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I also realized a lot of my personal philosophy was independently discovered on lesswrong when I was about 16.
As for doubting your ideas - there exists a healthy level, but it perhaps actually increases as you age. A little less doubt is useful for exploration.
Randomness does seem important to many algorithms. ET Jaynes argued that there is ~always a more clever and harder to find deterministic approach that outperforms any randomized approach. There do seem to be counter examples in some cases though, such as mixed strategies in competitive games. However, I guess the most well-studied version of this question is BPP versus P which is still open.
I've actually been recently thinking about randomness in ML, and I've come to a compelling case for it's specific role. The insights do seem to generalize to all problem-solving mechanisms in a way. I can expand if you want
If it’s worth saying, but not worth its own post, here's a place to put it.
If you are new to LessWrong, here's the place to introduce yourself. Personal stories, anecdotes, or just general comments on how you found us and what you hope to get from the site and community are invited. This is also the place to discuss feature requests and other ideas you have for the site, if you don't want to write a full top-level post.
If you're new to the community, you can start reading the Highlights from the Sequences, a collection of posts about the core ideas of LessWrong.
If you want to explore the community more, I recommend reading the Library, checking recent Curated posts, seeing if there are any meetups in your area, and checking out the Getting Started section of the LessWrong FAQ. If you want to orient to the content on the site, you can also check out the Concepts section.
The Open Thread tag is here. The Open Thread sequence is here.