Sounds like all you need is courage, which will come with experience.

I just learned how to ride a bike this year, and I've been progressing at overcoming various fears:

- Fear of descending
- Fear of being within 500 feet of cars
- Fear of collision with bollards and other objects
- Fear of riding at night.

I now commute to work by bike a couple of times a week. Once in a while a car will pass me closer than 3 feet away and it doesn't rattle me. Descending hills of various steepness - no problem. 2 night rides under my belt for this summer. My combo of dyno hub lights, USB-charged helmet light, wheel reflectors, and hi-vis pannier has been fine. I added some reflective stickers to my frame to personalize it a wee bit more on the cheap.

I might add some Monkey Lights spoke lights since they include a skull pattern, for my cycling group's Halloween ride. They would definitely take my lighting setup into the overkill category, but it's more for the festive look.