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I really enjoy watching speedruns and I'd like to try my hand at it but as the title suggest...where the hell do I start? I know a lot of streamers will say things like "Just start" but that's an extremely overwhelming task for myself. I'd like to try either Dark Souls or Half-Life 2. Should I start by just learning specific tricks? Or try runs and restart when I get stuck on a part for more than X amount of minutes? Try to finish entire runs regardless of time? I'm so lost.
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Everyone learns differently, you just need to find out what method works best for you. Personally, I think finishing entire runs regardless of time is a fine way to start. You will finish faster each time while getting more and more familiar with the route, tricks, etc.
The only traverse you could possibly encounter is if you're not having fun. So certainly don't grind a thing until it's no longer fun, it's not good learning that way either.

Certainly people only get into the "lost 2 secs restart" cycle after a LONG time running the game and only when going strictly for PB attempts.
Find a game that you like enough to play for hundreds to thousands of hours. Then do exactly that. Watch other speedruns of whatever game you decide to speedrun for strats.
It's important also to write about any findings of your own on the relevant thread (and update the wiki why not), but also do that whenever you feel you need feedback or information.
I think that for any game you're going to start running, the most important thing to do is research.  You should familiarize yourself with the route (if there is one) and any tricks, skips, or glitches in it.

Once you have a general idea of the mechanics you'll need and the route then usually the best place to start is the beginning.  It's important to practice, if possible, practice each section/level/etc of the game and then try to put them all together.  I play mostly on older consoles so I can use emulators and savestates for practice, but this may not be possible in the game you decide to start running.

Focus on finishing runs at first regardless of the time, then practice any trouble spots you might have.  I think that finishing your first complete run is a huge milestone and a great motivator for any runner, after that you can reset to your heart's content.

And lastly, if you don't have one yet, get a timer and make some splits.  Nothing like green splits to make you feel like a good speedrunner.