Hi Wyatt,
If you feel this way about women who have their lives together when it comes to dating, you are not happy with your own life. You need to be happy enough with yourself before thinking about making someone else happy in a relationship, whether you meet this person on a dating site or in real life.
Otherwise, you will just keep getting into short-lived relationships that aren’t fulfilling. This doesn’t mean that you have to become a CEO or something high and lofty to date, but, you do need to get to a point in your life where you truly feel happy about your life.
This could be something as simple as finding a more fulfilling job or even deciding to take some classes in something, whether it be academic or in a trade of some sort.
Work on getting yourself to a happier place before thinking about dating, whether that woman is on your level or doing better. Your attitude needs to change in order for you to have more fulfilling and healthier romantic relationships.