One thing you quickly learn when cutting your own firewood for heating with wood is that you need to become good at sharpening a chain saw. This is a skill that requires a lot of practice, but if you know what to look for, you can learn quite quickly.
Most people seem to have a tendency to not actually look at what they are doing, oddly enough. I know this because of my daily work as a plastic injection mold maker. I use my hands all day long and have trained many people to do what I do. Many of these apprentices realize that they are not really looking at what they are trying to work on.
It is the same when sharpening a chain saw. People tend to go through some kind of motions, but they fail to monitor what their sharpener or file is really accomplishing. They file away, then later discover that the chains saw chain is just not that sharp.
So, they give up and go out and buy another chain, which works great for a while. Then, they are back at the same point as before: dull chain and not very good results with sharpening it.
Some of the basics to remember are:
Learn how the cutting edge geometry actually should look
Look at what you are doing
Use a clean, sharp file
Keep the chain saw immobile while filing. If it moves back and forth, the geometry will not be correct.
It is almost always cheaper to sharpen than buy a new one
Wear gloves
Keep track of where you begin and end.
It is important to have the correct file size. If the chain calls for a 5/32 diameter, don't try to use some other random size just because that is what you have. It might work, sort of, but it certainly will not perform as it should.
It is worth the small investment to buy a file guide that is reliable and easy to use. There are many on the market and anyone should be able find a good chain saw sharpener guide. You really don't need to invest in a professional grade, unless, of course, you are a professional lumberjack!
When storing your files, don't just let them bounce around in a toolbox or something. If they jostle up against one another the cutting edges become damaged and the file teeth will quickly load up with filings.
Another option for sharpening a chain saw is to use a Dremel type hand held grinder. This can make the job go very quickly and the teeth will be much more accurately sharpened. One way to use this approach is to have 2 or 3 chains and just put on a new chain when the first one is dull. Then, when you get back home, use the grinder to sharpen all of them.
This takes a bigger investment, but then again, you can also use the grinder for other tasks around the house or garage.

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