@khatz : I agree with you that a lot of seemingly hard choices can be reduced to simple binary choice. However, I think it’s not the case for every choice.

I’ll use a mathematical metaphor: let’s assume that finding the best decision is like finding the minimum of a function. Binarization works for single parameter decision: it’s easy to find the minimum of a 1-D function by comparing the value of two points for several iterations. But if you want to find the optimum of a multi-objective function (= complex choices), you have to use other techniques, such as Pareto front (the “80/20” Pareto). And that’s why we get stuck when we have too much elements to make a decision.

But I’ve just realized, as I write this, that this is exactly what you suggest with you “shortest word algorithm” : a metaheuristic to transform multi-objective optimization into a simple problem…

Thank you Khatz, now I look like an idiot with this message 😉

Binary decisions are a great way to turn everything into yes/no, ranking questions. Hard to use sometimes when there is more than 1 person and the other person isn’t “into” proper decision making.

So one good thing to remember is – stop arguing with other peoples decisions for the sake of argument alone. If they want to eat Turkish food tonight, would it really harm you to just agree in 5 seconds rather than discuss the merits of Thai food for 30 minutes? I used to have groups of friends (engineers/science types mostly) that would wander around downtown for hours, bored, because nobody could agree what to do, or how to get there. Then I met a group of colleagues (sales/marketing types) who did not needlessly argue over which nightclub to go to, but instead whipped out phones and immediately made (often different) plans on how to get there and raced each other to arrive first. If anyone had a dissenting opinion, it was dealt with simply “well why don’t you go to your place, and we’ll be at the other place” – but it rarely happened because everyone knew that you had to pick a plan so why dissent all the time?

I also learned, you can double down on your decisions. For example, buying two black t-shirts instead of one (and you can do it again – what about 4 of them?). Because if you make a decision, and it feels like a good one, maybe you ought to double down – if one is “worth it” is two “worth it”? Get two for the price of two. (Great quote from Contact “First rule of government spending, why buy one when you can have two for twice the price”). I often buy two power adaptors for a new latop, or 3 identical trackballs for use in different locations.

And this idea can even be applied to help cope with loss/bad decisions. Back in student days when a buck was something that had to be spent wisely, a friend inserted a buck in the coke machine and got nothing out – the drink bottle was just short of falling down due to a small mechanical issue. So he spent $1 and got zero back. He pondered this for sometime, then inserted another coin. His reasoning – $2 for 1 coke is a better deal than $1 for 0 coke. So he doubled down and got a more expensive coke, although in the long term his 1 coke a day habit would pretty quickly average the cost down.

I apply this reasoning to a lot of things.
Don’t fight unimportant decisions with your unimportant opinions.
Don’t make a new decision if your previous decision is still good. Get 2 for the price of 2.
Decisions sometimes don’t work out, but that doesn’t mean it was a bad decision, get 1 for the price of 2.