I don't think the works are primarily a proof of our faith to ourselves but a witness of the authenticity of our faith, already known by us, to those around us. At least, that is what I think James is talking about.
Self-witness, I feel, comes from continuing acknowledgement of Biblical truths to your self, growing desire to obey God's commands, and continual turning away from sin.
I would also add that both the easy-believism and works-based crowds have a higher *perceived assurance because they are both point towards actions the have take as opposed to actions God has taken. The Reformed position is indeed less straight-forward but that is because we reliant on God's mercy... and I honestly believe that the recognition of the full need for Jesus to be our righteousness to be very comforting to me personally.
I would recommend getting a copy of <em>The Valley of Vision</em> as this has been very helpful for my own assurance and encouragement.
I’m terrible at them too. This is what helped me a lot and I would just read them and make them my prayer to God. https://www.amazon.com/Valley-Vision-Collection-Puritan-Devotions/dp/0851512283
I highly recommend you acquire this particular book: https://www.amazon.com/Valley-Vision-Collection-Puritan-Devotions/dp/0851512283/ref=sr_1_1?ie=UTF8&qid=1523284721&sr=8-1&keywords=the+valley+of+vision
Woo-hoo for wanting to deepend your relationship with God. What everyone else has said is great. But I've got a few things I'd add.
Praying scripture can also be helpful. The Psalms are a great way to start. Basically you read a few words, a line, a verse, however much and then reword it in your own words and add your own related thoughts, confessions, thanks, requests, etc.
Sometimes reading printed prayers can be helpful. The book The Valley Of Vision is one great example. https://www.amazon.com/Valley-Vision-Collection-Puritan-Devotions/dp/0851512283 There are many others.
For Bible reading, eventually, reading through the Bible cover to cover is a great idea. I like to use a chronological reading plan, as that helps me understand the overall story of the Bible better. I also recommend The Jesus Storybook Bible. https://www.amazon.com/Jesus-Storybook-Bible-Every-Whispers/dp/0310708257/ It looks like a kids' book and it is written on a level that kids can understand. But it also does an awesome job of explaining the story of the Bible and particularly God's plan and Jesus' place throughout all of it. The pictures are really cool too.