We cannot solve our problems with the same thinking we used when we created them. – Albert Einstein

Apart from the to-do list, there’s another type of list, and it may be even more forlorn. The pros-and-cons list is sometimes almost a punchline. “You should make a pros-and-cons list” is often said with the definite intimation that actually making such a list wouldn’t help. Like the to-do list, the pros-and-cons list doesn’t always actually exist as a list; it can simply be a thought in your mind. It represents the frustrating state of mind in which you’re unable to make a choice between multiple good alternatives.

I was hosting a dinner party recently, and I was trying to come up with a menu and in particular which cocktails I was going to serve. I had a lot of ideas, concrete cocktail recipes that I could make, but I couldn’t decide on the specific ones to include. I was considering their varied merits: one would add nice variety to the cocktails I had already chosen; another would offer a low-ABV option for a guest that might want something lighter; another would allow me to showcase an interesting ingredient. All were good options that had something going for them. I kept mulling this over, but I struggled to make a decision. Then I realized that I hadn’t really chosen a theme for the evening. I gave this some thought and it occurred to me that some of the things were roughly characterized by a connection to Latin America. Immediately the choice was clear: I would make the cocktail with Pisco.

The comparative process that had preceded this breakthrough – drawing up the mental pros-and-cons list – was the result of an impasse. But the pros-and-cons list wasn’t the solution: it was the sign that there was no more progress to be made at that level. The choices seemed more or less equally weighted, and I wasn’t going to draw a meaningful distinction through a more thorough analysis of the positives and negatives of each. I wasn’t going to uncover any new quality through a more detailed examination. What I needed to do instead – and unwittingly did do – was to go to a more fundamental level, the level at which the goals underlying the choice were situated. This perspective didn’t make me see anything new but did change the meaning or significance of the features of the choices. It made certain features more salient, such as that one of the drinks had a Latin American spirit.

There’s a scene in the latest season of Succession in which the siblings have gathered together and are forced to choose sides between their brother and their father. Each is asked in turn, and they’re all non-committal and cagey. This isn’t merely strategy, however. They are genuinely unsure who to choose because all they’re trying to figure out is who, of the father or brother, has the greater chance of winning the fight for control of the family company. They have no higher principles, such as filial loyalty or personal conviction, to guide them. Even once they do make a choice, they’re constantly second-guessing and hedging. They’re at the whim of events and information as they transpire, and are consequently always unsure whether they’ve made the right choice.

Hard indecision, of the sort that makes one inclined to turn to a pros-and-cons list, comes from a lack of a deeper purpose. The purpose might be entirely lacking, or else it might be ill-defined. Sometimes, there are competing purposes. Simply forging ahead, in the weeds of the details, and gathering more information, isn’t going to bring clarity or certainty. The list is a trap in which you get mired as a distraction. You need to zoom out and better define your purpose. In this way, the solution is harder.