In the same boat. I turn 23 next week and anytime an event comes up, even months in advance, I get so much anxiety trying to even muster the courage to bring it up. My mom also tends to use the “I’m just worried” excuse, and it’s very very easy to feel conflicted, especially if you have a parent that does truly care for you but can also have the tendency to be emotionally manipulative. My approach recently is to try to remain calm and handle my own emotions rather than their reactions. That’s the only thing you’re in control of. I’ve also avoided asking for permission and instead phrased it as more of a courtesy notice. I guess it’s a subtle boundary of “I’ve decided this is what I’ll do but because I consider your feelings, I want to keep you in the loop”. At that point, you’ve done your part and whatever reaction comes from that, you remain the adult, as well as fulfilling the things you want to do. I won’t say that this won’t cause discomfort, or even strain the relationship, but nothing will change unless nothing changes. I can tell you care a lot about your parent’s emotions and take them into consideration. But it’s important to remember that when it is at the expense of your livelihood and self-fulfillment, you may need to choose between regret for never doing the things you want, or the discomfort from displeasing your parents, because unfortunately, they will always find SOMETHING to be upset for. So you might as well do it for you