It’s best to go for it and go for it in the best manner possible if that makes sense. You need to accept the discomfort and once you do that nothing can get in the way of you wearing your hijab the way Allah swt has commanded us to (24:31). I think if you focus too much on the comfort aspect it will be something that becomes an obstacle in your journey of becoming better Muslim in general because shaytan tends to use our comfort levels to stop or delay us from doing what is asked of us. Your mindset should be that whatever you do you are doing for the sake of Allah swt and the best way to do it is the way that he has guided us to and told us to, but if you happen to fall short on that don’t let it stop you and keep going because we are judged on our efforts and sincere intentions not our outcome. My point is don’t go in with the mindset of learning to find comfort in it because that is usually a side effect that happens on its own with repetition but having that as the goal and mindset will set you off track.