wonderful.” That might be true for some things – health, happiness, golden retrievers, maybe.

But in so many cases the thing that helps you can be taken to a dangerous level. And since it’s a “good thing,” not an obvious threat, its danger creeps into your life unnoticed.

Take intelligence.

How could someone possibly be too intelligent? How do you get to a point where you realize you could have been more successful if you had been a little dumber?

Let me share three reasons why.

And if you're looking for another podcast to listen to, check out The Rundown by my friends at Public.com. It's a quick five-minute listen that gets you all caught up on the latest in the stock market, the economy, and in crypto. Hope you enjoy it. 

This episode discusses my take on what you should pay attention to when reading history. 

There’s a quote I love from writer Kelly Hayes who says, “Everything feels unprecedented when you haven’t engaged with history.”

It’s so true. History’s cast of characters changes but it’s the same movie over and over again.

To me, the point of paying attention to history is not the specific details of certain events, which are always random and never repeat; it’s the big-picture behaviors that reoccur in different eras, generations, and societies.

Let me share a little theory I have about optimism, and why progress is so easy to underestimate.

I’ll explain it in four parts.

Behavioral finance is now well documented. But most of the attention goes to how people invest. But the study of how you spend money might be far more interesting -- and practical. How you spend money can reveal an existential struggle of what you find valuable in life, who you want to spend time with, why you chose your career, and the kind of attention you want from other people.

There is a science to spending money – how to find a bargain, how to make a budget, things like that.

But there’s also an art to spending. A part that can’t be quantified and varies person to person.

There’s obviously a hierarchy of information. It ranges from life-changing good to life-changing disastrous.

That got me thinking: What would be the most interesting and useful information anyone could get their hands on?

Years ago I asked that question to Yale economist Robert Shiller. “The exact role of luck in successful outcomes,” he answered.

I loved that answer, because nobody will ever have that information. But if you did, your entire worldview would change. Who you admire would change. The traits you think are needed for success would change. You would find millions of lucky egomaniacs and millions of unlucky geniuses. The fact that it’s impossible to possess this information doesn’t make it useless – just thinking about how powerful it would be to have it forces you to ponder a topic that’s important but easy to ignore.

Keeping the idea that the most interesting information doesn’t have to be realistic – it can be impossible-to-obtain, magical-wish thinking – here are three other things that would get your attention.

There are two big ways to learn: 

Active learning: Someone tells you what to learn, how to learn it, on a set schedule, on pre-selected standardized topics.

Passive learning: You let your mind wander with no intended destination. You read and learn broadly, talk to people from various backgrounds, and stumble haphazardly across topics you had never considered but spark your curiosity, often because it’s the topic you happen to need at that specific time of your life.

I can’t be alone in realizing that most of what I’ve learned in life has come from passive learning.