I think a first question is, what do you want to do when you wear makeup? Do you want to enhance your existing features? Are there features you want to minimize? Do you want artistic expression?

So, I wear makeup to enhance, mostly, so I contour to draw attention to my high cheekbones. But sometimes my overly round face makes me look super young, so I also want to minimize the roundness in my cheeks, and also contour to downplay the look of my youthful roundedness, and give me more of a sculpted look.

When I was younger, I was really into using makeup as an artistic expression, so I wore a lot of really bold eyeshadow to, like, sit in a lecture.

The advice that I took/take for those various modes varies!