Like say you don't know how much you'll bring in in a particular year, you've got some money but not millions or even six figures where you can really relax, you're ok for now but you're trending down, and you get IOIs, should you go for it or just think "I can do something(not with this one, but there's always another) when I get myself fixed up"? I get that women aren't that into how much you have/make, where you live, what you drive, etc. But at the same time they're mirrors and if you're a wreck she will be too and then you get "maybe I should go", so why bother?

Let's say you're preparing for a boxing tournament, but you're scrawny and weak. Now, you know that you need to get better ("improve yourself"), so you're working on building a strong, muscular body that can take on the challenge. Are you going to wait until you get that body to begin training? No, you go out there and practice, i.e. you build that body and practice simultaneously.