I think the traditional way we think about comparing “pros and cons” is wildly incorrect.
The traditional way is this: we make a list of pros and cons, and whichever list has more items becomes our yes/no decision. I see a LOT wrong with this strategy.
First, not all items are equal. Let’s say I’m putting down the pros and cons of robbing a convenience store. “Pros: 1.) Pretty easy. 2.) Pretty fast. 3.) Would get like 30 dollars. Cons: 1.) Will go to jail for 5 years.” Well, only one con versus 3 pros! Guess I should do it!
Second, even if you were objective enough to only write exactly equally-weighted pros and cons, they don’t cancel each other out. Something could have lots of cons but still be something I want to do; those could be costs I’m willing to pay. Conversely, something could have lots of upsides but not be worth the price to me.
And lastly, something that has a lot of items in each column is probably not getting any clearer for you if you write them out. Because just listing a bunch of things doesn’t solve the hard choices that the first two problems present!
Let me propose an alternative method for you to use whenever you’d be tempted to use a pro/con format. I’ll call it “Pros & Dealbreakers.”
First, before you even start evaluating a potential course of action, list the top three things that would make you say “no,” no matter what potential upsides there might be. No matter what the “pros” are, for example, I won’t put my family’s well-being at risk. I won’t break my moral code. I won’t commit to spending more than $500 up front. There, those are my dealbreakers.
Next, set yourself a “pro” threshold – let’s go with 5 items. Start listing good reasons to do the thing; possible upsides, definite benefits, etc.
If you can get to 5, and The Thing doesn’t involve any of your dealbreakers, just do it.
5 good reasons is plenty to do a thing. Sure, you could probably come up with an equal number of potential bad outcomes if you wanted to, but so what? That’s another problem with the pro/con system – if you’re a pessimistic or risk-averse person in general, you can always come up with plenty of cons.
Life is full of potentially bad outcomes, but the worst one is never doing anything. If you can come up with 5 good reasons to do anything, do it.