TL;DR
Win at the wrong game, and you’ll still lose. Not all games are worth playing, and you are better off thinking deeply about how you choose, redesign, or create the games you play. Always remember that the prize means nothing if it costs you your meaning.
What does it mean to win?
If you are like most people you rushed to answering the question without paying more attention to the fact that a very important qualifier was missing: win at what? It may even be that it is the more important question. For although winning is very likely important to your wellbeing, winning at the wrong games is a good recipe for misery. If you were to win at all the games you are currently playing, would it improve your wellbeing?
As kids, we played at games that our parents, guardians, or societal expectations chose for us. Up till about the age of 17, winning is defined along the narrow corridors of academic performance, conquering a sport, and getting the girl or guy your peers think is the best pick. When we are younger, there are clear hierarchies around which winning is defined, and that frees us of the burden of asking the arguably more important question: what do I want to win at?
In a very general sense, every social interaction is a game that can be located somewhere on an axis that has no-rule (or hidden-rule) games on the one end, and many-rule (or hard-rule) games on the other end. To win at any game, one needs a combination charisma, discipline, and genius: charisma lends itself nicely to no-rule games, discipline to many-rule games, and genius is an advantage across the entire spectrum.
As an adult, if winning (mind you, you are always trying to win at something) will contribute to your wellbeing, you have to be intentional about the games you play; you would either have to 1) pick your games very carefully, 2) do all you can to redesign the games fate assigns to you so that winning is worth the effort, or 3) create your own games and win at them, and in 4) in the extreme case that one must play certain games, identify those compulsory games for which winning is worth the effort and those for which it is a source of misery, and then only put in the amount of effort required for a desired outcome.
Practical though it may be the fourth option is a trojan house that carries a recipe for disaster. First, because it is easy to label a game as compulsory when it is not, and secondly, because too many compulsory games with average winnings here and there may be a good way to live an average life. It seems more likely to build a rich and meaningful life if only the first three options are guiding lights.
It seems that no-rule (hidden-rule) games have the most rewards: they also, expectedly, have the most risks. Imagine for example, what it must have felt to be part of Nero’s court, one move away from having your head on a spike, and yet the rewards of gaining Nero’s confidence were limitless. Where there are no rules, the charismatic triumph because of their likability and their ability to create rules (which they sometimes do well to hide), and then compel others to follow them. We can infer that a high ranking official in Nero’s court was high ranking because: 1) they were liked, 2) they either knew the rules to which many were oblivious, and 3) other people looked up to them for guidance.
No-rule games tend to have more rewards because society rewards risk more than hard work, and charisma is a scarcer trait than discipline. If one is willing to do what few others are willing to do, they can charge a premium for it, and if one can do what others cannot do, they can charge a premium as well. This is precisely why entrepreneurship is both risky and rewarding. The point on risk is self-evident and is left as is. On the scarcity of charisma, it is important to notice that it arises from the fact that charisma is perhaps good proof that alchemy is a valid method: ask a charismatic person how they do it, and more often than not, they have no idea. Charisma is by definition and practice, a time-based, context-dependent, people-heavy trait whose essence cannot be contained in the same way that discipline can be contained.
On average, the relative abundance of discipline and the ease with which hard work mean that many-rule games are not as rewarding as no-rule games. However, every now and then, there is a game that combines such a number and difficulty of rules as to create scarcity with regards to the people who can (or are willing) play the game; think Investment Bankers. Many-rules can be very rewarding when they require seemingly unhuman feats and a strong exertion of personalities.
A good example that captures the relative greater value of no-rule games is the world of athletics. Long time ago, athletes were paid for achieving super-human feats, simple. It did not take so long for everyone to catch up to the fact that there is only so much one can push the human body and that the collective drive to shatter records here and there also follows the law of diminishing returns. That explains why the world of athletics (at least at the top levels) is moving closer to the no-rule category that relies on more charisma: athletes are making more money off the court, and sports teams are signing players just to increase matchday attendance and sell memorabilia.
There are certainly more dimensions along which we can frame games. One cannot pretend to exhaust those. This article has presented just a single frame, and the hope is that through your own exploration, you will come up with the frames that enable you to live the reality that you now have to pick (or create) the games in which you play carefully. Ultimately, the games you choose to play come down to a combination of your value system, your personalities, and other constraints like location, time, and network.
To quote Peter Thiel: “My advice for you — the advice I wish I could have given my younger self — is this: Before getting swept up in the competitions that define so much of life, ask yourself whether you even want the prize on offer.”
Choose your games such that you do not regret winning.