Examples escape me at the moment, but there have honestly been so many times I've hit a wall trying to do - what seem to me like - basic things in JIRA; I couldn't comprehend how such a complex tool could not accommodate them.
And the stuff that can be done is often so comically painful it's mind-blowing. Trying to do something as seemingly simple as create a useful saved search in JIRA is so painful I can't imagine its creation was not an act of sabotage.
I was late getting into computers, and back in '98 just got my first Windows PC. I struggled, but eventually figured out how to get MAME installed and loaded up a long forgotten arcade game I used to play as a kid at my local corner store.
It's hard to describe the sense of wonder I felt when when the ROM check sequence flashed to the title / insert credits screen and I knew it worked. It might sound silly, but few moments in my life have been so eye opening. It was definitely a key factor in me starting my path to becoming a developer.