Why is it so hard to sell

Can any of you Reddit psychologists weigh in here. I mean, some of us know the feeling. You Portfolio is in the green, you’re making more in a day than in a year of your shitty job. In your mind, you’re flipping your boss off, telling him to shove that email up his **** and hope it “finds him well”

Then why aren’t you selling?! I know you want more and more but when is enough enough? If and that is a big if - the bull ever returns I really need to make exit targets for my modest bags an stick to them. What are your experiences in this regard? We’re all in it for the wife changing money but when is it time … ??