There are no dumb questions, only dumb answers.
The first thing to consider is if ya have not been filing a chain very long, then it is likely you are not getting it really sharp.
It takes practice, and lots of it.
There are some people who are more gifted, and catch on faster. Mostly I have seen it takes about a season to learn what the tooth is supposed to look like. Then it takes another season to learn how to hold the file to achieve it.
I told one of my cutters the other day. First you have to be out on a nice day with a not so great chain. No spare chain, but a good set of files. You plunk the saw down and really do a first class filing job. You are proud of your work, and go back to cutting. You notice something funny. The saw is hopping on ya. You knock a couple more blocks off, and think about it. Boy, part of this chain is really working good. which implies... part of it isn't! You shut the saw off and go gaze carefully at each tooth as you pull it around. You noticed where you were getting sloppy and you file it up a few strokes to straighten the angles. Then you go around and touch the rakers to be certain that they are about .025 or so... You try again. It is a little better, but still not perfect. You plunk down and try again. Find and adjust a few more, hold that file steady. Straight lines. Eventually you get it pretty decent. It is cutting fast, and running smooth. You have achieved Satori. With all that fiddling to get it really good you now understand why it really ticks ya off when ya do something stupid like fall thru a cut and barely touch the sand :bang: knowing it will take a few minutes with a file to correct that damage, and you are filing off very precious metal to do so.
This is why I am going to a pay the cutter system, instead of them using my saws!