One thing that confuses people about The Bible is that it isn’t always in chronological order, I know that was one issue I had for a long time. Here are some things that I figured out and I hope this helps make studying The Bible easier and more enjoyable for you.
The first six books are pretty straightforward chronologically. The next eleven or so books are sort of chronological, after that it gets a little more jumbled.
The books of Genesis through Joshua tell the story of the Israelite people from the beginning petty much in order from the beginning of time, through The Patriarchs (Abraham, Isaac and Jacob), through their captivity in Egypt, their Exodus from Egypt led by Moses, receiving The Ten Commandments and other laws, 40 years in the desert, and finally moving into The Promised Land.
The first part of The Book of Judges is generally chronological but then it begins to cover several different events that were occurring at about the same time, but in different locations. The Book of Ruth is a completely “modular”; by this I mean that can basically stand on its own without any direct relationship to the rest of The Bible, It’s just the story of a family dealing with issues that families sometimes have to deal with and the narrative of The Israelites is essentially just a historical backdrop.
First and Second Samuel tell the story of the first few kings of Israel, King Saul and then King David. First and Second Kings and First and Second Chronicles overlap Samuel some but cover several hundred years of the history of the Israelites. First and Second Kings tell the history primarily from the viewpoint of the Northern Kingdom beginning with the death of King David, while First and Second Chronicles tell the story essentially from the perspective of the priests from the Southern Kingdom of Judah.
Chronologically speaking, Ezra, Nehemiah and Esther fit best near the end of The Old Testament. All three of these books take place after the Israelites began to return to Israel following the Babylonian captivity.
Like The Book of Ruth, The Book of Job is a “modular” story; it isn’t dependent on the rest of the Biblical narrative. It stands up well without much additional Biblical context as Job wrestles with some very difficult questions about pain and suffering and God.
Psalms, Proverbs and Ecclesiastes change gears as they don’t tell stories at all. Psalms is basically a collection of songs and prayers, The Book of Proverbs is just what it says it is, a collection of proverbs and wise advice, and The Book of Ecclesiastes has King Solomon looking back on his life and a list of ways that he unsuccessfully tried to find fulfillment in his life without God.
Isaiah ushers in the books of prophesy. Rather than looking at these books as telling a story, I find it makes more sense to look at them each as a Part of the story that is going on around them. For me it was most helpful to figure out where each of these books fits intothe larger story so that I could understand what role each prophet played in the overall narrative. When you know wherethey were writing from (northern or southern kingdom), who they were writing to (northern or southern kingdom) and roughly when they were writing, then their prophesies make a little more sense. The good news is that I put together a very simple chart to help understand the chronology and geography of the major and Minor Prophets that helped me and might just help you too. http://theminutebible.com/study-guide.php
This is The Book of Exodus on YouTube
This is The Book of Exodus on YouTube