Hi Jon!
Thanks for reaching out with your questions about streaming and I'm glad you enjoy my content!
I started streaming just over 18 months ago, in summer 2016.
There were some mental hurdles in getting started with my stream. I'll reference my Medium post in this answer: medium.freecodecamp.org/lessons-from-my-first-yea…
The main issue I had was that I felt like there was nowhere for me to hide, and it scared me. I thought, "everyone is going to think my code is bad, and that I’m a bad developer". I was worried folks would see my biggest weaknesses as a programmer and I'd become 'unhire-able' overnight.
Because of that, I rehearsed the first four streams the night before each one. That quickly ended up being too time consuming, and I felt I was being truly authentic with my viewers so I stopped doing that.
The first stream is the hardest one. Hitting 'Start Streaming' in OBS was terrifying the first few times. I do a lot of public speaking but this was just something else entirely.
My confidence and skills as a programmer have improved a lot since I started streaming. That's been worth the effort in swallowing the initial fears.