The Long Shots

I have a favorite type of hand in poker. I like it because it makes up a huge chunk of my winnings at poker, is good solid play, and looks idiotic to bad poker players. It’s the kind of hand that pulls hundreds of dollars in your direction, and sometimes a couple angrily-thrown cards from your opponent when he’s beaten, too.

Technically the hand would be called a plus-EV underdog draw, or something like that. In plain English, it’s a long shot where you have the right odds to take it.

An example might be if I have four cards to a straight and I’m missing one from the middle. So maybe I have 4 5 6 8 of various suits. Let’s say that there’s still one more card to come. There are forty-six remaining cards (just trust me on this one), and only four of them, the sevens, will help me. I have less than a ten percent chance at winning the hand.

And yet, sometimes it’s worth calling to see the next card. If it costs me thirty dollars to see it, but there’s six hundred dollars in the pot, then mathematically I’m way ahead.

This type of hand comes up pretty frequently. Good players understand it, but when a bad player loses to you, he sometimes gets furious. After all, you were behind the whole time, you kept putting money in, and you got lucky at the end. It’s not fair! What the bad player isn’t considering is how big the payoff is. Sometimes it’s worth persevering against steep odds because the payoff is so great.

I get called lucky a lot in real life. Sometimes it’s a compliment, and other times it’s something else. On one hand, I agree– being born to a loving middle-class family in a safe environment is such an incredibly great thing, that it alone has given me an unfair advantage over most of the world’s population.

But among those from similar backgrounds, considering the risks I’ve taken and the payoffs from those risks, I doubt I’ve gotten much luckier than the average person. If you were to calculate my chances of success, the benefit of that success, my chances of failure, and the costs of those failures, and then calculate where I should be, I bet I’m right on the money.

My secret is that I take long shots all the time. I love them. People shy away from high-risk / high-reward situations, so there’s often a lot more meat on the bone in those areas. In the short term these long shots add a great deal of variance (a nicer sounding word for chaos) to my life, but in the long run they keep paying off, making my life better and better.

Some examples:

— When I was nineteen I looked at online gambling and figured that their might be a way to beat it. So I risked some of my money and time, and it ended up funding my life for around seven years and teaching me a ton about decision making.

— Nine years ago I started this blog. I wasn’t taking much of a risk then, but a few years later, with only a small number of followers, I decided to commit to it and write consistently. The amazing things that have happened as a result are innumerable.

— When I learned about pickup as an introverted and inexperienced twenty-year-old, I bought a ticket to Chicago to try to meet the best guys in the game. They took me under their wings and taught me confidence and skills that have shaped who I have become.

You might ask what bad things happened to me. And, of course, most of my long shots don’t go well. That’s the definition of a long shot, though– usually they don’t pan out. But when they don’t pan out, the downside is pretty small. If I had lost a few hundred bucks gambling and then stopped, it would barely be a footnote in my life. If nothing came of my blog and it went by the wayside after a couple years, I would have barely noticed missing the time I spent writing. And if I’d never learned pickup, I would have only been out a ticket to Chicago.

I bother writing about long shots not because they’re the only way to have a life you want or because I think that everyone should take as many of them as I do, but because they’re overlooked opportunities. Long shots are seen as the territory of the lucky and the crazy, except to those who actually take them and realize that they pay off big enough and often enough to be worth it.

The key is to get out of the mindset that something has to be a sure thing, or even just most likely to work, before undertaking it. If you only focus efforts towards those narrow categories, you’re missing out on the vast majority of opportunities that will come your way. Any time you assess your life and notice that everything you’re doing is a sure thing, think further to your reach goals and fantasies about how life could be, and start working towards one or two of those. Go for enough long shots, and some of them work.

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Photo is the Rijksmuseum in Amsterdam. I thought I was really being clever by switching to cell phone photos, but my friend Amit told me they aren’t as good as the ones I took with a real camera.

You can now book cruises directly through Cruise Sheet, and all of them come with a bonus of onboard credit (money you can spend on the ship). I’ve also made a bunch of other changes to the site, so check it out.


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