To all Pentesters...how do you own/root a Machine all by urself (without walkthroughs or guides?

Im asking this because everytime I feel like Im getting the hang of it and I can "independently"

try my hands on a (equally difficult) machine I just get stuck at an impasse...

until I watch a Walkthrough guide or video and ask myself... "how tf was I supposed to arrive at this solution all by myself???(given that I never been taught this solution)"

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Is it just a matter of having seen every possible way to take advantage of …

ask asking can cybersecurity equally guide guides hands on machine own root try video walkthrough watch