That sample you posted seems pretty complex if you ask me. I barely know any of the words in the first two sentences. You say you should be able to understand this, but why exactly do you feel this way? When you attempt reading stuff like this, do you use a dictionary? At my current level I certainly couldn’t read something like this without a dictionary, and even then it would probably be a slog.
Hmm, I do use dictionaries a lot. Jisho has been a great companion to me for a long time now. I guess when I say I ‘should’ know that, it’s more of a strange way of saying ‘I’ll never get there’. Now that I think about it, it is kind of a weird thing to say, huh? I guess I’m just not aware of my own level, or other materials’ levels? Maybe I’m pushing myself too hard? It’s frustrating to think about it because, like I said, I’m just afraid I’ll never be able to get there… I wonder if it’ll take another ten years. I do understand the concepts behind a sample like the one I posted. I know the grammar, or can at least point out when it’s being used. The particles, conjugations, that sort of thing. I have a hard time with compound sentences and then combined that with all of the relatively unknown words, I guess I just feel lost. There’s that ‘what now?’ kind of feeling. And that is further compounded by the fear that I’m doing something wrong. I don’t know. Now I’m kinda confused. =/ I guess the way I interpret the language is lacking.
Try reading web articles with Yomichan.
It makes looking things up less tedious. Bonus points if you use a Japanese-Japanese dictionary, but you can plug in the same one that Jisho uses too.
Oh, I already have that, thankfully! It definitely helps a lot. 
Another problem I realized I have (and knowing it at least gives me some comfort), is that I often read or listen to something in Japanese… but my mind immediately tries to interpret it in English or my native language. I guess I’m just not thinking in Japanese enough… Which means my immersion is lacking? It’s a difficult habit to break.
It could also mean that what you’re reading is a bit above your level (maybe not by much though?). Personally, when I implicitly understand something I’m reading in Japanese I don’t translate. But if I had to look up a lot of words or if it’s a really long, confusing sentence, I often find myself translating it (at least in part) into English.
A lot of people replied already, but I wanted to +1 the idea of having actionable, concrete goals. The more specific, the better. When you say you “should” know words, or that you wish you knew them, what does that actually mean to you ? For example, does it mean that you would like to know, I’m making this up, the 8000 more common words ? Think about your specific goals and put them on paper. I had a tendency to have “goals” that weren’t measurable and that were more on the abstract side, ex. : “I want to be fluent”. This can mean so many things. By forcing yourself to choose specific, mesurable goals, you get many benefits :
- it gets way easier to track progress because you can actually mesure it, which in turn is very satisfying and encouraging
- you can easily break down your main goal into mini-goals or steps : what is needed for you to reach the goal ?
- by aiming for a certain date, you can check if your goal is realistic. Let’s say you want to learn 8000 new words in a year, but you know you don’t have more than 15 minutes to dedicate to this goal per day, and that on average, learning 10 new words takes you 15 minutes. Well, you can actually calculate that and adjust your expectations by either aiming for less words learned in the year, or pushing back your target date. (this one is really dependant on personalities, deadlines can work for some people, but trip others up)
- but most importantly : by actually having to think about your specific goal, you’re having to process your self-expectations and the emotional load attached to the goal. Let’s take the example of the “I should know these words”. I’ll speculate here a bit and use it as a starting point for how a thought process could go from there. So, if we break this down, you wish you knew more words. How many words ? Which ones ? Are you expecting yourself to one day know all of the words in the dictionary ? Sometimes, we don’t even realize what our expectations are before we force ourselves to truly examine and measure them. In this scenario, if you found yourself having this chain of thought, you would probably end up admitting : “I’m not being fair with myself. I can’t actually know all the words in the dictionary. Would I expect this of the greatest learner I know ? No. Now, what I actually want is to understand more [common words/words related to X field/etc.] or simply know that I am making progress and learning new words every day. How many words would make me happy, and give me the satisfaction of knowing I’m working on my goal ? 15 words a day sounds about right.” Etc.
You probably already know this, but try to use the SMART goals guideline as a starting point, it really helps !
Also, remember to celebrate your victories ! Break down your goal into milestones or mini-goals, and celebrate each 
and every one of them ! Get yourself a sticker. Some candy. Make a pretty board you hang on your wall and check the heck out of that step’s checkbox. You’re making progress, that is amazing ! And I can tell you’re dedicated, 10 years of study is so impressive, I really admire your focus !
I’d say so as well. While I don’t have any vocabulary problem with those sentences, the structure is quite convoluted too. Definitely not something I would have been able to read at an intermediate level (but then again, I have low pain tolerance).
I don’t know if this is encouraging to hear, but I passed N1 (twice) last year and my level of understanding for the screenshot is still probably the same as yours. Seriously, you have no context, no clue what is going on in the story, who all these people are, and the sentences are really really long and flowy as well.
I just want to say that just because you studied for 10 years, you shouldn’t feel like you have to be able to read everything that’s put in front of you. Your level is individual and not necessarily determined by how long ago you started Japanese.
I kind of understand how you feel. When I passed N2 and went to Japan for a month, I was extremely self-conscious of my speaking level. I felt like being N2 and not being able to speak properly would make people think that my Japanese level was much lower than they expected, and that I would embarrass myself. Which lead to me not really trying to speak, because „I should be at a higher level“, „I should be able to say this without much thought“, „I shouldn’t be making these simple mistakes when speaking“, and so on. But obviously not speaking didn’t help at all with getting my speaking skills on par with reading etc., which I of course realize now.
Seriously, I would stop thinking about „I should be at this level because it’s been ten years already“. That doesn’t matter. The only thing that matters is where your level is at now, and what the next best i+1 thing is for you to read.
If that’s a children’s book, that’s okay. If that’s a short NHK news article, that’s okay. If that’s a parallel reader with English translation, that’s okay too. There’s no shame in picking materials that you think are „supposed to be“ too easy for someone studying for ten years, because the only thing that matters is your level now and your reading needs now, and to find out what would be a good thing to read at your level. Yes, even if you don’t understand everything put in front of you, like that VN, that doesn’t mean there aren’t loads of other VNs, games, novels, that you could read with much less frustration, that would help you regain some of the enjoyment when engaging with Japanese content.
OP this might sound stupid and you might already be doing it but I also have a hard time with structure.
There’s no shame in breaking it down bit by bit then piecing it together. Especially if you’re only reading for your own entertainment.
If I’m really struggling I’ll open up a notepad and write down the sentence fragments and then piece them together afterwards.
I don’t know, you chose probably the go-to example for a difficult VN writer as an example. I don’t think there are many more difficult writers than Mareni in the VN scene so I wouldn’t expect it to be easy. You can read through reviews from Japanese people on erogamescape (18+) that gave up on it for being a chore to read so…
I feel a little more at ease reading through some of these replies again. At the very least, I feel like nothing will come of it if I’m hard on myself… I guess I just need to take a couple steps back and reassess what I’d like to accomplish, kinda like what @elisabeth said. Thinking back on my original goals. I wanted to learn Japanese at least enough to be able to read a visual novel and more or less ‘get it’ without requiring translations. And there are so many of them that still have none, so I guess my goal is still worthwhile. And it should be fun. Visual novels are such an incredible medium, and I really admire all the people that make them… Even if I will never be able to fully ‘grasp’ everything they write. 
This, for example, is definitely something I had an easier time with. I stumbled upon just a couple words, but was able to grasp the nuance of what was happening at least (I’m just lazily browsing through VNDB to find stuff to ‘test’ my reading comprehension ^^; ):
I guess it really is just a matter of stepping back, being okay with my level, and let the improvements find themselves.
Pretty much what I have to work on, I think. Which means more immersion. At my own level, of course. ^^;
This too. The fun part of the process is what I’d like to rediscover. The magic of what got me into it in the first place. I’ve actually been rewatching a few anime I really liked as a teen, to try and remember that. Maybe not ‘relive’ it, but just as a reminder of what got me here in the first place.
That’s a good call. I could write down some of the sentences I had the most trouble with and look back at them later. Then I don’t have to get bogged down trying to understand this one tiny bit of a larger work.
Yep, I had a feeling this was the case. Bit off more than I could chew. ^^;
Exactly.
Sometimes you just need to read on like you would in your native language or in English.
Even as a native speaker I’ll come across things I read in English that leave me scratching my head, so I’ll put in a sticky tab and move on or make a note of an unfamiliar word or turn of phrase. You can do the same in Japanese.
Just go with the basics and think to yourself:
“Okay, this word is marked by は so that’s the topic… ‘As for X’, and this one is を so this is the object of the verb which is… oh okay it’s got something to do with eating but it’s て form and we’ve got ourselves an auxiliary verb. Let me just piece this all together.”
I quite agree. Also, I couldn’t help but feel that you have a tendency to blame yourself, and to worry too much about getting ‘there’ (i.e. reaching the fabled land of Japanese fluency). My way of seeing it is this:
Firstly, you cannot keep telling yourself you ‘should’ be able to do something. It will just make you depressed, and even if it’s true, it won’t help you progress. I kept telling myself I ‘should’ be able to keep up in class when my physics teacher explained next to nothing and had all of us copying everything like nutcases so we could read it later. End result: getting through the notes on my own just frustrated me even more than it would have if I hadn’t thought about how little I understood, and I was exhausted each time I finished a chapter on my own. More importantly, it makes no sense to have expectations if you can’t justify them. It’s one thing to say, ‘I should know this kanji: I created a mnemonic for it last week and it took me half an hour. I’m pretty sure the mnemonic was meaningful…’ In that case, you should indeed be able to remember it since you’ve taken concrete steps that ought to lead to retention, and if you can’t, no problem: perhaps you need a different mnemonic. It’s quite another thing, however, to say, ‘I’ve been at this for [duration]. I should be done by now.’ My question is why? What justification do you have for that statement? I spent a year making an effort to follow my French teacher’s rambling and digressions in the hope of deepening my knowledge of democracy (which was the theme we were discussing). I ‘should’ have been able to follow his train of thought after a year of experience, no? It can’t possibly be that hard, right? Well… no. It didn’t work, and his thoughts were as convoluted as ever. If there’s no good reason for me to have such an expectation, I shouldn’t be putting pressure on myself.
Secondly, about reaching fluency, it’s quite a vague, grand goal, and it will definitely be easier if you set yourself intermediate goals. The last intermediate goal I completed was ‘understand as much of the Shield Hero anime as possible without subtitles, while checking the dictionary if necessary’. It taught me a lot. I’m not confident of understanding everything if I watch the anime without subtitles again, but I feel that I learnt a lot while enjoying myself, and I think that’s what matters. My current intermediate goal is to finish the Tobira textbook since I want to move on to more advanced material as soon as I can. Another thing you may need is a more structured view of the work required to reach fluency. It doesn’t just happen with time and effort. (I hope I don’t sound condescending or pedantic, because for all I know, your linguistics background means you know more about this than me.) My experience with becoming fluent in French showed me that the language learning process looks like a tree: you have to acquire core vocabulary and grammar at the lower levels before branching out into a very broad set of words and expressions at the advanced level. As such, it makes more sense to concentrate on that core knowledge in order to progress more rapidly over time.
Finally, just some random jumbled thoughts in no particular order: you said that perhaps your ‘immersion is lacking’. I think the truth is that you’re trying too hard to immerse yourself in anything and everything. Yes, it’s frustrating when you can’t understand something that you really want to absorb: I have 15 volumes of Konosuba sitting on a shelf at home, and I haven’t touched them because I know I’m not fluent enough. That irritates me. What we all need is immersion at an appropriate difficulty level. My experience is that only your listening abilities improve with mindless immersion. The same thing would probably happen if you immersed yourself by reading aloud texts with furigana for everything: your character recognition speed would improve, but you wouldn’t understand a thing. You learn to pick apart the symbols, be they auditory or visual, but you don’t learn how to understand them. Thus, I suggest you look at something where you don’t have to look up more than you can tolerate, whatever that percentage of vocabulary or grammar is. Perhaps you should try reading NHK News Web Easy articles – again, if you don’t find them ‘easy’, don’t fret. Everything will come in its time. Alternatively, as I suggested, try watching anime with subtitles, ideally with a transcription open in the background so you can look words up easily. As you get used to the structure of simpler Japanese sentences, you will gradually be able to parse more difficult ones. I can’t read the first screenshot you sent because there are too many words I don’t know, but I’m fairly confident that I’ll be able to parse at least some of it with a dictionary, because I have some sense of what each word is doing. This sense can only be developed by getting used to parsing simpler sentences in a context that makes them easy to understand. A year ago, I wasn’t able to parse the first sentences from Shield Hero Volume 18 on my own, because I couldn’t hold all the information in my head given that Japanese presents information in the opposite order to English. Now I can parse the sentences, because I’ve learnt to collapse sentence parts into blocks the way I do in English. This ability comes with familiarity, and you’ll be able to do it too. Also, I had help: I asked my friend to tell me how to parse the sentence, which opened my eyes to other possible structures. Whatever it is, don’t spend time being stuck alone: set limits on the amount of difficult material you’ll handle per day so you don’t get too tired and frustrated. Look up JLPT sites and other resources (like those from NHK) that may provide explanation. Come on the forums and ask your questions here – we’re not like WordReference, who insist that users make an attempt of their own, and I’m sure many of us will be happy to help. People in the book clubs on the forum ask each other about sentences they can’t understand all the time, and users from outside the club (myself, for example) often come on to try to help decipher these sentences. I know it may not come naturally right now, but let other people help you, at least in Japanese, so you won’t have to spend time mired in frustration with no way out. I wouldn’t have progressed as quickly without my friend’s help, and I’m sure it’s the same for many of us.
I have never done this in any of my languages
I think they meant that OP needs to generate more, rather than trying to absorb more.
I don’t think producing more output than input is even possible, even in one’s native language. (Maybe if you are a salesperson or a politician?)
OP, here’s a pencil. I want you to sell me this pencil in Japanese.
i hope people get this reference! this is great!
Oh jeepers.
I’m not sure even I get this reference and I made it. I was asked to sell a pencil at a scholarship interview and the previous post made me think about it. 
Its from the movie wolf of wall street. When he is trying to teach them to be confident sales people! great line