Being Good at Roulette

Luck causes problems.

July 31, 2020 • 5 min read

The first time I visited Las Vegas was on a business trip. I was 21. My official mission: train a large customer on our new software. My unofficial mission: try my hand at a Vegas table game.

Now, I’m a pretty logical person. Given that there is no such thing as luck, I knew that betting at a casino is irrational – unless perhaps you’re cheating, or you’re very good at poker. Still, I thought it would be fun. Pay $20 to say I lost some money in Vegas.

So on my first night, once I was happy with my slides, I ventured down to the casino floor of our hotel. I observed the various games as I passed by, but I knew where I was headed: roulette. It seemed to me that there was no simpler, no purer a way to lose your money in Vegas than roulette. The nakedness of its terrible odds were part of the charm.

I approached a table, and watched the guy ahead of me play, studying the etiquette. When he cashed out, I sat down and turned my $20 into 4 chips, $5 each.

Nervously, I reached out and made the simplest bet I could. $5 on black; I won $5. I put another $5 on black, and again won $5. “Okay, I get how this works.” But I wasn’t there to try and beat the house. I was there to lose my $20. So I took $5, and put it on 17. And won $175.

Of course, I made the next logical move: I cashed out immediately. I had gotten temporarily lucky, and I cashed out feeling like king of the world. I bought a hideously expensive whiskey cocktail and felt proud for trying something new.

The next day, as I was gearing up to fly home, I found myself passing near that casino floor again. Remembering how much fun I had last time, I thought I might as well take a second crack at my goal of losing $20. I sat down at a different table, but this time went right to my patented strategy: I bet $5 on 17. And holy shit, I won $175.

Now, this is not a great thing to happen to somebody. I mean, in one way it was extremely great – sweet, another $175! And cerebrally, I knew that hitting two single bets in a row is an extreme fluke, a 1444 to 1 chance. But the emotional high from that hit, the endorphins and adrenaline, it messes with you. You can enter a casino a logical human being, yet next thing you know you’re asking yourself, “Huh. Am I… good at roulette?”

You will be surprised to learn that I am, in fact, not good at roulette.

After promptly losing $100, I cashed out and headed to the bar. This time I felt less like king of the world, and more just a participant in the human condition. Still, I suppose, $100 was a small price to pay to learn conclusively that I am not good at roulette.

Luck tends to cause problems. When I say luck in this context, I don’t mean the fostered luck that results from being open minded, observant, and keeping a positive mindset. It does seem that people who think of themselves as chronically lucky do have more positive things happen to them, partially due to how they approach life.

Random luck, though, that just happens. Random luck is something you stumble upon. It’s the privilege you were born into, and the coin flips that have gone your way since. While it’s certainly nice to receive random luck, it’s not all roses. When something goes your way, your instinct is to feel like you’ve earned it. Random luck can initially make people feel guilty, and that cognitive dissonance often leads to people reframing their good fortune as the product of skill or hard work. The next thing you know, people feel entitled to the spoils of chance.

Besides the thorny problems of entitlement, if you’re not careful random luck can also make you a less effective person. At best, an unearned windfall can make you less motivated, less hungry to make things better. More dangerously, a lucky success can make you overestimate your skill, leading to a kind of luck-generated Dunning-Kruger effect.

As it happens, most great leaders seem to intentionally stay mindful of the role luck has played in their successes. When luck comes up, Barack Obama is eager to acknowledge the factor it played in his life – skill and hard work were necessary, but not sufficient to achieve what he did. Meanwhile, if you ask his successor about luck, you’re more likely to hear about how luck just amounts to hard work, or that success is not due to luck at all. Such are the differences between a thoughtful leader and a lucky idiot.

In fact, the majority of the highly successful CEOs they study in the book Good to Great name luck as a key factor in their success. While that is kind of strange – the whole point of the study was to determine what objective factors lead to successful companies – luck-awareness seems to actually make people more effective. Correctly attributing some of your success to luck seems to inoculate you against arrogance, and foster that lucky mindset, which we know can itself be helpful.

So, it seems, that’s the formula. Next time you have an unexpected success, don’t let it rob you of your humility. Don’t let your mind trick you into believing you’re somehow good at roulette. But do try to be mindful of your good fortune.

I bet you can think of five reasons you’re lucky right now, and you can create even more luck just by adopting a positive and open perspective on things. All because you happened to read some blog post about roulette.

I suppose you’re just lucky.

Liked this? Follow along to see what's next.

© Allen Pike. You can find me on Twitter, contact me, or check out Steamclock.