How do you get the courage to wear a kippah in public? I feel more comfortable wearing my kippah, but I'm also scared so I only ever wear it to shul
I might not be the best person for this because my process of wearing kippah was sheer hubris.
But unironically, I do think it helps to remember that in many places, the worst that happens is that you'll be looked at. The worst reception I've had so far is that I'll get stared at blatantly - not necessarily in an intimidating way, but moreso in that people just like to stare. I definitely am more cautious in new areas - I never wear two earbuds anymore, and I look around my surroundings more. You may want to keep a beanie or inconspicuous hat with you for quick coverage just in case.
I definitely relate with you about being scared, and how I worked through that is just... wearing it one day. I got sick and tired of feeling intimidated, so I impulsively decided, "well, today is the day." I don't even remember what day I started wearing it because I just... did it.
That might not work for you, so perhaps you could work up to wearing it everywhere if that's your goal. You could perhaps pick public places that have smaller crowds - a local bookstore, a café, maybe a walk down Main Street. It doesn't have to be much. See how you feel. And then once you get used to that feeling, maybe you could try pushing yourself. First and foremost, this is something between you and g-d (at least, I think). However, don't feel guilty if you can't wear it all the time - it can actually set you back in that you'll just feel guilty and ashamed. It's okay if your journey in this is not linear - in fact, most of the progress we make isn't linear. For a while when I was manic, I couldn't even remember to wear my kippah, so I understand how it can be. Just take a deep breath and give yourself the chance to have a clean slate every day, because g-d certainly gives us that mercy. You deserve to give it to yourself.
