Pros of Pro-Con Lists
They allow you to look at the benefits and drawbacks of a decision, and sometimes it becomes glaringly obvious that one side outweighs the other.
They force you to see a decision from two different perspectives, and prevent that, “Oh, shit, I didn’t think this through!” moment of regret after the decision has already been made.
They force you to be logical and even-handed in your approach, rather than impulsive and fuelled by emotion.
There is something deeply satisfying about treating every decision as though it can be figured out through rigorous list-making, and the objectively ‘best’ outcome can be reached. (Even if this is actually just an illusion.)
It can help you realise what you actually want. It’s sort of like when you couldn’t decide between two options as a kid, so your mum would hold them both behind her back and make you choose one. If you were disappointed with the one you got, that’s how you found out what you wanted all along. Likewise, if you look at all the reasons on the ‘con’ side and think, damn, I hope this doesn’t mean I shouldn’t do it. Bam! You just found out what you truly want.
Cons of Pro-Con Lists
They might give you the illusion of a logical, even-handed decision-making process, but you usually end up subconsciously writing them in a way that leads to the outcome you secretly wanted all along.
Without a system for weighting the points, you can end up treating a minor inconvenience in the ‘cons’ column with the same level of importance as a massive benefit in the ‘pros’ column, or vice versa.
You end up listing unimportant points, just as a way to give the illusion of balance and to fill up the page.
In general, people are very bad at predicting what will make them happy, so pro-con lists are almost always doomed to be inaccurate anyway.
Pro-con list-makers tend to be overly too obsessed with making the ‘correct’ or ‘best’ decision. No choice is perfect. All decisions will lead to both positive and negative outcomes. Studies have actually shown that the more time you spend making a decision, the less satisfied you are with it in the long run.