The revelation for me was when a school friend of mine in the early 2000s told me about a site called crack.cd which had serials or keygens for practically any software I wanted. It was a whole new world, I loved it. Only had to nuke my computer once after a keygen turned out to be a virus! (The other occasion on which I lost everything was when I was installing Ubuntu 5.10 ‘Breezy Badger’ for dual booting with Windows on the family computer and accidentally wiped the entire disk instead of just the old Linux partition - that was a bit more awkward because it had all our family photos on it ever since digital cameras started coming out, but luckily I found a CD backup of them all and also tried my hand at downloading and using a cracked file restoration program. Definitely took some time to rebuild trust and explain that I know what I did wrong and wouldn’t do something like that again.)
I had lots of learning experiences with this kind of stuff that I’m very glad I could have in my little years of first being online, when it wasn’t tied to anything really important, it was all just for fun. Everything would be different for me today if I didn’t have the opportunity to play with non-zero but relatively little risk.