I'm judging you right now, just not condemning
.
At least you know you suck, that's the first part of "recovery"
.
I feel this is where the jigs and guides come into play, they help you to learn proper file placement and help you to gain the muscle memory needed to sharpen a chain.
Step one, knowing what a sharp chain looks like/ what you desire your chain to look like after filing it (some people need some sort of magnification to help see it, im in this bracket of folks). If you don't know what you are trying to accomplish, then how will you ever know when you get there.
Step two, the proper tools. Without good sharp files, you'll be wasting your time, just like cutting wood with a dull chain.
Step three, knowing how to accomplish sharpening your chain, not just filing a chain. A filed chain is not necessarily a sharp chain, and a sharp chain is not necessarily a chain that will cut well if the rakers are not set properly(hence this conversation).
Step 4, doing it.
As the saying goes and as has been stated here, experience is what you get when things dogo as planned.
Filing a chain freehand is typically the result of practice with some form of a guide.
It's important to remember that what works for one doesn't work for everyone, find what works for you through trying different techniques until you find what works best for you. May guys get sick of trying to file and buy a grinder (which has its own learning curve), and they never look back. Others use a dremel attachment and like that. There are guide such as the roller guide, the guides that mount onto the file, the 3 in 1, and even guides that mount onto your bar and hold the file and the angles are set for you.
Keep seeking and you will find.
Ask, Seek, Knock, that's what I've read anyway, and it's worked for me
.