Sometimes its based on situations going on in your life, that certain passages draws you in, or you find more value later on in life. Or sometimes you have a question in mind, and thats how you get drawn into a certain book or books of the Bible. So understanding your frame of mind, or your motive in reading is good to identify.
The other part is to understand the framework of the Word itself. The Bible isn't just a step-by-step instruction, these are books inspired by God, but have different authors, with different authors, and different style of writing. Some books are more poetic, and some are more step-by-step, some are allegory, and some are more direct accounts. There's themes, design patterns, narratives, parables, cross references, the styles goes on so it is a very rich book.
So alot of people, I would argue most times, don't know if they need to know a certain that they are reading. But part of it, besides not seeing the need at the time, is because usually we are not taught to go with a reading plan, and part of it is because we often read without getting the gist of the big picture nor the intent of the writer when reading it.
A good way to start is to jot down your questions or concerns. Going with a goal that is more personal, will make it easier for you to take in the Word. Its not a sprint, is a marathon so allow yourself to learn as you live out your life. So then approaching the Word its, make sure that you first know the big picture, if you can find a good youtube video even to give you a gist of what each book's theme and style is, I think it will help you have better direction. Once you know which book contains what type of insight/message, and you have the questions you want to seek out, then it will be easier to navigate through the text.
The Bible Project Channel on Youtube is excellence on giving a gist of the Bible and its cohesiveness throughout the Word.
The Bible Project
Also for inspiration, this sermon discusses why God gave us such a tough text to us. This is one of my favorite sermons to date, and I hope it inspires you to get to know more about the heart of God and how to desire more of the things of God.
Why God Inspired Hard Texts
Usually, Psalms and Proverbs are good places to start since they are considered the wisdom books if I was to recommend. But Genesis is good too.
Also make an effort to memorize a verse or two that sticks out to you or write it down.i'm learning to do this, because sometimes when I hit a tough situation, the Word is my only saving grace.