It’s a holiday week, and the markets aren’t even moving a centimeter, so we’re going to do a little navel-gazing.

I asked my mother a question the other day. I asked her if I met or exceeded expectations. Meaning: what kind of adult did she think I would turn into, and how did I do relative to the forecast?

She was a bit taken aback by the question. She said that financially, I had succeeded beyond her wildest dreams. She also said that I picked an amazing partner (I have been happily married for 21 years). She said she never would have predicted that I would serve in the military. And that she never thought that I would make a career out of writing.
I don’t have children, but I suspect most parents mentally measure their children’s success to a certain extent.

Yes, I have been financially successful. Why?

Before we answer that question, let’s talk about billionaires. In my lifetime, I have known a few billionaires. I can count them on one hand. They all have two things in common:

• They are really good at doing a thing.

• They are relentless in the pursuit of that thing.

There’s no trick. Social skills help, connections help, luck helps, organizational politics help, but none of these things on their own will push you over the edge. You need to be the best at something, and you need to be relentless about it.

I really like markets and I really like writing and I really like writing about markets! I will never get to be a billionaire writing about markets, but that has never been my ambition.

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Talent and Relentlessness

I have not met many people who are making high six or seven figures by half-assing it. You have to be a little bit crazy and obsessed. Take a guy like Michael Phelps. Everyone knows he spent a lot of hours in the pool. Take a guy like Tiger Woods. Everyone knows he spent a lot of hours on the golf course.

Take a guy like Jeff Bezos. He spent a lot of hours in the office! Although he does seem to have a bit more free time these days.

Talent, you are born with. Can you cultivate relentlessness? I don’t know.

Growing up, nobody put a lot of pressure on me to succeed. I put it on myself.

The people at the highest level of government, the highest level of business, and the highest level of academia are all a bit relentless.

I am far from the only person in the world who works hard. In fact, I have been semi-retired since 2008.

But if you trained a camera on me all day, you would see that I don’t sit still. I’m always doing something.

It’s funny—I actually kind of have a reputation as being one of the few young people on Twitter (and certainly perhaps the only libertarian) who are against marijuana.

I’m not against legalization—it should certainly be legal—but I think that any drug with a reputation for destroying ambition should be viewed with great suspicion. I guard my ambition with my life.

Why It Is Good to Be Underpaid

I never want to be overpaid.

I have known a few overpaid people in my life, including one person right now. That person is having an existential crisis of massive proportions.

Rationally, we should all want to be overpaid. Everyone wants to get paid more for less work.

But if you are underpaid, you are scrappy. You are always trying to make what you think you are worth. It’s also how you stay grounded. (Hard for the richest man in the world to stay grounded.)

The moment that you become overpaid, you lose your relentlessness. I have seen it happen many times before.

Since I like to write about personal finance, this is my challenge. I can teach people how to save, I can teach them how to manage expenses, I can teach them how to optimize their taxes, I can teach them how to invest, but it is very, very hard to teach relentlessness. And relentlessness determines the top line, which is a lot more important than the bottom line.

One last thing. James Holzhauer, who is currently mopping the floor with the competition in Jeopardy! and setting records left and right, was asked by Alex Trebek if he acquired all his knowledge in school.

“I hated school,” he said. “I read what I wanted to read. And I forced myself to read stuff I didn’t want to read.”

I am also relentless about music. Please enjoy my latest creation, The Lost.

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