This brings back some great memories. I learned so much from the HOWTOs, and I think they played a big part in getting me my first proper tech job. I just had to sit and figure it out, and the process of persevering through the mistakes and dead ends ultimately gave me a level of confidence around computers and technology in general which has been incredibly useful in work and in life.
This brings back memories for me, but I don't know if they are "great." I have memories of being in high school and downloading Linux binaries and HOWTOs over a dial-up modem, messing around with Debian on the family computer. So much of my youth spent (wasted?) on this. I wish I had spent more time making friends and playing sports, or learning something more fundamental like math or programming. I don't even work in the tech industry.
Not squandered at all because it's not too late to learn something like programming, for example, and knowledge of Debian will help you get started. Linux is a great platform for programming. Languages, libraries, IDEs/editors are only an `apt-get` (or what have you) away. It's so powerful, even Microsoft had to come up with WSL to try to remain relevant to developers.
Eh. I played football as a kid for who knows how many hours, and never became a professional player. It isn't a waste if you enjoyed and learned something from it.
I had a similar feeling installing Gentoo on my graphite iMac in 2004. Except in my case I received so, so much help from the IRC channel, particularly Joseph Jezak (JoseJX) who helped me with some very deep problems I had involving patching X to start on the iMac because it hadn't been used on my model before.
I saw just now that JoseJX went on to do Google Summer of Code with Gentoo in 2006 to work on the X.org Configuration Tool.
I believe it took me most of the high school summer to get X working. In the meantime I got to use links CLI web browser, IRC, and instant messenger clients (AIM etc) for 2-3 months until GUI was functional.
I became completely comfortable in command line as a result. It's sad to me that I can't help students replicate a simklar experience today because the internet seems largely unusable in a text-only browser now.
Those communities are incredibly for new users. For me it's been critical to have others around who can get me past roadblocks while I work hard to genuinely learn on my own.
And yes, the Gentoo docs were superb. The forum and IRC had incredibly patient people who genuinely loved helping people of all skill levels.
If someone was running a non Ubuntu distro on a personal laptop, I used it as a proxy for some amount of technical ability and it was mostly justified.