Having spent nearly a decade in IT professionally, I am a bit ashamed to admit that I never felt like there was a good time for me to “break” into the Software discipline. I was always worried that as soon as I began to learn JavaScript or Python or Bash, the next big thing would become popular, and I would have completely wasted my time learning x, y, or z. From outside of Software it felt like new magical technologies were popping up everyday (they kind of are), and it was just a matter of time before something huge completely reshaped how we access our bank accounts, schooling portals, and social media.