check the boxes! then what?

Every perfectionist handbook out there tells you to stop checking the boxes - it won't make you happy. But why do so many of us feel the need to? We understand that checking the boxes won't make us happy, yet we get upset when we don't check them anyway. Being in a field where every aspect of your life is going to be evaluated to some extent as the gateway for you to be "successful" in your career, I find myself checking boxes that I don't even want to check. How does someone be happy with working towards a goal while also feeling like they are already enough? Let's talk about it.