Poker, Chess and Life – Part 3: Skill

Skill in anything is an attractive thing to strive for. It’s something we can develop and hone to achieve the things we want. To put it simply: skill grants access to success. But what exactly composes skill in poker and chess, and can the same thing be applied to life? Can we simply develop our skills in the same structured way and guarantee ourselves the same level of prosperity as we can in the realms of strategy games?

This is part of a series of articles, and if you haven’t already read it, you can find part 2 here.

1. Skill As Decision Making (poker and chess)


As always we set off by looking at our concept in question through the lens of the chess player. You win a game of chess by being more skilled than your opponent. Being more skilled than your opponent is represented by the fact that you make superior moves to the ones he makes. Therefore, being skilled at chess is simply to possess some faculty that consistently enables you to make good decisions. Good decisions lead to better outcomes than bad ones do with a firm degree of reliability in the purity of the chess world and so skill translates directly and instantly to success.

In poker there’s no real fundamental difference here. Skill is still the underlying currency of success and it can be reduced here also to brute force decision making; it’s just that now there exists a delay in the translation of this skill to success as we saw last time when we examined luck and learned that this game contains a great deal of it. A common misconception about poker held by the uninformed outsider is that since poker is a game of luck, it can’t also be a game of skill. This is completely false and to quickly explain why I’ll use the following analogy that I so often find myself falling back on at social events.

Imagine we each have a coin and decide to play a coin tossing game where the idea is to toss your own coin and flip heads more than your opponent does with theirs. When someone flips heads, he/she scores a point but scores nothing for tails. Our coins are perfectly normal apart from one small but crucial detail: mine is weighted in such a way that it lands on heads 51% of the time. Your coin, on the other hand, is just a regular two pence piece from your pocket and lands on each side 50% of the time.

What would happen if we played a match of ten tosses each? Well, I’d flip heads 5.1 times out of 10 on average to your 5 times out of 10, but on one occasion in isolation, anything could happen. There will be many times where you toss more heads than me and over this small sample it would be impossible for an onlooker to determine that any one coin was favourable to the other. However, if we toss 100,000 times instead of 10, we’ll find the 0.1 extra heads I toss per 10 to be decisive. I will flip more heads than you than you due to the law of large numbers which says that statistical likely hoods hold true over large numbers of trials. I am crowned champion over a 100,000 toss match thanks to my ever so slightly better coin.

Now let’s imagine this small edge of being able to toss more heads was not in fact due to me holding a bogus weighted coin, but was a result of my superior skill in coin tossing. Now we can see how skill can generate a positive long term expectation in a hybrid game of skill and chance, but that the more skilled party can easily still lose over the short term. Here in lies the unreliable nature of success in poker over the short term but near certainty of long term profit for the more skilled party in the long run. In poker, this skill equates to choosing what action to take with a certain hand in some distinct situation. The player who makes the better decisions wins the money in the long term so again skill is just this ability to choose good options.

2. Skill As Decision Making (life)


Jerry (50) dropped out of university at the age of 19 as it wasn’t for him so he’s chosen instead to travel and pursue his passion for music for the last 25 years. He’s now making his way through Australia with his wife teaching the guitar while she teaches piano. He says couldn’t be happier.

Sally (50) has worked as a solicitor for the last 25 years and grown to loathe it. She feels like her life has passed her by without her even realising, each day a meaningless blur in a procession of routine drudgery. She’s thought about changing her life at various points, but never found the moment to join the police force like she’d always fancied.

So what do Sally and Jerry have in common? They’ve both made choices for the last 25 years that have resulted in different levels of satisfaction with how life has gone. It seems pretty obvious that Jerry has chosen better than Sally and thus lived a far more positive life over the years. Just as in poker and chess, there’s a sense in which skill is simply a person’s ability to make good decisions. Of course Sally’s knowledge of the legal system and Jerry’s knack with the guitar are sub-skills, but if we want to generalise away form sections of life to the bigger picture of life itself then skill is at least partly decision making.

There are two issues rearing their heads here so I’m calling for a short time-out to deal with them.

The first is the subjectivity of success. ‘Success’ as intended from now on is subjective to the agent in question and not comparable to how others perform on an objective scale. Mike might not be as intelligent or brilliant as Fiona, but he could be more successful in life if he achieves more good stuff (whatever that turns out to be) than she does relative to their respective natural abilities and opportunities. Fiona might be a natural born world class pianist who received world class lessons from infancy. Mike didn’t have this chance so this needs to be taken into account. Of course there will be external factors governing overall achievement in life, but success should be measured in an equal manner so we’ll be overlooking any of these natural strokes of luck from now on.

The second issue and the one I’m going to need to leave on the sidelines until part 5 is what exactly constitutes success in life. Could Sally not be considered more successful than Jerry if she’s saved a lot of money, bought a house and raised a family in the last 25 years where as Jerry has not? Maybe her sacrifice in doing something she hates was worth it should we zoom out and see the bigger picture. Sure, maybe! it depends on what we think the currency of the good actually is in this baffling realm. Maybe that currency is different from person to person. This question is worthy of more space than can be allowed for in this section so stay tuned for fuller exploration soon.

That aside, I want to investigate why some of us are more skilled in life than others. Why do some of us repeatedly make bad decisions and end up in bad spots while others seem to chose prudently and reap the rewards? I have three explanations for this that might lead us down a path to improving our skills in life. They are: desire invasion, decision discipline and decision automation.

By desire invasion I refer to something more than just a lack of willpower or lapse in judgement. Many types of people, for example, addicts, criminals and mentally ill people suffer from an inner programming so profound that it overrides any hope of decision making carrying out it’s normal duty of pursuing the best outcome. The poker equivalent is the enraged recreational player who has a gambling problem and chases his losses without rationality or sense of limiting the damage. The chess equivalent is extremely rare and even more bizarre than the rest of the chess community, but i suppose he’d be the board trashing, abusive type of player who gets so mad at the game he starts to make moves in a shortsighted emotional manner and hence gives up decision making in any rational sense. These people are not necessarily unskilled at life, they simply suffer from something debilitating that prevents that skill from being exercised. Even the most gifted poker player in the world will be a loser if he can’t keep it together for long enough to think clearly and implement his ability.

For the rest of us, success in life I believe is very much a case of skill in decision making. We understand this on some level yet many of us constantly make decisions we know deep down to be mistakes.

The first culprit here is decision discipline or lack thereof. Just about every poker player suffers from this deficiency at some time or another. We know that we should fold the river because analysis shows calling to be unprofitable, yet we chose to call anyway and convince ourselves somehow that it’s okay. We know playing h5 and opening up the kingside is probably theoretically bad, but we can’t resist the chance of winning via a brilliant (or lucky) mating attack. We resolved to run 3 times a week this year and give up Papa Johns pizza as this was much better for our well being, but hey, it’s two for tuesdays today and it’s really cold outside.

Those who succeed find ways to keep discipline levels high more frequently and enforce strict codes of decision making upon themselves. Those who fail succumb to bad decisions they could have avoided with a stronger faculty of discipline. Success in life requires discipline, otherwise the brain will just make the bad decisions it seeks for whatever irrational or emotional purpose. Discipline here usually involves the overriding of emotional interference of any type. It takes Sally discipline to quit her job as a lawyer and pursue actual happiness just as it takes me discipline to stop ordering pizza. Her job is controlling her fear enough to make the change where as the rouge desire I’m trying to reign in is temptation or perhaps gluttony.

If we separate emotional urges from our rational analysis, we’re better placed to make the right decision. Sometimes, however emotions can lead us to the correct choice. The saying “follow you heart” has a hell of a lot of truth to it in my opinion. However, other times we’re best placed ignoring emotional impulse and reasoning out the problem. The real skill in life then is using our cold calculating abilities to decipher which emotions are worthy of listening to and which are striving for unwanted ends. This isn’t going to be easy, but as a friend of mine likes to maintain, large problems need to be broken up into steps and now at least we have a starting point.

Finally we come to decision automation. I came up with this concept thanks to a poker illness many poker players are afraid of developing – the dreaded autopilot! This is a frame of mind that can exist in almost any mental activity where the brain, due to distraction or fatigue, stops thinking authentically and begins to rely on habitual patterns to make decisions. We suddenly find ourselves on the turn without any idea of how we got there. We have to trace the hand backwards to reason that we must have open raised KJs from an early position and been called by the big blind. Then we must have continuation-bet the flop and been called again. Our minds switch off when they lack the focus or energy to create new thoughts to deal with a situation and shift into this autopilot mode so damaging to our win rate.

Perhaps unsurprisingly by now, I’m now going to say that the same thing happens in life all the time. How many decisions do we make, completely unaware of the fact we’re making a decision at all. And how good of a decision can we possibly make where this is the case? I didn’t go for a run today because I didn’t even think about it until I was in bed, yet at every point of the day where this was a possibility, my subconscious was choosing not to bring it to my attention. If we can develop a system of flagging up important decisions as and when they occur, we can minimise decision automation. We may also need a system of bookmarking certain things so we remember to consider them and consciously make a decision about if and when to do them. The more you automate your life, the firmer the grasp routine will have on your mind and the quicker the mould will grow over that beautifully dynamic creative and inspired part that’s always seeking to make great choices and better your life.

So to recap, in order to not end up like Sally, we need to build decision discipline to quell the destructive randomising effect of emotion while still using it as a guiding beacon the times we find we agree with its impulse. We also need to banish autopilot decision making and keep fresh our inspired originality and creative pallet so that we may paint things into our lives that aren’t staring us right in the face. Be aware and be disciplined; in chess, in poker, and in life!

3. Skill Beyond Decision Making – Immersion


If skill in life leads to success, and decision making isn’t always sufficient for success, then skill must be more than just decision making. Why would I say decision making isn’t always enough? Well, when we make a good decision we gain useful things that can be enjoyed or transferred into happiness. In order to experience happiness or pleasure from the things we’ve gained though, there’s one ingredient missing, and this ingredient I’m going to call ‘immersion.’

Let’s imagine Julia read this article, but stopped before this section. She became obsessed with making decisions every moment of her conscious waking day and making the right ones. She built an amazing career, made a beautiful family with her successful husband and became very rich (all thanks to me). Unfortunately, her days are now nothing but a massive fest of stress and worry as she battles with decision after decision, adamant that she’ll make lots of right choices about important things.

So Julia isn’t very happy and that’s because she never allows herself to blend in with the world and enjoy the fruits of her labour. If we’re doing nothing but choosing what to do next, we can’t savour the present. We enter some bizarre self contradictory loop where we spend the present always setting up the future so that it will be better but then we chose not to cash in that betterness and instead set up the next future so it will be better so on and so on. I think we’ve all encountered neurotic stress-heads like Julia. She has a great decision making faculty but lacks the other half of skill in life – immersion.

Immersion is the ability to switch off the decision making brain and allow yourself to profit through endorphins and positive inner well being. I find that some of the most enjoyable times in life are those where you get completely lost in the moment. The times you remember forever are those which felt the most special at the time. The very things we try to manage and even suppress in order to make good decisions are the things we need to let loose in order to gain from those decisions….emotions! We are supposed to thrive by becoming one with our environment and simply being sometimes.

As someone with very hedonistic views, I may be biased here, but I’m going to go ahead and state the weak claim that no achievement is really anything if life is void of pleasure and happiness. The happiest people seem to me to be those who can successfully flick the switch of decision making on and off at the appropriate times. Switching it on to create the circumstances conducive to happiness and turning it off again in time to enjoy them.

In poker and in chess we have no need for such a balance. Skill is not measured by how much we enjoy the trip but by the destination that is the winners’ circle. In life though, I;d say you’re pretty bad at life though if you create an empire of resources that noone ever enjoys. The poker equivalent would be building a massive stack in a tournament to then leave the computer and let your stack disappear along with any hopes of winning money. To be like Julia is to create a winning endgame in chess then blunder it all away in horrific fashion.


Skill is vital to success in chess, in poker, and in life. Decision making is vital to skill in all three realms. We need to control our emotions in order to proposer at this and make sure we stay vigilant enough to have the right factors up for decision in the first place. The more we avoid the natural inclination to autopilot our way through the world, the more beneficial the topics of our decision making become. The more we conquer our irrationality and channel emotion in the right way, the better the choices we make on these matters. At the end of it all though, it’s totally irrelevant how much we achieve if we neglect immersing ourselves in the world and enjoying what we’ve created. Life is a finite blip in the grand scheme of things. Don’t blunder it all away in the end game.

Skill in life is just the ability to achieve what is good for us to achieve. More about that in part 5.

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