What Machiavelli Understood About Luck

If it’s all luck, why bother?

I’ve heard some version of that question several times since July, when I wrote We Live in a Sample Size of One, an essay expanding upon a topic from my book. In it, I argued that variance plays a bigger role in our lives than we like to admit, and that the “long run” it takes to even out is often longer than most of us will live.

Some of you wrote back to say it resonated. Two of you pushed back with the same question: If so much of the outcome is out of my hands, why should I work so hard?

I understand that question, because I’ve asked it myself.

During the pandemic, I tried to shift from cash games to tournament poker. I worked hard and started seeing some success online. Thinking this would translate to live tournaments, I traveled to the World Series of Poker three times, hoping to make a deep run in a larger event. Over those three years, I entered about fifteen tournaments and cashed in only one.

Fifteen tournaments is nothing. Online, I’d sometimes play that many in an evening and cash in zero or one; other nights I’d cash in seven and make a final table run in two.

But that’s hard to keep in perspective when those fifteen are spread across three trips and three years. I remember wondering why I was putting in all that work when so much of the outcome came down to things out of my control. In the middle of a bad run, it’s difficult to stay consistent and trust your process.

That “why bother?” mindset is fatalism. I get its appeal, especially for anyone who has spent time on the wrong end of the luck distribution.

But “much of life is variance” and “so why try” are two different claims. I believe the first — luck decides more of life than most of us are comfortable with.

I also believe that good inputs and consistent effort shift the odds in our favor. Luck scatters our results around a baseline. That baseline — the expected value of our efforts — is the part we can move.

History’s best thinkers wrestled with this same question. One of its sharpest strategic minds answered it five hundred years ago.

Niccolò Machiavelli has a mixed reputation. We call someone “Machiavellian” when they scheme, deceive, and manipulate to get ahead. I think that reputation is only partly earned.

Machiavelli spent years as a diplomat and official for the Florentine republic. In 1512, the Medici family returned to power, and he lost his post. Early the next year, he was arrested on suspicion of plotting against them, jailed, and tortured. After his release, he retreated to his farm outside the city and wrote The Prince. The book’s dedication ends with a line about how he suffers “a great and continued malignity of fortune.”¹

This is a man writing from the wrong end of the luck curve. He had every reason to be a fatalist. He opens Chapter 25 with the fatalists of his own day:

That’s more or less the objection I’ve been hearing, written in 1513. Machiavelli even admits that he’s sometimes “in some degree inclined to their opinion.” But he turns back to say:

I don’t know whether half is the right number. Machiavelli wasn’t sure either — “or perhaps a little less” is him hedging. The exact share matters less than the fact that we can influence some of the outcome.

Machiavelli then compares fortune to a river in flood. No one can stop it. But as he writes, “it does not follow therefore that men, when the weather becomes fair, shall not make provision, both with defences and barriers.”

We can’t stop a hurricane or a flood. But we can build levees before it arrives. The levees won’t guarantee that the city survives, but they improve the odds.

Most of our levees are far smaller decisions. Keeping junk food out of the house is one. You make the decision on a calm day, so it’s already made the night your willpower runs out. A savings cushion is another. If you lose a job or your income drops, the cushion carries you through for a while. Neither stops the storm, but both can help you get through it.

Preparation works for good luck, too. In Chapter 6, Machiavelli writes that history’s great founders owed fortune nothing beyond opportunity. He adds: “Without that opportunity their powers of mind would have been extinguished, and without those powers the opportunity would have come in vain.”

Nassim Taleb makes a similar case in modern terms in his Incerto series: protect yourself against the catastrophic bad breaks, and stay in position to benefit from the rare good ones.

I’m a big fan of Robert Greene’s books. In the past few years, I’ve read The 48 Laws of Power, Mastery, and The Laws of Human Nature, and I’m currently reading The Daily Laws, which explores one idea from his books for each day of the year.

Greene gets some of the same criticism Machiavelli does. He addresses it in his introduction to the September entries:

Greene goes on to credit the ancient Greeks with the idea that stupidity and incompetence do more harm in the world than outright evil. We can see evil coming and fight it. We don’t recognize incompetence until it’s too late.

I agree. Being strategic and being devious are different things. Plenty of devious people are strategic. So are plenty of good ones.

This is where a philosophy comes in. Mine is Stoicism. Virtue and principles act as constraints, and as David Epstein argues in his excellent new book, Inside the Box, constraints tend to improve outcomes.

Virtue decides what I’m willing to pursue and which lines I won’t cross. Strategy is how I pursue it well.

This is the idea I built The Stoic Systems Thinker on. Systems thinking is a way of being strategic: it shows you how the system in front of you works. Stoicism sets the priorities and boundaries you operate within.

In the past month, I’ve come back to Greene’s September 5 entry multiple times. There’s a line I’ve underlined: “The essence of strategy is not to carry out a brilliant plan that proceeds in steps. It is to put yourself in situations where you have more options than the enemy does.” Sun Tzu made the same point roughly 2,500 years earlier. Don’t follow a script. See the whole board, and adjust as it changes.

None of this guarantees a win. It puts you in a far better position. And we can see what that looks like.

I couldn’t write about luck without a poker chart. Let’s bring back our hypothetical poker player from July.

As a quick refresher, he played fifty Saturday nights a year and won an average of $200 per session — about $10K a year.

In July, I simulated one hundred copies of him. The only thing separating their results was variance. The luckiest made almost $30K. The unluckiest lost about $10K. Nine of the hundred lost money over the year.

This time, I’ve added two players at the same Saturday game. A weaker one averages $100 a session. A stronger one averages $300.² I simulated each of the three one hundred times, with every run getting its own good and bad breaks.

The first thing to notice is that the swings don’t go away. Each of the three has great years and awful ones.

What moves is the baseline. The whole cloud of results shifts. Of the $100-per-session players, thirty-five lost money on the year. Of the $200 players, nine did. Of the $300 players, only one. The unluckiest of the $100 players lost almost $13K on the year. The unluckiest of the $300 players lost about $1K. Bad luck still arrived, but the stronger player absorbed it.

The better player doesn’t always come out ahead, though. Sixty-nine of the $100 players finished the year ahead of the unluckiest $300 player. As we learned in July, one year proves nothing. But the overlap only goes so far. Eleven of the $300 players finished above the best year any $100 player had.

A higher baseline changes which results are within reach.

The world is made of systems. Understanding how they work doesn’t take the luck out of them. But it does raise your odds of success inside them. That’s why I wrote The Stoic Systems Thinker: to help you think strategically through a problem and nudge your baseline a little higher.

Others are making the same case. Last year in Harvard Business Review, Tima Bansal and Julian Birkinshaw called systems thinking “the best way to anticipate the many secondary effects of change in an interconnected world.” And on a July episode of Lenny’s Podcast, Elizabeth Stone, Netflix’s chief product and technology officer, named it the skill she’s hiring for: “We need more systems thinkers in a world with AI.”

The small systems we start today can compound over time. My own writing is an example. In 2020, I started a poker blog and began writing consistently. The blog led to a commonplace book, then to a Zettelkasten, a system of small, connected notes. None of it was aimed at a particular goal. I just enjoyed the practice. But by the time I thought seriously about a book, I had years of material to draw from and enough finished writing behind me to believe I could do it. I never planned the head start. I kept building in fair weather, and when the opportunity came, I was ready.

The Stoics are often misread as passive, people who shrug and accept whatever comes.

In practice, they governed. They served their communities. They raised families. They prized phronesis, the practical wisdom to do the right thing with whatever is in front of them.

Consider Marcus Aurelius. He became emperor in 161 AD, after his adoptive father, Antoninus Pius, had reigned for twenty-three largely peaceful years, one of the longest such stretches in Roman history.

Marcus’s own luck ran the other way. War with Parthia broke out in the east that same year. Soldiers returning home carried a plague with them that killed millions. And then came years of war along the Danube. He controlled none of that. He governed anyway, and wrote the private notes that became Meditations.

Machiavelli admired Marcus Aurelius, too. The label “Five Good Emperors” traces back to a list Machiavelli made in his Discourses on Livy, with Marcus as the last name on it.

Machiavelli gives Fortune half. The Stoics give her every outcome and keep every choice. Neither leaves room to sit still and do nothing.

Last month, I gave my first talk about the book at Booksweet in Ann Arbor. Thank you to those who came out. I’m working on a few more speaking and podcast dates for this fall. I’ll share them here as they firm up.

If you haven’t picked up The Stoic Systems Thinker yet, you can find it on Amazon. And if you have, a review goes a long way.

All the best,
-Michael