Having played a fair amount of blackjack (I learned card counting when I was 21), I’ve noticed some interesting patterns in the way people play the game that seem to reflect larger life patterns.

Background Story

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Feel free to skip ahead to the “Interesting Observations” section if you just want to read the lessons. This part simply provides some background info for the curious.

When I was 21 years old and living in Los Angeles, some friends and I decided to take a weekend trip to Las Vegas, my first trip there as an adult. I decided to read up on some of the casino games before I went, so I could be prepared.

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I quickly learned that most of the casino games were skewed to give the house an advantage — how unfair is that? — but blackjack was supposedly beatable if you learned a technique known as card counting. So I bought a book on blackjack, learned the rules of the game, memorized the basic strategy, and then studied a simple +/- card counting system. It took a heck of a lot of practice and was tedious to learn, but I eventually felt comfortable with it. Then I was off to Vegas to try my luck with a whopping $40 of gambling money. Not much of a bankroll I know….

My friends and I stayed at the Aladdin Hotel (before it was demolished and rebuilt). Since there are many variations on blackjack rules, I scoped out the nearby casinos to find one that had the best player-favorable conditions. That turned out to be the Barbary Coast on the Strip (across the street from Caesar’s Palace), which had a nice double-deck game with liberal rules (the fewer the decks, the better for the player, all else being equal). Plus they offered a $2 minimum, so my $40 had a chance of lasting. $400 would have been a more adequate bankroll for that limit, but at the time I didn’t want to risk $400.

I felt a bit intimidated playing blackjack for the first time in a real live casino. But I trusted I was as prepared as I could be, so I sat down and dove in. The preparation paid off, and after a few minutes I began to feel at ease. Aside from making a few minor etiquette mistakes, I played my hands perfectly and had no trouble keeping track of the cards. After a few hours of playing I had turned my $40 into $165 while betting only $2-10 per hand… making more than enough to pay for my trip expenses. This was during the time when you could still find buffets for about $5.

After that first trip I was hooked on the game, not so much for the money but for the challenge of it. Card counting appealed to the nerd in me far more than the entrepreneur. I made many return trips to Vegas and played in dozens of different casinos all around the city. One of my favorite places to play was the Frontier Hotel, which used to have a single-deck game with generously player-favorable conditions. That was very lucrative until they changed their rules, like many other casinos eventually did, probably in large part due to card counters.

Between Vegas trips I studied blackjack and card counting ever more deeply. I read 10-12 books on the subject and mastered different counting systems (Thorpe, Uston, Revere, etc.). I practiced advanced counting systems that keep a side-count of aces. I drilled myself until I could count down a deck of cards in under 14 seconds. I learned to vary the play of hands according to the count, memorized optimal strategies for different rule sets, and learned the subtleties of the game that would increase my edge even the slightest degree. We’re talking a total edge of maybe 1%.

As I gained experience, I became comfortable doing all these mental gymnastics under actual casino conditions. I learned to play cat-and-mouse with the pit bosses. I even got a lot of comped meals for myself and my girlfriend (now my wife), although we got tired of eating at the same places over and over. Casinos have grown stingier with the comps, but back then you could play $5 blackjack for about 30 minutes and get a free buffet for two without much difficulty (and without being asked to join a players club).

Card counting isn’t illegal, but casinos will kick you out for it and sometimes ban you for good. Fortunately I was never banished for life anywhere, and I was only kicked out once (from the Barbary Coast of all places). Mostly this was because I played only in the $5-25 or $10-50 range of betting… too small for the casinos to care much. At that level I certainly wasn’t going to get rich, but I was doing this more for fun than for profit.

The funny thing is that now I live in Vegas, I hardly play blackjack at all… I’ve played only twice this whole year for a total of about 45 minutes (and won both times). Even though I found that card counting worked, I never seriously considered trying to make a career out of it. For one it’s very hard work, and for another it doesn’t contribute anything. I still enjoy blackjack as a diversion sometimes, and I like meeting people from around the world at the table, but I wouldn’t want to try to make a living from it.

Interesting Observations

While learning to master the game of blackjack, I made a number of observations in the way players approached the game, especially the contrast between novice and expert players. Most people who play blackjack are novice or intermediate players. During all the times I played blackjack, I felt I had identified another card counter at the same table with me on only two occasions. In both situations we could each tell the other person was counting cards, and we gave each other knowing looks. But card counters are extremely rare as a percentage of total players… way, way below 1%.

1. Novices will make correct decisions most of the time. About 80-90% of the time, novices will play their hands the same way an expert player would. But the house gains a big advantage on the 10-20% of decisions they don’t make correctly. That 10-20% makes all the difference in the world between winning and losing because it’s cumulative. How is this different from other parts of life? An extra 10% makes a big difference. Eat 10% less food, and you lose weight. Save 10% of your income, and you retire a millionaire. Spend 10% of your day on some key goal, and by the end of the year, you’ve written a book, started a business, or found a mate.
2. Novices miss golden opportunities. Novice blackjack players will almost invariably play their hands too conservatively. They’ll stand too often when they should hit, and they’ll fail to double down and split pairs as often as they should. They hesitate to hit 16 against a dealer’s 7 or to split a pair of 2s against a dealer’s 4. They give up a lot more to the house by playing defensively, trying not to bust. But expert players exploit every opportunity to maximize their wins, meaning that they’ll double and split far more often when the odds favor doing so. Expert players will bust more often, but they’ll also hit their big hands more often. You see a similar pattern in life too. High achievers will bust more often, while underachievers play too conservatively, afraid to take calculated risks for fear of losing what they have. In blackjack, it’s those splits and double down hands where you make your real money. Novice players think it’s the ten-ace blackjack hand that’s the best — the guaranteed win. Expert players know it’s those hands where you split pairs 4x and double down on each one and see the dealer bust, winning 8x your original bet (but also risking 8x) instead of the mere 1.5x you get from a made blackjack. The big wins come disguised as garbage hands, like a pair of 3s. So it is in life — real opportunities come disguised as problems.
3. Novices don’t put in the time to fully understand the game. Expert players understand the game inside and out because they’ve invested many long hours studying it. Experts work harder. Novices have a strong understanding of certain parts, but their knowledge is very fuzzy in other areas. They often get confused on how to handle situations that arise infrequently. But eventually those situations do arise, and that’s where novices lose. Novices can’t handle the exceptions as well as the experts. But aside from a lack of understanding, novices also have some false understanding. If you could play blackjack and be dealt an 18 every hand, would you do it? A novice will usually say yes, thinking 18 to be a pretty good hand because a dealer has to hit 19-21 to beat it. But an expert player knows that 18 will lose more often than it will win — if you have an 18 every hand, in the long run, you’ll lose money. Experts have a more accurate understanding of the strengths and weaknesses of each hand than novices. It’s the same with life. Novices don’t take the time to master the basics, like goal-setting, time management, motivation, and self-discipline. They do OK most days, but whenever an exception occurs such as the loss of a job, they’re thrown completely out of whack, and it takes them a long time to recover. You can throw a bankruptcy or a divorce at certain people, and they recover quickly and then keep on going. But novices are more likely to allow temporary setbacks to drift into long-term ruin.
4. Experts are more disciplined. Novice players tend to play their hands inconsistently. When the same situation arises, they often make different decisions with no rhyme or reason. They exhibit poor discipline and will often drink alcohol while playing. Experts understand that you can make the correct decision and still lose, but they focus on making correct decisions, not on trying to force a particular outcome. Experts have the patience to know that making correct decisions is all it takes to win in the long run. You see this in real life too, don’t you? Achievers tend to be more consistent in making decisions and taking action; they focus their energy. Underachievers, however, waste their energy, never applying enough force in a consistent direction to bring about a breakthrough.
5. Private victory precedes public victory. Novices learn how to play in the casino. Experts learn how to play at home and then apply their knowledge in the casino. Experts spend a lot more time practicing, which takes tremendous patience. Their real victories are unseen. Talented people who perform in public have often spent many years honing their skills in private.

#2 is the observation I find most applicable to business. Even winning blackjack players will lose most of their hands. They typically win about 48% of the hands they play. That’s just the nature of the game; you’re going to lose more hands than you win. But on average the winning players will bet more money on the 48% of winning hands than they will on the 52% of losing hands. These bigger bets are made in two ways. First, with card counting you can recognize when the deck composition is in your favor and when you’re more likely to win than lose, so you increase the amount of your initial bet. But also you can recognize situations to double down or split pairs where you can increase your bet after you see your first two cards.

Novice players miss opportunities in these same two ways then. They don’t know when the odds are in their favor, so they don’t know when the conditions are right for a bigger initial bet. And secondly, after they see their first two cards, they don’t know when it’s a good idea to put more money out. And by missing these two key opportunities, they lose money in the long run, typically giving the house around a 5-8% edge.

How does this lesson apply to real life? Life isn’t about the quantity of successes and failures you experience. You also have to consider the magnitude. When you perceive the conditions of your life are ripe for success in some area, that’s the time to bet big. Plus there are also situations where you have the chance to see what results you’re getting, and if they show promise, you can raise your bet even higher.

For example, suppose your goal is to find a long-term relationship. When the conditions in your life suggest you have a better chance of succeeding at this goal than you did in the past, that’s a great time to push yourself. Perhaps you have a stable job and money in the bank and your health is great. It’s time to place a big bet by focusing hard on your relationship goal. Go out on a lot of dates. Ask! Don’t sit on the sidelines waiting and miss the opportunity. It will be a lot harder to achieve this goal under less optimal conditions.

And then when you find a person who seems compatible with you, double down and raise your bet. Find ways to spend more time with that person, and put your lesser goals on the back burner. Don’t neglect the opportunity to grow closer. Strike while the iron is hot. Have a lot of fun together. Build your relationship when the conditions make it easy to do so.

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When the conditions in your life are right to seek out opportunities instead of merely holding your ground, get out there and take advantage of them! And when you start getting promising results in some area that show you the odds are in your favor, push yourself to capitalize on the situation as best you can. Don’t sit around waiting and waiting.

Sometimes the conditions in your life aren’t right for going after opportunities. Maybe it’s a struggle just to hold your ground or to dig yourself out of a pit you find yourself in. Be patient and stay your course. Eventually there will come a time where things are going your way again. And when that happens, do NOT allow yourself to be complacent. Everyone loses when the deck is stacked against them. But the biggest losses come not from the no-win situation but from the could’ve-won-but-failed-to-act situation. Could’ve started the business but didn’t. Could’ve gotten the date but didn’t. Could’ve lost the weight but didn’t.

As in the game of blackjack, the could’ve-but-didn’ts are the biggest losers in life. Don’t join them.

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