How do you decide to spend money?

As far as I know, I’ve never really asked myself this question before. I usually just ask, “Should I spend money on this?” But I don’t ask the more general, “Why spend money on something in general?”

It’s an interesting question for me especially because a lot of things are free now. So often it’s a decision between tracking down what I want for free or buying it now.

Of course, many, many things still cost money and don’t have free substitutes. So which ones should I pay for… which ones should I do without?

How do you decide?