There are lots of things that feel uncomfortable. Doing those things again and again can make them feel more bearable. You get used to them.
For me many of the uncomfortable things are unexpected. You just can't be prepared for everything that comes up during the day. Not at least if you don't stay at safe places where you can control and predict all the things. But that would be limiting, boring. You need to get yourself out there.
But you can't repeat to get used to them. What I should prepare for?
I have tried to get comfortable with the feeling of uncomfortable itself. Making myself handle that better. Build up tolerance. It's easier to face that feeling when you can fsce them in the safe places. Decide what, when and where. Do something uncomfortable when you are safe. Notice that feeling. Notice how it's not that bad. I'll survive!
Remember that feeling. It might feel uncomfortable but you'll survive. It's a small victory, an accomplishment.
It can be simple thing. One thing I have been doing is washing my face with cold water in the morning. Perfect thing for this kind of practice. You put the water running, put your hands under the tap. Feel the coldness in your hands, anticipating the shock in your face. But it's not that bad. You actually feel refreshed, more awake. Less uncomfortable. You are ready to face anything today.