Words are interesting when you try to translate them from one language to another. A language is grown from the collective imaginations of the people, and as much of a language is words as it is ideas. One television show dealt with this by having the characters speak in analogies. When to people look at each other and say, "Tristin at the station," no one could understand them because the rest of the world had no idea that, "Tristin at the station," meant sadness because Tristin lost the love of his life in the station.
What is really important to a person has more meanings than what is not important. A basketball is a basketball, but love has so many shades of meaning that only someone with those same ideals can understand. We say Puppy Love, and we know that it's love between children. We say Caustic Love and we know that they aren't good for each other. True love may or may not last, but it's the love of their lives. But how do you translate those terms into Aramaic when they have controlled relationships and the very concept of love is a bit alien to them? You don't. You can't. You have to start with kindergarten and then build up the concepts into ideas, and when you do that, you change the person and make them understand, but then when they go back to their people and try to explain the new concepts, they're stumped.
Separate this by time, and distance, and let the culture die out, and you get a set of concepts that are displayed in letters or pictographs, and while you may eventually understand what the word is defined as, you will never truly know what it "Means."
Words have meanings. Those meanings are dictated by the society of the speaker or writer, and are as defined by definitions as by the speakers personal experiences. When reading an old document or text, if you allow your experience to define how you read the words, then you deny yourself the truth of what you read, because you deny the ideas of the writer and substitute your own. You get what you want to out of the words, instead of what was intended, and this is dangerous.
The bible is unique book, in that it is large enough to generally define itself. But even this is not true in some cases, because different books were written in different languages. A word that is translated as, "Submit," has different definitions, and in some places, has meanings that are so different that it should have been translated into a different word altogether - but when English is a composite language, and we don't have compatible concepts, then how do you translate it? Again, you can't. But there is something you can do.
The context and meanings of words within the books of the bible are somewhat defined by looking at the words in context within multiple passages. It's easy to make assumptions, however, and overlook at simple meaning that is culture based. Look at the "Look at a woman with lust... adultery," verse in Matthew, or the "each man should have his own wife... women her own husband..." verses. In one, you would think that everyone that looks at his wife with the desire to sleep with her would be committing adultery, and in the other you can look up every word in the passage, and most likely you would not bother looking up the word "own," and discover that the passage does not say what it appears to say.
But while this is a great start, occasionally that's not enough and you'll need to look deeper. Seeking out a native speaker of the language (those languages which are not dead) but even that's difficult, and to make matters even worse, even languages like Hebrew, which are thousands of years old, have evolved over the years. A word may not mean now, what it meant then. Look at fag in English, it means something now, but once it meant a cigarette or even earlier, it meant a match. Punk means an out of control rude kid, but it once meant rotten wood used to start a fire. Yada means to get to know someone, but yada yada yada now also means to REALLY get to know someone. Like as in the bumping uglies sort of way. Get it?
So how do you understand the Bible?
Read it. A lot. Let it sink in.
Then, start to question the words. Look them up in free places like Blueletterbible.com and then go to the bible and find each instance of that word, and read how it's used in sentences.
This will get you a long way toward understanding.
Or, you can pray. You can read, pray and ask to understand. It may be your gift, it may not. If it is, then that's fantastic, and if not, then seek someone out who does have that gift.
But in everything remember this. Your salvation is based on Jesus, not the bible. The bible is a great book, both sweet and bitter, and to those who understand it, it opens amazing doors, but if you don't understand it, rely on your faith. If every bible on the planet were destroyed, then we would still have our faith. Never forget that.