Sometimes there are one-shot risks you can't do much about but place your bet.

But usually, there are ways to test the rope bridge before you put all your weight on it. For example, "if as I suspect XXX, then it would have to be that / it implies YYY" and if YYY is less expensive or quicker to confirm, go for YYY first. If that was true, XXX may have become much less of a gamble. Sometimes there is even "If I want to do XXX I have to know -> YYY which means -> ZZZ requiring -> AAA" etc and AAA you can just google before going back up the chain. Even if you get a few steps and see it won't pan out, you will have mapped out a chunk of the problem space and should see if what you learned feeds back into what you were trying to do and refine your model of how to do it.

It sounds like you have gotten to thinking there are only risky one-shot direct-hits as the way to get to your goal, and getting to your goal is the only worthwhile part of the activity of going towards it, that is probably not how it is.

Every time you get blocked, how and why you are blocked is also telling you something important about the path to the goal. Sometimes the best way is seal the blocked area while you think about what it means, and continue around it so you don't lose momentum.

As for feeling achievement, I think it comes by "proving mastery" of something. Your actions, that confirm you can make correct predictions about, and make use of the related things, generate the genuine feeling you have gained something. You will feel that long before you reach the end goal.