Honestly, the way it’s got easier for me is by forcing myself to do it more. Like go out even when you don’t need to. If my roommates went grocery shopping, I’d tag along even if I need to because it was a way to scope out a safe space for when I needed to go shopping later. Go in brief intervals. The best thing you can do is just jump into it like it’s a pool. Just make that grocery list and map out in your head where everything is and then go in. When you wish you’d have stood up for yourself, think about if you still can and if not, make a plan for what you’ll do next time. If you fall short again, make a plan for that next next time! The point is, it’s going to be goofy, but you have to jump in and adapt. It’s scary because it’s new and so much can go wrong. The more you experience the “wrong” then the less wrong it feels. I hope this made any sense lmao!