I will tell you a secret. I am a mediocre chess player. I don’t have much experience playing and I managed to lose against a computer at the lowest level of difficulty. I don’t plan 10 moves in advance and I am not a pro Risk player.

But I still like to win at games. Therefore I looked for techniques which fit my style better: making moves where I can only win.

Here are my 4 favorites:

Diversified bets

It is similar to investing. Pick a set of uncorrelated choices which you expect to win overall. Some choices can hedge others. Obviously, the result will depend on the reliability of the predictions. I expect my predictions to be wrong more often than I expect and to an extent larger than I thought. For that reason, I have other techniques.

Options

The Oxford dictionary describes it as “the freedom or right to choose something”. That is the key part, there is nothing mandatory in an option. Many know about options in finance, stock options, for instance. But as noted by N.N. Taleb, we tend to overlook the other types of options in life. For instance, a free trial of a software is an option. If the need for the software is low, I can simply cancel the subscription (or forget about it until the reminder I receive on the very last day. Or when I see that I have been billed without reminder. In that case, the company goes into my “hate list”). Another option I discovered in college was joining many clubs at the beginning of the year. There is an upfront time investment to get to know them all but you can stay in the ones you prefer. Clubs are less likely to recruit new members later during the year and by then you will have filled your calendar with other activities. However all options are at the expense of another party. So you won’t be able to rely only on options.

Asymmetry

Asymmetrical pay-offs are what I am after. Win big or lose small. Or, high upsides, capped downsides). We can think of angel investing, a $50k check can turn into millions but it won’t be worth less than $0. Creating content also has asymmetries. The creator can connect with people and share content they both enjoy. Worst case scenario, the content is ignored (that is the case of most of what we see or hear) but the creation process was enjoyable.

The ultimate solution

The equivalent of “heads, I win, tails, you lose” but hopefully without cheating. Winning no matter the outcome. It is rare and easier to see in retrospect (everything is obvious once you know the answer, right?). An example was learning digital marketing at the beginning of the e-commerce era. Either you got more traffic and customers for your website and/or you developed expertise in a domain very few knew about.

A personal example: choosing a “classe préparatoire” (a 2 year intensive program) as a starting point for my engineering degree, as opposed to a more relaxed university program. All of those who succeeded in this intensive program could join more selective engineering schools. Those who failed ended up becoming good students in regular university programs. Probably better than they would have been, had they not done this intensive program.

How to spot them

Diversified bets are found through a study of the pay-offs and probability of the bet. Or with a good rule of thumb.

Options are found by looking for things you can do but don’t have to, if you change your mind.

Asymmetries are simple to see from the probability distribution of a phenomenon. Heavy-tailed distribution for instance.

I am afraid I don’t have a way to spot the ultimate solutions easily.