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Literature Text
Perspective is probably one of the most difficult concepts in art to grasp. I suppose pretty much everyone has or has had problems with it, even some more experienced artist. I can tell you I'm not exception to that. Even thought I wasn't extremely bad at drawing, it still took me 6 years to even figure out where I needed to work on before I could address the deeply rooted issues I had.
I have basically based all of my artistic understanding on perspective and 3D. Although I can't say I'm perfect in my execution, by looking my gallery you can see that pretty much all of my drawings tries to convey the feel of depth and 3D. I think that's one of the factors that make my drawings stand out and maybe you also feel that way. Drawing depth has become a second nature for me.
You may also have noticed that I have about four tutorials (depending on how we define perspective) that tries to explain a thing or two about perspective. I have also few practices/demonstrations about perspective. Here they are:
I feel I haven't been able to convey my understanding quite as well as I have wanted though. I have a decent idea what makes perspective so difficult for many, but I'm also having problems with translating my own understanding into tutorial format. It's like there is a missing bridge somewhere that I haven't been able to tell you about. I'll keep trying to find it.
The first challenge I have is that my way of thinking might be so out of the box that it doesn't make sense to others unless they know all the factors about it. Things I find very straightforward and self-evident probably are very alien for an average person. I can relate to this to a degree because I originally didn't think the way I do now and I'm sometimes perplexed with my own findings.
The second challenge is that my approach is pretty much completely opposite to how perspective is commonly addressed. I don't think about vanishing points or guidelines (in fact, they were the reason I initially went astray), but I have confirmed that the way I think doesn't violate any of the rules of traditional perspective. I think in very spatial way, as if I personally were within the drawing and then I just analyse how I see or should see the objects in the scene. It's a lot more difficult to draw a good perspective drawing without using perspective guidelines. I tend to draw reference objects (bounding box) trough eyeballing and its reliability depends solely on my ability to get look somewhat right. I think my approach makes perspective feel more lively and real. I often see very well executed perspective drawings that are... how to say it... dull and artificial. That's not to say my approach is ultimately a better choice, but it has served me surprisingly well because it's applicable in any possible scenario.
The third challenge I have is how to tie concepts and reality together. It's good to note that I didn't figure out perspective from still images or examples. It dawned to me trough motion and movement (I worked on a 3D model and orbited around it) and witnessed how the rules of perspective changes the view). That said, if I truly wanted to explain my understanding, I would need to present an animation or other video material to truly express my ideas (later in this post you will find my best attempt to demonstrate the idea). I think that normally people aren't able to piece things together from several still images. Hence there are life drawing courses where you can actually "orbit" around the model and see how the subject looks from any angle, that's the whole point in those courses in my opinion. Also, if things are too simplified and conceptual, the examples lose their meaning. People have no problem understanding how the real world unfolds in front of them because there are so many visual cues, but to make them perceive something specific in just one simple cube or plane... to make them see something that isn't there... that's a huge challenge. These were the biggest obstacles for me to figure out, not to mention how to actually work on them.
I believe that you won't go too badly wrong if you try to ponder these things as well. If anything, it's worth checking out.
The fourth challenge is that even if you figured a thing or two, you still need to transfer that into your drawings. That requires a lot of practice which isn't exactly tied to perspective alone. It's also up to you to identify your deeply rooted issues, they may be different from what I have found myself.
I have had some quite deep discussions with some people who have asked me about perspective in comments. In these discussions people often have had some sort of enlightenment. Here is a short comment thread you may be interested to read trough: comments.deviantart.com/1/5940… (I should have saved all such instances, now I should browse trough all the comments to find more). I don't know to what degree it has been thanks to my understanding, I feel the people I discussed with have figured something out on their own while they have processed things in their mind or experimented on their own. I suppose it's important for everyone to find their own way to approach concepts like perspective.
If there is something common with several people I have talked with, it's the "pole" concept. Like on the aforementioned comment thread, the person comes up with the infinitely long pole that vanishes at the horizon (horizon is infinitely far away). You could say there is a vanishing point there. If you move that pole around, its other end still vanishes somewhere. That means that where ever that pole ends, there has to be a vanishing point. So if you anchor the other end in place and just rotate the pole along that anchor point and plot every vanishing point, you form a spherical point cloud (that pole is the radius of the sphere). This image shows how that spherical point cloud could look:

So the idea is that you as the beholder are in the center of the perspective system, i.e. in the center of that point cloud of vanishing points. The point you are looking at is the other end of the pole (the one that is infinitely far away). You only need a handful of vanishing points from that point cloud when drawing though. Which particular vanishing points you need depends on the orientation of the objects you are about to draw. I think traditional perspective tutorials that focus on 1-, 2- or 3-point perspective fail to explain this and it can seriously cripple your ability to learn perspective. A cube has 6 vanishing points in total, because if you have one vanishing point, say, above, then there also has to be one below. The same apply with left vs right and front vs back. Here is an animation I once made (modelled in Sketchup):

Does this make any sense to you? Did you find the bridge or just another cliff?
I'm interested hearing whether I managed to show you the missing bridge or not. Maybe I still wasn't able to define the bridge properly. Maybe some more animated examples would do the trick. Maybe I should explain the rules of a cube in meticulous detail, because its essential to understand how it behaves in order to understand how any other form behaves. Maybe I'm still missing something absolutely crucial.
I hope to find that out.
Nsio of the Hermit Mystics
I went to read this just after my first comment on your webtoon. 'v' My main difficulty with perspective is I think I'm unable to picture things in 3D, and even less to picture myself in a 3D place. Hence why I have a sense of direction nearly nonexistent. I'm always lost, even in my own village, my friends are always trying to teach me about it when we are walking together and end up being shocked by how much I can't picture things they see as evident. So when I draw, I'm having huge difficulties with seeing my characters in 3D, and I'm terrible with depths... It did not really help me to make a bridge when I read this journal, but it is not a cliff either. Because, while it did not help me to picture something precise, when I still tried to see myself in the cloud of vanishing points, and to chose any of them to draw the lines of the pole, I think I saw things another way... I'm not sure if it was clear in my mind, but I feel it was different.
I'll keep using references like the website posemaniacs for my official works, 3D being clearly what helps the most when drawing I agree, but I'll keep in mind what I read here, and take a look at the links to do trainings and warm-ups with that point of view on perspective. 'v' Plus, I'm trying to teach about art to some students I have, and I did not know how to help them on perspective. I will try to talk about it with them using your tutorials and journal, to help them think about it too and try to work together on it. >v< Thank you for your work.♥