Hey, that’s definitely not a dumb question! The way I’d recommend watching something that is harder to follow in real time is actually twice – once to get a general understanding of the steps that you’re going to be taking, and then one more time to actually follow along.
Try to practice replicating a ‘task’ rather than an exact set of clicks. E.G. instead of thinking “extrude these vertices, inset, then move slightly over”, think “create the loop around the eyes” and challenge yourself to rely on what you already know to get you there. Think more about the bigger picture and trust yourself. Then, if you find that your version looks different, you can focus more on each individual click if you need to to see where the difference came from.
Thinking of a set of smaller steps as one single step is just something that happens naturally as you get more comfortable with modeling (or any skill) and it may take a lot of practice, but it’ll come. Hope that helps!